The RegScale Playbook: Landing Enterprise Customers as an Early-Stage Startup
Landing enterprise deals is challenging for any startup. But in a recent episode of Category Visionaries, RegScale co-founder Travis Howerton revealed how they secured major contracts with financial institutions and defense contractors while still building their initial product.
Their success came down to three key strategies:
- Find Visionaries Who Share Your Pain Instead of trying to sell to everyone, RegScale focused on finding what Travis calls “visionaries who are excited about the vision.” As he explains: “What we kind of found that both helped us and hurt us was finding other visionaries who are excited about the vision. Because when you’re an early stage product, you don’t do everything you want to do in the vision.”
- Lead with Deep Domain Expertise Travis’s two decades in the nuclear weapons program gave RegScale instant credibility. “You’re kind of looking for something that you’re passionate about, that you’re good at, and that you think you’ve got some competitive advantage,” he notes. This expertise helped them understand and articulate problems in a way that resonated with enterprise buyers.
- Start with the Highest Bar Rather than working up to enterprise requirements, RegScale started with the most demanding use cases first. “When you sell to the Department of Defense and they’re using it there, it’s kind of hard to say it’s not good enough for your bank,” Travis explains. This strategy established their enterprise-readiness from day one.
The combination of these approaches helped them land two significant early wins: a major financial institution and a large defense contractor. As Travis shares: “We were able to land two really big contracts early on, as well as some smaller ones. But those two sort of wells we landed, I think, got the attention of the investor community because you don’t tend to get contracts of that size at the maturity were and with organizations that have that much diligence in procurement.”
Their approach to building trust with large organizations had several key components:
First, they demonstrated deep understanding of enterprise pain points. “I’ve lived a lot of the same problems that they’re dealing with,” Travis notes, which helped establish credibility in early conversations.
Second, they offered a genuinely innovative solution. Travis explains: “We’re just doing some stuff that’s very forward leaning… we just have the benefit of building on a modern tech stack versus starting ten years ago where everything was harder and the tooling wasn’t quite there.”
Third, they focused on exceptional service. “Some of it’s just being young and hungry, so great customer service and really bending over backwards to make our customers happy,” Travis shares.
This combination of domain expertise, technical innovation, and customer focus has helped RegScale continue their enterprise momentum. They’ve exceeded growth targets and are now positioning for their Series B, with recognition in four Gartner hype cycles this year.
For B2B founders targeting enterprise customers, RegScale’s journey offers valuable lessons about the power of deep domain expertise and the importance of finding the right early adopters. As Travis puts it: “We found like minded people who were feeling the pain and felt like something should be done about this. They helped us get our start, and so forever grateful to those folks.”
The key is understanding that early enterprise deals aren’t just about your product – they’re about finding customers who share your vision for industry transformation and are willing to partner in making it happen.