Wilmington-based product development firm CloudFruit is betting that a mix of AI-assisted workflows and old-school product fundamentals will set its new ERP platform apart in a crowded market. The bootstrapped company, founded in 2022 by CEO Sam Hilsman, has one hospital signed on as a design partner for its ERP Drift platform, with revenue from its services business funding the product work.
CloudFruit started as a custom software development and analytics shop and has evolved into a full product development firm handling design, build, marketing, and go-to-market strategy. Its analytics and integration work now focuses on ERP integrations for hospitals, health systems, and manufacturing clients.
Hilsman's path to founding the company included time as an ERP architect and a stint at Sean Penn's disaster-relief nonprofit CORE, where he helped develop a disaster response tool now sold as Relief Compass. COO Ana Yant joined in 2023 after working as a product owner and designer at Wilmington-based Synply.
Learning from early missteps
The pair's product experiments have not all worked. In 2023, they built HiiBo, an AI chat app created before OpenAI upgraded ChatGPT's memory recall system. Originally marketed to "AI beginners," the company scaled too soon and has since sunsetted the app.
"We've made every mistake you can make as a business," Hilsman said. "We started as a services-based business, then tried to pivot to product too early, overscaled, hired too many people, didn't hire properly, tried to build a consumer-facing app before we had the resources to do so… just every possible mistake."
Those failures shaped how the company now approaches client work. Hilsman said CloudFruit intentionally pushes back on customer requests early in the process.
"We challenge our customers a lot on what they need - do you really need this, what exactly do you need?" he said. "We intentionally create friction upfront so we don't deliver something no one uses or that doesn't work with their process."
Standing out in an AI-saturated market
Yant acknowledged that AI has lowered the barrier to entry for product development, making it harder for firms to differentiate. She said CloudFruit's advantage comes from combining AI tools with established product skills. For product development professionals, the distinction matters: knowing how to ship software people actually use, not just how to prompt a model.
"I think what sets us apart is that we already had the foundational skills of knowing how to build products, and on top of that we use AI," Yant said. "So, it's not just 'we have AI,' it's that we actually know how to design and ship something people will use."
That foundation includes hands-on user acceptance testing and training sessions for newly developed modules, work that goes beyond what clients typically expect from a product development firm. Those skills are also the focus of training resources like AI for Product Managers, which covers how to apply AI within existing product workflows rather than treating it as a replacement for core competencies.
CloudFruit has grown without outside capital, relying on services revenue to fund product experiments. Once ERP Drift signs on additional design partners, Yant said the company expects to hire more people and continue expanding. The company's broader approach to AI-enabled product work is covered in its AI for Product Development resources, which address similar integration challenges.
Why this matters for product development professionals
CloudFruit's trajectory offers a working example of how AI fits into product development without becoming the whole story. The company uses AI to speed up work, but its differentiator remains the fundamentals: user testing, client training, and pushing back on requests that don't solve real problems. For product teams, the takeaway is that AI tools are table stakes now - the firms that ship useful products are the ones that pair them with disciplined process and honest client conversations.
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