The response, honestly, surprised me.

My LinkedIn has been a fury of activity ever since—messages, connection requests, and a noticeable spike in profile views.

And it reminded me of something I used to believe for far too long:

“If I just do great work, my career will take care of itself.”

That belief is comfortable.
It’s also incomplete.

Because here’s the reality:

Two equally qualified leaders don’t get the same opportunities.

The one with the stronger visibility does.

Why this matters more than ever in Customer Success

Customer Success leaders are some of the most impactful operators in SaaS.

We:

• Drive retention and expansion

• Influence product and GTM strategy

• Sit at the intersection of revenue and customer experience

And yet… many of us are invisible outside our own companies.

Not because we lack expertise.

But because we’ve been taught to:

• Stay heads down

• Let results speak for themselves

• Avoid “self-promotion”

Meanwhile, the market rewards something different:

Perception shapes opportunity.

If people don’t know how you think, what you stand for, or the problems you solve…

They can’t bring you into bigger conversations.

The experiment: What happens if you build your brand on purpose?

About a year ago, I decided to test this.

Not as a marketer.
Not as an influencer.

But as an operator who wanted to see:

What would actually happen if I showed my thinking consistently?

No viral hacks.
No polished content strategy.

Just:

• Sharing what I was learning

• Starting more conversations

• Being visible on purpose

What changed (in 12 months)

Here’s what happened:

• 285 LinkedIn posts

• 253 meaningful conversations with GTM leaders

• 2,000+ new connections

• 12,500 followers

But the numbers aren’t the point.

The quality of opportunity changed.

I started getting:

• Inbound requests from other CS Leaders

• Invitations to speak

• Strategic conversations with CROs and CEOs

• Advisory opportunities

And the biggest shift?

People already understood how I think before we ever spoke. In fact, a lot of people who I have just met will say that they feel like they already know me.

The biggest mindset shift: You can’t build a brand in private

This is where most CS leaders get stuck.

We think:

• “I need a better title first”

• “I’ll start once I’ve perfected my framework”

• “Who would even care what I have to say?”

• “What will my company think?”

But here’s the thing:

You can’t build a brand in private.

Your brand doesn’t come from:

• Your resume

• Your job description

• Your internal reputation

It comes from:

• What you share

• Who you engage with

• The conversations you create

The Visibility Flywheel

Once I stepped back, I realized this wasn’t random.

It was a system.

1. Conversations → Content

Start by talking to people.

Peers. Other GTM Leaders. CROs. Former colleagues.

The best content doesn’t come from sitting alone; it comes from real conversations about real problems.

2. Content → Credibility

Then you share what you’re learning.

Not what’s perfect.
Not what’s polished.

Show your thinking.

When you do that consistently, people start to associate you with:

• Certain ideas

• Certain problems

• A specific point of view

That’s credibility.

3. Credibility → Opportunities

This is where things compound.

Because now:

• People tag you in discussions

• They refer you into conversations

• They reach out proactively

And those opportunities?

They rarely come from job applications.

The real opportunities come from conversations.

4. Opportunities → More conversations

And the flywheel continues.

More exposure → more conversations → better insights → stronger content → more opportunities

What actually makes posts work (no fluff)

A lot of people overcomplicate this part.

Here’s what I’ve found works—especially in CS:

Every strong post has at least one of these:

• A real problem

• A personal experience

• A practical takeaway

• A strong opinion

That’s it.

You don’t need:

• Perfect graphics

• Long essays

• “Thought leadership” language

You need:
clarity + honesty + relevance

People want to know what works (and what doesn’t) when it comes to CS.

The simplest way to start (steal this)

If you’re thinking, “This sounds great, but I don’t have time”…

Start here:

Per week:

• 5 new connections

• 2 meaningful conversations

• 1 LinkedIn post

That’s it.

No content calendar.
No pressure to go viral.

Just consistency.

The LinkedIn mistake most CS leaders make

Your profile is not a resume.

It’s your digital first impression.

And most profiles:

• Undersell impact

• Focus on responsibilities instead of outcomes

• Don’t reflect how you actually think

If someone looked at your profile today…

Would they understand:

• The problems you solve?

• The value you bring?

• The way you think about CS?

If not, that’s your first unlock.

A reflection for you

Here’s the question I left the audience with:

What’s one thing on your LinkedIn profile that doesn’t reflect the value you actually bring?

Because that gap?

That’s where invisibility lives.

Final thought: Visibility isn’t about ego. It’s about access.

This is the part that changed how I think about personal branding entirely.

Visibility isn’t about:

• Being loud

• Posting constantly

• Building a “personal brand” for the sake of it

It’s about access.

Access to:

• Better conversations

• Better opportunities

• Bigger rooms

Because right now?

There are people with less experience…
less depth…
and less impact…

Getting those opportunities.

Not because they’re better.

Because they’re visible.

If you take one thing from this:

You don’t need to become someone else to build a brand.
You just need to stop being invisible.

So far, we’ve covered:

• How to Lead Value-Driven Customer Conversations

• How to Map the Customer Journey

• How to Get Yourself Fired as a CS Leader

• How to Turn Customer Success into a Revenue Driver

• How to Scale Customer Success (Without Breaking Your Team)

• How to Forecast

• How CROs Should Think About Customer Success

• How to Hire Great CSMs

• How to Grow in Your Career When Things Feel Stagnant
  

  You can read the posts here

Each post has been read by upwards of 280 people, and I continue to get 10+ new subscribers every week, which is incredible to see.

If you’re finding my posts helpful, share my substack with someone in your network.

Share Real Talk with CS Impact

And if you’d like to collaborate on a future post, I’d love to hear from you. Just reply to this email with the topic you are interested in writing about together (think something you are passionate about, an experiment you tried, a project you worked on in CS and had good results).

Now onto this week’s topic: aligning Customer Success and Sales.

This relationship gets talked about a lot.

And yet… it’s still one of the biggest reasons Customer Success strategies fail.

I would’ve been remiss not to include it in this series, because the reality is:

You can have a great CS strategy on paper, but if Sales and CS aren’t aligned, it won’t work in practice.

Why?

Because your teams are deeply interconnected, whether you like it or not.

You need to know:

• How many deals Sales is projecting to close (for capacity planning and account allocation)
  

• What expectations were set during the sales process (Was implementation promised in 4 weeks instead of 6? Was a 24-hour follow-up committed?)
  

• How Sales is performing relative to targets (Are you about to get flooded with new customers or is something off in the market and sales is missing their number?)
  

• How Sales is compensated (Do they lose commission if a customer churns early? Do they get paid on expansion?)
  

All of this directly impacts how your team operates and, more importantly, how your customers experience your company.

Okay, I’m getting ahead of myself.

The bottom line is this:

If you’re in Customer Success, a good relationship with Sales isn’t optional, it’s foundational.

Something I will never forget

Now let me tell you a story …

I joined a new organization as Vice President of Customer Success and brought my team together to map the customer journey.

We started with the current state.

It was incredibly insightful. I could clearly see how the business was operating, where things were breaking, and what needed to be fixed.

But on my flight home that night, I couldn’t stop thinking about one thing:

There was a single point of failure across the entire journey.

And it wasn’t process. It wasn’t even the product.

It was distrust between Customer Success and Sales.

That distrust was showing up everywhere:

• AEs didn’t trust CSMs to deliver value, so they stayed involved in accounts far longer than they should—pulling focus away from new business
  

• CSMs didn’t trust AEs to sell the right customers, so when things went wrong, they blamed Sales for poor-fit deals or bad expectations
  

• Communication was strained at best and at worst, confrontational

At one point, things escalated so much that a CSM and an AE had a confrontation in the office… and they were no longer allowed to be there at the same time. There were rumours that a fist fight had broken out between them, but I never heard if it was actually true.

Needless to say, things were BAD.

What I realized

I knew we could fix onboarding.

We could improve renewal readiness.

We could launch new in-app customer messaging.

But none of it would matter if we didn’t fix the relationship between CS and Sales.

Because process doesn’t fix distrust. People do.

What I did

First, I talked to my team.

I told them plainly:
We can make all the improvements in the world, but if we don’t fix this relationship, we won’t see the results we want.

Then I spoke with the VP of Sales.

He was candid. The relationship with the previous CS leader had been strained for a long time. They had tried to repair it—even going as far as inviting them to dinner—but nothing worked..

So the teams defaulted to what many companies do:

They operated in silos.
Stayed out of each other’s way.
And quietly built resentment and distrust.

I told him that’s not how I work.

If we were going to succeed, we had to operate as partners.

What actually moved things forward

We brought both teams together for a two-day onsite.

Not to review metrics.
Not to point fingers.
But to reset how we worked together.

We:

• Aligned on go-to-market vision and how we would get there
  

• Reinforced that Sales and CS are two sides of the same coin (one can’t be successful without the other)
  

• Identified breakdowns across the journey (via sticky notes across the room)
  

• Mixed teams in exercises to build real relationships
  

• Spent time together outside of work—dinner, conversations, a few laughs
  

It wasn’t magical

But it was a turning point.

What changed after

I continued showing up in Sales meetings.

I shared what we were improving in CS and how to set expectations with customers accordingly.

Over time:

• Handoffs improved

• Expectations became more aligned

• Customers had a more consistent experience

• CSMs and AEs started working things out directly

Was it perfect? No.

But it was functional, collaborative, and moving in the right direction.

And that made all the difference.

The takeaway

If you take nothing else from this:

Alignment between Customer Success and Sales is not a process problem, it’s a relationship problem.

You can’t fix it with:

• Better documentation

• More detailed handoff forms

• New tools

You fix it by:

• Building trust at the leadership level

• Creating shared context

• Spending time together as humans and having candid conversations

Because at the end of the day:

Customers need to experience your company as one team.

If this resonated, share it with someone navigating this challenge.

And if this is something you’re working through right now, I’d love to hear how it’s going.

Subscribe now

They’re packed with slides, heavy on reporting, and rarely lead to meaningful conversations.

Over the past year, I’ve been helping teams run them in 15 minutes instead—focused on customer outcomes, not presentation decks.

I’m going to walk through exactly how this works in a live session with PracticalCSM.

We’ll cover:

• How to structure a 15-minute QBR

• What to focus on (and what to leave out)

• How to make it valuable for executives and not just your team

📅 Wednesday March 25th
🕐 1 PM ET

If QBRs feel too long, too tactical, or just not that impactful, this will be worth your time.

Also, if you are wondering how to scale QBRs for your long tail SMB customers, this could be a the perfect solution.

👉 Reserve your spot here:
https://www.linkedin.com/events/7434535828565090304/

Hope to see you there!
Andrea

About a month earlier, I wrote about how to turn Customer Success into a revenue driver — what it actually takes for CS to own renewals and expansion.

But structure alone isn’t enough.

Even if Customer Success owns revenue, growth only happens when CSMs can lead meaningful, value-driven conversations with their customers.

And this is where we see many teams struggle.

Many CSMs are excellent relationship managers. They care deeply about their customers and work hard to support them. But they are often not trained to connect their product to the customer’s business goals, metrics, and outcomes.

Without that connection, conversations stay tactical — focused on features, support tickets, or status updates — rather than strategic discussions about business value.

Recently, Nakul Kadaba, a customer success leader who prioritizes customer growth, shared a framework he has been using with his teams to address this exact challenge.

His approach helps CSMs move from reactive account management to consultative value positioning, enabling them to translate customer business goals into meaningful conversations that support retention and expansion.

He calls it the Consultative Value Positioning (CVP) Framework.

I asked Nakul to share the framework in his own words with the CS Impact community.

The Consultative Value Positioning (CVP) Framework

In Nakul’s words:

Customer Success is often described as a revenue engine, but many organizations still struggle to translate customer value into predictable expansion.

Teams may see high NPS or positive customer sentiment, yet still experience surprise churn or flat renewals. One reason is a persistent value gap — the difference between the value customers receive and the value that gets communicated during strategic conversations.

Customers who experience value-focused conversations are far more likely to renew and expand. Yet many CSMs do not feel equipped to lead those discussions.

To address this challenge, I developed the Consultative Value Positioning (CVP) Framework.

The goal is simple: empower CSMs to translate a customer’s business goals into clear conversations about how your product or service drives measurable value.

The framework is built on three pillars:

• The Customer-First Mindset

• Business Acumen

• The Iterative Feedback Loop

1. The Customer-First Mindset

Most organizations claim to be customer-first. In practice, however, many customer conversations are still driven by internal agendas.

CSMs often focus on their own checklist:

• Product updates

• Feature releases

• Adoption & Engagement metrics

• Support issues

While these topics are important, they rarely drive strategic conversations.

A truly consultative CSM starts with the customer’s outcomes.

This requires three capabilities.

Stakeholder Analysis

Are CSMs mapping stakeholders across the organization, or only speaking with the person who accepted the meeting invite?

Value-driven conversations require understanding:

• Who owns the budget

• Who owns the business outcomes

• Who influences the decision-making process

Without that visibility, it is difficult to connect your solution to the broader goals of the organization.

Resource Orchestration

Consultative CSMs act as conductors.

They bring in the right internal experts at the right time — product, sales, marketing, or voice-of-the-customer teams — to help the customer achieve a milestone or overcome a challenge.

This shifts the relationship from vendor to partner.

Accountability Over Availability

Being customer-first does not mean being constantly available.

It means designing conversations and cadences that are focused on the customer’s outcomes, not simply responding to requests.

The goal is to create high-impact conversations that move the customer forward.

2. Business Acumen

True partnership begins when you stop talking about your product and start talking about your customer’s business.

Research from Mixology Digital indicates that 56% of B2B companies do not feel vendors understand their business goals. When that happens, conversations remain superficial and value becomes difficult to articulate.

This is where business acumen becomes critical.

CSMs need to understand several key elements of the customer’s organization.

The Profit Engine

How does this company actually make money?

Understanding the revenue model, cost structure, and market dynamics allows CSMs to position solutions in a way that aligns with the customer’s financial priorities.

The Central Goal

What is the most important business goal the organization is trying to achieve this year?

This could be:

• Increasing revenue

• Reducing operational costs

• Improving efficiency

• Entering a new market

When CSMs understand this goal, they can align their conversations accordingly.

The Key Performance Indicators

Which metrics matter most to the key stakeholders?

These are often the KPIs that influence promotions, bonuses, and executive priorities.

When CSMs connect their solution to those KPIs, the conversation becomes significantly more strategic.

The Initiative Bridge

Finally, the CSM needs to connect the dots.

How do your products or services accelerate progress on those goals and KPIs?

This bridge is where expansion opportunities often emerge naturally.

Instead of selling additional features, the conversation becomes:

“Here is how we can help you move faster toward your business goals.”

3. The Iterative Feedback Loop

Frameworks like CVP only work when leaders reinforce them consistently.

This is where Customer Success leadership plays a critical role.

Many 1:1 meetings between CS leaders and their teams focus on status updates or operational discussions.

Instead, leaders can use those sessions to coach value-driven conversations.

One approach I recommend is structuring 1:1s around rotating themes.

Metrics Progress

Review the CSM’s book of business and discuss changes in retention, expansion, or risk indicators.

What trends are emerging?

Where are the opportunities?

Book of Business Strategy

Identify a stagnant segment of accounts and brainstorm a strategy to re-engage them.

What business outcomes matter most to those customers?

How can the team reconnect the product to those outcomes?

Skill Development

Assess the CSM’s progress against key competencies, including discovery skills, consultative conversations, and business acumen.

What capabilities need further development?

Feedback and Growth

Review call recordings or meeting notes to refine how the CSM communicates value and leads customer conversations.

This type of coaching helps teams continuously improve their ability to translate product value into business impact.

Bringing It All Together

One of the biggest gaps we see in Customer Success organizations is this:

Teams want Customer Success to drive revenue, but they do not always equip CSMs to lead commercial conversations.

Nakul’s Consultative Value Positioning framework provides one practical model for bridging that gap.

When CSMs understand their customers’ business goals and connect product capabilities to measurable outcomes, conversations become more strategic.

Renewals become more predictable.

Expansion opportunities become easier to identify and close.

And Customer Success moves closer to the role many organizations say they want it to play — a true driver of long-term customer value and revenue growth.

Nakul and I would love to hear from you:

What is the biggest challenge your team faces when it comes to leading value-driven customer conversations?
I’m also inviting more CS leaders to collaborate on future Substack posts and share their frameworks with the community.

If you’re interested, just respond to this email.

The purpose of this series is to give CS leaders practical advice from my own experience leading Customer Success teams and working with organizations on their CS strategy — particularly how they turn Customer Success into a revenue engine for their business.

Also, thank you for reading my somewhat sarcastic post last week on how to get fired as a CS Leader.

The post was meant to be funny and serious at the same time — and clearly it resonated, as over 500 people read it.

Either a lot of you are afraid of getting fired…
Or perhaps you are wondering how to get yourself fired and collect severance.

Either way, it struck a nerve in the CS community.

This week’s post is much more tactical.

Let’s talk about how to map the customer journey.

Most CS Leaders Don’t Do This

I am always surprised by how many CS leaders don’t map the customer journey.

It is the first thing I do when I join a new organization.

Without mapping the journey, it is really hard to know where things need optimizing and where the problem areas are.

For instance:

• Is our onboarding too long or too short?

• Do we have enough resources for customers to self-serve?

• Are we running QBRs at the right time with the right audience?

• Are we starting renewals early enough?

• Where are customers getting stuck?

• Where are we losing momentum?

If you don’t map it, you are guessing.

I think the reason most leaders avoid this exercise is that it feels like a lot of work.

When people think about mapping the journey, they imagine getting Sales, Marketing, and CS in a room with a giant whiteboard and a wall full of sticky notes.

You can do it that way.

But it’s hard to coordinate, expensive (those people could be out selling and renewing), and honestly — not necessary to get started.

Here’s a much more straightforward way to do it with your own team.

You can always layer in cross-functional insights later.

How I’ve Mapped the Customer Journey in the Past

First, get your CS team together — ideally in person or onsite if you can.

From that group, select 3 people who:

• Have been with the business for a while

• Know the customers well

• Understand how things actually work

Now map the current customer journey.

And do this separately for each segment.

If you have SMB, Mid-Market, and Enterprise customers, map each journey independently.

They are not the same.

Step 1: Map the Current State (No Matter How Messy)

Start with reality.

Even if it’s disjointed, inconsistent, or nuanced.

Begin at the Sales → CS handoff and map all the way through renewal.

For each stage, capture:

• What is happening?

• Who is involved (internal and external stakeholders)?

• What role do they play?

• What resources are available to customers (community, knowledge hub, etc.)?

• Where are customers likely to expand?

• What does that expansion motion look like?

• When does renewal start?

• What are common reasons for churn?

• How is product feedback collected and shared?

• How are new features disseminated to customers?

Write down as many steps and processes as possible — but keep it high-level.

For example:
“Renewals start 90 days in advance and typically follow these steps.”

You don’t need to document Salesforce stages or forecasting mechanics.

Focus on the experience from the customer’s perspective.

Also note differences:

Do brand-new customers need more handholding than customers who have been with you 3–5 years?

Capture those nuances.

Step 2: Map the Ideal Customer Journey

Now shift.

Put yourself in your customer’s shoes.

How would you want to move through the journey?

This is not “money is no object.”

Be realistic.

For example:

• It’s not realistic for SMB customers to have a year-long onboarding and four QBRs.

• That wouldn’t be scalable (an SMB CSM could only manage 20 accounts).
  
  

But do challenge yourselves:

• Would in-app messaging make onboarding smoother?

• Should renewals start earlier?

• Do customers need QBRs — and if so, how often?

• What should be covered?

• Where could the experience feel more intentional?

If you have customer feedback, incorporate it.

Again, map this separately for each segment.

And remember:

This does not have to be perfect.

You are going for done.

You can always refine later.

If you’re doing this virtually, it will take a little longer — but it can absolutely be done. I highly recommend using a Miro board. Even if you do this in person, you can capture everything digitally afterward.

Step 3: Find the Delta

Now look at the difference between:

Current State and Ideal State

The delta between the two is your action plan.

Capture every change required to move from current to ideal.

Examples might include:

• Build a scalable QBR for SMB customers

• Create onboarding videos

• Redesign the sales-to-CS handoff

• Implement in-app onboarding guidance

• Start renewals earlier

Put these items into:

• Asana

• Monday.com

• Or a spreadsheet

Next to each item, write down:

• Effort (High, Medium, Low)

• Priority (High, Medium, Low)

Then step back and look at the list.

Is it realistic?

Are there items that are aspirational but too expensive or too time-consuming right now?

Refine.

Now identify:

• High impact + Low effort → Do these first.

• High impact + High effort → Plan these carefully. Identify dependencies, owners, and timelines.

If you have a CS Ops or Enablement team, there will likely be clear ownership opportunities.

If you don’t, lean on your team.

When I had a team of 10 CSMs:

• One built the QBR deck.

• One recorded onboarding videos.

• One created a kickoff deck.

We built working versions and refined them together.

Progress over perfection.

“This Sounds Like a Lot of Work…”

I know what you’re thinking.

You said this wouldn’t be time-consuming.

Mapping the current and ideal state should take about two hours.

If you have multiple segments, it might take an afternoon.

I’ve seen billion-dollar organizations with over 100 products map their customer journey in less than a day.

It can absolutely be done.

And once it is done, you have your roadmap.

Everything else becomes clearer:

Where to invest.
Where to hire.
Where to automate.
Where to fix process.

Mapping the customer journey is not busywork.

It is foundational work.

If you want Customer Success to be a revenue engine, you have to understand the system your customers move through.

You can’t optimize what you haven’t mapped.

This post is part of my “How To” Series for CS Leaders. We’ve covered a range of topics so far — from how to grow in your career when your role or company feels stagnant, to how to hire great CSMs, how CROs should think about CS, how to forecast, how to scale without breaking your team, and how to turn Customer Success into a revenue driver.

If you missed any of those, you can find them on my main Substack page.

If you follow me on LinkedIn or have been reading from the beginning, you know I spend a lot of time telling CS leaders what they should do.

I rarely talk about what not to do.

So this is a tongue-in-cheek post on how to straight up get yourself fired.

It mixes some sarcasm with some seriousness — so you know exactly what not to do.

In all seriousness, though: the average tenure of a VP of CS is now around 15 months (about the same as a CRO). Getting fired at some point in your leadership career is a very real possibility.

So let’s talk about how to do it efficiently.

1. Don’t Understand the Magnitude of Your Role

As a CS leader, you are not “just” leading a team.

You are responsible for recurring revenue — the lifeblood of a SaaS business.

Renewals fund growth. They fund product innovation. They fund marketing spend, sales headcount, and future investment.

So if you want to get fired quickly?

Don’t forecast.

Or forecast wildly inaccurately.

ARR businesses survive on predictability. If you say revenue is coming in, it better come in. If you refuse to call a number at all, your CFO, CEO, and CRO are flying blind. They don’t know whether they can invest, hire, or conserve cash.

And if you lose a million-dollar customer — especially at sub-$25M ARR — and have no idea how that happened?

That’s not just a retention hit. That can impact funding, valuation, hiring plans — everything.

Bottom line: own your numbers. Forecast with accuracy. Know your largest accounts inside and out. Spot risk early and mitigate it.

(There I go telling you what to do again.)

2. Stay Permanently in Reactive Mode

Another excellent way to get yourself fired?

Live in firefighting mode.

Jump on escalations all day. React to churn. React to executive asks. React to your team. React to Sales.

When you are constantly reacting, you’re stuck working in the business — not on the business.

You’re not proactively reducing risk.
You’re not seeding expansion.
You’re not planning capacity.
You’re not building scalable systems.

At some point, this catches up with you.

You don’t look in control. You look overwhelmed.

And executive teams rarely reward overwhelm.

So yes — align to company priorities. Advocate for resources. Be explicit about tradeoffs. Make it clear what will and won’t get done with the current budget.

You cannot do everything.

But if you pretend you can, you’ll burn out — and eventually lose credibility.

3. Avoid Sales at All Costs

Or better yet, create a culture of silos.

“This is my zone.”
“That’s yours.”

Talk about Sales behind their backs. Blame churn on bad deals. Blame escalations on poor handoffs. Refuse to collaborate with the Sales leader.

Focus only on “your” metrics.

This works beautifully — right up until it doesn’t.

Sales and CS cannot succeed without each other.

Sales depends on CS for referrals, expansion signals, and a strong customer experience.

CS depends on Sales for quality deals, accurate expectation setting, and clean handoffs.

When mistrust creeps in, finger-pointing follows.

And when fingers start pointing, let me be very clear:

In most companies, Sales wins that argument.

The pecking order is real.

So, if you plan to stay employed, align early and often.

4. Make Your CS Team Your “First Team”

Now this one is subtle.

There’s a leadership concept that your “first team” is your executive peer group — not the team that reports to you.

If you flip that?

You won’t get fired immediately. But you will slowly erode trust.

Protect your team from accountability. Make excuses for missed outreach. Justify lost renewals. Explain away expansion misses.

Over time, you’ll be seen as someone who shields underperformance instead of raising the bar.

Great CS leaders care deeply about their teams.

But they also hold them accountable.

You cannot be the advocate and the excuse-maker at the same time.

5. Fundamentally Disagree with the Company’s Direction

Healthy debate is good.

The best executive teams challenge each other.

But if you fundamentally disagree with growth targets, exit strategy, product direction, or how the company is run — and you continue to resist publicly?

You’re not “being principled.”

You’re misaligned.

Companies need speed. They need cohesion. They need leaders rowing in the same direction.

If you can’t align after debate?

It may be time to leave — before you’re pushed out.

6. Treat Expansion Like It’s “Not Your Job”

If you want a fast exit, this one works well.

Say things like:

“If my team wanted to sell, they would have become AEs.”

Ignore expansion targets. Refuse to forecast revenue influence. Focus solely on renewals.

Meanwhile, the executive team is staring at NRR targets and board pressure.

Whether you like it or not, most SaaS companies expect CS to contribute to growth.

If expansion is part of the model — and you resist it — you are misaligned with the revenue engine.

And misalignment at that level doesn’t last long.

7. Look Like You’re Leaving

Gone are the days when “looking around” results in a retention bonus.

There is too much talent on the market.

If leadership senses you’re disengaged or halfway out the door, they may accelerate the timeline for you.

Unless you have undeniable revenue impact, your leverage is smaller than you think.

It always comes back to revenue, revenue, revenue.

Two Hard Truths

Let me leave you with two things.

1. It’s Easier Than You Think to Fire a Leader

There are no performance improvement plans at the executive level.

There are few warnings.

Once the executive team and the board decide you’re out, you’re out.

It’s fast. It’s quiet. It’s final.

That’s why seasoned executives negotiate their exit terms upfront.

They understand the risk.

2. Sometimes… You May Want to Get Fired

I used to think this was crazy.

But sometimes you know it’s over.

The company is missing targets. Cash is tight. Layoffs are likely. You’re unhappy.

As a leader, you are expensive.

Waiting to be laid off — or negotiating a dignified exit — can be strategic.

This must be handled carefully. Reputation matters.

But severance plus time can be a lifeline.

Leadership is not just about staying.
Sometimes it’s about knowing when to leave well.

Final Thought

If you read this and felt slightly uncomfortable — good.

None of this happens because CS leaders are incompetent.

It happens because the role is hard.

Because revenue pressure is real.

Because alignment is fragile.

Because scale exposes gaps.

Leadership at this level is commercial, political, operational, and emotional — all at once.

And if you want to stay in the seat longer than 15 months?

You have to understand the game you’re playing.

First, let me say this.

“Turning Customer Success into a revenue driver” is becoming an overused saying.

In fact, I’ve considered changing the tagline for CS Impact, my consulting business, several times. However, each time I decide against it because I truly believe that in today’s environment — where companies are increasingly focused on driving recurring revenue — Customer Success plays a pivotal role.

It is high time that we directly tie Customer Success to company revenue.

So let’s break it down.

How do you actually turn Customer Success into a revenue driver?

TL;DR

Turning Customer Success into a revenue driver requires:

• Delivering measurable business outcomes that drive renewals

• Building a structured expansion motion rooted in value

• Aligning compensation with commercial accountability

• Owning and forecasting renewal and expansion targets

• Participating in go-to-market and pricing decisions

• Understanding how retention and expansion impact the P&L

Customer Success is already responsible for a significant portion of company revenue.

The real shift happens when it takes full ownership of that responsibility — commercially, operationally, and financially.

Customer Success Is Sitting on All the Money

There is something I believe wholeheartedly:

Customer Success is sitting on all the money.

Companies rely on their CS team to renew revenue that the business depends on — to invest in product, people, and future growth.

If you have a $30M ARR business and Sales is projected to bring in $8M in new ARR this year, Sales is responsible for $8M.

Customer Success is responsible for protecting $30M (assuming annual contracts).

That $30M is what keeps the lights on. It funds product development. It funds hiring. It funds expansion into new markets.

That is a lot of responsibility, and it should not be taken lightly.

Now, if you have a land-and-expand model or multiple products, CS may also be responsible for driving an additional $2–5M in expansion ARR.

At that point, the revenue coming from existing customers can start to rival — or even exceed — new business revenue.

This is where Customer Success truly starts to own revenue, not just in the form of renewals but also expansions.

Now, companies have many different models.

Sometimes Customer Success owns renewals and sometimes not.
Sometimes Customer Success owns expansion and sometimes not.

When I talk about “turning Customer Success into a revenue engine,” I am talking about the model where CS is sitting on the money — renewals and expansion — and is accountable for it.

Renewals: Delivering Recurring Impact

Let’s start with renewals.

Customer Success needs to renew as many customers as possible to drive recurring revenue. The only sustainable way to do that is to deliver recurring impact.

When I say “impact,” what I am referring to is helping customers achieve their business outcomes.

Your product needs to help customers:

• Make money

• Save money

• Drive efficiency

If your product or service is not doing one of those three things, you will struggle with retention.

Whenever I am consulting for a B2B SaaS company, one of the first things I look at is whether the product is solving a meaningful problem and delivering real business outcomes for its customers.

If it isn’t, the organization will always struggle with churn because customers will either decide:

• They don’t need you as badly as other solutions

• Or the problem isn’t worth spending money to solve

Now, I know what some of you are thinking.

“What about the things CS can’t control?”

What if the product doesn’t deliver as promised?
What if Sales closed bad-fit deals?
What if the customer’s company goes out of business?

There are many things Customer Success cannot control.

Which is why I often say: choose your company wisely.

There were over 100,000 new SaaS companies created just last year, many with AI at the forefront. Not all of them will survive, and not all of them are solving a core business problem.

In Customer Success, you can never fully control whether a customer stays or leaves. But you can choose to work for a company that:

• Has a strong product

• Solves core challenges in the market

• Has a sales team focused on closing good-fit deals

When you combine product-market fit with strong customer outcomes, retention becomes a very powerful revenue lever.

Expansion: Easier and Cheaper Than New Business

The next way to drive revenue from Customer Success is through expansion.

It is much easier — and much cheaper — to sell to existing customers than to acquire new ones.

But expansion does not happen simply because you ask for it.

It happens when you deliver value consistently.

If you deliver on the outcomes your customer is looking for, they will want more — or at the very least, they will be open to a conversation about what else you can do for them.

This is where what I call a “consultative approach” becomes critical.

A strong CSM:

• Deeply understands the customer

• Understands their industry and challenges

• Understands your product or service

• Has built trust and credibility

When customers see their CSM as a partner who is trying to help them maximize value — not just sell something — they are far more likely to collaborate on additional solutions.

If you can consistently deliver outcomes, you increase the likelihood of both renewal and expansion.

Compensation Drives Behavior

Everything above sounds good.

But if CSMs are not compensated on retention and expansion, they may not focus on it.

The easiest way to motivate behavior is to put money behind it.

If you want to turn Customer Success into a revenue driver, then driving retention and expansion needs to be part of the compensation plan.

I am not going to argue whether 80/20 is better than 60/40. It depends on how much you want to motivate commercial behavior and how mature your expansion motion is.

I have even seen CS teams with a 50/50 split, similar to Sales.

What I will say is this:

The more aggressive the target and the more variable-heavy the compensation plan, the stronger your foundation needs to be.

You cannot layer an aggressive expansion target on top of:

• A shaky product

• Weak onboarding

• No clear expansion motion

• CSMs who have never been trained in discovery or objection handling

If you expect CSMs to drive revenue, you need to equip them for it.

That means commercial training.
That means account planning.
That means teaching consultative conversations and even negotiation skills.

Commercial Ownership: CS Needs to Own the Number

Now all of this is fine, but CS needs to own the numbers.

Owning the number does not mean being handed a top-down target and told to “figure it out.”

It means being part of determining what is realistic.

Customer Success should be in discussions with the CEO and CFO about:

• What renewal rate is achievable next year?

• What needs to change to increase it by X%?

• What is a realistic expansion number based on what CSMs can sell and conservative conversion rates?

• What are the leading indicators that tell us we are on track or off track?

You are not going from 85% renewal to 90% renewal without serious changes to product, onboarding, pricing, ICP targeting, and customer experience.

Renewal rates are the output of operational and product decisions.

The same applies to expansion.

Does the attach rate of the second product support the target?
How many customers actually have a need for it?
What is the likelihood they will buy?

Some simple math can quickly show you whether a number is realistic or purely aspirational.

I have seen top-down models.
I have seen bottom-up models.
The combination of the two tends to work best.

Ambition plus data.

Forecasting and a Seat at the Table

If CS owns revenue, CS must forecast revenue.

That means calling the number weekly:

• What will renew?

• What is at risk?

• What will expand?

• Are we up or down versus last week?

• What is the plan to close the gap?

This is similar to Sales — and it should be. Owning revenue is a big responsibility.

If Sales is ultimately closing expansion deals and CS is generating warm leads, CS needs to be part of the sales forecast call. They need visibility into what is projected to close so they can accurately forecast Net Revenue Retention.

CS also needs to be included in major go-to-market decisions.

GTM includes Sales, Marketing, Product, and Customer Success.

If Marketing increases pricing beyond what the market can bear, customers will churn.

If Sales starts targeting a new ICP, retention and expansion will be impacted.

If Product builds features only 20% of customers are asking for, that affects value delivery.

If CS is accountable for revenue, CS needs a seat at the table where those decisions are made.

Board-Level Visibility and Understanding the P&L

Lastly, Customer Success needs visibility at the board level, and Net Revenue Retention needs to be viewed as a primary growth lever.

The board ultimately influences the strategic direction of the company.

If CS is not represented in those discussions, it doesn’t matter how strong your renewal rate is — your voice will not shape the future direction of the business.

But here is where I see many CS leaders struggle.

They understand their metrics.

But they don’t always understand how those metrics flow into the P&L.

If retention drops from 92% to 88%, that doesn’t just mean “more churn.”

It means:

• Revenue becomes less predictable.

• Sales must spend more to replace lost revenue.

• Customer acquisition costs increase relative to lifetime value.

• CAC payback periods lengthen.

• Profitability is impacted.

High Net Revenue Retention improves capital efficiency and makes growth more sustainable.

These are financial conversations.

If CS leaders want to be seen as commercial leaders, they need to understand how retention and expansion affect revenue, margin, and ultimately valuation.

This is where financial literacy matters.

Bringing It All Together

Turning Customer Success into a revenue driver is more than a tagline.

It is about taking responsibility.

Responsibility for:

• Delivering measurable business outcomes

• Driving renewal and expansion

• Owning and forecasting the number

• Participating in GTM decisions

• Understanding how your metrics impact the P&L

Customer Success is already sitting on the money.

The question is whether we are willing to take full ownership of it — and operate accordingly.

Because when CS truly owns revenue, it changes how the function is perceived, how it is structured, and how it shows up in leadership conversations.

And that shift is long overdue.

—

If this resonates, I’d love to hear:

Where is your biggest gap right now — renewals, expansion, compensation, or commercial ownership?

Summary

Scaling Customer Success isn’t about hiring fewer CSMs or pushing teams harder. It’s about replacing heroics and intuition with systems that hold up as the business grows. In this post, I share the real lessons I’ve learned — as a CS leader and advisor — about what actually works (and what quietly breaks) when you try to scale CS without burning out your team or sacrificing the customer experience.

One of the questions I get asked most often is how to scale Customer Success effectively.

More specifically:
How do you bring on more customers without hiring more CSMs?

And while that can sound harsh, it’s actually good business. That’s how companies move toward becoming profitable and durable. (More on that another time.)

This question comes up constantly — in conversations with CS leaders, in advisory sessions, and in almost every engagement I do through CS Impact.

Over the past year alone, I’ve helped teams:

• map customer journeys

• build playbooks

• train CS teams

• roll out brand-new CRMs and Customer Success platforms

• build forecasting models

• redesign customer segmentation and account load

In my experience, most teams don’t struggle to scale because they lack effort or intent.

They struggle because they try to scale what worked — heroics, intuition, and a handful of exceptional people — instead of building systems that hold up as the business grows.

And when you put more customers on a shaky foundation, the whole system can crumble.
(Trust me — I’ve been there too.)

What follows aren’t theoretical frameworks.

These are the lessons I’ve learned — sometimes the hard way — from leading Customer Success teams and helping other leaders scale theirs without burning out their people or breaking the customer experience.

1. Scale requires a defined revenue system

(You can’t scale on heroics)

When I became a Vice President at a $15M ARR B2B SaaS company, Customer Success was built on the heroics of a few exceptional CSMs.

They were the kind of CSMs every leader wants:

• always available

• willing to jump in wherever needed

• deeply invested in the customer experience

They were rockstars.

They retrained customers multiple times.
Designed custom workflows for individual accounts.
Convinced Product to build for one-off use cases.
Offered special pricing and discounts to keep customers happy.

And for a while, it worked.

But the entire CS motion depended on a small number of people doing extraordinary things. There was no clearly defined customer lifecycle, no shared understanding of success at each stage, and no explicit handoffs — just effort.

As we added more customers to their books of business, my CSMs started burning out.

The risk became obvious very quickly:

• none of this was scalable

• if we lost those CSMs, retention would fall through the floor

First, we tried paying them more to show how much we valued them.

But eventually, even the money wasn’t enough. They weren’t unmotivated — they were exhausted.

That’s when it became clear that scale requires a defined system:

• clear customer lifecycle stages

• explicit ownership

• documented processes and workflows

• rules of engagement and escalation paths

• clearly defined commercial negotiation tactics

• onboarding stages and success metrics

Heroics are not a strategy.

2. Ownership must be unambiguous

(CS can’t own everything and still scale)

Earlier in my career, as a Director of Customer Success, my team spent an enormous amount of time making good on promises that were never designed to scale.

Things like:

• longer onboarding timelines

• customer data migrations

• training and retraining teams

• onsite troubleshooting

• after-hours availability

• white-glove support for one-off situations

All of it was framed as “doing right by the customer.”

But what was really happening was that CS was compensating for promises made during the sales cycle — without any shared agreement on what was actually sustainable.

So I started tracking these situations:

• what was promised

• what CS had to do to deliver

• how often it happened

I brought the data to our sales leader — not as a complaint, but as an operational problem.

Together, we reset expectations:

• what CS would deliver on

• what CS would not deliver

• what required explicit approval

We documented everything and reset expectations with our teams.

The result?
Fewer exceptions, better alignment, and significantly less burnout.

3. Roles should be specialized, not overloaded

(Generalists don’t scale)

I’ve inherited CS teams where CSMs owned everything:

• onboarding

• adoption

• renewals

• expansion

That can work when companies are small.
It does not hold as the business grows.

The issue isn’t effort — it’s skill mismatch.

The skills that make someone great at onboarding:

• teaching and training

• deep product knowledge

• project management

…are not the same skills that make someone great at driving adoption and outcomes:

• consultative conversations

• holding customers accountable through success plans

• driving outcomes

Renewals require:

• comfort with commercial negotiations

• understanding how procurement works

• finding win-win outcomes

Expansion requires:

• strong discovery and positioning

• matching customer needs to product capabilities

• the ability to demo and create a vision of what’s possible

When we ask one role to do all of this, people don’t become well-rounded — they become stretched.

I learned that when everyone does everything, no one becomes truly great at anything.

So I started asking my team:

• what part of the role they enjoyed most

• what skills they wanted to develop

I learned that some people were great at onboarding, some thrived in renewals and forecasting, and some were natural sellers.

That insight allowed me to redesign roles in a way that both improved outcomes and made the work more sustainable.

Even light specialization dramatically reduces cognitive load and improves results.

4. Process beats intuition at scale

(Even experienced leaders get burned by gut feel)

Early in my career, I relied far too heavily on intuition.

I spoke to customers regularly.
I talked to my team constantly.
Everything felt okay.

“They’ll renew,” I told myself.

But I didn’t actually know they would.

I couldn’t be everywhere. I couldn’t know everything all the time. And that gap caught up with me when a few large customers canceled — and I was completely blindsided.

That’s when I put a rigorous forecasting process in place, built on:

• leading indicators

• CSM sentiment

• customer health scores

CSMs updated it weekly.
We reviewed it weekly as a leadership team.
Every Monday, I pulled the numbers, tracked week-over-week changes, and rolled them up to the executive team.

After that experience, I rebuilt forecasting in every leadership role I held — because it’s that important.

If you don’t know:

• where the risks are in your book of business

• how your team is mitigating those risks

• and whether customers are actually likely to renew

…then the business can’t make informed decisions about growth or product investment.

It’s like not knowing how much money will be in the bank in six months — how would you decide whether to take on a bigger mortgage?

5. Leaders design the system — teams execute it

One of the hardest parts of being a leader was accepting that I could no longer know everything.

I didn’t have the time — or capacity — to be:

• a product expert

• in every customer conversation

• designing every process

• hiring and onboarding

• aligning with the executive team

What I had to learn was this: my job wasn’t to know everything — it was to put the right foundation in place.

The very first thing I always did was map the customer journey.

That allowed me to see:

• where processes or systems were missing

• where we were letting customers down

• what was actually working well

I mapped:

• the current state

• the ideal state

I always did this with my team — because I couldn’t be everywhere, and they saw things I didn’t. I also involved Sales and Marketing when possible so I could understand the full lifecycle of a customer.

I mapped journeys by segment, because the journey for an SMB customer is fundamentally different from the journey for an enterprise customer.

Once the journeys were mapped, I compared the current state to the ideal state to identify gaps.

From there, I created a list of everything that needed to change.

Then I prioritized ruthlessly:

• High priority, low effort → quick wins I tackled immediately

• High priority, high effort → structured projects executed with Operations and cross-functional partners

Those quick wins alone created meaningful improvements in clarity, efficiency, and customer experience.

And for the first time, I no longer felt like I had to be everywhere.
I just needed to understand what was happening along the customer journey.

A few final thoughts

• You can’t scale ambiguity

• You must design for the average, not the exceptional — not every CSM will be a rockstar, and that’s okay

• Specialization reduces cognitive load

• Metrics and forecasting are the backbone of any healthy business

• Scale without humanity creates attrition

That last one matters most.

I always involved my team in the scaling process, asked for feedback early, and kept refining what we built. I also closely monitored key indicators:

• how many customers were in onboarding

• how many were at risk post-onboarding

• time to value

• customer usage vs benchmarks

• expansion timing and size

Scaling isn’t a one-and-done effort. It’s iterative.

Closing

Frameworks can tell you how scale should work.

Leadership is figuring out how to apply them in the real world — with real constraints, real people, and real pressure (ever tried to scale while the exec team is breathing down your neck about the forecast?).

That’s the work most CS leaders are doing right now.

And it’s exactly the work I do through CS Impact.

I partner with CS leaders and executive teams to:

• design scalable customer journeys

• clarify ownership and operating models

• build forecasting systems leaders can trust

• reduce heroics without sacrificing the customer experience

• put playbooks and processes in place

• train CSMs and cross-functional teams

If you’re being asked to scale Customer Success and it feels hard, I hear you.

You don’t have to figure it out alone.

Forecasting in Customer Success wasn’t always required — but today, it’s non-negotiable. In this post, I walk through:

• Why CS didn’t forecast 8+ years ago (and why that changed)

• How we first forecasted using a simple spreadsheet

• How forecasting evolved into Salesforce and Gong

• Where things got messy (carryovers, non-payment, win-backs, product swaps)

• Best practices I learned the hard way
  What CS leaders and ICs should understand about forecasting today

If you’ve ever felt like forecasting was more complicated than it needed to be — or wondered if everyone else was struggling too — you’re not alone.

Why CS Didn’t Have to Forecast (And Why That Changed)

Eight years ago, most Customer Success teams didn’t forecast.

Not because we didn’t care about revenue — but because we didn’t have to.

There was so much new business coming in the door that as long as churn wasn’t egregious, things worked out. Retention was “good enough.” Expansion happened organically. And CS looked at numbers in retrospect, not ahead of time.

At the end of the quarter, we’d say things like:

“That was a good quarter. Lots of new business and we retained most of our revenue. Great.”

That world doesn’t exist anymore.

Why Forecasting Is Non-Negotiable Today

When COVID hit, everything changed.

Customers’ budgets tightened. Buying decisions slowed. New business dropped. Suddenly, leadership wanted answers CS hadn’t been expected to give before:

• How much revenue are we actually going to retain this quarter?

• What’s at risk?

• What’s likely to expand?

• Where should we intervene now to change the outcome?

This is when forecasting became mandatory — not just for Finance or Sales, but for Customer Success.

And this is also when CS became undeniably tied to company revenue.

We were always tied to revenue — recurring revenue is the lifeline of a SaaS business — but forecasting forced CS to own revenue outcomes explicitly, not just relationships and health scores.

How We First Forecasted: Start Simple

Our first forecast wasn’t fancy.

It was a spreadsheet.

For each renewal in the quarter, we tracked:

• Account name

• Revenue up for renewal

• A health score

• A prediction: renew, downgrade, expand, or churn

• A column for expected dollar change (upgrade or contraction)

We then used a simple formula to calculate the forecasted renewal amount.

For example:

• $30k up for renewal

• We predicted a $10k contraction

• The formula calculated $20k as the forecasted renewal amount

If we predicted an expansion, that amount was added. If we predicted a downgrade, it was subtracted.

We totaled everything and calculated GRR and NRR.

Simple.

Moving Forecasting Into Salesforce

As forecasting became more important, spreadsheets stopped scaling.

Salesforce became the most natural place to forecast.

Every renewal was created as an opportunity and moved through the same stages as new business. Each stage had a probability attached.

For example:

• Qualified → 50% probability

• Pending Signature → 90% probability

That probability was applied to the renewal ARR, giving us a weighted forecast.

CSMs were responsible for:

• Adding notes about risks and next steps

• Flagging potential expansions

• Logging expected downgrades

Expansion and contraction fields were structured so product selection auto-populated ARR, keeping the math consistent.

Where Gong Came In

We fed Salesforce data into Gong’s Deal Board, which gave us a consolidated view of:

• ARR up for renewal

• Forecasted churn

• Forecasted expansion

• Salesforce stage and probability

• Health score

• Touchpoints and recency

• CSM notes and next steps

Salesforce was our system of record, but CSMs mostly worked out of Gong.

Not all fields were bi-directional. Core forecast and revenue fields lived in Salesforce, while Gong surfaced that data alongside activity, conversation insights, and CSM inputs. Some updates synced back to Salesforce, but Salesforce remained the source of truth.

In practice, CSMs worked primarily in Gong unless they were executing a contract, in which case they worked directly in Salesforce.

This setup allowed us to forecast in Salesforce while using Gong to validate assumptions, highlight risk, and understand whether customer activity supported what we were predicting.

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Where Forecasting Got Complicated (And Why You’re Not Alone)

This is the part no one talks about enough.

Renewals That Didn’t Close on Time

Not all renewals closed in the quarter they were due.

A renewal might be up in Q1 but not close until Q2.

That raised uncomfortable questions:

• Do we go back and change Q1 numbers?

• Or do we roll the renewal into Q2?

I’ve seen both approaches.

Personally, I strongly prefer rolling renewals forward. Changing numbers already communicated to the board is risky and makes the company look like it doesn’t understand its own numbers.

Once a quarter is closed, it should stay closed.

Customers Who Said They’d Renew — Then Didn’t Pay

Some customers told us they were renewing, but the revenue was never recognized.

We chased them for a quarter or two before eventually wrote it off as churn.

Again, the question came up:

• Is this churn in the original renewal quarter?

• Or do we change historical numbers?

Best practice here is simple:
If revenue isn’t recognized, it’s churn — recorded in the period the decision is made to write it off.

Win-Backs

Sometimes customers churned and then came back within a short window.

We were tempted to erase the churn.

But rewriting history creates more problems than it solves.

Best practice:

• Record the churn when it happens

• Treat the win-back as new or reactivated revenue in the period it closes

Product Swaps

This one comes up constantly.

A customer drops one product and picks up another. We counted the dropped product as churn and the added product as expansion.

The result:

• Churn looked worse than reality

• Expansion looked better than reality

Best practice:

• At the account level, this is neutral

• At the product level, it’s contraction and expansion

Be explicit about which lens you’re reporting through and apply the rule consistently.

Weekly Forecasting and Executive Roll-Ups

All of the data flowed into a spreadsheet that automatically calculated GRR and NRR.

We forecasted entire quarters out, and the expectation was that CSMs updated their forecasts weekly. We pulled the forecast at exactly the same time every week and kept historical versions.

This allowed us to see whether we were closing the gap or getting further away, meaning we were predicting more churn.

Every Monday, I rolled up the GRR and NRR forecast to the executive team and shared whether it was higher or lower than the previous week and why.

I also walked them through:

• The largest accounts up for renewal

• The biggest risks

• How we were mitigating those risks

• Next steps for expansion on the largest accounts or where we had the greatest opportunity

What I Learned About Forecasting

After doing this multiple times, here’s what actually matters:

1. Salesforce must be the system of record

2. Gong should validate forecasts, not replace them

3. Separate facts from judgment

4. Forecasting is forward-looking, reporting is historical

5. Consistency matters more than precision

Final Thought

Forecasting isn’t about being right.

It’s about being early enough to change the outcome.

If you’ve struggled with messy renewals, confusing churn math, or forecasts that felt more political than factual — you’re not alone.

I hope this post gave you some ideas for how to tackle this head on.

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This is becoming increasingly common. Many CEOs think it’s only natural for CS to report into sales if CS is driving revenue through renewals or expansions.

However, many CROs step into this role assuming CS works like sales.
It doesn’t.

If you’re a CRO and Customer Success is reporting to you for the first time, here are 7 things you need to know.

1. Customer Success is not Customer Support

Support is reactive to customer needs.
Customer Success is proactive.

CSMs anticipate customer needs, proactively spot risk and expansion, and focus on delivering customer outcomes. They don’t reset passwords or troubleshoot technical issues.

When CS is treated like an escalated support function, retention suffers, as CSMs start waiting for customers to come to them rather than proactively reaching out to ensure customers are getting maximum value from your product or solution.

2. Customer Success Managers are not trained like your sales team

In many cases, CSMs may never have been formally trained at all.

There aren’t many books on Customer Success, and there certainly aren’t widely adopted frameworks like MEDDICC or Value Selling on the post-sales side.

Most CSMs learned the role on the job. That doesn’t mean they aren’t capable — it means they need structure, clarity, coaching (and ideally training) in a very different way than sales reps do.

3. Forecasting exists — but it’s different

Yes, you still forecast — but instead of forecasting bookings, you’re forecasting:

• Whether a customer will renew

• How much revenue is likely to renew

This forecast is far more nuanced than sales forecasting.

Even healthy customers can churn for reasons completely outside your control: mergers and acquisitions, bankruptcy, budget cuts, or product consolidation. You’re managing probability, and it is both an art and a science.

Note: More on this in my “How to Forecast in Customer Success” post next week. Stay tuned!

4. If you want to reduce churn, start with two things

First: The product.

• Is it embedded in your customer’s workflows?

• Is it mission-critical to the customer’s organization (i.e., can they live without it)?

• Do customers clearly understand the value they’re getting, and can they articulate that value?

If the answer to any of those is no, start there.

Second: Onboarding. Onboarding. Onboarding.
Customers who don’t realize fast time-to-value during onboarding are far more likely to churn later. Poor onboarding creates renewal risk before the contract even gets going. If you ask a handful of CS leaders where to focus first when preventing churn, they will all say onboarding.

5. Everything is more complex post-sales

Post-sales is less predictable than sales.

There are more data points to consider — TTV, CSAT/NPS, NRR, GRR, LTV, and many more things to analyze: license utilization vs. purchased seats, health scores, cost to serve, cost of expansion, renewal discount rate. I could go on!

Retention is also nuanced. When I examine churn in an organization, customers are usually leaving for a whole host of reasons, not just one or two. It can be very hard to pinpoint where the problem is.

In fact, when I asked CS and GTM leaders why churn is up across the board in SaaS right now, I got a hundred different answers — ranging from budget cuts, to poor sales-to-CS handoffs, to selling to the wrong ICP, to product issues, to tech stack consolidations, to an increase in the number of competitive solutions on the market. The list went on and on.

6. CSMs don’t like the word “selling”

Even when they’re driving expansion opportunities like your best Account Executives, many CSMs will insist they’re not selling.

You’ll hear things like:
“If I wanted to do sales, I’d be in sales.”

This matters because language, incentives, and expectations all need to be handled carefully.

Expansion works best in CS when it’s positioned as additional value creation — not quota chasing.

Customers expand when they are getting recurring impact from your product or service and want even more impact. Therefore, when CSMs “sell,” they sell from a consultative perspective and from the same side of the table as the customer, which is very different from new business sales.

7. Resources are tighter than you think

Most companies still concentrate the majority of resources on acquiring customers.

So unless you’re prepared to redistribute some budget from your sales team, expect Customer Success to operate on a shoestring — while being asked to protect and grow a massive portion of your revenue base.

This mismatch is one of the biggest hidden risks CROs inherit with CS — but it’s also within your control. By becoming a strong advocate for the revenue that can be generated from the existing customer base, and by backing that up with numbers (which I know you can do), you’ll be in a position to ask for more resources or redistribute them across your entire function so the company benefits from both new business and customer expansion.

Feeling Over Your Head? You Have Two Real Options

If you’re a CRO and this feels overwhelming, you’re not alone. I talk with CROs regularly who don’t have a good handle on Customer Success.

You have three good options:

Option 1: Dig in and figure this stuff out. Start reading my posts and my Substack, and follow other well-known CS leaders.
Option 2: Hire a very strong CS leader who can take the function off your plate.
Option 3: Hire a consultant who can put the right frameworks in place and teach you how to manage Customer Success effectively with a more junior CS leader (contact me if you’re interested in this last option).

What doesn’t work is ignoring it, under-investing in it, or managing it like a sales team.

Customer Success is now a core revenue function.
If you own revenue, you own CS — whether you planned to or not.

If this is you right now, you’re not failing — you’re learning a function most CROs were never trained to run.

More practical “how-to” posts like this coming every week.

• Don’t post the job right away. Start with your network to avoid being overwhelmed by hundreds of applicants.

• Write a job description that reflects the actual role — including book of business, customer segment, level of scrappiness required, and compensation range.

• Define real, practical skills needed for the role and design interview questions that test for those skills.

• Strong interviews depend on preparation. Ask questions that reveal whether a candidate can actually do the job.

• Use a case study to see how candidates think, follow instructions, present, and handle feedback.

• Always check references and ask specific questions to understand strengths, gaps, motivation, and performance.

• When making an offer, don’t lowball. Good CSMs will negotiate — and that skill matters in the role itself.

January = hiring season

It’s January, which means many companies are hiring (assuming they have plans to hire this year).

New budget.
New growth targets.
More people needed.

If you’re a CS leader, you’re likely hiring at least one new CSM — if not many. So how do you hire well in today’s job market?

1️⃣ Don’t post the job right away

Unless you enjoy having your inbox blow up.

It’s not uncommon for a CSM role to get 600 applicants, plus countless emails and LinkedIn messages.

When this happens, hiring teams get overwhelmed. How can you realistically process that many applications?

What usually happens is:

• The company hires a recruiting firm, or

• The job posting is taken down and they try to fill the role through their network anyway

My advice: start with your network first.

2️⃣ Write a job description that actually reflects the role

So many job descriptions are:

• Recycled from previous years

• Written by AI

• Or so generic that everyone thinks, “I can do that.”

As a result, they don’t reflect the actual job.

Be specific.

If the CSM will:

• Own a $1.5–$2M book of business, say that

• Work with mid-market customers, say that

• Need to be scrappy because processes aren’t fully built, say that

Be honest about what the role entails and what to expect.

And if you don’t fully know yet because things are still being built out — say that too.

Too often, candidates apply for a role only to find out during the interview process that the job is completely different than they expected.

Also: put the compensation range in the job posting.
There shouldn’t be any surprises.

3️⃣ Get clear on the skills you actually need

I mean real skills — not:

• “Ability to solve problems”

• “Drives adoption”

• “Manages a book of business”

• “Works well on a team”

Get clear on what the person actually needs to do, such as:

• Driving customer oucomes

• Forecasting

• Objection handling

• Discovery

• Working in Gainsight

• Building and managing Success Plans

Then create interview questions that actually test for those skills.

4️⃣ The interview is made or broken by the questions you ask

This is where many hiring processes fall apart.

Hiring managers don’t prepare enough, and the questions don’t actually tell them whether the person can do the job.

Instead, they walk away thinking:

• “I can’t see this person on my team,” or

• “I really liked them, but I’m not exactly sure why.”

Neither is very helpful.

Here are examples of interview questions that do test for the skills above:

• Walk me through how you forecasted your book of business. What was your ARR, GRR, and NRR last year?
  If someone can’t answer this, they don’t know how to forecast.

• Tell me about a time you overcame a customer objection and either saved a customer from churning or convinced them to expand.

• Walk me through how you do discovery with a customer and why it’s important for expansions.

• Tell me how you managed your tasks and time in Gainsight or another CS platform.

• Walk me through how you used Success Plans. What purpose did they serve, and how did you hold the customer accountable?

5️⃣ Have candidates complete a case study

I highly recommend having CSM candidates do a case study.

Why?

It helps you evaluate:

• Can they follow instructions, or do they go rogue?

• Do they overthink the assignment or over prepare?

• How do they approach problem-solving?

• How do they think (what did they do first, second and third)

• Do they present professionally?

• How do they handle feedback?

This gives you insight you won’t get from conversation alone.

6️⃣ Ask for references — and ask good questions

References are hand-selected, so yes — they will speak positively.

That doesn’t mean they aren’t valuable.

Speaking with references can tell you a lot about someone’s:

• Strengths

• Shortcomings

• Motivation

If you’re speaking with a former manager, ask questions like:

• What was their book of business (number of accounts, ARR, GRR, NRR, industries)?

• How did they manage and prioritize their accounts?

• What was one thing you were coaching them on?

• What is one skill you would have continued to develop?

• What motivates them?

• What feedback did they receive in their last performance review?

• What is their superpower?

• Would you rehire them today?

7️⃣ Don’t lowball the offer

You put the compensation range in the posting — your offer should land around the middle of that range.

If you’re offering below the midpoint, be prepared to explain why (for example, the role requires 3 years of experience and the candidate has 1).

Also be prepared to explain:

• How often compensation is reviewed

• What typically leads to increases

Good CSMs will negotiate.

And in my experience, CSMs who don’t negotiate often struggle to negotiate renewals too.

Are you hiring? Reach out, I have a huge network.
Are you looking for your next CSM role? Put what you are looking for in the comments so others can see it. Who knows, maybe this post will help you land your next role or help you make your next hire.

The webinar idea came from something I hear almost every week from CS and GTM leaders:

They’re not necessarily unhappy enough to leave.
But they’re not energized enough to stay as-is.
And they’re stuck in that uncomfortable gray zone.

During the session, I shared a simple framework I’ve used repeatedly in my own career — especially during moments when the path forward wasn’t obvious.

I wanted to share it here so you can come back to it anytime.

The core question behind the framework is this:

Can I be successful in this role — by my definition of success?

Not your company’s definition.
Not your manager’s.
Yours.

Here are the five questions I recommend asking.

1. Financial Reality

Does this role support the life I want — or need — to have right now?

This isn’t about maximizing comp at all costs.
It’s about being honest.

Ask yourself:

• Does my compensation align with my current responsibilities?

• Does this role give me enough financial stability to reduce stress?

• Am I constantly trading personal well-being for financial security?

If the financial reality of a role is unsustainable, it will eventually distort every other decision you make.

2. Professional Goals

Is this role helping me become who I want to be next?

Career growth isn’t just about titles — it’s about trajectory.

Ask yourself:

• Am I building skills that will matter in my next role?

• Would this experience be valuable outside this company?

• If I stayed here another year, what would I be better at?

If the role doesn’t align with where you want to go, staying may still be possible — but it needs to be intentional.

3. Energy, Capacity, and Balance

Is this role sustainable for me in this season of life?

This question is especially important — and often ignored.

Ask yourself:

• Do I have the energy to show up consistently?

• Is the workload realistic, or am I in constant recovery mode?

• Given everything else in my life, what can I actually sustain right now?

A role can be “good on paper” and still be wrong for the season you’re in.

4. Culture, Trust, and Toxicity

Is this environment making it harder for me to succeed?

No company is perfect.
But some environments actively undermine success.

Ask yourself:

• Do I trust leadership to act with integrity?

• Is feedback safe and constructive?

• Am I spending more energy navigating politics than doing meaningful work?

One critical red flag in this area can outweigh strengths elsewhere.

5. Future Growth and Optionality

Does staying expand — or limit — my future options?

This is about leverage and optionality.

Ask yourself:

• Am I gaining visibility, influence, or credibility?

• Is my network expanding or shrinking?

• Would staying here make my next move easier — or harder?

Even imperfect roles can be powerful if they build long-term career capital.

How to Use This Framework

In the webinar, I asked participants to score each area from 1–5. With 5 being “this is working well for me right now” and 1 being “this is a real problem.”

The exact score matters less than the patterns you notice:

• Where are you strong?

• Where are you constrained?

• What’s costing you the most energy right now?

Most importantly, this framework isn’t about forcing a decision.

It’s about replacing vague discomfort with clarity.

Sometimes the answer is: I should stay — but differently.
Sometimes it’s: It’s time to start preparing for what’s next.
And sometimes it’s simply: I need more information before I decide.

One Final Thought

Feeling stuck doesn’t mean you’re failing.

It usually means you’ve outgrown something — or that the way you’re engaging with your role needs to change.

You don’t need perfect certainty to move forward.
You need clarity, honesty, and the willingness to act with intention.

This framework is meant to help with that — and you can revisit it anytime your career starts to feel noisy again.

If this resonates, I’ll be sharing more practical guidance like this as part of my CS Leader’s How-To Series here on Real Talk with CS Impact.

And if there’s a topic you’d like me to cover next, just reply or message me.
I’m building this series based on what CS leaders are actually wrestling with.

You’re not alone in this.

If the first week back from the break left you questioning your job, your company, or your next move — you’re not alone.

Many CS and go-to-market leaders are burned out, under-resourced, and unsure whether staying or leaving is the right move in today’s market.

The core idea of this post is simple:

👉 You don’t need to change roles to grow your career.

Before making any big decisions, it’s important to define what success actually means to you, understand your real constraints, and get honest about the realities of the job market.

And if now isn’t the right time to leave? Growth is still possible — and powerful — right where you are.

This post kicks off a new How-To series focused on practical, real-world guidance for CS leaders navigating uncertainty.

How to grow in your career when your company or role feels stagnant

You made it through the first week back from the break.
You’re officially back in your routine.

For some of you, this feels great — a welcome return after holidays that dragged on, or kids who were quietly (or not so quietly) driving you nuts while they were off school.

For others, this first week back has been hell.

It reminded you why you hate your job.
What you were dreading about the new year.
That task or project you’d been successfully avoiding.

It feels like a wilderness — and you’re longing for the holidays, when you could watch three movies a day while eating a box of chocolates. I hear you.

Or maybe last week brought unexpected news.
A layoff.
A change in company strategy.
A leadership shift.

Maybe you’re feeling uncertain.

Wherever you are after this first week back, you may be thinking about your career.

If you’re happy in your role, maybe you’re wondering how to progress this year.
If you’re unhappy, maybe you’re questioning whether this is the year to look for something new.

Wherever you are in your journey, this post is for you.

Step one: get clear before you make a move

I speak with a lot of go-to-market leaders every single week.

Many are burned out.
Many feel like targets are impossible to hit.
Many feel bored, unmotivated, or stuck.

The past few years have been tough on everyone. Budgets have tightened, teams have been cut, and companies are expecting a whole lot more with a whole lot less.

I’m often asked what the job market and interviewing look like right now. (For context, I interviewed with over 30 companies last year before deciding to start my own consulting business.)

I’m also asked a lot about being fractional — how I got started, how I get clients, and what that path really looks like.

What I see most leaders doing right now is gathering information and trying to determine their next move.

Here’s my advice when thinking about how to grow this year — whether that’s in your current role or outside of it.

1. Determine whether you can be successful in your current role.
And by success, I don’t mean your company’s definition. I mean yours.

Do you have the support and resources to achieve what success looks like to you?

2. Look at what else is happening in your life right now.
Do you have the time, energy, stamina, and financial means to look for another role — or is something else taking priority?

3. If something else is higher priority, focus on that first.
Looking for a new role in today’s market will test you in ways you may not expect.

If there’s something more important in your personal life or at work, do that first. You can always revisit the decision to look for a new role in 1, 2, or 6 months.

In the meantime, look for ways to upskill in your current role.

If nothing else is higher priority and you do have the capacity to explore something new, don’t immediately quit your job.

You need more information first.

Before you start looking:

• Assess the size of your network. If it’s not strong enough, build it first.

• Talk to people in similar roles and recruiters to understand what’s actually moving in the market.

• Take a hard look at your finances and your runway.

Ideally, you look for your next role while still employed. Severance is rarely enough to sustain a long job search unless you’ve been in a senior role for a long time or you work for a generous company.

Now — let’s say you determine that this is not the right time to leave.

That’s perfectly okay.

You don’t need to change roles to grow

This is the part many people miss:

You don’t need to change roles to grow in your career.

You can grow a lot right where you are — even if you don’t love your role and don’t see a clear light at the end of the tunnel.

Here’s what that can look like.

1. Decide where you want — and need — to grow.
Let’s use one example: increasing your commercial acumen.

If you’re being honest, maybe much of what your CFO says about budgets, targets, P&L, and company valuations goes over your head.

First — that’s very common among CS leaders. There’s no formal training for this. Most people are expected to just “pick it up.”

2. Get intentional about how you build that skill.
Brainstorm ways to learn — both inside and outside your current role.

Could you:

• Meet with your CFO for 15 minutes once a week?

• Ask questions like:

  • How do you define success for the CS organization?

  • Where do our expansion targets come from? (i.e how did you come up with the numbers?)

  • How should I think about the P&L for my department?

  • Do you view Customer Success as a growth driver or a cost center — and why?

You can also learn through external resources:

• Subscribing to newsletters where leaders and even CFOs talk about this

• Taking courses like Pavilion’s Introduction to P&L Fluency

• Learning SaaS fundamentals through Winning by Design’s Revenue Architecture

There are also thought leaders whose work can dramatically increase your understanding over time. I personally read almost everything from Cassie Young and John Gleeson at Success Venture Partners to better understand what boards, investors, and strong operators care about.

And there are books worth exploring, such as The SaaS Playbook by Rob Walling or Subscribed by Tien Tzuo. If you do these things — regardless of how much you dislike your current role — you are growing.

You may not feel successful today, but you are building success for tomorrow.

Now commercial acumen is just one example.

Maybe you want to become a better people leader.
Maybe you want to start your own business one day.
Maybe you want to improve your forecasting or data analysis skills.

No matter where you are in your career, growth is always possible.

Your career growth is your responsibility

This brings me to my final point:

You are responsible for your career growth.
Not your company. You.

That means taking ownership — even when you hate your job, the job market is tough, and your company is heading in a direction you don’t agree with.

I’ve had roles with less-than-ideal companies, strategies, and situations — and I still continued to grow.

My approach was simple:

1. Know my definition of success

2. Regularly reevaluate whether I could be successful in my role

3. Keep a pulse on the job market

4. Continually grow my network

5. Always be learning

Feeling stuck doesn’t mean you’re failing.
It usually means you’ve outgrown something and it’s time to get out of your comfort zone and try something new.

Join me live: January 20th

If this topic resonates, I’m going deeper on it in a live webinar on January 20th at 12:00 PM EST.

We’ll talk specifically about:

- How I evaluated when it was worth staying vs. when it was time to go in my own career
- How I continued growing in roles that felt limiting on paper
- What I’d do differently earlier in my career

There will also be space to ask questions and openly share how you are planning to grow in your career this year.

If you’re trying to figure out your next move — or just want to feel less alone in the process — I’d love to have you there.

Register for the Webinar

I’m launching The CS Leader’s How-To Series to share practical, real-world lessons from my time as a VP of Customer Success and from working closely with CS leaders today — what’s working, what isn’t, where leaders tend to get stuck, and what I recommend.

These are meant to be things you can put into action right away, and I’d love to hear from you on what you’d like me to cover in this series.

Subscribe now

When I was a VP of Customer Success, I often found myself asking:

What are other CS leaders actually doing?

The problem was that I rarely had time to connect with other leaders, so I often felt like I was operating in a vacuum.

Now, as a fractional leader, I talk with upwards of 25 CS leaders a week about their toughest challenges.

They all want advice.
And almost every one of them wants to know the same thing:

What are other CS leaders doing right now?

So for the next month or so, I’m going to share a series of “How-To” posts.

I’ll cover:

• Some of the things I worked on as a VP of Customer Success

• What I see working (and not working) across multiple companies today — including what I’ve personally been involved in

• Where leaders tend to get stuck, and recommendations for moving forward

• What I would absolutely never do again

These are meant to be practical posts — things you can actually put into action right away.

The first few topics I’m planning to cover:

• How to grow in your career — even when the company you’re in feels limiting

• How to hire strong CSMs (or uplevel your existing team)

• How to build a forecast your CEO and CFO will actually trust

• How to reset expectations with your team after a tough year

I’ll also be going deeper on some of these topics through webinars and LinkedIn Live sessions, starting with a topic many CS leaders struggle with in January: career growth and what to do when your role or company feels stagnant.

If you’re a CS leader trying to figure things out — either in a sea of information or in a vacuum — this series is for you.

And if there’s something you’re wrestling with as you head into the year, email me and let me know. I’m happy to share my experiences on topics that are relevant to you.

Because you’re not alone.
We’re in this together.

You can email me at any time at andreabumstead@gmail.com

Join my webinar on what to do when your role or company feels stagnant on January 20th at 12:00 PM EST. Register here ASAP as space is limited.

Register here

Since leaving my full-time VP of Customer Success role and building CS Impact, I’ve started seeing CS leadership very differently.

In this post, I share:

• Why stepping outside one company changed how I think about strategy, influence, and accountability

• The patterns I now see across CS teams that I couldn’t see from the inside

• Where CS leaders are being set up to fail — especially around churn and unrealistic expectations

• And why, despite all of this, I’m genuinely optimistic about the future of Customer Success heading into 2026

This isn’t a tactical post.
It’s a perspective shift — and an honest reflection on what CS leadership really requires today. Let’s dive in …

When I left my VP of Customer Success role to start CS Impact, I assumed I’d always think like an operator.

That’s all I had ever known.

Urgency. Execution. Problem-solving.
Move fast. Fix things. Deliver.

What surprised me most was how quickly that mindset shifted.

Today, I think much more like a consultant.

Instead of asking, “How do we execute this?”
I now ask, “Should we even be doing this?”

And more often than not, my advice isn’t to speed up — it’s to slow down, step back, and look at the strategy from a different angle.

As an operator, I did what was asked and didn’t push back much.
As a consultant, I question everything — and I push back when I believe a company is heading in the wrong direction.

That shift has taught me more about Customer Success leadership than I expected.

What surprised me after leaving the VP seat

Inside a company, trust is largely assumed.

People know you. They’ve seen your work. You’ve built credibility over time.

Outside a company, that trust doesn’t exist.

You have to earn it quickly — and you have to prove that you understand the business, the pressure, and the tradeoffs, not just CS theory.

That reality has changed how I communicate. I’m far more intentional about tying CS decisions back to revenue, risk, and outcomes executives actually care about.

Another surprise was how much context protects you when you’re inside one organization.

As a full-time operator, I thought I had more influence over strategy than I actually did. From the outside, it’s much clearer: company strategy is set at the board level — and it almost always comes down to one thing.

Revenue. Revenue. Revenue.

That doesn’t make leadership wrong — but it explains why CS leaders often feel like they’re pushing uphill.

Patterns I couldn’t see from the inside

Once I started working across multiple companies, clear patterns emerged — ones I couldn’t see when I was focused on a single org.

The biggest one?

Most CS teams aren’t equipped to do the job they’re being asked to do.

CSMs are often hired because they’re “good with people” or great at solving customer problems. Far fewer are hired — or trained — to help customers realize measurable business outcomes.

Those are very different skill sets.

As an industry, we’ve underinvested in CS upskilling. There’s a massive gap in training, capability, and commercial acumen — and most teams are trying to close it on their own.

Another pattern I see constantly: CS leaders internalizing churn.

They take it personally. They assume the buck stops with them.

But churn is rarely just a CS issue.

It can be product. Sales. Pricing. Positioning. Expectations set long before CS is ever involved.

When CS leaders carry all of that alone, burnout isn’t a surprise — it’s inevitable.

Where CS leaders are being set up to fail

Here’s the hard truth I see over and over again:

CS leaders are held accountable for churn without being truly empowered to influence all the factors that drive it.

CS can impact churn — but they don’t own it in isolation.

Another unrealistic expectation? That CS leaders should be great at everything post-sale.

Just like any other role, CS leaders are specialized.
Some thrive in SMB, others in Enterprise.
Some are data-driven. Others excel in enablement, change management, or scale.

No one is great at everything — yet CS leaders are often expected to be.

What’s missing isn’t effort.
It’s support.

Support looks like outside enablement.
Experienced coaches or fractional leaders.
Help with critical projects that don’t fit neatly into day-to-day work.

Trying to do all of this alone is one of the fastest paths to exhaustion.

If there’s one thing I wish more CS leaders knew, it’s this:

You are not alone.
Most CS leaders feel this way.

The key is asking for help in the right way — speaking the language of the CFO, using data, and clearly showing how targeted support improves both revenue and expenses.

What gives me real optimism going into 2026

Earlier this year, it felt like Customer Success was under attack.

There were endless posts about the “death of CS.”
A lot of doom and gloom.

I don’t see that anymore.

What I see now is renewed energy — and better questions.

CS isn’t going anywhere. In fact, it’s becoming more important than ever as companies are forced to focus on helping customers actually achieve outcomes with their products and solutions.

I’m hearing leaders ask:

• How can I strengthen my business acumen?

• How can I use AI efficiently instead of chasing noise?

• How do I upskill and stay ahead of the curve?

• What are the best leaders doing differently?

That curiosity gives me hope.

Personally, I’m most excited to support CS leaders who are tired of doing it all — and ready to make a real business case for help.

Leaders who speak in dollars and cents.
Leaders who understand that progress doesn’t come from more effort — it comes from better leverage.

Building CS Impact has reinforced something I believe deeply:

The future of Customer Success isn’t about doing more.
It’s about doing the right work — with clarity, support, and intention.

And finally — Happy New Year

As we step into 2026, I just want to say how grateful I am for this community.

I’m excited to continue this journey with you — sharing what I’m seeing, what I’m learning, and where I believe CS leadership is really headed.

As always, your feedback on these posts means a lot to me.
Tell me what resonated. Tell me what didn’t.
And if there’s something you’d like me to write about in 2026, I’d genuinely love to hear it.

Here’s to a thoughtful, grounded, and impactful year ahead.

— Andrea

👇 Watch the webinar + access the slides

In this session, I share:

• How I attracted roles and opportunities without applying

• Why I decided to create my own business instead of taking another full-time role

• The exact steps that led to my first signed clients

• The habits and systems I still use to grow CS Impact today

⬇️ Access the resources below

👉 Slides from the webinar (see download link)

From Job Search To Signed Clients My Pivot Story Webinar (3)

4.75MB ∙ PDF file

Download

Download

👉 Access the Webinar recording

What we cover in the session

This isn’t a highlight reel — it’s a real look at what worked, what didn’t, and what I learned along the way, including:

• Building visibility and momentum during a job search

• Using LinkedIn, relationships, and thought leadership intentionally

• Turning “no” into paid project work

• Reframing rejection into opportunity

• Creating a business around the work once clients were already in hand

If you’re curious about consulting or fractional leadership but unsure where to start, this session will give you a concrete reference point.

How to use this resource

I recommend this session if you’re:

• In between roles or thinking about what’s next

• Exploring consulting or fractional leadership as a path

• Wanting a more honest look at career pivots — without the hype

You don’t need to have it all figured out. You just need to start building momentum.

Want to talk through your own pivot?

If you’re navigating a transition and want to pressure-test your thinking, I offer free 15–30 minute intro chats.

👉 Grab a time here

👇 Watch the webinar + access the slides

In this session, we cover:

• Where AI is actually being used in CS today (and where it isn’t)

• Why AI isn’t the strategy — your operating system is

• How to start small with AI workflows that remove noise and free up CSM time

• When AI agents make sense — and when they absolutely don’t

⬇️ Access the resources below

👉 Download the slides

The Ai Powered Cs Org How To Scale Smarter (1)

8.35MB ∙ PDF file

Download

Download

👉 Access the webinar recording

AI in Customer Success Webinar Recording

What we cover in the session:

• AI trends in Customer Success (Andrea)
  A clear look at how CS teams are actually using AI today — and the biggest takeaway: you haven’t been left behind. There is still plenty of time to get started the right way.

• Using AI across the customer journey (LeeRon)
  How to think about AI from onboarding through renewal, and the foundational pieces you need in place before AI can create real leverage.

• Building and scaling an AI agent in CS (Theeba)
  A behind-the-scenes look at Nora, an AI agent that answers customer questions. Theeba walks through how Nora was built, how she’s trained, and how she’s being used today as a valuable member of the CS team — not a replacement for humans.

• Moving along the AI continuum (Kate)
  How to think about AI maturity, when agents make sense, and how to get started safely. Kate also shares a bad example of an AI agent and a good one, and why most teams get this wrong the first time.

The common theme across all four perspectives: start small, focus on real problems, and use AI to reduce noise — not create more of it.

How to use this resource

I recommend this session if:

• Your team is experimenting with AI but hasn’t seen real impact yet

• You’re trying to align CS, Ops, and Product on how AI fits into your model

• You want to avoid buying tools before fixing process and data issues

This is a strong starting point for leaders who want to move from curiosity to execution.

Want help applying this to your CS org?

If you’re thinking through AI adoption, digital CS, or scalable engagement models, I offer advisory and implementation support.

👉 Book a free 30-minute CS strategy chat
Book time with me here

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This launch kit is designed to help you:

• Replace bloated, slide-heavy QBRs with short, high-impact conversations

• Equip your CS team with a repeatable, executive-friendly structure

• Roll out the 15-Minute QBR in a way that sticks — not a one-off experiment
  
  👇 Download the 15-Minute QBR Launch Kit

The 15 Minute Qbr Launch Kit Aug16 (1) (3)

530KB ∙ PDF file

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What’s inside the Launch Kit

This isn’t just the framework — it’s everything you need to implement it across your team, including:

• Why the 15-Minute QBR works (and why traditional QBRs fail)

• A clear breakdown of the 3-part QBR structure:

  1. The impact or value the customer is getting

  2. The impact or value they could be getting

  3. Three tailored recommendations for next steps

• How to implement the framework in your org, including:

  • Leadership buy-in

  • Team enablement

  • Pilot → learn → scale rollout phases

• Answers to FAQs from CS leaders, covering:

  • Exec attendance and engagement

  • Prep time and data overwhelm

  • Expansion, upsell, and value conversations

  • What to do when ROI isn’t obvious

This kit is meant to help you turn QBRs from a calendar obligation into a strategic lever for retention, expansion, and trust.

How to use this launch kit

I recommend using this kit when:

• You want to standardize QBRs across your CS team

• You’re re-training CSMs on executive-level conversations

• QBR attendance is dropping — or never existed

• You want QBRs to support value realization and revenue, not just reporting

Start small. Pilot with a few accounts. Refine. Then scale with confidence.

Want help implementing this with your team?

If you want guidance rolling this out — from leadership alignment to team training — I offer implementation and enablement support.

👉 Book a free 30-minute CS strategy chat
Book a strategy call

Let’s make your QBRs shorter, sharper, and more strategic.

Just over a year ago, I was a full-time VP of CS with a team of 13 at a ~$30M ARR SaaS company. The business was navigating familiar scaling challenges: two acquisitions, an attempt to create a new category, and increasing pressure around churn and growth.

I was hired to merge Customer Success teams, rethink the end-to-end customer experience, and stabilize retention — with the implicit expectation that CS would also begin to play a more meaningful role in revenue.

On paper, it made sense.
In practice, it exposed a reality many CS leaders are living right now.

When CS Is Asked to Carry Revenue Without Real Authority

Shortly after joining, I made one of the hardest decisions of my career: exiting three of my direct reports who were CS leaders. It was the right decision for the business — and it immediately put me underwater.

At the same time, expectations accelerated.

Customer Success was expected to:

• Improve retention

• Influence expansion

• Absorb post-acquisition complexity

• Support a shifting go-to-market strategy

All while operating inside an organization that hadn’t recalibrated around those outcomes.

Churn worsened. Priorities multiplied. The three companies had different products, customers, and operating models.

From the outside, this often looks like a CS execution problem.
From the inside, it’s a systemic go to market problem.

This is where CS leadership starts to become high-risk for both the leader and the company.

I knew that if I couldn’t get things turned around fast, the company would have no choice but to find a new leader or change directions.

The Moment It Became Unsustainable

A few months in, I felt like I was drowning.

I was running the day-to-day while trying to operate strategically. The backlog never cleared. Context switching became constant. I had trouble sleeping as I thought about the growing customer churn.

This is the moment many CS leaders hit — when accountability expands faster than authority, and success is defined by outcomes you don’t fully control.

When churn worsened and expansion and new business revenue slowed, the company went through a major leadership restructure - almost every go to market leader was exited, including the CEO and I found myself looking for my next role. I felt two things at once: relief and dread.

I knew the job market would be tough. So I treated the search like a race that I was going to win in record time.

What the Interview Process Revealed

I got to work right away and hired an executive coach I’d worked with earlier in my career. I spoke with recruiters, resume writers, and former colleagues. I prepared for interviews and researched companies tierlessly.

Over seven months, I interviewed at more than 30 companies (I know because I tracked them all in a spreadsheet).

Four times, I came in last.

And by “last,” I mean I was the only candidate still standing — and the company still didn’t hire anyone.

That’s when the pattern became clear.

Hiring a senior CS leader is a high-risk decision for companies — the role is expected to solve multiple systemic problems quickly, often during periods of uncertainty.

Also, the need to hold onto as many customers as possible (prevent churn) while brining in new revenue (expansion) is stronger than ever so companies can’t afford to take a chance on a leader. They have to know that they are the right fit and that they will deliver.

The interview process wasn’t broken.
In today’s macro, economic climate of uncertainty, it was completely rational.

Two Hard Truths I Couldn’t Ignore

1. Companies Are Risk-Averse — and CS Leadership Is Inherently Risky

In uncertain markets, companies optimize for certainty.

That’s why interviews stretch to eight or nine rounds. Why candidates are asked to complete data exercises and meet with boards. Why every box needs to be checked.

Customer Success leadership doesn’t offer certainty — especially when companies want CS to drive revenue without fully rethinking incentives, ownership, or decision rights.

Most companies say they want Customer Success to take care of their customers.
What they actually want is revenue.

That gap creates risk — for the business and the CS leader.

2. I Didn’t Want to Take the Risk Either

At the same time, I had to be honest with myself.

Every company I interviewed with was dealing with some combination of churn, stalled growth, incomplete integrations, go-to-market misalignment, or leadership change.

The roles were framed as “strategic,” but the expectations were immediate and expansive.

I started to imagine the likely outcome: come in, absorb the complexity, move fast — and if the numbers didn’t change quickly enough, be gone in 15–18 months.

Without meaning to, I began thinking of these roles as temporary.

That realization changed everything.

Why Fractional Became the Answer

If the role was temporary anyway, doing it fractionally made more sense.

Fractional leadership isn’t a downgrade.
It’s a way to reduce risk by aligning expectations with reality.

It creates:

• Senior-level insight at a price point companies can afford

• Clear scope instead of open-ended accountability

• Momentum without a long-term gamble

After the fourth rejection — this time for “cultural fit reasons” — I went back to one company with a different proposal.

I said:
You have a real problem to solve. You don’t have someone in this seat, and waiting to hire the perfect candidate is costing you time. You’ve already seen how I think through your data and your challenges. Let’s start fractionally and focus on outcomes.

They hired me the next day.

That’s how my company CS Impact was born.

Why This Substack Exists

I didn’t start CS Impact because I wanted to build a company.
I started it because the way we hire, position, and support Customer Success leaders isn’t working and it is changing.

CS leaders are being asked to own revenue outcomes without real revenue authority — and then quietly blamed when systemic go to market issues surface.

This Substack is where I’ll write about:

• Why CS leadership has become such a high-risk role

• What it actually takes to make CS work inside a real go-to-market system

• When fractional leadership makes sense — and when it doesn’t

• And how CS leaders can make clearer, more strategic decisions in uncertain environments

No platitudes. No generic playbooks. Just real talk from the operator seat. I will share everything I know and everything I am learning from working with real companies.

If you’ve ever felt set up to fail in Customer Success, you’re not alone — and you’re in the right place.

Thank you for being here.