Full-length episodes and replays from The Insurtech Leadership Podcast. New here? Start with the newest episode and work backwards.
The Insurtech Leadership Podcast
Claim This Podcastby The Insurtech Leadership Podcast
4.5(24 reviews)
229 episodes
Updated Daily
Accepts GuestsHas SponsorsLocation 🇺🇸
59
Podcast Authority
BetaFairBased on show quality, social media presence, reviews, charts, and more
Quality85
Social0
YouTube0
Engagement84
Podcast Overview
Full-length episodes and replays from The Insurtech Leadership Podcast. New here? Start with the newest episode and work backwards.
Language
🇺🇲
Publishing Since
10/8/2020
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59
Podcast Authority
BetaFairBased on show quality, social media presence, reviews, charts, and more
Quality85
Social0
YouTube0
Engagement84
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excellent
Episode Length
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Recent Episodes
July 1, 2026
Your Health Coverage Ends With Your Job. His Doesn’t.
IntroductionWhat happens to your health coverage the day you leave a job, go independent, or pick up seasonal work? For more than 90 million Americans who earn outside a traditional employer plan, the answer is usually that it disappears. Felix Ortiz, founder and CEO of Smirk Health, joined host Joshua Hollander to explain why the benefits system built in 1929 for full-time employees no longer fits the way people work, and what it takes to build something that does. The conversation covers portable coverage that moves with the worker, modular plans that start at $19, and an AI layer that does more than answer questions.Guest BioFelix Ortiz is the founder and CEO of Smirk Health, an AI health benefits infrastructure company in Austin building portable coverage for 1099, part-time, hourly, and seasonal workers, underwritten and insured by Chubb. He is a repeat founder whose earlier companies spanned education technology, talent intelligence, and a banking-and-insurance platform for Americans of modest means. He is also a U.S. Army veteran and a marathoner who has finished five of the seven World Marathon Majors. Much of Smirk traces back to watching insurers decide his younger brother's care during a childhood heart condition, and to his own coverage gap leaving the military.Key TopicsThe 1929 problem - Group benefits were designed for full-time employees, so the fastest-growing part of the workforce gets priced out or left ineligible.Coverage that follows the worker - When a member changes employers, the plan, the price, and the benefits stay the same instead of ending with the job.Modular plans from $19 - Smirk rebuilt the plan chassis so members can add or remove coverage and see what is covered and what it costs before they buy.From supplemental to fully insured - Smirk took a product category damaged by bad actors, re-engineered it into a fully insured medical plan, and stacked it on an AI layer.An AI layer, not a chatbot - Because the plan is tied into Smirk's infrastructure, the concierge can take a member from a question all the way to a booked appointment with known costs.The AI divide - Ortiz argues a gap is opening between people on free AI models and people on paid ones, and that health is the wrong place to let that gap decide outcomes.Getting a carrier to say yes - How Smirk earned Chubb as an underwriting partner, and what Ortiz tells founders about approaching a large carrier.Notable Quotes"Somebody will have a Toyota, somebody else will have a Mercedes-Benz, but ultimately they still have access to a car. And when it comes to health, they don't. That's the big pain point.""We've gutted the whole thing and re-engineered it to be a fully insured medical plan.""You actually are starting to get a divide in AI infrastructure. That's a topic no one talks about.""Three years out, Smirk will be the infrastructure stack for AI within the health and financial intersection."ResourcesGuest:Smirk Health: https://www.smirkhealth.comSmirk Health on LinkedIn: https://www.linkedin.com/company/smirk-healthFelix Ortiz on LinkedIn: https://www.linkedin.com/in/fwoiii/Host & Organization:Joshua R. Hollander on LinkedIn: https://www.linkedin.com/in/joshuarhollander/Horton International (USA): https://www.horton-usa.com/Insurtech Leadership Podcast (LinkedIn Showcase): https://www.linkedin.com/showcase/insurtech-leadership-showSubscribe & ReviewIf this episode was useful, subscribe and leave a review. The Insurtech Leadership Podcast is on YouTube, Podbean, Apple Podcasts, and Spotify.
June 26, 2026
The 30-Year-Old Software Running Your Underwriting Is Already Obsolete
Host Josh Hollander interviews William Steenbergen, CTO of Federato, about replacing obsolete underwriting software with AI-native platforms for improved efficiency and accuracy.
June 23, 2026
AI Is Breaking the Old Rules of Monetization
Host Michael Pollan interviews AI expert Dr. Andrew Ng about how artificial intelligence revolutionizes traditional monetization strategies in business.
229 total episodes available with 35 transcripts
Recent guests on The Insurtech Leadership Podcast
Guests from recent episodes — sign up to see every guest that has ever appeared on this show.
William Steenbergen
Guest
Woody Klemmer
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Ido Deutsch
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Matt Connolly
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Dan Griffith
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Paul Wauquiez
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Jon Kelly
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Hamesh Chawla
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Valkyrie Holmes
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Eliron Ekstein
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Jake Sloan
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Wayne Slavin
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This podcast is available on 8 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
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