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How I Became a Senior Sales Leader Before the Age of 30
Podcast
June 10, 2026
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3 mins

How I Became a Senior Sales Leader Before the Age of 30

Brett Runyan was promoted to a senior sales leadership role before the age of 30. On episode two of Sales Rewritten, the EZRA Coaching VP explains what that rapid rise cost him and how he redefined success.

How I Became a Senior Sales Leader Before the Age of 30
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TL;DR

  • Brett Runyan joined Groupon as employee number 200, was part of its IPO at 24 and was leading international sales teams before he turned 30. On Sales Rewritten, he looks back on that rapid rise and what it cost him.
  • A run of layoffs, an acquisition and a difficult VP role led to burnout, after years of tying his self-worth to job titles and promotions. His advice is to find fulfilment in your work without letting it become everything, and for leaders to set healthy boundaries by example.
  • Brett also shares hard-won sales lessons, including why you should multi-thread every deal instead of relying on one contact, and how to write emails that are short, personal and sound like you.

When people ask Brett Runyan what he does for a living, he often says he works in tech and leaves it at that. But this undersells a career that took off fast: employee number 200 at Groupon, part of an IPO at 24, leading international sales teams before 30.

But in episode two of Sales Rewritten, the VP of North American Sales at EZRA Coaching tells host Alex Wood that his rapid rise came at a price.

Right place, right time

Brett's first job out of college was selling printed merch. It wasn't working. In the corner of the same office, a team of 20 or 30 people were having far more fun on the phones. They were working for early-stage Groupon.

He quit the next week, applied, and four weeks later was working as an account executive at the company.

"Every day was different and I was working with my friends and at the time it felt like we were doing meaningful work."

He was part of the IPO at 24 and leading a team of people his own age soon after. Later, at Glassdoor, he helped grow the Chicago office from 20 people to 300 in two years, then moved to Dublin to do the same in Europe. He had turned down an earlier chance to move to Ireland because the timing wasn't right. Waiting paid off.

The cost of the climb

Then came a run of tough breaks. Brett left Glassdoor in 2020 as the European team was cut from around 120 people to 20 or 30. He had been involved in 119 interview processes there.

A VP role at Lessonly followed, but on his first day the company signed to be acquired by Seismic. He went back to Glassdoor to lead go-to-market, only for another round of layoffs. Then came a VP of global sales role he calls a nightmare.

The stress took a physical and mental toll. It also changed how he saw himself.

"I started questioning my own capabilities... Should you be in tech? Should you be in leadership? Was everything that got you to this place just kind of luck? Like was it right time, right place?”

His husband, John, stepped in. Brett left with nothing lined up and took time to reset.

You are not your job title

Brett's message to sellers chasing the next promotion is simple. Enjoy your work, but don't let it become everything.

"It is okay and a good thing for you to feel fulfilled by the work that you're doing on a day to day basis. Where it gets dangerous is when it is the majority of your fulfillment, where you are so wrapped up in what you do every single day."

As a leader, he sets boundaries by example. Work done on a Sunday goes out on scheduled send for Monday.

Who's in the room?

At Glassdoor, Brett's team ran a hugely successful proof of concept with Revolut. Then their one contact put the renewal on hold - nobody else in the business knew it was happening.

They rescued it by sharing candid employee reviews about the leadership team. Within days, everyone was in a room in London, and the deal renewed.

Years later at EZRA, the lesson came back. A Hilton RFP showed every buying signal, but they lost to the incumbent provider.

"The first question my chief sales officer asked was, who is in the room? Who was making this decision? Who were you selling to?"

His advice is to multi-thread, and get every stakeholder you can in front of you.

Signals tell you when to act, but you need the whole buying group too. Our guides to signal-based prospecting and data enrichment cover both.

Write like you talk

Brett sees email as the core of his job.

"When people, younger people ask me what I do, I say I'm a professional emailer. That's my job, I try to emulate how I talk in person."

His emails are short, mention something from the last conversation, and end with a simple ask for 15 minutes. He also treats research as part of the role, and would pay for a prospecting tool himself if his company wouldn't.

Better research starts with better data. Here's what sales intelligence is and how revenue teams use it.

Hear the full conversation

There is plenty more in the episode, including what Brett learned selling in Europe as an American, the art of the boomerang, and why video is his top tip for building a personal brand.

About the guest

Brett Runyan is VP of North American Sales at EZRA Coaching. He has led sales teams at Groupon, Glassdoor and Lessonly, and holds an MBA from Trinity College Dublin. Find him on LinkedIn.

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