EST. LOS ANGELES · READ WORLDWIDE
OCTOBER 2026 · VOL. X
InsurTech.me
Where insurance, technology, and capital meet
← ALL EPISODES
EPISODE 8 · INSURTECH TALKSNOV 30, 2020 · GILAD SHAI

Ryan Mathisen, Co-Founder and CEO of GloveBox

WATCH ON YOUTUBE · ALSO ON SPOTIFY

Everything After the First Policy

Ryan Mathisen is co-founder and CEO of GloveBox, based in Denver. He grew up in insurance: his father started an independent agency about 35 years earlier, and Ryan remembers licking stamps and envelopes at the kitchen table for direct mail. He graduated in 2008, into the recession, took an internet marketing job, and in 2011 joined the family agency, which was about a $5 million premium shop with three producers. He started as an agent, wrote about $2 million in premium over two years, then built the sales team. Roughly nine and a half years later, the agency had grown to around $100 million in premium, more than 200 agents and ten states across the western US, and in the summer of 2019 it was sold to a private equity firm. GloveBox started right after.

About Ryan Mathisen

Ryan Mathisen is co-founder and CEO of GloveBox, a platform for independent insurance agencies to serve, cross-sell and retain clients after the first policy is sold. His co-founders include his brother and a friend since elementary school, Sean.

Why Work With People You Know

Ryan likes to build with people he knows, likes and trusts, which skips the interview process and adds accountability, since you answer to them and their families. The day they sold the agency, he told Sean to pack up because they were starting GloveBox. By September 2019 they had no office and no technology, but they marketed hard, selling the hype while the developers built, which is why GloveBox was initially described as the Mint of insurance.

The Problem GloveBox Was Built For

At the agency, Ryan found that with about 40,000 to 45,000 clients, they received 13,000 to 14,000 service requests a month and staffed 30 to 35 customer service reps, and couldn’t keep up. The requests were nominal: a copy of a policy, who the policy was written with, who to pay, who to call. He thinks agents forget that consumers care about insurance only in the moment they need it. GloveBox set out to create clarity for the policyholder, and to direct communication based on how the independent channel really works, offsetting those service requests.

It has since evolved from a self-service platform into a solution for everything after the first policy: service, cross-sell, renewal, reshop, referrals and general communication, which no good system aggregates. “While we have your clients’ attention,” GloveBox helps agents cross-sell, get referrals and let consumers request reshops, and directs people, for instance, to pay bills with the carrier on agency-billed policies.

The Marketplace Is Next

At the time, GloveBox was focused on personal lines, with life, health and commercial coming the following month, which Ryan calls pillars that complete the platform: clients should be able to manage all their insurance in one place, from any device. The marketplace will show customers what policies they have and, more importantly, the ones they don’t have. Most agencies focus on one or two lines and don’t want to touch pet, travel, cyber, drone, dental or vision, though their clients want to buy them from an agent they trust. With the marketplace, the agency can offer these lines digitally through its own app, with GloveBox automating notifications and quote-and-bind, and paying the agency the revenue. He said it is due in 2021.

Gilad called himself a pro-agent person, noting about 200,000 licensed agents and 2 million working in US insurance, and that some products, like annuities, commercial or D&O, are hard to digitize. Ryan said Germany is ahead: consumers want a mix, buying some products digitally and some through an agent, and GloveBox wants to marry the two so people don’t have to choose.

Agency Clusters and Wholesalers

GloveBox announced a partnership with an agency cluster, and Ryan said clusters are becoming popular: about 26 percent of agencies, over 10,000, belong to one. A cluster is a group of agencies that pool premium to gain market access and bonuses from carriers, and help mitigate loss ratio problems across regions (hail in Colorado, fires in California). A wholesaler, by contrast, is an MGA that specializes in products agents can’t place in the standard market, such as high-risk flood property in Florida, and sells through agents without dealing with the end consumer.

Traction

Since launching its first agency the day it went on stage at Plug and Play in San Francisco, GloveBox had over 100 agencies live and 22,000 users, with another 100 agencies due within 45 days, which Ryan said maxes out the team. It receives four to five inbound demo requests a day. The company was 100 percent self-funded and planned its first fundraise to build the marketplace by July 2021 by hiring developers. His reasoning for self-funding: as former agents who lived the problem, he didn’t want an early investor steering the product in a direction they disagreed with, and it gave the freedom to operate unconventionally, like walking around ITC with a spaceman. Writing personal checks early on was tough, which is why they marketed so ambitiously before the product was built.

Why Carrier Apps Hurt Independent Agents

Insurers didn’t respond well at first, Ryan said, because GloveBox moves attention back to the agent, away from carrier platforms. His argument is that independent-channel clients servicing through carrier portals is the number one mistake in the business:

  • Revenue: a client using a carrier app is not shown or allowed to buy more, so no one cross-sells.
  • Service: service in the independent channel is split between carrier and agency, so a client using, say, one carrier’s app gets maybe 30 percent of their needs met, and it’s worse with several carriers.
  • Referrals: clients refer the carrier whose app they use, not the agency.

Gilad related it to embedded insurance and customer journeys, where carriers have invested heavily in their own journey. Asked about captive agents, Ryan said GloveBox isn’t focused there, but notes that captive carriers are inching toward the independent channel, appointing independent agents or letting agents place risks elsewhere, which he sees as a pendulum that moves slowly, like an iceberg.

The Astronaut Suit and Guerrilla Marketing

His wife volunteered to wear an astronaut suit at ITC in Las Vegas in 110-degree heat, a sign of her commitment after seeing the checks written into the business. Gilad recalled Hippo’s green shirts and Bold Penguin’s yellow ones as other branding stunts, plus his own cow, calf and goat on Fifth Avenue from his gaming days.

Ryan said he first met the CEO of Risk Genius at a New York conference and pitched him on adapting the product for consumers; he thinks AI that explains policy language would be valuable on the consumer side as well as the broker side, especially as a quote of 30 pages gets sent out with a note that the premium looks good, which can be an E&O exposure.

Advice: The One Thing, and The Queen’s Gambit

Ryan has trained mixed martial arts for six and a half years and trains at Factory X in Denver, where his kids do jiu-jitsu. His recommendation for agents is The One Thing by Gary Keller, co-founder of Keller Williams: do one thing extremely well. His agency only sold home and auto, no life, health or financial planning, and sold for a nice amount. He also recommended The Queen’s Gambit.

Key Takeaways

  • Ryan’s family agency grew to roughly $100 million in premium with 200-plus agents before being sold to private equity in 2019.
  • GloveBox targets everything after the first policy (service, cross-sell, renewal, referrals), not just self-service.
  • Its marketplace, planned for 2021, lets agencies sell lines they don’t staff for, such as pet or travel, digitally, paying them the revenue.
  • By late 2020 it had over 100 agencies live and 22,000 users, entirely self-funded, with a first raise planned for the marketplace.
  • Carrier apps cost independent agents cross-sell revenue, service completeness and referrals.
  • Focus on one thing: his agency sold only home and auto and still built a business worth selling.