For the first episode of the Revenue Mavericks podcast, I sat down with Esther Friend, VP of Revenue Operations at Udemy. What stood out wasn’t just her global experience or her track record of driving complex GTM transformations–it was the through-line behind it all: intentional learning, adaptability, and a marathoner’s mindset.

1. The Experience That Changed Everything

Before Esther ever stepped into sales or RevOps, she lived abroad in Sevilla, Spain for a year and a half. Immersed in a culture with completely different rhythms, norms, and assumptions, she learned a lesson many leaders miss:

There’s never just one “right” way to operate.

That openness–to questioning existing processes, to challenging assumptions, and to seeing alternative paths–is a foundational RevOps skill. Her early international experience made her more adaptable, more curious, and more willing to ask why something is done a certain way.

2. The Inflection Point That Accelerated Her Career

Her career took a turn during what she thought was a simple networking breakfast. The COO of Angie's List saw something in her she didn’t fully see in herself: a highly technical business leader who could translate vision into systems, processes, and engineering roadmaps.

That conversation led to leading sales platform transformation, owning Sales Ops and PMO, and ultimately driving a major integration between Angie’s List and HomeAdvisor.

A reminder for all of us:

Career-defining opportunities often show up when we’re not “trying”–they show up when we simply show up.

3. The Secret Sauce: Empathy Meets Scale

Esther’s superpower is her empathy for frontline teams–because she’s been one of them. She’s run outbound motions, saved at-risk customers, and led sales teams. That experience anchors how she designs systems:

  • Talk to frontline sellers.
  • Understand their day-in-the-life.
  • Capture winning behaviors.
  • Automate and scale them.

One example: redesigning a contracting process so reps could draw a circle on a map to generate a quote–dramatically reducing time and improving customer experience.

This is design thinking applied to RevOps:

human input → repeatable workflow → scalable system.

Why This Matters for GTM Leaders

Esther embodies what today’s GTM orgs need:

  • Leaders who are students of the game
  • Operators who listen before architecting solutions
  • Builders who combine empathy with automation
  • Athletes who play the long game

If you want a masterclass in modern RevOps leadership, her episode is worth your time.

Listen to the Revenue Mavericks Podcast on Spotify.