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From OK grades to Dartmouth Hall of Fame: Remitly’s Matt Oppenheimer on his ‘strengths and shadows’
Nearly 25 years after enrolling at Dartmouth College to study psychology and embarking on a path that led him to co-found Seattle fintech giant Remitly, Matt Oppenheimer has been inducted into the Ivy League school’s Entrepreneur Hall of Fame.
The honor, presented Thursday night in San Francisco as part of Dartmouth’s annual Entrepreneurs Forum, comes seven months after Oppenheimer stepped down as Remitly’s long-time CEO to become chairman of the board.
Created by the Magnuson Center for Entrepreneurship, the Hall of Fame honors Dartmouth alumni who have made lasting positive impacts through their ventures. Oppenheimer joins a select group of honorees with Northwest ties — including Smartsheet co-founders Brent Frei and Mark Mader — and used his acceptance remarks to express deep gratitude to the admissions officers who took a chance on a kid from Boise, Idaho, with “OK grades” and “below average SAT scores.”
Speaking with GeekWire ahead of the event, Oppenheimer recalled how his early college years studying social psychology helped shape his understanding of business.
“I think a lot of business and entrepreneurship does come down to interpersonal dynamics,” Oppenheimer said. “I am a people person. But how do you find what I call career-market fit when it comes to really understanding and connecting with people? That’s ultimately my strength, but it was really hard to define earlier in my career.”
After graduating from Dartmouth in 2005, Oppenheimer earned an MBA from Harvard Business School and worked in Kenya for Barclays Bank, where seeing families hit with steep fees on cross-border money transfers inspired him to start Remitly in 2011.
He served as CEO for nearly 15 years, guiding the company through its 2021 NASDAQ IPO and building it into a fintech powerhouse serving over 9 million customers across more than 170 countries before transitioning to chairman in February.
In his acceptance speech on Thursday, Oppenheimer focused on a central philosophy he calls leading authentically through “towering strengths and shadows.”
“Each of us has a few towering strengths — things we are in the top 10% of the world at doing. Not good at. Towering,” he said. “And almost always, that tower casts a shadow. The same trait that makes you exceptional at one thing quietly makes you a liability at another. They aren’t two traits. They’re one trait, seen from two sides.”
He pointed to his own extreme tenacity as an example, noting how it helped him build Remitly through years of investor rejections and early product stumbles, but how it also had a darker side.
“That same tenacity can lock onto things that are unhealthy, or unchangeable, or both,” Oppenheimer shared, candidly discussing his personal experiences with OCD-related anxiety and depression. “This isn’t a character flaw sitting next to my strengths. It is the shadow of my greatest strength, from the same place. Which means it’s something to work with … harness the tower, manage the shadow … rather than something to be ashamed of.”
Seven months into his transition from operational CEO to board chairman, Oppenheimer says the shift has felt surprisingly comfortable. Free from managing daily execution, he now channels that same intensity into coaching current leaders and serving on corporate boards.
“I have so much trust in Sebastian [Gunningham], our CEO, and it’s super exciting to support him in a chair capacity,” Oppenheimer told GeekWire. “I get to share reflections on the journey, mentor, and coach. I didn’t know that would be the case, because you hear so many examples of founder-CEOs who transition and have a really hard time with it.”
That mentorship extends to Seattle’s broader startup community, where Oppenheimer is an active member of Foundations, a collective of local tech founders and AI leaders. When advising early stage entrepreneurs, he urges them to remain hyper-focused on solving a single, deep customer problem rather than spreading themselves thin.
And while AI has vastly accelerated product development, Oppenheimer notes that the core fundamentals of building a business haven’t changed.
“With fintech, you still have to build the trust, get the licensing, and build out the compliance infrastructure and banking relationships,” he said. “The actual building and deployment of product got a lot faster, but if you don’t have great judgment, you can go down the wrong path pretty quickly.”
Looking back 25 years later, Oppenheimer noted that the Dartmouth admissions officers who took a chance on him didn’t look past his test scores by accident — they told him years later that they were drawn to his personal qualities and humanity.
“Two strangers in an office in Hanover found my tower before I had any idea what it was, and then they handed me the place to build on it,” Oppenheimer said in his closing remarks. “That isn’t a debt. It’s a privilege. And the only sensible thing to do with a privilege is use it well.”
