August 13, 2025 | Raistone

Meet the Team: Everett Doolittle, Vice President, Alliances Acquisition

As Vice President of Alliances Acquisition at Raistone, Everett Doolittle is helping grow the Raistone’s reach by connecting with platforms that integrate well with the firm’s working capital solutions. What excites him most about Raistone is its ability to scale, thanks to its multi-funder model, tech-forward approach, and growing operational discipline.

A career-long business developer, Everett brings decades of experience turning innovative ideas into scalable ventures. His entrepreneurial drive took root early — fixing and selling bikes as a kid and later building a career defined by uncovering and scaling new business opportunities.

While going to school at University of Wisconsin Stevens Point where he studied business, finance, economics, and computer science, Everett faced a fork in the road. Specialized, a bicycle manufacturer, presented him with the chance to travel the country, racing mountain bikes and representing the brand.

“Mountain bikes were just getting popular, and they had a new program that provided a van and a daily stipend. I seriously considered it,” he laughed. “But my parents were very thankful I chose to continue with school.”

Instead, Everett continued honing his problem-solving skills in the insurance industry before pivoting to tech platforms. He began working for Skyward, one of the largest ERP software providers for school districts in the U.S. From there his career continued to evolve as he worked across the technology sector.

Later, Everett helped launch two ventures at Deluxe Corporation, including a desktop publishing tool that enabled small business owners to design and electronically submit professional-grade marketing materials for print production. The software was adopted by FedEx and integrated into its Kinko’s retail operations.

He then joined U.S. Bank as one of the original team members behind PowerTrack, a global payments network, where he led business development and sales as the platform scaled to process $22 billion per year. The platform was eventually acquired by Visa and rebranded as Syncada.

Following that success, Everett joined Optum, part of UnitedHealth Group, where he helped build and scale global operations leveraging offshore teams and automation to support complex, 24/7 back-office systems in the healthcare space.

Most recently, at European fintech Lenderwize, Everett helped double financing volumes from $15 million to more than $35 million per month. But scaling further proved difficult due to capital constraints, an experience that helped shape his next move.

“There were many lessons learned along the journey,” he recalled. “Even with great tech and customers lined up, you need the financing backbone to support real growth. That’s what drew me to Raistone. Our multi-funder model and ability to initiate business on our terms before rapidly expanding is unique and exciting.”

Everett’s path to Raistone is a classic case of the fintech world coming full circle. While at Lenderwize, a potential partnership with SAP led to an introduction to Raistone CEO Dave Skirzenski. Years earlier, in his time at U.S. Bank and Syncada, Everett worked closely with the legal team at Citibank, including Matt McAlpine, who is now Raistone’s General Counsel.

“It’s a small world,” Everett said. “I look back and think about the numerous individuals who are still active in our industry and how many of the same great people resurface at key moments.”

At Raistone, Everett is focused on working with software platforms who have customers that can benefit from Raistone solutions. Engaging with software platforms creates a multiplier effect for Raistone where Raistone integrates once, and by leveraging the platform data we can help companies gain access to working capital.

With a career spent in business development, Everett thrives on the challenge of understanding how a partner’s business operates, uncovering where Raistone can complement their platform, and aligning incentives so everyone benefits. He sees success not just in closing deals, but in creating systems where everyone wins.

While he no longer fixes and sells bicycles like he did as a young entrepreneur, Everett continues to be an avid cyclist and all-around active adventurer. He and his wife enjoy spending as much time as they can outdoors.

With their four adult children out of the house, they’ve embraced an active lifestyle by exercising and walking daily, along with logging as many 20+ mile tandem, road, or mountain bike rides as possible. Recently, they set a personal record of skiing 32,000 vertical feet in a single day — a call back to their time together on the alpine ski team in college.

“We love it all. Water sports, motor sports, motorcycles, bikes, cars, boats, camping, canoeing, hunting, golfing, pickleball — you name it. We’re all play,” he said. “I always joke, if it slides, glides, rolls, or I can jump it… I’m in. And if I can do it upside down, even better!”

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