How I went from entry-level CSM to Strategic CSM in 4 years

Hi there,

In 2020, I made a decision that changed my career.

I stepped back from my leadership role and went all in on Customer Success.

Four years later, I moved from entry-level CSM to Strategic CSM, managing global enterprise accounts.

It wasn’t luck.
It wasn’t timing.
And it definitely wasn’t waiting around for someone to hand me a bigger title.

It was intentional.

Here are the 15 things I did differently.

If you’re an early-career CSM and want to move into enterprise, this is your roadmap.

1. I invested in myself

I read every Customer Success book I could get my hands on.

A few that shaped me:

• The Outcome Generation – Paul Henderson

• Selling to the C-Suite – Nicholas A.C. Read & Stephen J. Bistritz

• The Customer Success Professional’s Handbook – Ashvin Vaidyanathan & Ruben Rabago

• The Chief Customer Officer Playbook – Jeanne Bliss

• Doing Discovery – Peter Cohan

• The Seven Pillars of Customer Success – Wayne McCulloch

• Chief Customer Officer 2.0 – Jeanne Bliss

• The Chief Customer Officer Playbook - Rod Cherkas

• REACH – Rod Cherkas

• Never Split the Difference – Chris Voss (with Tahl Raz)

• The Strategic Customer Success Manager – Chad Horenfeldt

I absorbed as much knowledge as I could in a very short period of time.

Every book changed how I show up with my customers and got me closer to where I am today.

2. I listened to the best

Podcasts during workouts.
CS webinars at night.
Industry panels on weekends.
I attended CS conferences and events.

I studied how strong CSMs ask questions.
How they position value.
How they think about revenue.

I stopped consuming random content.
I consumed strategically.

3. I tracked my numbers obsessively

This is where things shifted.

I stopped saying “my accounts are doing well.”

Instead, I tracked:

• GRR

• NRR

• Expansion rate

• Adoption trends

• Product usage

• YoY growth

• Risk indicators

At one point, I closed a year at 136% NRR.

Strategic CSMs think in numbers.
If you don’t know your metrics, you can’t lead.

If you want to learn more about how to track your metrics, this YouTube video is for you.

4. I learned to read and analyze 10-K reports

Most CSMs never open a 10-K.

I started downloading them before every executive conversation.

I looked for:

• Cost reduction initiatives

• Lease liabilities

• Strategic risks

• Executive commentary

• Investment priorities

When you quote their annual report back to them, the conversation changes.
You start sounding like a business partner.

5. I built frameworks where none existed

I’m not naturally organized.

So, I built systems.

• Research frameworks (Industry, Company, Executive)

• Discovery templates

• Success Plan structure

• Milestone trackers

• Health score models

• AI prompts for research

Strategic work depends on structure. 

6. I surrounded myself with people smarter than me

I joined Slack groups.
I engaged in CS communities.
I built relationships on LinkedIn.

I asked questions publicly.

I shared ideas and put myself out there.

I learned from operators who were way ahead of me.

Your environment matters more than you think.

How’s that saying go?

“You are the average of the five people you spend the most time with.” — Jim Rohn

7. I shared my journey online

I started writing consistently.

No big audience.
No polished strategy.

Just lessons I was learning in real time.

That grew to 19,000+ followers on LinkedIn.
And +2,500 subscribers on this newsletter. (Thank you for being here)

Building in public did four things:

1. It forced clarity.

2. It forced me to level up.

3. It built authority before the title caught up

4. And… it landed my first Enterprise CSM role 5 years ago.

8. I invested outside of my job description

I built:

• Internal coaching sessions

• Onboarding resources

• EBR Templates

• Success Plan Playbooks

• Internal processes

• CS training decks

• AI initiatives

No one asked me to.

I saw gaps and filled them.

That’s how leaders are built.

9. I embraced revenue ownership

I stopped thinking:

“I manage accounts.”

I started thinking:

“I own a business portfolio.”

That changed how I approached:

• Renewals

• Expansion timing

• Risk mitigation

• Executive engagement

Revenue is not only a Sales problem.

If you want to manage enterprise accounts (especially in 2026), you need a revenue-driven mindset.

10. I learned cross-functional influence

Instead of escalating product issues emotionally, I translated them into ARR impact.

Instead of saying “this feature is broken,” I said:

“This impacts $X in expansion potential or retention.”

Product (and leadership) listens when you speak in business terms.

11. I did the role I didn’t have yet

This one matters.

Before I ever managed enterprise accounts, I started treating my existing customers like enterprise customers.

I researched their industry.
I mapped stakeholders.
I documented goals.
I tried to understand how their teams were measured.

The habits I built became the foundation for managing global enterprise accounts.

Strategy is a muscle.

You build it long before you actually need it.

12. I got comfortable with executives

I stopped fearing C-level titles.

CIO.
VP.

They are measured on KPIs like everyone else.

When you understand what they are measured on, conversations become easier.

Executives don’t want feature updates.

They want clarity, context, and direction.

13. I adopted AI early

I bought my ChatGPT premium subscription the day it was available and long before Copilot was adopted in my company.

I used AI to:

• Summarize 10-Ks

• Prepare executive questions

• Research industries

• Draft milestone plans

• Refine value messaging

• Better communicate ROI

Strategic CSMs move faster by using tools well.

AI won’t replace strategy.

But it will replace tactical work.

14. I narrowed my focus

When I moved from hundreds of accounts to Enterprise, I used the space wisely.

I went deeper.

• More research

• Better documentation

• Stronger executive relationships

• Clearer success plans

Depth creates authority.

15. I documented everything I learned

Early in my career, I realized something.

Every problem I solved…
Every discovery call that went well…
Every mistake I made…

There was a lesson in it.

So I started documenting everything.

Frameworks.
Strategies that worked.
Lessons from churn.

Over time, those learnings turned into templates.
Then playbooks.
Then training sessions.

Eventually, they became the foundation for the resources and content I share with you today.

Growth compounds when you capture what you learn.

What changed?

I didn’t wait to be promoted.

I started operating at the next level.

That’s the difference.

If you’re feeling stuck, here’s what I want you to remember:

Being busy is not the same as being strategic.

Strategy is built intentionally.

And it’s learnable.

You don’t need 10 years of experience.

You need:

• Curiosity

• Systems

• Executive awareness

• Revenue mindset

• Consistency

That’s how I went from entry-level CSM to Strategic CSM in four years.

And if you’re willing to do the work, you can do it faster.

Are you looking to get promoted? What’s the one skill you know you need to work on next?

Best,
Erika