Quick Summary: To be a true leader in customer success today, you must think like an operator, aligning with investor goals, proving impact with data, and treating the customer journey as a revenue engine. Business fluency, strategic use of AI, and proactive decision-making aren’t optional.
Most customer success leaders today are navigating shrinking budgets, rising expectations, and the relentless pressure to prove value. It’s a perfect storm that’ll take more than management alone if you’re in the driving seat, says Jan Young. This requires true leadership.
So how do you become a true leader in customer success in the new investor-driven, efficiency-focused environment?
You’ll need to rethink your role, build your business fluency, and go all-in on AI as a strategic tool, says Jan. (Here’s how to get started with AI if you haven’t already.) At the same time, leading means championing AI adoption throughout your team, even when it means challenging the status quo—a role that modern CS leaders must fully embrace. And no, AI isn’t replacing CSMs—it’s elevating those who learn to use it.
In her recent ChurnZero webinar, NextGen CS, Jan explained the essentials that you should know.
Use the tips from Jan’s webinar (you can watch it in full below) to earn your seat at the leaders’ table rather than waiting for it. Here are our top five takeaways for current and future leaders in customer success.
1. Know your investors. They’re shaping your strategy.
“Investors have impacted you every day of your career,” says Jan, “even if you haven’t thought about them.”
Whether your company is backed by venture capital or private equity, your funding model defines the rules of the game. Venture capital investors push for growth, often with a 7–10 year runway. Private equity investors seek leaner, more profitable operations, which often occurs post-acquisition.
Knowing your investors’ expectations helps you position your team—and your tools—in alignment with the boardroom agenda.
2. Build your business cases with the data you have.
“You are the one who needs to manage for your team’s profitability, says Jan. “No one else is going to do it.”
If you’re waiting on finance to give you pristine numbers, that means… don’t. Instead, start with what you know, such as revenue per account, and time spent per activity. From here, you can estimate your costs to start building business cases for tools, strategy, and even new headcount.
What if your CFO hesitates to share margins?
“Tell them you’re trying to help them show we’re doing this profitably,” Jan suggests. “Then they get on board.
3. Your customer journey is your revenue system.
One of the most potentially game-changing shifts from Jan’s webinar is to reframe your customer journey from a map to an operating system. In this framing, your milestones, outcomes, and exit criteria become the foundations of predictable revenue, targeted automation, and smarter investments.
When you can show who’s on track, who’s at risk, and where time is being wasted, you can stop chasing intuition and start leading with insight
“This is your success path,” says Jan. “It’s how you prove and scale your impact.”
4. AI isn’t optional—it’s a performance expectation.
“Before asking for more headcount and resources, teams must demonstrate why they cannot get what they want done using AI.”
This, from Shopify CEO Tobi Lutke’s now famous April 2025 memo, encapsulates the new era of leaner teams and investor expectations of efficiency.
AI isn’t extra, says Jan. It’s expected. Use this four-question framework to help prioritize your AI projects: 
Don’t wait for permission. Start with a small, strategic win—like automating QBR prep or segmenting at-risk accounts.
5. Business leadership is learned, not inherited.
“None of us were born knowing how to sell, manage, or draw a P&L,” Jan says.
Her point: you might not think of yourself as a leader in customer success today, but leadership ability isn’t fixed. It grows with practice. If you’ve ever said: “I’m not good at math”, or “I don’t think like a CEO”—simply add one word: “yet”.
You’re not just allowed to learn business fluency, says Jan—you’re expected to. The best place to start: your customer journey (see above) your data, and your willingness to ask hard questions.
Watch Jan Young’s NextGen CS webinar in full here.
You can also see Jan’s answers to our audience’s questions below.
Our top audience questions, and Jan’s answers.
Q: If you don’t currently have access to your company’s finance data, how can you gather the metrics you need to tell a strong business case?
Jan: Start with what you do have—revenue at the account level. That’s the foundation. Then, begin tracking key activities and estimating the time your team spends on them. From there, you can calculate costs using an average FTE (full-time equivalent) salary. If your finance team won’t share internal averages, use public benchmarks and adjust them. Once you have revenue and cost, you can estimate your margins. When you bring this model to finance, they’re more likely to engage and refine it with you—especially if you frame it as supporting their goal of demonstrating profitability.
Q: Which roles are most at risk of being replaced by AI or automation?
Jan: It’s less about replacing roles and more about transforming how we work. In support, for example, AI might handle first-level responses, but it increases the importance of skilled team members who can handle complex, nuanced issues. What changes is how we grow—rather than hiring more people, leaders should ask, “How can I be more efficient with AI?” Roles will evolve to focus on oversight, customization, and higher-value work.
Q: What’s the biggest mistake CS leaders make when trying to build a business case for tools?
Jan: Starting with the tool, not the business objective. Many leaders get caught up in product features or debate minute ROI details. Instead, begin by aligning the tool to a key business goal—whether that’s reducing churn, increasing NRR, or improving onboarding efficiency. Show where your current system falls short and how the tool helps close that gap. That’s how your request becomes a priority among competing internal asks.
