The Insurance Technology Podcast

The Insurance Technology Podcast

The Insurance Technology Podcast brings together interesting people from across the insurance ecosystem to discuss and debate technology’s impact on insurance products, businesses, and the industry. While “InsurTech” seems like the buzzword of choice these days, insurance technology has been around for decades. As a true believer that the past informs the future, podcast host Reid Holzworth speaks to both insurance industry “godfathers” – the original innovators who paved the way for tech at a time when bell-bottoms were still in fashion – and today’s trailblazers, who are busy disrupting one of the world’s most traditional industries. Join Reid as he distills wisdom from these radically different vantage points in his continued quest to create innovative insurance technology that brings simplicity and value to the entire insurance ecosystem. As Chief Executive Officer of IVANS, Reid leads the company’s strategic direction. He is a prominent insurance industry leader with extensive insurance experience in both broker and insurer distribution environments. Reid was the founder and CEO of TechCanary.TechCanary built an innovative set of insurance solutions on the Salesforce platform to create choice and flexibility for agencies who prefer Salesforce.com, which has since been incorporated in Applied’s portfolio under the name Applied Epic for Salesforce. Reid’s extensive industry experience, innovation-first mindset and commitment to simple, valuable customer experiences will be hallmarks of his leadership of IVANS and the expansion of its compelling innovation strategy.

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Sneak Peek: The Evolution of Agency Management Systems with Dennis Chookaszian

Sneak Peek: The Evolution of Agency Management Systems with Dennis Chookaszian

Full episode coming starting May 7! Get a sneak peek of Episode 2 of The Insurance Technology Podcast with Reid Holzworth. Back with his guest from Episode 1, Dennis Chookaszian joins Reid to discuss the history of the agency management systems. You’ll be amazed by the people involved, who went on to build some of the biggest insurance technology companies in the world. About the GuestDennis Chookaszian is an Adjunct Professor at the University of Chicago Booth School of Business and teaches courses in Corporate Governance. Before his professorship, he was with CNA Insurance for 26 years, serving as chairman and CEO for seven years, then chairman of the executive committee for three years. Prior to that, he was President for two years and CFO for 15 years. After CNA, he was chairman and CEO of mPower Inc., an internet financial advisory service. Prior to CNA, Dennis was a management consultant with Deloitte for eight years.

Episodes

The Insurance Technology Podcast’s Year-End Wrap

The Insurance Technology Podcast’s Year-End Wrap

Ready to reflect on a transformative year and gear up for even bigger tech leaps in 2025? Our latest podcast episode with Reid Holzworth and co-host Christen Kelley is your perfect year-end roundup. We'll dive into the standout moments from 2024, from groundbreaking technologies that shifted the industry to the invaluable insights shared by our amazing guests.Join us for a forward-thinking conversation that sets the stage for another incredible year of digital transformation.Episode Highlights2024 reflections, from download to other dynamic innovations (1:21)Ivans Connect success (5:28)Spearfishing and work travel (6:59)Unmissable moments in our top podcast episodes (9:00)Navigating challenges like the CrowdStrike incident (12:35)Storm Watch: Analyzing 2024 hurricane trends (16:03)Looking forward to 2025, call for podcast feedback (19:20)The coffee-wine ratio (22:55)Final thoughts for 2024 (25:24)You can also watch this episode on YouTube!

Best of Giving Back

Best of Giving Back

In this exciting episode of The Insurance Technology Podcast, co-host Christen Kelley highlights some of the inspiring stories of giving back that we’ve gathered from our incredible guests this year.Join us as we explore the heartwarming ways our guests are making a difference—from lending a helping hand to their neighbors to tackling hunger relief to championing under-represented founders to engaging in missionary work. We’re thankful for all of our guests this year and the difference they’re making in our communities, and we can’t wait to see what they’ll achieve next!Episode HighlightsJason Cass: Missionary work in Cuba, aiding in Immigration, Centralia Youth Initiative (00:56)Taylor Rhodes: World Vision & being a good neighbor (5:42)Pat Caldwell: NYC Cares, working with schools, aspirations related to medicine (7:58)Jack Ramsey: Church families, supporting the youth, children’s hospital, hurricane relief (9:58)Adam Denninger: Dress for Success, supporting the people you work with (11:09)Kate Terry: Hunger relief + Greater Boston Food Bank + mentoring young women in the industry (14:26)Jen Linton: Under-represented founders – female founders (16:12)Leticia Trevino: Heffernan’s giving & Poder Scholarship Fund (investing in Latinas) (17:10)Bradley Flowers: Monthly Ask Me Anything, mission work, Little Sparks Project (19:19)

The Insurance Guy Behind Portal Insurance

The Insurance Guy Behind Portal Insurance

In this episode of The Insurance Technology Podcast, Reid chats with Bradley Flowers, founder of Portal Insurance and co-host of the Insurance Guys Podcast, to explore how family influences, personal struggles, and triumphs paved the way for a successful career. Grab a cup of coffee, sit back, and listen as they unravel the challenges of business ownership and the beauty of building meaningful relationships along the way. Episode Highlights Rural roots in Atmore, Alabama – known for its casino and high-security prison (0:55)Getting progressively safer with hobbies, from bull riding to skateboarding to golf (5:22)A near-death experience that had nothing to do with bull riding (14:00)Starting out in insurance to have time for golf (16:37)Bradley’s biggest regret…it might surprise you (18:47)Starting an agency and creating the Insurance Guys Podcast (37:46)

From Shy, Small-Town Kid to Insurance VP

From Shy, Small-Town Kid to Insurance VP

In this episode of The Insurance Technology Podcast, Reid chats with Jack Ramsey, the vice president of agent channels at NEXT Insurance, to dive into Jack’s life journey – from his humble beginnings as a shy kid in a small town to his pivotal role at NEXT Insurance. Tune in to hear how Jack broke through his shyness to create an impact in the insurance industry for a fully digital carrier and is giving back through mentorship and his passion for disaster relief, including the disaster that recently impacted his hometown. Episode Highlights Big family, small town (00:45)Turning shy-kid experiences into mentorship opportunities (5:36)From door-to-door greeting card salesperson to insurance leader (13:43)Waking up excited to represent something different that agents are looking for (23:53)The growing talent gap in insurance (35:48)A heart for giving back to youth and supporting disaster relief (52:55)

Cultural Pride and Personal Drive

Cultural Pride and Personal Drive

In this episode of The Insurance Technology Podcast, Reid chats with Leticia Trevino, COO at Heffernan Insurance Brokers, to discuss Leticia’s remarkable story, from growing up in the San Francisco Bay Area to a thriving 24-year career at Heffernan.Tune in to dive into the intricacies of the insurance technology landscape, the challenges and triumphs of leading a major organization, and the importance of staying connected to one's culture and values amidst it all. Episode Highlights· Music, culture, and connection (2:30)· Starting out as a claims adjuster (3:35)· Targeting Latino markets (7:45)· Finding satisfaction in team building (9:45)· The “golden record” (20:47)· Success equals having a body of work you’re proud of (42:40)· Setting up the Poder in Action fund for Latina females (44:21)

From Dreams of Flight to Insurance Heights

From Dreams of Flight to Insurance Heights

In this episode of The Insurance Technology Podcast, Reid chats with Adam Denninger, global industry lead for insurance at Capgemini, to discuss everything from musical interests and fighter jet dreams to an appreciation for history and a passion for insurtech. Tune in to hear about Adam’s dream of going into flight as a fighter jet pilot in the US Air Force evolved into entering the world of insurtech – you won’t want to miss his insights and stories. Episode Highlights From fighter jet dreams to insurance impact (1:43)A taste of modern family life and historical interests (2:20)Entering insurance at The Hartford, from intern to director (13:56)Being a newbie at Capgemini (24:34)The right place, the right time, the right data (28:19)Leading without fear and being ready to work (1:03:03)Doing the right thing (1:09:24)

Sending Off Good Startup Culture Vibes

Sending Off Good Startup Culture Vibes

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 HighlightsDocumenting 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)

Flying Solo: Reid Hits the Road

Flying Solo: Reid Hits the Road

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 HighlightsEmbracing 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)

Finding Tuxedo Moments to Sail into Success

Finding Tuxedo Moments to Sail into Success

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 HighlightsAn 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)

Driven with the Soul in the Driver’s Seat

Driven with the Soul in the Driver’s Seat

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

From Salt Lake Serenity to the Startup Scurry

From Salt Lake Serenity to the Startup Scurry

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 HighlightsGrowing 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)

Chasing the Challenge

Chasing the Challenge

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)

A Live Panel Recap from Insurtech Boston ‘24

A Live Panel Recap from Insurtech Boston ‘24

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)

Best of Reid Holzworth

Best of Reid Holzworth

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.

From Fast and Furious to a Mission for Safer Roads

From Fast and Furious to a Mission for Safer Roads

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 HighlightsReading 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)

Seasoned Investigator Turned Tech Innovator

Seasoned Investigator Turned Tech Innovator

In this episode of The Insurance Technology Podcast, Reid sits down with Joe Stephenson, Director of Digital Intelligence at INTERTEL, kicking things off on a light note with the amusing story behind Joe’s impressive title and moving onto heavier topics like Joe’s encounters with drunk drivers, law offenders and scammers during his time as a police officer and investigator.Tune in to hear how Joe has brought his skills as a seasoned investigator into the world of insurance and technology.Episode HighlightsA rural Maine upbringing (1:50)Joe’s scariest story in policing (11:46)Career “ADD” (18:15)Uncovering insurance claims scams (20:01)Embracing life as a director of digital intelligence (47:53)

Deb Smallwood’s Journey of Self-Empowerment

Deb Smallwood’s Journey of Self-Empowerment

In this episode of The Insurance Technology Podcast, Reid sits down with Deb Smallwood, founder and creator of SELFPOWERMENT (Deb M. Smallwood LLC), to discuss Deb’s deeply planted roots on the seacoast of New Hampshire and her impressive career – from starting out as a developer for Liberty Mutual to co-founding Strategy Meets Action (SMA), selling SMA, and embarking on a legacy to help women become empowered to manifest their own goals.As we wrap up National Women’s History Month, tune in to hear how Deb’s admiration for women trailblazers like Amelia Earhart and her family of strong women shaped her own 'Why not me?' philosophy.Episode HighlightsA happy life on the New Hampshire seacoast (2:08)The root of Deb’s ‘Why not me’ philosophy (5:22)Pursuing entrepreneurship with Strategy Meets Acton (18:46)Focusing on women empowerment in semi-retirement (26:22)

Building a Culture that Breeds Innovation

Building a Culture that Breeds Innovation

In this episode of The Insurance Technology Podcast, Reid sits down with Taylor Rhodes, CEO of Applied Systems, to dive into Taylor’s career journey of building great teams in technology with humility and customer-centricity.Plug in to listen to how Taylor left his 11-year tenure at Rackspace to pursue a new mission he could pour his heart into and eventually landed at Applied, reinvigorating a culture of innovation for the company’s family of brands.Episode HighlightsThe last act of leading at Rackspace (1:12)Entering the SAAS space (2:08)Leading a customer-centric mission at Applied (14:17)Creating a safe harbor and making the industry better with tech (29:49)

Hard Work That Started on a Cattle Ranch

Hard Work That Started on a Cattle Ranch

In this episode of The Insurance Technology Podcast, Reid sits down with Taylor Rhodes, CEO of Applied Systems, to chat about his fascinating journey from childhood to starting his career in technology.Get ready for a ride down Taylor’s memory lane to hear about his early life experiences, from childhood summers on the ranch to serving in the Marines, and how these experiences have shaped who Taylor is today.Episode Highlights· Summers on the cattle ranch (4:15)· The “team over self” Marine mentality (13:40)· Entering the tech space at Rackspace (22:21)· Being a good neighbor (35:41)