For this episode, we tried something a little different. Instead of interviewing a leader in philanthropy, Maya turned the mic around and had a true back and forth with her close friend Alex Hanley, CEO and co-founder of WinWon, on what it actually takes to build an early stage company in a sector technology has largely passed over.
Welcome to Inside Impact, Temelio's monthly video interview series featuring honest, unfiltered conversations about what's working, what isn't, and where philanthropy and the sectors around it are headed. No sales pitches, no jargon, just real conversations with people doing the work. Most months, that means a leader from the philanthropic space. This month, it means a fellow founder who has run into the same problem from a different industry: sports operations, like philanthropy, has never had the tools built for it that other sectors take for granted, and building for an overlooked sector raises a lot of the same questions no matter what that sector is.
WinWon, where Alex is CEO and co-founder, streamlines operations for sports organizations, from college athletic departments to professional and youth sports programs. It helps coaches, administrators, and athletic directors manage athletes at every stage of their journey, from scheduling and recruiting to academic eligibility tracking.
Two different sectors, the same founding story: technology that arrived too late.
Before building WinWon, Alex and her co-founder Sarah went on the road, visiting athletic departments across California, Seattle, Iowa, and Alaska to watch firsthand how coaches and administrators were actually working. What they found, again and again, was people managing complex, high stakes processes on legacy systems or plain pen and paper, including manually reviewing academic transcripts for hundreds of athletes each semester just to confirm eligibility.
"People were not complaining... but seeing that academic eligibility piece by hand being done by people who cared so much, really stayed with me."
Maya's own aha moment came from a completely different industry.
Before Temelio, Maya was chief of staff at a software company that automated tax credit discovery for small businesses, often uncovering tens of thousands of dollars those businesses didn't know they were owed. Watching that transformation made her realize the same infrastructure gap existed in philanthropy, just with no one building for it yet.
"If we can do this for the for-profit sector, we should be able to do this for the sector that's trying to make the world a better place."
Neither company started building until they had real validation.
Both founders described leaning hard on future users before developing a product. Maya and her team built a 50-person advisory board split between grantmakers and grant recipients to sanity-check every early product decision. Alex and Sarah talked to coaches, athletic directors, compliance staff, and student athletes alike, and have since launched a new partner advisory board of current customers.
"If the industry you're trying to serve isn't telling you that you're building the right thing, you're probably not building the right thing."
Fear doesn't disappear. You just decide the problem is worth it.
Both founders pushed back on the idea that starting a company requires fearlessness. For Alex, building for a sector she believed in made the decision feel less risky than it looked from the outside. For Maya, building in a space technology had largely ignored gave her a conviction that outweighed the fear.
"It's so rich in experience, and in how you're spending your time on this planet, making an impact and making a difference. That, for me, it's been very risk adjusted in that way."
On being women founders: empathy and deep listening as a real advantage.
The conversation turned to the gap in venture funding for women founders, and what each of them has seen firsthand about how it shapes the way they lead. Both pointed to empathy and listening, traits they associate with how they were raised as women, as core to how they build product and teams. Maya built the connection between empathy and leadership directly into Temelio's earliest engineering interviews, and Alex described a similar instinct at WinWon, looking for the same quality in the people they hire.
"Empathy is about understanding people's pain and motivation, and then being able to build something that solves that."
The moment each of them knew it was working.
Alex pointed to a partner campus that started using WinWon's unified calendar, originally built to consolidate scheduling and compliance tracking, to boost game day attendance across teams, something the platform wasn't explicitly built to solve. Maya's example came from Find Your Light Foundation, a small arts funder that saw applications triple after federal arts funding cuts. Because Temelio automates much of the work behind multi-year grants, the foundation shifted a third of its grants from one year to three, giving nonprofits more stability without adding staff.
"That's when you know something's taking root, when people are using the product for what it's meant to do, but then also taking it one step further."
Inside Impact is a monthly video series by Temelio featuring candid conversations with leaders across foundations, corporate giving, and philanthropy tech. New episodes every month at trytemelio.com.
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