Will Geiger

The insider who defected to the applicants

Will Geiger has read your college essay. Or 10,000 just like it. For years he sat where the verdicts get handed down - Senior Assistant Director of Admissions at Kenyon College, the person who decided which applicants got in and, just as importantly, who got the scholarship money. He directed the school's merit scholarship program and sat on the financial aid appeals committee, the quiet room where families plead their case for a few thousand dollars that change everything.

Today he runs Scholarships360, the cofounder and CEO of a free platform that does the opposite of what his old job did. Instead of guarding the gate, it hands students a map. Find scholarships. Vet them. Win them. Pay for college without drowning in debt. The whole thing is built on a simple, slightly subversive idea: the person who used to score the applications now works for the people filling them out.

It started where a lot of good companies start - with a problem the founders lived. Will is a first-generation college student. So is his brother Brian. When the two of them went looking for legitimate scholarships, what they found instead were dead websites stuffed with expired opportunities and advertisements, the digital equivalent of a bulletin board nobody had updated since 2004. The scholarships you needed were buried under the ones that no longer existed.

In 2010, the brothers decided to fix it. Brian brought the operator's toolkit - investment banking at Barclays, growth and operations at Toptal, a public policy degree from Princeton. Will brought something rarer: a decade of knowing exactly how the money actually moves. He had recruited students across the country, read the essays, run the merit program, heard the appeals. He knew which scholarships were real, which were traps, and how a teenager could actually win one.

From the admissions desk to the dinner table

Before Scholarships360 became a startup with a seed round, Will did a tour of duty that most edtech founders never get. After Kenyon, he crossed to the other side of the desk entirely - Associate Director of College Counseling at Hopkins School in New Haven, the third-oldest independent school in the country. There he counseled more than 100 students through the admissions and financial aid gauntlet, one nervous family at a time. He had now seen the process from every angle: as a first-gen applicant, as the gatekeeper, and as the guide.

That triple vision is the whole pitch. Most scholarship sites are built by marketers. Scholarships360 is built by someone who spent years reading the actual applications and signing off on the actual checks. The platform vets scholarships so students don't get scammed, replaces the graveyard of expired listings with live opportunities, and offers what Will describes as a personal advisor - the kind of guidance that, in his old world, only the most resourced families could buy.

Somewhere along the way he picked up a master's in education from the University of Pennsylvania, layered on top of the bachelor's in history he earned at Wake Forest. A history major running a data-driven scholarship platform is a nice tell: he is fundamentally interested in how systems shape who gets ahead, and in rewriting the ones that don't.

The $250K bet

In October 2021, Scholarships360 raised a $250,000 seed round and launched a data-driven version of the platform, one that lets a student build a personalized plan for finding funding that actually pencils out. The promise is not just more scholarships. It is the right scholarships, matched to the student, vetted for legitimacy, free to use. In a category crowded with sites that exist mainly to sell ads against desperate searches, that positioning is the product.

Will also hosts the company's Office Hours podcast, where he interviews the people who run the system he used to be part of - VPs of enrollment, edtech founders, directors of college counseling. It is the same instinct that built the company: pull back the curtain, let students see how the machine works, and hand them the lever. In one episode, he and Brian sit down to tell their own origin story and dispense the kind of advice the two of them never had access to when they were the ones filling out the forms.

The mission statement is unglamorous and exactly right: make finding and funding education simpler, faster, and more accessible for all Americans. Coming from most founders that would be a slide in a deck. Coming from a man who has personally read 10,000 essays, run a merit program, and sat on a financial aid appeals committee, it reads less like marketing and more like a confession - and a correction.