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
10:00 Global perspective and customer centricity
14:00 Designing culture from day one
18:00 Evolving values as strategy evolves
23:00 Hiring executives for stage, not sentiment
28:00 Managing leadership transitions thoughtfully
33:00 Founder development plans and 360 reviews
36:00 Moving from “doing” to leading at scale
42:00 IPO preparation and avoiding IPO as the sole goal
46:00 Becoming a public company CEO
49:00 Imposter syndrome and board dynamics
53:00 Advice for founders scaling their leadership

Follow Matt on

LinkedIn: https://www.linkedin.com/in/mattoppenheimer/
Website: https://www.remitly.com/

Connect with Alisa!

Follow Alisa Cohn on

Instagram: @alisacohn
Twitter: @alisacohn
Facebook: facebook.com/alisa.cohn
LinkedIn: https://www.linkedin.com/in/alisacohn/
Website: http://www.alisacohn.com

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#113 – Matt Oppenheimer, from Founder to Public Company CEO of Remitly: Why Falling in Love with the Problem Builds Enduring Companies

From Start-Up to Grown-Up