From CSM to CEO: Why Customer Success Leaders Are the Next Generation of Founders and Executives

Customer Success has quietly become one of the best training grounds for executive leadership. I come at this with a first-person perspective as I started success at Boomi when, as I used to say, it was 3 people and a cat in the corner that no one knew about. By the time I left as COO success was 100+ people globally driving 95%+ gross retention and ~120% net retention. CS leaders are stepping into the CEO role, and this is because CS can be a capstone role for future CEOs.

Customer Success is under pressure.

Churn is up. Renewals are harder. Budgets are tighter. And success teams are being asked to do more, with less.

In recent months, we've seen a surge in thought leadership highlighting the strain CS leaders are under. It's no longer just about onboarding and renewals, it's about driving value across the entire customer journey, influencing product strategy, and owning revenue outcomes.

But here’s the thing: The very pressure that’s reshaping CS is also forging tomorrow’s CEOs.

Customer Success is CEO School.

Think about it. A great CS leader doesn’t just manage customers, they sit at the crossroads of everything that matters in a company:

Product: CS sees what’s actually being adopted, and what’s not. They hear firsthand what features are loved, which are confusing, and what’s missing. And they have to understand how the product and engineering teams work and prioritize.

Sales: They’re deeply involved in initial adoption and understanding “what was sold” compared to what is adopted. They are also knee deep in expansion and upsell, working side-by-side with account teams to grow revenue.

Support, Services, and Finance: CS leaders connect the dots across functions, aligning internal teams to deliver value and outcomes.

Board & C-Suite Visibility: Success leaders are often asked to report on health, renewals, NRR, and strategic risk, giving them exposure to investor-level conversations earlier than most.

In short, Customer Success is one of the few roles that sees the entire lifecycle, from onboarding to expansion to advocacy. And that makes it a perfect proving ground for executive leadership.

‍Christina Kosmowski: From CS to the Corner Office

No one embodies this path better than Christina Kosmowski, now CEO of LogicMonitor.

Before taking the helm, she built and led Customer Success teams at Salesforce and later Slack, where she scaled success orgs during periods of hypergrowth. Her success playbooks weren’t just operational, they were strategic, tightly aligned to revenue and product decisions.

In interviews, Christina has been vocal about how her CS background shaped her CEO approach: “I saw early on that if we really listened to our customers and helped them succeed, the business would follow.”

And it has. Under her leadership, LogicMonitor has grown rapidly (6x its initial valuation in 2018 and 650% organic growth in that same time) and continues to expand globally, all while keeping the customer at the center.

Gabby Wong: Another Signal in the Noise

Another standout example is Gabby Wong, CEO of FranConnect. Her rise from a customer-facing role to CEO reinforces a growing trend: companies want leaders who deeply understand the customer, not just the balance sheet.

Gabby has spoken about how CS taught her to drive alignment across departments and to lead with empathy, skills she now leans on to guide the entire organization.

If you’re in CS today, take this as permission to think bigger. Yes, the job is hard right now. But it’s also preparing you for something more.

Because when you’ve learned to:

✅ Manage risk across dozens of accounts
✅ Align cross-functional teams around outcomes
✅ Navigate product gaps without panic
✅ Drive revenue without overselling
✅ Make customers feel seen and heard

You’re not just leading success.
You’re building CEO muscles every day.

‍

• Don’t wait to be tapped. Start thinking like an exec today.
• Push for clarity on how your team impacts revenue.
• Build relationships with product, finance, and the board.
• Frame CS work in terms of strategic risk, not just operations.
• Learn how your company actually makes money.
  

Final Thought

Customer Success is no longer a supporting role. It’s a launchpad.

And the next wave of great CEOs might come from sales, product, or finance, but they might also come from the team that knows the customer best.

For those leading with clarity, Noded AI is inviting the next generation of CS first executives to join our early access. It’s free, fast, and built from my leadership learnings in Customer Success.