Matt Oppenheimer’s journey with Remitly feels like one of those classic American entrepreneurial tales, the kind where grit meets vision and turns a simple idea into a global powerhouse. For nearly 15 years, he steered the ship as co-founder and CEO, transforming a tiny startup from seed to sea. Now, at this pivotal moment, Oppenheimer is handing over the CEO reins to Sebastian Gunningham, a seasoned executive from Amazon’s marketplace and payments ranks, while he himself slips into the role of chairman. It’s a transition that’s all about intentionality, as Oppenheimer told GeekWire, echoing his lifelong drive for impact and purpose. Remitly, once a humble Techstars Seattle venture, has evolved into a remittance giant, empowering over 9 million users to send money across borders with the ease of an app—no more tedious forms or agent visits. The company’s Q4 revenue hit $442.2 million, a 26% year-over-year leap, and it boasts its first full year of profitability in 2025. But beneath the numbers lies a story of human connections, where families reunite through smart tech, and Oppenheimer’s leadership mantra—build with intention, lead authentically, prioritize customers over ego—keeps ringing true.
The seeds of Remitly were planted in a moment of real-world frustration. Oppenheimer, fresh from a stint in Kenya working for Barclays, witnessed firsthand the agony of families struggling to wire money overseas. The process was archaic, rife with hassles, and it lit a fire in him. Teaming up with co-founders Josh Hug and Shivaas Gulati, they embarked on a rollercoaster ride through a Techstars program, cranking out an MVP and navigating early missteps. Their initial concept, which leaned heavily on mobile wallets, met a reality check when customer feedback at a makeshift booth in Seattle’s Southcenter Mall painted a clearer picture. “We had to follow customers,” Oppenheimer recalls, embodying the humility of pivoting not once but dramatically, toward cash pickups, bank deposits, and even door-to-door delivery. It wasn’t just about building a product; it was about solving a raw, empathetic problem that touched lives every day. Along the way, they raised around $400 million, weathered the storms of funding rounds—each demanding that unyielding perseverance—and thrilled at their 2021 IPO valuing the company at nearly $7 billion. For Oppenheimer, the early days were a blur of logistics: securing licenses, leasing an office, even mundane tasks like emptying the trash, all to support Hug’s product smarts and Gulati’s engineering wizardry.
As Remitly scaled from a scrappy trio to a 3,000-person outfit, Oppenheimer’s playbook became a blueprint for success. He preached falling in love with the problem, not the product—a lesson carved from watching founders chase shiny ideas that flop because they ignore what customers truly need. Stubborn insistence on a failing concept, he warns, burns through time and resources. Instead, he advocates getting intimately close to users, drawing inspiration from Airbnb’s “non-scalable” marketing tactics. That booth at the mall wasn’t for flashy growth; it was a feedback goldmine, revealing why legacy systems appealed and where Remitly could shine differently. Culture, too, wasn’t a vague slogan but a living, breathing thing: behaviors like “be a compassionate partner” and “lead authentically” that get rewritten every couple of years to stay vibrant. Oppenheimer and his team doodled their culture on a whiteboard before launch, refining it through shared values that trickle into hiring and reviews. Customer centricity reigns supreme, a litmus test for every decision, ensuring that Remitly’s values aren’t just words but engines driving real-world impact.
Surrounding yourself with complementing talents is another cornerstone of Oppenheimer’s wisdom. He credits Hug and Gulati for bringing the product and tech prowess he lacked, stressing mutual respect for diverse skills while aligning on core values. Early on, his role was more enabler—handling the red tape and hands-on chores—so the real innovators could focus. Raising capital? Raise more than you think necessary, Oppenheimer advises, because ambitions always stretch timelines, and dilution’s worth it if it fuels progress. Fundraising is a dance, not a monologue; listen to investors’ questions, gauge their fit for your board, and show no desperation. He’s savored that tenacity, turning no’s into momentum, and now channels it into his own growth, treating leadership evolution like a product roadmap. From board-led performance reviews that gathered candid input to coaching sessions honing his blind spots, Oppenheimer built a deliberate system for self-improvement. Even in his new chairman seat, personal development remains a driving force, a testament to his belief that growing as a human outpaces any title.
Community ties make Remitly’s saga even more heartwarming. Seattle isn’t just a backdrop—it’s the pulse. Techstars provided the launchpad, and the region’s talent pool, drawn from giants like Amazon and Microsoft, infused the startup with expertise. In a city with fewer massive growth stories, Remitly beckons mission-driven folks seeking scale, attracting a workforce committed to global good. Their shiny new downtown headquarters symbolizes that commitment, a space where impact gets crafted daily. Oppenheimer’s dedication to the community goes beyond bricks and mortar; he wants Seattle to be Remitly’s home for decades more, fostering that ecosystem of innovation. It’s a reminder that entrepreneurship thrives on connections—mentors, peers, and a city that believes in bold dreams. As he passes the CEO torch, Oppenheimer carries this ethos forward, ensuring Remitly’s culture of authenticity and customer love endures.
Reflecting on 15 years, Oppenheimer’s transition isn’t an endpoint but a fresh chapter infused with joy and purpose. Stepping into chairmanship, he feels a profound sense of fulfillment, echoing his intentional approach to building something meaningful. From Kenya’s money-transfer woes to millions of users globally liberated by seamless tech, his story underscores that real leadership is about adaptability—flexing solutions while staying rooted in the core problem. Advice to budding entrepreneurs? Persevere, but direct that energy wisely; build teams that balance strengths; fund generously for the long haul; and never stop evolving yourself. In a world where tech can empower the underserved, Remitly stands as Oppenheimer’s legacy, a beacon of human-centric innovation. As he mentors from afar and chases his own growth, one can’t help but feel inspired—entrepreneurship as a lifelong odyssey, driven by empathy, community, and an unwavering focus on making the world a little more connected. Seattle’s skyline might change, but Oppenheimer’s footprint, etched in compassion and resolve, promises to influence Remitly for generations. His shift isn’t just a handover; it’s a celebration of how one man’s vision, backed by grit and goodwill, rewrites the rules of remittance—and perhaps, of business itself. In an era of rapid shifts, Oppenheimer reminds us that true success blooms when we lead with heart, pivot with humility, and build bridges between dreams and realities.
