Would you regret leaving before a massive exit?
Jason Oakley walked away from a stable job, great coworkers - and life-changing stock options. Here’s why he still says he’d do it again.
Hey 👋 I’m Andrew - and welcome to the Delivering Value Substack, where I write about the stuff growth leaders don’t always talk about: lessons from the trenches, honest convos with other leaders, and what I’m learning as I build my business solo.
This post is part of my Candid Convos series, where I chat with SaaS leaders to unpack the toughest moments in their careers - and explore how they navigated ‘em.
Jason Oakley was out to dinner with his closest friends when they finally gathered the courage to bring up a touchy subject.
"Hey man, are you okay?"
A few years ago, Jason made a huge change.
He left a job that he loved. That was paying him extremely well. At a company he liked, with great co-workers - to work at a friend’s startup.
It was a move he felt great about, at the time.
There was less pay, and way more risk. But a massive opportunity to learn and have an impact. That's what motivated him.
But a few years later, Verafin (his former employer) announced a massive 2 billion dollar acquisition. It became a life-changing event for many of his former co-workers.
Jason had some options, but missed the big payday.
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Jason started a campus publication in college - called Recess.
It was inspired by free flyers, full of games and crossword puzzles, you’d see in coffee-shops - but for students.
He wanted to make something fun students could enjoy between classes. It was a printout filled with puzzles, horoscopes, and games. It was his first experience running a business - and it won him a couple of scholarships! He used that scholarship money to see if he could scale Recess into a franchise business. Something that could exist at many universities across the country.
That fizzled out and Jason found himself looking for a new opportunity.
Eventually he landed an entry level AE role at Verafin - one of the main SaaS companies in Newfoundland. When he joined, it wasn’t just another job. It was the job that everyone in-town wanted.
The company was growing fast, the product was excellent, and he had a clear path forward.
Jason had been at Verafin for a little over three years, when the big opportunity came.
He had transitioned from sales into marketing, and steadily grown his scope and visibility inside the company.
So when leadership decided to open another office in Toronto, they tapped Jason to help lead it. That was a big deal. A chance to help expand the company beyond Newfoundland. A visible vote of confidence from senior leadership. For Jason, it felt like a sign he was leveling up.
But this wasn’t just a professional opportunity. Jason had grown up in St. John’s his entire life. Moving to Toronto (several hours away) was a big personal change too.
He scouted out apartments.
Signed a lease.
Packed-up his life.
…and moved to Toronto.
Then the same day he signed his lease, he found out that Verafin tried to cancel theirs.
“The day that I'd signed my lease, I got this, I think an email or I went into this temporary office that we had and they were like, yeah, they're trying to back out of the lease.”
The office existed, but barely.
A beautiful downtown space built for 50 people, never held more than six. He kept showing up. But it became obvious: the Toronto expansion wasn’t happening.
Everyone he worked with was back in St. John’s.
He had uprooted his life for this adventure. And the career changing opportunity he’d signed up for no longer existed. He could have moved back. But he didn’t want to.
Instead, he stuck it out in Toronto for a while, even after it was clear the office wouldn’t grow.
He liked the work, liked the company, and part of him hoped things might shift. But slowly, it became obvious: the opportunities were back in St. John’s. Leadership, mentorship, growth, they were all rooted at HQ. And Jason wasn’t moving back.
So when a friend invited him to join their early-stage startup, he said yes.
It meant walking away from a great salary and real stability. It meant way more risk, way less money, and almost no safety net. But it also meant momentum. Autonomy. A new kind of challenge.
He was about to lose the financial cushion he’d worked hard to build.
But he made the leap and left Verafin in 2015.
Then in 2021, Verafin was acquired by Nasdaq for $2.75 billion.
“That was a massive acquisition, life-changing amount of money for a lot of people that were in that company.”
Not long after the acquisition was announced, Jason was out to dinner with some friends, when someone cautiously asked: “How are you doing?”
Their tone said what they didn’t: we’d be devastated.
Jason smiled. "I never regretted it. Not for a second."
When he made the leap, Jason wasn’t chasing a big idea or some dream of entrepreneurship. He didn’t count his options or wonder how long he needed to stay to maximize a potential payout. He just knew he wasn’t learning anymore.
"If I look back, I would've told myself to do it sooner" he shared.
The startup he joined didn’t work out. But it was an amazing stepping stone for his product marketing career. He gave him the opportunity to lead teams at companies like Uberflip, Chili Piper, and Klue.
Then he took another leap: going out on his own.
Today he runs Productive PMM and Demo Dash. He writes, coaches, consults. And he’s built a reputation that wasn’t possible if he’d stayed comfortable.
Jason knows what it feels like to stare down an opportunity that makes no logical sense and say yes anyway. He knows the fear of leaving something great, and the quiet confidence that comes from betting on yourself - and making it work.
When asked what advice he’d give to others considering a move, he doesn’t flinch:
"Don’t plan your career around a maybe. Plan around what you’re going to learn."
Catch Jason’s entire story on YouTube
Listen on Spotify
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