From Receipts to Rewards: What Scaling Loyalty Really Looks Like in Practice

In a packed room at Startup Boston Week, founders, students, operators, and ecosystem leaders gathered for a conversation that went far beyond loyalty points and receipts.

Moderated by Suffolk’s Center for Entrepreneurship Director Chaim Letwin, the fireside chat featured Wes Schroll, the founder and CEO of Fetch Rewards. What unfolded was a candid, tactical look at what it actually takes to identify a durable pain point, survive years without product-market fit, scale a consumer platform, and rebuild an organization for an AI-first future.

The full event video is embedded below if you’d like to watch the conversation start-to-finish, or keep reading for an overview.

Finding the Pain (and Sitting With It)

Schroll traced the origin of Fetch back to a frustration many in the room recognized instantly: loyalty programs that promised value but rarely delivered anything meaningful.

As a college student shopping for himself for the first time, Schroll found himself juggling grocery store rewards, airline miles, and restaurant punch cards…none of which added up to much on their own. “If you could combine them,” he explained, “you’d have something meaningful. On their own, they never got there.”

That insight didn’t immediately become a company. Instead, it became a question, one Schroll would spend years pressure-testing. He immersed himself in the grocery and restaurant industries, talked to operators and brands, and eventually turned the idea into a business plan. Notably, Fetch launched without code, customers, or revenue, just a PowerPoint deck and a written plan.

To fund the earliest version of the company, Schroll did something few founders think to do: he entered business plan competitions at universities across the country, often through friends enrolled at those schools. In just 45 days, Fetch raised roughly $180,000; enough for Schroll to drop out and commit full-time.

The Long Road to Product-Market Fit

What followed was not a straight line.

Fetch spent nearly four years iterating before landing on the version of the product users know today. During that time, Schroll openly questioned whether the company or his leadership would survive. “I don’t trust founders who don’t question it,” he said. “If you’re not wondering whether this is going to work, that’s a red flag.”

The turning point came in 2017, after Fetch launched its receipt-scanning app. A sudden surge of users overwhelmed the system, breaking receipt processing for weeks. What surprised the team wasn’t the failure, it was that users kept submitting receipts anyway.

“That’s when we knew,” Schroll said. “The product was broken, and people still used it.”

That moment…users choosing to stick with a flawed product because it solved a real problem…became Fetch’s clearest signal of product-market fit.

Building (and Rebuilding) Teams at Scale

As Fetch grew from a handful of scrappy generalists into a company with thousands of employees over its lifetime, Schroll emphasized that team composition had to evolve just as fast as the product.

Early on, Fetch hired anyone willing to jump in, engineers found through campus flyers or even casual conversations at gas stations. Later stages required specialized leaders with deeper functional expertise. The hardest lesson, Schroll noted, was learning when someone who helped get the company to one stage couldn’t take it to the next.

“I used to take it personally when people left,” he admitted. “Now I understand that timing matters. Not everyone is meant for every phase.”

To maintain culture at scale, Fetch leans heavily on repetition and transparency. Schroll personally welcomes every new hire each week, shares company context monthly, and prioritizes information flow across leadership levels to avoid silos. “Context is the CEO’s job,” he said. “If people don’t understand why you’re doing something, they’ll pull in different directions.”

Fundraising as a Tool, not a Trophy

Fetch raised roughly $8M before launch and another $500M between 2017 and 2022. But Schroll pushed back hard on the idea that fundraising itself is a milestone.

“Raising money is dilution,” he said bluntly. “It’s not the outcome. It’s a tool.”

For Fetch, that capital was necessary to reach the scale where the business could sustain itself—particularly as a marketing-driven platform that rewards users directly. Today, with profitability in sight, Schroll expressed relief at no longer needing to fundraise simply to keep growing.

Rebuilding Fetch for an AI-First Era

One of the most striking sections of the conversation focused on how Fetch has restructured itself around AI.

Rather than incremental adoption, Fetch made a radical move: the company shut down for a full week. Employees broke into teams, learned directly from frontier model providers, and rebuilt workflows using AI tools. The result? Marketing teams shipping code, faster iteration cycles and a company that now operates with roughly 20% fewer employees while growing faster than before.

Schroll was clear that this transition wasn’t optional. “To be world-class talent now, you have to be fluent with AI,” he said. Fetch now dedicates weekly time for employees to stay current as tools evolve.

Importantly, Schroll challenged common assumptions about data risk. Fetch deliberately avoids collecting highly sensitive personal data and focuses instead on maintaining trust through value creation. “The relationship with the consumer is the asset,” he said. “If users stop opening the app, the data doesn’t matter.”

What Founders in the Room Took Home

Throughout the audience Q&A, Schroll returned to a few consistent themes: talk to users directly, don’t outsource early learning, and don’t confuse activity with progress. When asked how Fetch initially acquired users, his answer was unglamorous: standing outside stores, onboarding people one by one, and explaining the value face-to-face.

“There’s no shortcut,” he said. “You have to intercept people where they already are.”

For founders navigating today’s landscape, where AI lowers barriers but accelerates competition, the message was both sobering and energizing. This may be the hardest time to build a company. It may also be the best.

The full event video is embedded above (or you can watch it directly on YouTube) to catch the complete Q&A and founder stories shared from the stage.