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Pipedrive's VP of Sales on Former Life as Professional Footballer
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July 29, 2026
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3 mins

Pipedrive's VP of Sales on Former Life as Professional Footballer

Sean Evers played professional football for eight years before starting again as an estate agent. On episode five of Sales Rewritten, Pipedrive's VP of Sales explains how elite habits carried him to the top of a second career.

Pipedrive's VP of Sales on Former Life as Professional Footballer
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TL;DR

  • Sean Evers spent eight years as a professional footballer with Luton Town, Reading and Plymouth Argyle. On Sales Rewritten, Pipedrive's VP of Sales shares why only around 2% of players can retire after football, and how he started again in sales.
  • From estate agency to Pitney Bowes, Sage and Pipedrive, his rise was built on hard work, curiosity, a strong network and the resilience he learned on the pitch.
  • He explains why AI should take on low-value admin, not replace sellers, and why the best modern salespeople act as guides with a clear point of view.

Most of us dreamed of playing professional football. Sean Evers, Pipedrive VP of Sales, did it. Then, like almost every player, he had to work out what came next after retiring in his early 30s.

In episode five of Sales Rewritten, he tells host Alex Wood how he went from dressing rooms to deal rooms, and what it takes to start again.

Living the dream

Sean grew up in Hertfordshire with a ball at his feet. Scouts spotted him playing county football, and he joined Luton Town at 14. A youth contract followed, then a first-team debut in midfield.

He didn't stop to take it in. Until one match day interaction with a young fan in the car park.

"I remember this, like, it must have been, I don't know, maybe a child of seven or eight years old that came running up to me and said, 'Hey, can I have your autograph?' And I was like, 'Yeah, of course you can!' And I remember walking up thinking, 'I have made it.'"

A transfer to Reading came next, with a loan spell in the Scottish Premier League along the way, before a move to Plymouth Argyle. Eight years as a pro in total.

The 2% problem

Football pays well. Just not well enough for most players to stop working once they retire.

"There's only about 2% of professional footballers that ever make enough money to live the rest of their life off it. The kind of thing that was always in your mind is there's always kind of a window where your body won't allow you to play at a top level."

By his early 30s, Sean could see he had found his level. Over coffee, a friend suggested estate agency.

Within weeks he was a negotiator, under a manager he describes as the “Gordon Ramsay of estate agents”.

It was the ultimate crash course in sales. Sean learned to qualify buyers early, running 25 to 50 serious applicants while colleagues juggled hundreds. It worked, mostly. 

One Sunday, a man in flip-flops and shorts walked in, and Sean immediately passed him to a colleague. He assumed he wasn’t a serious buyer.

The man in flip-flops went on to buy a million-pound house.

Qualify too hard and you miss the flip-flop millionaire. Qualify too little and you waste your week. Get the balance right with our guide to why qualifying leads matters as much as closing them.

There's still time left

From there, Sean built a contact centre for Spicer Haart from scratch, learning from Barclays, Next and Carphone Warehouse. He joined Pitney Bowes, moved to the US to run North America for 18 months, then led sales at Sage and Funding Circle before joining Pipedrive.

The common thread? Hard work, curiosity and a big network to lean on when a new role feels out of your depth. And a resilience that started on the pitch.

"Because you're going to have good months, bad months, but you need to be able to bounce back. And you need to get off that call that's not gone so good and get on your next call and go, okay, I need this call to be better than that last call."

Let AI do the admin

Sean believes AI won't replace sellers - it will free them up. The winners will hand off note-taking and CRM updates, and spend more time with buyers.

He can now run a prompt across thousands of calls to see which competitor shows up most. And he sees data as the fuel for better outreach.

"There's also kind of personalization in terms of outreach and, you know, tools like [Surfe] are amazing for that because, you know, they're pulling in different data points and pulling in signals."

Want to reach buyers at exactly the right moment? See how signal-based prospecting gives you the right reason, at the right time.

Be the Sherpa

So what does a modern seller look like? Not a persuader, says Sean. A guide.

"And that's the way I see a salesperson is they're there to help guide. They're not there to persuade or influence... I actually just talk about like being a Sherpa, like how do you be a Sherpa that's going to guide someone up the mountain?"

The best guides also have a point of view. Share something a buyer hasn't thought of, and they'll remember you when they're ready, even if that's a year from now.

Hear the full conversation

There is plenty more in the episode, including what footballers earned in the late 90s, why Sean would never sell a product he didn't believe in, and the three questions he asks every member of his team.

About the guest

Sean Evers is VP of Sales at Pipedrive. A former professional footballer with Luton Town, Reading and Plymouth Argyle, he has since led sales teams at Pitney Bowes, Sage and Funding Circle. Find him on LinkedIn.

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