I’ve been quiet. Here’s why.

2025 forced me to level up. So I did.

Hi there,

It’s been more than six months since my last newsletter.

That wasn’t the plan.

If you’ve been here for a while, you know I care about consistency. But 2025 stretched me in ways I didn’t expect. Instead of sending something rushed, I stepped back and focused.

For those of you who joined recently, let me reintroduce myself.

I’m Erika. 👋🏻
Strategic CSM. Enterprise, global accounts. Revenue ownership.
Obsessed with becoming the most strategic, high-impact CSM I can be.

And for those who’ve been here a while — thank you.

I stepped away for a reason.

Over the past two years, I’ve been building something that demanded far more time and energy than I expected: The Success Plan Playbook.

It’s the most strategic work I’ve created so far. And it required my full attention.

But the bigger reason I’ve been thinking differently isn’t just the playbook.

It’s what I’ve seen happening around me.

The CSM role has changed

The post-sales environment for SaaS shifted toward higher scrutiny and tougher retention math: tech layoffs stayed elevated, budgets tightened, procurement influence increased, and expansion became harder.

I’ve seen this firsthand in my own business portfolio.

  • My customers experienced layoffs.

  • The champions I built relationships with? Gone.

  • Executive stakeholders changed.

  • Budgets froze.

  • Procurement analyzed every subscription line with a microscope.

  • Executives demanded more.

And I felt the pressure.

Not just to manage my accounts.
To defend them.

And layered on top of all of this — AI.

I follow earnings calls. I read what CEOs are saying.

Last week, Block (Fintech company) announced it was laying off roughly 40% of its workforce — around 4,000 people — as it leans further into automation and AI-led efficiency.

And I’m seeing this all around.

Companies are no longer asking, “Should we experiment with AI?”

They’re asking, “How can we use AI to operate leaner?”

And when that question gets asked, every function is examined.

Including Customer Success.

If reporting can be automated, it will be.
If onboarding flows can be standardized, they will be.
If risk alerts can be surfaced automatically, they will be.
If decks can be generated from usage data, they will be.

So the real question becomes:

What remains uniquely human?

Judgment.
Context.
Influence.
Strategy.

AI can surface churn risk.
It cannot defend a budget in front of a CFO.

AI can show usage trends.
It cannot navigate stakeholder politics mid-renewal.

AI can optimize the renewal process.
It cannot earn executive trust.

When execution becomes automated, value concentrates in IMPACT.

That forced me to rethink how I show up in my role.

What this means for you

If you’re in Customer Success right now, the bar is rising.

Tactical work is easier than ever to replace.

What’s harder to replace?

  • Thinking in business outcomes.

  • Influencing executive decisions.

  • Connecting usage to revenue, cost savings, or risk reduction.

  • Anticipating renewal risk months before it surfaces.

  • Aligning stakeholders around measurable value.

That’s strategy.

It protects your role.
It expands your influence.
It moves you from vendor to revenue partner.

Being strategic doesn’t mean doing more.

It means understanding how your customer makes money.
Knowing how your executive is measured.
Framing every recommendation around impact.

The CSMs who operate at this level become indispensable.

And that’s what the next chapter of this newsletter will focus on.

Where this newsletter is going

Over the past five years, I’ve documented my journey as a CSM. As I’ve evolved, so has my content.

This space won’t be about generic CS advice.

It will be about how to think, operate, and show up like a Strategic CSM in an environment where “good enough” is no longer safe.

Six months from now, if you’re reading consistently:

  • You’ll build real business acumen.

  • You’ll prepare for executive meetings differently.

  • You’ll ask sharper discovery questions.

  • You’ll tie your product to financial outcomes naturally.

  • You’ll protect renewals before they’re at risk.

  • You’ll own revenue.

That’s the shift.

One thing you can use today

Before your next customer call, ask yourself:

Do I know how this stakeholder is measured this year?

If you don’t know their KPIs, you’re not operating strategically yet.

Start there.

It will change how you listen, what you say, and what you recommend.

One quick question

Before I shape the next few issues, I want to understand who’s here.

Where are you in your CS journey?

Login or Subscribe to participate in polls.

I’m so excited for the next chapter of this newsletter.

Thanks for being here!

Best,
Erika

Erika Villarreal

 

Reply

or to participate.