During a 45-minute interview, the founder and CEO of a fintech company known as Captain told Carrier Management a little bit about his career path to his current leadership role.

Along the way, Demetrius Gray also spoke briefly about his recent experience of learning to ski.

“Why are you such a good skier for your first time?” Gray recalls the instructor asking.

“Well, I’ve been used to leaning forward,” was the response.

Gray, who is now leading a technology company that advances capital to building contractors and helps homeowners recover quickly after natural disasters, worked for several roofing contractors before starting up two technology companies with ties to the property/casualty insurance industry. He was leaning forward once he had climbed up onto damaged roofs. He also climbed up the executive ladder, serving as vice president of operations at one roofing restoration firm and as chief executive at two others, according to his LinkedIn profile.

Working as Operations VP at a company that chased hailstorms and cleaned up after national disasters, however, wasn’t in his career plan when he pursued a degree in accounting in college. Nor was starting Captain or a predecessor technology company known as WeatherCheck.

“I hate to quote Lemony Snicket, ‘A Series of Unfortunate Events,’ but it was really just a confluence of all the right things happening,” Gray said when asked to fill in the blanks in the career timeline.

“I started out in the banking industry at PNC Financial Services and really loved that—but [that was] right during the ’08 banking crisis. Interestingly enough, when I was there, I didn’t realize I was there because I loved their online banking platform. They had rolled out a product called Virtual Wallet, and I should have known then that technology is something that I’m interested in.”

“I then got an opportunity to join a small family office out of western Kentucky that was in the restoration business. That offered me a glimpse into what goes on after hailstorms and tornadoes…Frankly, that line of business was very messy. It was disorganized. There were some really distinct challenges in terms of cash flow. So, as a young accountant, I would sit there pulling my hair out, trying to figure out, ‘How am I going to pay all these material bills? And how am I going to pay the laborers?'”

“The inverse reaction ends up being that you try to bill the [insurance] carrier for more, right, because the cash flow within the companies is so poor,” he said.

That experience would ultimately prompt him to develop the idea for Captain. After homeowners claims get approved by insurance carriers, Captain purchases insurance receivables and advances money to contractors to make those labor and materials payments, charging them a percentage of the face value of the claim every month to incentivize quicker rebuilding efforts.

“If you help the contractor with cash flow, then you solve for their need to bill you so often—and so much.”

“It’s a strange bedfellows situation where the carriers really do need a lot of contractors in the country and the contractors need the carrier,” he said.

Before starting up Captain, Gray found and led WeatherCheck, a tech application predicting where severe hail was about to strike and when it actually impacted a particular property. The seed for WeatherCheck was planted in Gray’s mind when he was working at one of the contracting firms, Champion Restoration, which turned out to be an early adopter of “all things technology,” he said, referring to AccuLynx roofing contractor software and EagleView, a provider of geospatial software, aerial imagery and analytics.

“It wasn’t really until I went to EagleView Technologies in Seattle, in their early days. The company I was working for was Customer No. 10, and I thought, ‘Wow. People are doing aerial imagery in this room,'” Gray said. “It really got me thinking, ‘What are the things that I can do from a technology perspective having seen this?'”

“I wasn’t on the roof. I was really in the back office trying to figure it all out. It was that moment in which we got to thinking, ‘OK. What about WeatherCheck? Why don’t policyholders know that they should or shouldn’t file a claim?'”

And later, Captain was born out of Gray’s experience on the financial side of the contracting business. “What the industry really needs is another pool of capital to finance the disaster insurance market so that there’s relief all the way around,” he says.

(Read the related article, “How a Fintech Named Captain Helps Homeowners Rebuild After Natural Disasters,” published in Carrier Management’s second-quarter magazine, to find out more about Captain and WeatherCheck.)