TL;DR:

Natalie Wolf, VP of Customer Success at People.ai, joins Kelly and Tiffany for a candid conversation about career growth, stepping into your power, operationalizing customer outcomes, and how AI is changing go-to-market for good. If you want tactical advice for thriving in today’s chaotic GTM world, this episode is a must-listen.

Full Description:

In this episode of The Revenue Insiders, we sit down with Natalie Wolf, VP of Customer Success at People.ai, to explore the future of customer success, AI, and go-to-market leadership. Natalie’s story is proof that career success isn’t handed to you—you have to step into your power and create it.

Natalie’s journey started in consulting, where she built an obsession with operational excellence and solving for pain. Later, she transitioned into customer success leadership, not by waiting for a promotion, but by spotting a gap at Anaplan and declaring a new path forward. She shares how stepping into an undefined role, without permission or playbook, helped her build a customer success function from scratch—and why today’s leaders must do the same if they want to stand out.

A few key themes we explore:

• Leadership isn’t about being the smartest person in the room—it’s about unlocking others’ superpowers.

• Revenue growth is a team sport—CS, sales, and support must drive shared outcomes, not siloed KPIs.

• AI is powerful only when tied to real, painful workflows—not hype.

• Career opportunities today are hidden inside messy, unstructured problems, not job postings.

Natalie drops an important truth: Too many leaders use AI as a shortcut instead of solving fundamental go-to-market problems. She shares how People.ai embeds AI into critical rituals—like customer health scoring and value reviews—to drive meaningful outcomes, not just automate busywork.

We also dive into Natalie’s personal process for evaluating career moves (hint: it’s way more thoughtful than most people’s). She breaks down why product-market fit, culture, executive alignment, and stage-appropriateness matter—and why a great brand name or big title should never be enough.

And it wouldn’t be a Revenue Insiders episode without a little humor:

• Kelly shares her firm policy of paying someone else to take her kids to Disneyland.

• Natalie proudly embraces her status as a Disney adult—with spreadsheets to prove it.

• Tiffany and Natalie bond over their shared obsession with planning (and purple leopard aerobics outfits).

If you’re a:

• GTM professional worried about staying relevant

• CS leader navigating this volatile economy

• Sales or CS practitioner trying to embed AI into real outcomes

• Rising leader wondering how to create your next opportunity

—this conversation will hit home.

Natalie leaves listeners with a powerful challenge:

🎧 Tune in to hear why simplicity wins, why declaring your leadership is non-negotiable, and how operationalizing outcomes—not just activities—can future-proof your career in 2025 and beyond.

“What’s the one shared customer outcome you could align your entire go-to-market team around today—and how would it change your revenue path?”