In this episode of The Insurance Technology Podcast, Reid chats with Send Chief People Officer Pat Caldwell about his early lessons in leadership, work ethic, acceptance and culture that influenced his career trajectory.

Tune in to hear how Pat’s aspirations evolved, from wanting to become a paramedic to going to law school and eventually sending off his good startup culture vibes within the HR insurtech space for an underwriting platform.

Episode Highlights

• Documenting culture and leadership tips as an author (1:08)
• Venturing into insurtech HR at Send (1:11)
• Giving back, realizing work is not your identity (1:27)
• Reminiscing on first-job lessons and “vintage” video stores (12:56)
• Starting in HR at a large Australian mining company (24:09)
• Leaving for London and entrepreneurial dreams (33:27)

In this episode of The Insurance Technology Podcast, co-host Christen Kelley puts Reid in the hot seat to look back at a summer packed with fun and zoom ahead to a season brimming with industry events.

Tune in to hear about Reid’s upcoming work travel adventures and learn about some of the latest trends and news, including the buzz around the Applied Systems/Planck acquisition.

Episode Highlights

• Embracing the summer vibes (00:30)
• Nashville bound for Ivans Connect & Applied Net (3:20)
• Taking center stage as panel moderator at IndieTech (8:35)
• Mingling with C-suite executives at CIAB (12:32)
• Sparking industry-wide connections at ITC (15:19)
• Elevating the AI game with Planck (26:44)

In this episode of The Insurance Technology Podcast, Reid chats with Jason Cass, managing partner of the Insurance Alliance and founder of the Insurance Podcast Network, to share Jason’s story of entrepreneurship that started at an early age on a business venture to milk cows and has led to being a successful insurance entrepreneur.

Get ready for these two podcast hosts and insurance gurus to discuss the rewards of working in the industry and the importance of connectivity. You’ll also discover how to find what Jason calls “tuxedo moments” to sail into success.

Episode Highlights

• An ambitious spirit that started with milking cows (5:22)
• Tuxedo moments and how being different matters (10:01)
• Leading by listening and putting people first (29:42)
• Sailing into success (30:42)
• Giving back, seeing a need and trying to fix it (32:40)
• A love for building things, boating, animals and dive bars (38:15)

In this episode of The Insurance Technology Podcast, Reid chats with Dr. Douglas Brackmann, author and psychologist, for a deep conversation about neurodivergence related to being what Dr. Doug calls “driven.”

Tune in to hear how Doug self-identified as neurodivergent and driven at a young age, and how seeing a psychologist drove him to inspire others to put their soul in the driver’s seat. 

Episode Highlights

• Neurodivergence and imposter syndrome (14:30)
• The “driven” trait to thrive in chaos (18:39)
• The hunter-farmer theory (21:43)

In this episode of The Insurance Technology Podcast, Reid chats with Fenris CEO and Founder Jen Linton for another insightful interview live from House of Blues at Insurtech Boston ’24.

Tune in to get inspired to dream big as we explore Jen’s journey from growing up in a large family in the Salt Lake City suburbs, becoming a microbiologist, obtaining her MBA, and founding an insurtech startup.

Episode Highlights

• Growing up with an entrepreneurial mom, siblings and livestock in the Salt Lake City suburbs (00:57)
• The pivot from microbiology to education software to insurtech startups (3:31)
• Venturing into insurance and telematics (8:45)
• Creating her startup vision with the help of bottomless coffee (18:45)
• Leading with vision, and a little bit of necessary stubbornness (27:23)

In this episode of The Insurance Technology Podcast, Reid chats with Surround Insurance CEO and Co-founder Kate Terry for an engaging conversation from Insurtech Boston ’24.  

Tune in to get to know Kate, from her Boston upbringing and work ethic that started at an early age to a new passion for tap dancing and how she’s always chasing a challenge.

Episode Highlights

·       Boston roots (1:01)

·       Right place at the right time (19:14)

·       Becoming an insurtech co-founder (24:41)

·       Success equals a sense of growth (47:25)

In this episode of The Insurance Technology Podcast, Reid covers key post-event takeaways from Insurtech Boston ’24, captured live from House of Blues with Nick Lamparelli, managing partner of Insurance Nerds, and Charles “Chip” Bacciocco, CEO of TrustedChoice.com.

Get ready to be inspired as these three insurtech thought leaders reflect on the event topics, comparing insurance to hide-and-seek, sharing excitement about the “golden age of innovation,” and speculating on how factors like AI and telematics will impact the industry.  

Episode Highlights

·         The speedy pace of Generative AI (2:45)

·         The roller coaster of a startup (11:45)

·         Understanding the economics of this industry (19:20)

·         Three magic words to double success (36:15)

In this episode of The Insurance Technology Podcast, co-host Christen Kelley puts Reid in the hot seat for the first time in a new format we will occasionally use. Reid shares his thoughts on current industry topics.

Tune in to hear Reid fly solo as the guest, sharing his point of view on the industry, from single sign-on solutions to connectivity challenges, transparency, fraud and more. 

Episode Highlights

·         Connectivity as the lifeblood of innovation (2:00)

·         The need for tech adoption (3:45)

·         Transparency of data is key (12:20)

·         Single sign-on as a real thing in the industry (14:40)

·         Coming together for the betterment of insurance (30:37)

In this episode of The Insurance Technology Podcast, podcast co-host Christen Kelley picks some of the best insights from host Reid Holzworth as we celebrate the podcast’s third anniversary today!  With more than 70 episodes, Reid has interviewed a ton of industry greats, but he’s also shared a lot of his own passion and industry insights. 

Tune in to get a glimpse into his passion for entrepreneurship, technology and more. 

In this episode of The Insurance Technology Podcast, Reid sits down with Ryan McMahon, Senior Vice President of Strategy & Corporate Development for Cambridge Mobile Telematics, to talk about how early aspirations to go into law enforcement eventually transitioned to a career in insurance telematics.

Catch a ride on Ryan’s journey, including an attempt at a fast and furious move that was pivotal in driving his passion for safer roads and reduced crash risk. 

Episode Highlights

• Reading actuarial review magazines as a kid (1:56)
• From park ranger to EMT to volunteer rescue squad (3:35)
• Entering the world of insurance (5:08)
• A fast and furious attempt gone wrong (11:51)
• Thinking outside of the box to make roads safer (34:54)