A Hard Market – An Insurtech CEO’s Perspective


In this episode of Awkward Insurance hosts, Dustyne Bryant and Ashley Fitzsimmons, have a heart to heart with Rick McCathron, CIC, CPCU, CEO of Hippo Insurance to unpack the intricacies of a hard insurance market, shedding light on its impact and opportunities for insurance agents and consumers.

 Join us as we discuss the factors driving the hard market, insights into the narrowing property market, and expert advice for those feeling the market’s challenges. Plus, we tackle misconceptions that both agents and consumers may have about today’s property market. Tune in for a concise yet informative dive into the current state of the insurance landscape from an Insurtech CEO’s perspective.

To hear more valuable insights from top CEOs and experts like Rick McCathron, register to attend InsurTech Insights NYC with an exclusive Awkward Insurance discount code:

Over 5,000 industry leaders, entrepreneurs and investors will take over the Javits Center for two days of insights, inspiration and networking.  Hear from over 400 speakers and over 500 companies in the expo hall on the most electrifying advancements in insurance innovation.   

Richard McCathron, CIC, CPCU

Richard McCathron, President & CEO of Hippo, has served as a member of the Board of Directors since February 2017. Prior to Hippo, Mr. McCathron held senior executive positions at various insurance companies including First Connect Insurance as its President & CEO from October 2012 to February 2017, Superior Access Insurance as its President & CEO from June 2007 to October 2010 and Mercury Insurance Group as its Regional Vice President from April 2004 to June 2007. Mr. McCathron is both a Chartered Property & Casualty Underwriter and a Certified Insurance Counselor and sits on the board of directors of Spinnaker Insurance Company, First Connect Insurance, The National Alliance of Insurance Education and Research, and Players Health. He is an advisor to several insurtech companies and holds a BS in finance from Oregon State University.

Dustyne Bryant, MBA, CIC, CISR

Personal Lines Academic Director & Awkward Insurance Co-Host

Dustyne Bryant, is the Personal Lines Academic Director for The National Alliance for Insurance Education & Research. In her role, Dustyne collaborates with National Alliance faculty and industry colleagues to research and analyze Personal Lines segment trends, data, and coverage in an effort to deliver relevant and quality educational content to growing insurance professionals. 

Ashley Fitzsimmons, CISR

Director of Professional Development, Ohio Insurance Agents Association, Inc.

Awkward Insurance Co-Host

Known as the Beyonce of Insurance, Ashley has grown up in insurance. She has real life experience on the agency side – for nearly the last decade. She has had to overcome the same daily struggles and has personally researched and implemented many tools and programs to help her family agency run more efficiently.

Nine years spent as the fourth generation in a family agency located near Scranton, PA, obtaining her CISR designation, multiple speaking engagements across the country as well as being nominated the 2018 National CSR of the year has given her the knowledge and experience to help other agents thrive instead of just survive.

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