Summer’s Enterprise Sales Playbook: How a Former Government Insider Built Trust with Financial Institutions

When most founders think about enterprise sales experience, they don’t picture government service. But for Summer founder Will Sealy, five years at the Consumer Financial Protection Bureau became the foundation for building relationships with major financial institutions like Intuit and Fidelity.

In a recent episode of Category Visionaries, Will revealed how his unique background shaped Summer’s approach to enterprise sales. The journey begins with a pivotal moment at the CFPB: “I was actually the first person at the agency that was looking into what the CFPB could do on a regulatory standpoint in student loans,” he explains. This position gave him unprecedented insight into both the problem and the institutions he’d later sell to.

Building Trust Through Domain Expertise

Will’s approach to enterprise sales starts with deep domain knowledge. Rather than rushing to market, he spent years studying the student loan crisis: “I spent the next few years writing reports to members of Congress, briefing other bodies of government on the issues at hand, and writing white papers on potential solutions.”

This expertise became crucial when approaching financial institutions. As Will notes, “When you start doing that, you’re obviously going B to B to C. And so inevitably you have to be very thoughtful about how to acclimate and adapt to the clients preferences or the channel partner’s preferences.”

The Power of Face-to-Face Meetings

Even in today’s digital world, Will emphasizes the importance of in-person connections for building trust. He shares a recent example of landing three competitive hires: “I took each one of them out to dinner and had a proper conversation with them about the business, why I’m passionate about it, where we’re heading.” For one candidate, he even “rerouted a trip back from California to New York and went to his hometown in Atlanta.”

This approach extends to enterprise sales. Will notes that while Summer is remote-first, “I never forget the value of an in person face to face and showing the other party whether that be someone you’re recruiting, a client you’re trying to win over, or investor of actually making the effort to show up face to face and just how powerful that can be.”

Creating Flexible Partnership Models

Summer’s success with financial institutions comes from their adaptable approach to partnerships. Will explains: “We work with a number of financial institutions – Intuit, Fidelity, and a host of others… there’s usually very bespoke models that work within their ecosystem.”

This flexibility extends to their revenue model: “We do all sorts of things such as either still charging the employer through with a revenue share to the channel partner, or in some cases we do allow for an actual employee to opt into our services as a fee for service.”

Building Product Credibility

The foundation of Summer’s enterprise sales strategy is their product. Will describes it as “almost a TurboTax like product to navigate borrowers through over 120 federal and state loan assistance programs.” This sophisticated technology, combined with their understanding of regulatory requirements, helps build credibility with financial institutions.

For founders selling to enterprises in regulated markets, Will’s journey offers a crucial lesson: sometimes the best sales advantage comes from deeply understanding the problem space and regulatory landscape before building the product. As he puts it, when “you’re solving something, moving it a hairline to the side for 350,000,000 people” in government, that experience can translate into building products that create meaningful change at scale in the private sector.

The key is leveraging that expertise to build trust while remaining flexible enough to adapt to each enterprise partner’s unique needs. It’s a playbook that’s helped Summer build relationships with some of the largest financial institutions in the country, proving that government experience can be a powerful asset in enterprise sales.