Intro

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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