What does it really take to evolve from first-time founder to public company CEO without losing conviction, culture, or clarity?
In this episode of From Start-Up to Grown-Up, Alisa Cohn sits down with Matt Oppenheimer, Co-Founder and CEO of Remitly, the global financial services company serving customers in more than 170 countries.
Matt shares the leadership evolution behind building Remitly from an early-stage startup into a publicly traded company. From spotting the broken experience of international money transfers while living in Kenya, to navigating executive transitions, IPO readiness, board dynamics, and imposter syndrome, Matt reflects on the real work of founder to CEO leadership growth.
This conversation explores how conviction differs from stubbornness, why great founders fall in love with the problem rather than the solution, and how culture must evolve alongside strategy. If you are building, scaling, or leading a growth-stage company, this episode offers a practical and deeply human roadmap.
You’ll learn:
Why founders must apply grit to the problem, not the solution
How to balance curiosity with decisiveness as a leader
The difference between startup execution and public company leadership
How to design culture intentionally and evolve it over time
Why executive transitions are about stage-fit, not loyalty
What IPO readiness really requires behind the scenes
How to manage imposter syndrome and board pressure
Why psychological safety with investors matters
How “towering strengths” create leadership shadows
What it means to grow into the CEO your company needs
We talk about:
00:00 The origin of Remitly and identifying a global problem
03:00 Grit, flexibility, and falling in love with the problem
06:00 Growth mindset, curiosity, and listening to feedback
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