As the founder and CEO of CloudFruit, a Wilmington-headquartered product development consultancy and software development firm for growing businesses, Sam Hilsman is keenly aware of the struggles of pushing a startup along the racetrack. 

Today, CloudFruit operates as a growing, bootstrapped software service firm, showing positive momentum from multiple shipped products and promise for its enterprise resource planning (ERP) platform, ERP Drift, which has one hospital signing on as a design partner, Hilsman said. Some of the company’s top clients include Walmart, Novant Health, Alaska Native Tribal Health Consortium and Infor. 

The firm is run as a “family tech company,” as couple Hilsman and chief operating officer Ana Yant navigate a competitive software and product development landscape. 

“We’re really focused on understanding what our customers need and delivering it to them,” Hilsman said. “We challenge our customers a lot on what they need – do you really need this, what exactly do you need? We intentionally create friction upfront so we don’t deliver something no one uses or that doesn’t work with their process.” 

Hilsman’s path to CloudFruit has been anything but linear. After starting his career as an analyst working in a corporate environment, Hilsman eventually worked his way up to the title of ERP architect – responsible for designing, planning and overseeing the architecture and efficient implementation of ERP systems for businesses or clients. 

Following roles in the healthcare and nonprofit sectors – including a stint at Sean Penn’s disaster-relief nonprofit, CORE, where Hilsman helped develop a disaster response tool now on the market at Relief Compass – Hilsman decided to start his own company, CloudFruit, in 2022. The company quickly gained traction with clients, some of which, he said, are still with the company today. 

CloudFruit launched as a custom software development and analytics company, but has since evolved into a full product development firm, handling design, build, marketing and go-to-market strategy. Over time, its analytics and integration work has narrowed to focus on ERP integrations for hospitals, health systems and manufacturing. 

Along the way, both Hilsman and Yant – who joined the company in 2023 and previously worked as a product owner and designer at Wilmington-based Synply – have tried their hand at developing several products, which Hilsman said has been a learning process. 

In 2023, Hilsman and Yant built an AI chat app, called HiiBo, created before OpenAI upgraded ChatGPT's memory recall system. Originally marketed to "AI beginners," Hilsman said the company scaled too soon and has since sunsetted the AI 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.”

Now, with momentum from recent product launches, client relationships and stable revenue, Hilsman and Yant said they are optimistic about the company’s growth and potential; though, in an industry dominated by AI, the duo understands that an AI-centric product development company is a dime a dozen. 

“There’s a lot of bloat with product development,” Yant said. “Everybody can develop, especially now with AI, so yeah, it can be really hard to stand out in that space.”

Yant added that CloudFruit’s up-front AI usage, paired with experience from both Hilsman and Yant, sets the company apart from others operating in the same space. 

“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,” she added. “So, it’s not just ‘we have AI,’ it’s that we actually know how to design and ship something people will use.” 

CloudFruit’s client relationships – which include hands-on user acceptance testing and training sessions for newly developed modules – go beyond what a client may typically expect from a product development firm, Yant said. 

As a bootstrapped company, CloudFruit has grown without outside capital, Hilsman said, relying on revenue from its services business to fund product experiments. Once the firm signs on additional design partners to ERP Drift, Yant said, officials expect to hire more people and continue expanding.