Founding-team VP Product at Paper: buyer discovery, logo and product UI, +25% session starts, Paper Review from chat demand.

Join the founding team

Philip Cutler and Roberto Cipriani, GradeSlam's founders, brought me onto the founding team with a specific shift in mind. They had a classical tutoring marketplace, pay-as-you-go and pay-as-you-use. Students could get help when a tutor happened to be online. They wanted a platform that could offer tutoring around the clock, across every subject, without a student landing in an empty queue.

The hard part was supply. We built an algorithm to predict demand across topics, time of day, and season. It scheduled tutors before the rush and held backup capacity in a tolerance band so sessions almost always had someone ready. Early forecasts were rough. As usage data piled up, the model learned the patterns and accuracy tightened toward 90% on surges and dips.

We worked from talent. Instead of hiring generalists and spreading them thin, we built departments around strong leads in product, engineering, operations, and tutor quality. I designed the logo and multiple generations of the product UI while the company grew from an accelerator office toward fifty people.

Behind the live sessions we built what schools would eventually need: session analysis before LLMs existed, tutor reports summarized for teachers, dashboards that showed which students struggled with which concepts. We scored roadmap ideas by impact and complexity and turned raw user feedback into prioritized product work.

Later we worked with a research team connected to Yoshua Bengio, a pioneer in artificial intelligence, on algorithms that surfaced knowledge gaps and fed them back to teachers. That product story, in decks and investor meetings, helped close the $2M seed round alongside the CEO and CTO.

Test who pays

Early go-to-market was experimental. We tested students, then parents, then schools, then districts.

Students loved the idea of on-demand tutoring, but even when we priced it as cheap as a pizza, they were not the ones paying. Parents had the cards, but too many had unanswered questions about how to judge educational choices. Teachers were different. They understood the value immediately: less time grading, richer feedback on the homework they assigned, faster turnaround, and a clear view of the gaps each student had so they could personalize what came next.

In parallel we narrowed the product. GradeSlam had started as 24/7 tutoring across elementary through higher education, all subjects. The SaaS we sold to schools was focused and structured around what teachers and administrators could buy and renew.

Once the school motion worked, deals grew from single campuses to full districts. We learned who signed the check before we polished the logo, fixed the session start flow, or built Paper Review.

Design a logo students and teachers both trust

GradeSlam needed a logo that worked for students, teachers, and investors. EdTech identities often skew too childish or too corporate. We landed on an icon that merged a student and a tutor into one symbol: playful and colorful enough for younger students, restrained enough that older students would not feel talked down to.

We sketched concepts, explored alternate directions, and refined the approved logo for screen-first use on app icons, marketing, and tutor-facing surfaces. Directions that did not read at small sizes dropped out. Contrast tightened for product chrome. The same period saw multiple generations of the product UI ship alongside the logo, before the company later rebranded to Paper.

Logo exploration

Concept sketches through alternate directions to the approved logo, before the Paper rebrand.

Fix the session start flow

While scaling, I reviewed the session start flow. Something felt off.

Students landed on a plain white screen with a box prompting them to select a topic. Students hesitated.

I overlaid that same topic selector on top of the actual chat interface. Just a peek. A preview of what was underneath.

They saw what came next, and it clicked. Session starts went up by about 25%. Students called it obvious in hindsight.

Paper Review became the product

As usage grew, a pattern kept showing up in chat: "Can someone help me review my paper?"

Tutors were already doing it manually. We built a dedicated Paper Review flow so students could submit work, get structured feedback, and teachers could track it transparently. Teachers logged in, saw all their students at a glance, spotted who was struggling, and read tutor notes alongside session insights. It saved them 30%+ of their time while keeping the human connection.

The product had started with live tutoring sessions. Paper Review became the core value, and the company rebranded from GradeSlam to Paper.

What stayed with me: test who signs the check before you polish the product. Small UX moves compound when users can see what comes next. The best features often start as something users already hack together in chat.