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LuckyTruck raises $2.4M for insurtech, taps industry veteran as CEO

Company automates 3-day process down to 10 minutes

LuckyTruck democratizes carriers insurance processes. (Photo: Jim Allen/FeightWaves)

Insurtech company LuckyTruck announced Thursday it has raised a $2.4 million seed extension led by Candid Insurance Investors with participation from Markd, Draper University Ventures and SiriusPoint as the company scales its retail insurance platform that reduces time spent shopping insurance. Since its founding in 2019, LuckyTruck has raised a total of $6.5 million.

While founder and president Devin Bostick is new to the trucking industry, he has dedicated the past three years to consuming industry data, learning from leaders in the space and combining his past work in venture capital and insurance to give fleet operators an insurance experience that mirrors a modern insurance practice.

Funding detailsLuckyTruck
Funding amount$2.4 million
Funding roundExtended seed
Lead investorCandid Insurance Investors
Secondary investorsMarkd, Draper University Ventures and SiriusPoint
Business goals for the roundExpand insurance and financial solutions
Total funding$6.5 million

“Truckers are the backbone of our economy, yet their insurance process is still very complex,” he said in an interview with FreightWaves.

Bostick said conversations with trucking leadership revealed that their insurance processes often lack the analytics to help bring costs down and the automation to make purchasing insurance easier, getting drivers on the road faster.

Bostick and his team of engineers have built a simple, automated process for carriers. After entering their Department of Transportation number and company and driver information, they can receive a quote back in less than 10 minutes, a process that otherwise takes up to three days

According to LuckyTruck’s website, carriers can either pay in full or receive financing, and within a matter of minutes, they have the proper insurance documentation to get back on the road.


Leadership for growth

The company also reported it has recruited industry expert and LuckyTruck board member Julie Zimmer as CEO. Zimmer has over 30 years of experience working with fast-growing companies like Flexport (head of insurance), Embroker (chief operations officer) and HUB International’s middle market team.

(Photo: LuckyTruck)

“Lucky Truck would not be where it is today without Julie,” said Bostick, who stressed the importance of having someone with industry and startup experience to lead the company while he focuses on leading more of the technology-driven decision making.

Zimmer commended Bostick’s leadership style and technology-driven approach to solving problems and creating a work atmosphere similar to the one she had grown used to at Flexport.

Now with Zimmer in place and the extra infusion of capital, the duo looks to continue improving the workflow of its platform and adding more financial solutions to a roster of offerings that have already attracted over 700 active customers.

“Trucking has become more complex and that requires a higher level of company flexibility. The modern reality of trucking needs a solution like LuckyTruck. I’m eager to see LuckyTruck bring the space into the future, and I am confident in their vision,” said Parker Beauchamp, managing partner who led the deal for Markd, an insurance venture capital firm.


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Grace Sharkey

Grace is an entrepreneur and former supply chain executive who has held positions in sales, operations, and consulting. She is passionate about the future of the industry and how technology can improve the experience for all supply chain members. She believes supply chain is the one industry that affects every human directly, and is looking forward to creating content that mirrors that sentiment. If you have a story to share, please contact me at [email protected]