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S2E12: Gregory Bailey’s Journey to Build Denim®


In this week’s episode, we’ve turned the tables on Denim Rivet. Brian Hemesath, Managing Director of the Global Insurance Accelerator (GIA), interviews the CEO & Co-Founder of Denim and the founder and host of this podcast, Gregory Bailey. On today’s show, Brian guides the conversation as Gregory shares his journey through his more than two decade insurance industry career and how he founded Denim.

From Insurance Agent to Startup CEO

Gregory started selling insurance as an agent for Northwestern Mutual at the age of 20. At the time, he was full-time student at the University of Missouri where he struck a chord with the marketing discipline in his business studies. He landed his first corporate job through Mutual of Omaha, where his skills in sales and sales management gave him the experience to help create training programs, marketing plans and go-to-market strategies. Next up, he was director, product management at CUNA Mutual Group, where he led the P&L, product development and product lifecycle management for the life and health related products of the company. After brokering a strategic partnership with Pacific Life Insurance Company, Gregory moved to southern California to lead marketing in the life insurance division of Pacific Life. After three years in southern California, Gregory’s career continued with a move back to the Midwest where he became the Chief Marketing Officer of a large life and annuity carrier in Des Moines. This is when he first crossed paths with Brian. Gregory became a lead mentor for the GIA’s 2015 cohort, and quickly realized that after spending two decades in the insurance industry, his newfound passion was in founding an insurtech startup. Thus, this podcast and Denim itself was born.

Denim’s Digital Platform

Denim has multiple avenues to add value to a carrier’s marketing strategy. The first is Denim’s ability for corporate marketers to highly scale their social media advertising on behalf of their local agents, advisors and brokers. This is a huge deal, because locally targeted ads perform up to 250% better than taking a corporate brand approach to social advertising. Denim also aggregates an enormous amount of data within its platform specific to consumer advertising behavior on social media. In the first five months Denim was in the market, the company’s patent-pending platform captured more than 250 million aggregated data points.

Denim’s Team

Leading and growing the Denim team (the core team is currently made up of five people), Gregory has brought wicked smart people together to achieve the company’s transformative tech vision. From his technical co-founder and friend building the first code on nights and weekends from southern California to recent hires in Des Moines, he’s focused on building a team that is far from just nose-in-the-keyboard programmers. Nearly all team members can speak intelligently about the company in front of an audience – it’s a work culture Bailey is especially proud of. Through this episode, listeners are able to get a glimpse into many of the positive aspects of building an insurtech startup. However, it’s those at home (including family members) that experience it all – the joys, the tough moments and the roller coaster ride that is starting a business.


Denim’s Website

Gregory Bailey on LinkedIn

Brian Hemesath on LinkedIn

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