To Infinity and Beyond with Ryan and Andy Mathisen


In a galaxy far far away Awkward Insurance hosts, Dustyne Bryant & Cat Ferris, explore the habits, perceptions, and expectations of insurance buyers (particularly millennials and gen Z’s) with brothers Ryan and Andy Mathisen, the founders of Glovebox, and hosts the podcast Cease & Desist. Ryan and Andy started insurTech company Glovebox to address dire needs in the industry… easy CRM tasks (like ID cards) are bogging down producers and account managers alike while their clients are getting lost in space and confused by carrier/agent, agent/client, client/carrier relationships.

InsurTech, like the Glovebox app, gives independent agents and agencies tech advantage to play on the same field with big insurTech companies. It elevates the client experience into the next universe by communicating with clients how they want to be communicated with and frees up precious time for professionals to focus on production, retention, and working on being FREAKING awesome at cross-selling.

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Andy Mathisen

Along with his brother, Andy was fully ingrained in the insurance industry through the family-owned agency started by his Dad. At a young age he learned the basics of insurance, guiding him to a path of future involvement in the industry. After officially joining the agency in 2012, he took the reins in heading up marketing and lead generation. This position evolved into a role as Director of Sales, providing experience in everything from quoting, sales, service, and business management. 

By 2019, Andy had grown passionate about providing a much-needed solution to the insurance industry. As co-founder and CMO of GloveBox, he now strives to show the immense value of this technology to agents, agencies, and carriers alike. The product will continue to grow, adding features/functionalities for a modernized experience aimed at both clients and agency operations.

Ryan Mathisen

Growing up in an insurance family, Ryan watched as his Dad make the jump from being a captive agent to starting his own independent agency with the help of a small loan from family. 

Ryan joined the family agency in 2011, which at that time, was a $5 million in premium agency. In the nine years since, his Dad, Ryan, and the GloveBox team were able to grow the agency to $100 million, expanding with over 200 agents across ten states in the western half of the United States.

The agency has since sold to a private equity firm, allowing Ryan and the GloveBox team to focus solely on growing the most needed innovation in the independent channel.

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