Best InsurTechs.io Podcasts (2025)

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Navigating the M&A Landscape for Independent Agencies with Mike Mensch & Colby Allen 50:30

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2d ago50:30

50:30

In this powerhouse episode of Insurance VC, PE, and MA, host Jeff Shi is joined by Michael Mensch and Colby Allen from Agency Brokerage Consultants to explore the complex, ever-evolving landscape of mergers and acquisitions in the independent insurance agency space. With over 500 transactions under their belt, Mike and Colby share insights that are…

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From Captive Agent to annuity Leader: Tracy Lownsberry on Scaling Education-Driven Sales 32:37

4d ago32:37

32:37

In this powerful episode, host Jeff Shi sits down with Tracy Lownsberry to unpack his evolution from a captive insurance agent to the founder of the largest social media community for annuity professionals. Tracy shares how his early experiences shaped a deeper commitment to transparency, education-based sales, and doing business the right way. He …

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Navigating M&A, Lending, and Growth Strategies in the Insurance Industry with Kelly Drouillard 1:15:33

6d ago1:15:33

1:15:33

In this episode of Insurance VC, PE, and M&A, Jeff Shi sits down with industry icon Kelly Drouillard to unpack the complexities of insurance M&A, lending strategies, and agency growth. With over 30 years of experience spanning carrier, reinsurance, and capital markets, Kelly brings a deep well of insight into insurance transactions. She breaks down…

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Building Scratch Agencies & Podcasting Community with Sean Fitzgerald & Stephen Turnbull 41:46

9d ago41:46

41:46

In this episode, host Jeff Shi welcomes Shawn Fitzgerald and Stephen Turnbull, the dynamic duo behind the Scratch Agency podcast. Together, they share their journey of launching their own scratch agencies in New York and how their similar-but-different paths led to the creation of a podcast that has grown into a vibrant community for independent in…

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Bootstrapping a Flood MGA: Inside Flow Flood's Growth Story with Abbe Sulton & Michael Pallas 38:20

11d ago38:20

38:20

In this episode, host Jeff Shi sits down with Flow Flood co-founders Abbe (A.B.) Sulton and Michael Pallas to explore their unique path from insurance distribution to building a flood-focused insurtech MGA. The conversation dives deep into their early days running a retail agency during the 2008 financial crisis, discovering market inefficiencies i…

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Global Insurance Transformation, Community, and the Power of Mindset with Rory Yates 36:22

13d ago36:22

36:22

In this thought-provoking episode, Jeff sits down with Rory Yates, Group Vice President of Corporate Strategy at EIS, to explore his dynamic journey from a tech-savvy athlete to a global leader in insurance transformation. Rory opens up about growing up in poverty, using sports to earn an education in the U.S., and his pivot from launching one of t…

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Fixing the Insurance Data Problem: Roman Stepanenko on Conversions, Governance & RecordLinker 32:04

16d ago32:04

32:04

In this episode of Founders Journey, Jeff sits down with Roman Stepanenko, founder of Record Linker and co-founder of RiskMatch. Roman shares his fascinating transition from software developer to insurtech entrepreneur, starting with the creation of RiskMatch and continuing with his latest venture, Record Linker. They dive deep into the overlooked …

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How Melon Local Became a Powerhouse for Insurance Marketing with Whitney Olson 21:30

18d ago21:30

21:30

In this episode of Founders Journey, Jeff sits down with Whitney Olson, co-founder and CEO of Melon Local, to unpack the story of how a boutique digital marketing agency became a trusted partner for some of the nation's top insurance agents. Whitney is joined by Senior Director of Paid Search, Megan, and Senior Director of Business Development, Kat…

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The Evolution of insurtech with Denise Garth, Chief Strategy Officer at Majesco 46:28

20d ago46:28

46:28

In this powerful episode, Jeff sits down with insurtech trailblazer Denise Garth, Chief Strategy Officer at Majesco. With over three decades of experience in both business and IT across insurance carriers, vendors, and global industry organizations, Denise brings unmatched insight into the evolution of the insurtech landscape. From launching Majesc…

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Revolutionizing Insurance Tech and Lead Gen with Steve Mohr 34:16

23d ago34:16

34:16

In this episode of Industry Voice, we sit down with Steve Mohr, a seasoned insurance technology entrepreneur and founder of The Insurance Index. Steve takes us through his multi-decade journey in the insurance and insurtech space, from starting out as a producer in Florida’s non-standard auto market, to building revolutionary agency management tool…

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The Evolving Role of Strategic Partnerships in Insurance Distribution with Jeff Pireu 36:12

25d ago36:12

36:12

In this episode of Industry Voice, host Jeff Shi sits down with Jeff Pireu, Vice President of Strategic Partnerships at First Choice, a MarshBerry company. With over 30 years in the insurance industry—spanning claims, sales, and executive leadership roles at Nationwide—Jeff shares his journey from carrier-side leadership to the forefront of agency …

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Rethinking Insurance Distribution with Patrick Tullius 33:39

27d ago33:39

33:39

In this episode, host Jeff Shi sits down with Patrick Tullius, Managing Director at INS Capital Group, to dive deep into the evolving world of insurance distribution, insurtech innovation, and the critical role of MGAs in bridging the gap between carriers and cutting-edge technologies. Patrick brings his extensive experience in investment banking a…

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How to Sell an Insurtech Startup in a Down Market with Daniel Metcalf 32:50

1M ago32:50

32:50

In this episode, we sit down with Daniel Metcalf, co-founder of Smart Harbor, to explore the complete lifecycle of building and exiting an insurtech business. Daniel shares the origin story of Smart Harbor, a company born out of the belief that independent insurance agents needed modern digital tools to compete with direct writers. He talks about t…

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Embedded Insurance, Risk Carriers, and insurtech Innovation with Theresa Blissing & Michael Waitze 1:06:36

1M ago1:06:36

1:06:36

In this episode of Insurtechs.io, host Jeff Shi is joined by Theresa Blissing and Michael Waitze to unpack the dynamic evolution of embedded insurance, the strategic role of risk carriers, and what drives the next generation of insurtech innovation. The conversation dives deep into how customer-centricity is reshaping product development, the diffe…

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Building a Software-Enabled Underwriting Company with Bobby Touran 44:30

1M ago44:30

44:30

In this episode, Jeff Shi sits down with Bobby Touran, the two-time founder and CEO behind leading insurtech startups Pathpoint and Rainbow. Bobby shares his journey from building software-driven companies to founding two specialized underwriting and distribution platforms within the commercial insurance space. Hear how Bobby transitioned from the …

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Using AI to Drive Underwriting Efficiency at Scale with Sarah Reeves & Matthew Sutika 53:01

1M ago53:01

53:01

In this episode, we dive into the future of underwriting transformation with Steve Reeves, Chief Insurance Officer at Voxel, and Mico Sutika, VP of Sales. Hosted by Jeff Shi, this conversation explores how Voxel is applying advanced AI and machine learning technologies to solve long-standing inefficiencies in commercial underwriting. From automatin…

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From the NFL to Insurtech Vegas: Marcus Ogden’s Unbreakable Mindset and Story of Redemption 37:33

1M ago37:33

37:33

In this powerful episode of Industry Voice, Jeff sits down with Marcus Ogden — former NFL offensive lineman turned motivational speaker, entrepreneur, and insurtech advocate. Marcus opens up about his extraordinary journey from football stardom to personal and professional rock bottom, and how he clawed his way back through grit, authenticity, and …

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Crypto Meets Insurance: Risks, Regulation & Real-World Use Cases 38:39

1M ago38:39

38:39

In this episode of Industry Voice, Jeff Shi sits down with two industry veterans, Susan Holliday and David Crosbie, for a deep dive into the intersection of crypto, blockchains, and the insurance world. Susan shares her extensive experience leading strategy at Swiss Re and her early encounters with blockchain technology, while David recounts his tr…

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Modernizing Insurance Sales Enablement with Caleb Cramer of Launch 20:39

1M ago20:39

20:39

In this episode of Industry Voice, Jeff Shi is joined by Caleb Cramer, Chief Revenue Officer of Launch. Caleb shares his journey from traditional B2B sales into the insurance space and discusses how Launch is transforming the producer-client relationship. From his days at AgencyZoom and Ascend to helping agencies improve enterprise risk management …

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Navigating Executive Search in Insurtech: Clarity, Talent, and Market Trends with Ira Ziff 24:24

2M ago24:24

24:24

In this episode of Industry Voice, we sit down with Ira Ziff, a veteran in executive search with nearly three decades of experience. Ira shares his expertise on bringing clarity to hiring strategies in the insurtech sector, offering insight into the challenges of dysfunctional job descriptions, retention issues, and misaligned expectations between …

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Building Community & Talent in insurtech with Josh Hollander 31:21

2M ago31:21

31:21

In this episode of Industry Voice, host Jeff Shi welcomes Josh Hollander, President of Horton International USA, host of the insurtech Leadership Podcast, and co-founder of the insurtech Association. Josh shares his remarkable journey from investment banking and fintech entrepreneurship to becoming a key community builder and talent strategist in t…

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From Selling Shoes to Building a $15M Insurance Empire with Dan Kitajima 36:29

2M ago36:29

36:29

In this episode of Industry Voice, host Jeff Shi welcomes Dan Kitajima, founder of one of the largest farmer’s insurance agencies in California. Dan shares his journey from working at a sneaker store in college to becoming a top-performing insurance agent. He opens up about the grind of building his agency from scratch—starting with two people in a…

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Building Careers in Insurance Through TikTok and Empowerment with Samantha Ridgewell 45:20

2M ago45:20

45:20

In this episode of Industry Voice, Jeff Shi sits down with Samantha Ridgewell, Managing Director of Empower Development, to explore how social media—particularly TikTok and LinkedIn—can reshape the way young professionals discover and enter the insurance industry. Samantha shares how her engaging content has influenced over 200 people to find roles…

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Building a Legacy of Impact: From Insurance to Philanthropy with Anthony Gruppo 42:49

2M ago42:49

42:49

In this powerful episode of Insurance Dads, hosts Matt Sutika and Jeff Shi sit down with the ever-inspiring Anthony Gruppo—a serial entrepreneur, board chair, author, and philanthropist. Anthony opens up about his incredible journey from blue-collar beginnings and early sales jobs to leading major organizations like USI and Marsh, and ultimately fo…

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Transforming Insurance Through Embedded Distribution: Charles Merritt on Building Buddy 46:45

2M ago46:45

46:45

In this episode of Founders Journey, host Jeff Shi sits down with Charles Merritt, co-founder and CEO of Buddy, to unpack his entrepreneurial path from cinematography and tech startups to founding a pioneering insurtech platform. Charles shares how his curiosity and creativity led him from media production to product innovation, ultimately co-found…

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From Engineer to insurtech Founder: Sivan Iram’s Journey with Flow Specialty 1:10:25

2M ago1:10:25

1:10:25

In this episode of Founders Journey, host Jeff Shi sits down with Sivan Iram, Co-Founder and CEO of Flow Specialty. From coding in his childhood bedroom in Israel to navigating the complexities of venture-backed growth in Silicon Valley, Sivan shares a detailed, candid look into his entrepreneurial journey. He talks through his transition from soft…

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Building Better Insurance with Data, AI, and a Mission-Driven Mindset with Martin Ellingsworth 42:21

2M ago42:21

42:21

In this episode of Industry Voice, host Jeff Shi sits down with analytics and insurance veteran Martin Ellingsworth. With a career spanning over four decades—from the Air Force to corporate America to startup culture—Martin shares invaluable insights on transforming the insurance industry through data, ai, and human-centered innovation. The convers…

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From $16M Exit to Building Intelligent Agencies with Mick Hunt 44:26

2M ago44:26

44:26

In this episode of Industry Voice, Jeff sits down with Mick Hunt—consultant, serial entrepreneur, and founder of Premier Strategy Box and Mic Unplugged. Mick shares his incredible journey from a promise he made to his mother at age 10 to building and selling his insurance agency for $16 million by age 32. The conversation dives deep into lessons in…

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Building AI-Powered Claims Solutions: A Deep Dive with Timon Gregg 17:26

2M ago17:26

17:26

In this episode of Founders Journey, host Jeff Shi sits down with Timon Gregg, co-founder of a cutting-edge claims technology company. Timon shares his journey from Oxford to launching an AI-driven third-party administrator (TPA) in the U.S., tackling inefficiencies in the insurance claims process. He breaks down how AI-powered automation is transf…

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Innovating Insurance Brokerage: Michael Malfa on the Growth & Future of BoardWalk Insurance 32:40

2M ago32:40

32:40

Welcome to another insightful episode of Founders Journey! In this episode, Jeff sits down with Michael Malfa, the co-founder of BoardWalk Insurance, a leading Canadian property and casualty brokerage specializing in commercial P&C. Michael takes us through his journey into the insurance industry and how he co-founded BoardWalk with a vision to bri…

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Crypto Meets Life Insurance: Building the First Bitcoin-Based Carrier with Zachary Townsend 43:12

2M ago43:12

43:12

In this episode, Jeff sits down with Zachary Townsend, co-founder and CEO of Meanwhile, the world’s first bitcoin-denominated life insurance company. Zach walks us through his journey from working in government and fintech to building a YC-backed startup acquired by Silicon Valley Bank, and now pioneering in insurtech. He dives deep into the origin…

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Bridging Finance and Technology: A Fintech Vision for Insurance with Timothy Li 38:06

2M ago38:06

38:06

In this episode, host Jeff Shi sits down with fintech innovator Timothy Li to explore the evolving intersection of financial services and insurance. With a background spanning consumer lending, banking, and tech startups, Timothy brings a deep understanding of how fintech infrastructure can revolutionize traditional insurance operations. The discus…

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Growing Insurance Trends and Legal Challenges With Lauren Ybarra’s Expertise 25:43

3M ago25:43

25:43

Welcome to this insightful episode of Founders Journey! Today, Jeff is joined by Lauren Ybarra, an accomplished legal expert specializing in insurance law. Lauren takes us through her career, from her early ambition to become a judge to her eventual transition into the complex world of insurance law. She shares her work experiences with major compa…

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AI-Powered Sales in P&C Insurance: Scaling Mav AI with Matthew Black 45:11

3M ago45:11

45:11

In this episode of Founders Journey, Jeff sits down with Matthew Black, founder of Mav AI, to explore how AI is revolutionizing sales and lead management in the P&C insurance space. Matthew shares his journey from a tech-obsessed teenager to building cutting-edge AI solutions for agencies and brokers. They discuss the evolution of AI from chatbots …

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From Marketing to Ethical Hacking: Josh Crumbaugh’s Cybersecurity Journey 53:51

3M ago53:51

53:51

Welcome to another insightful episode of Founders Journey! In today’s episode, Jeff interviews Josh Crumbaugh, an influential figure in the ethical hacking world and the founder of PhishFirewall. Josh shares his inspiring transition from a marketing career to becoming a leader in cybersecurity, recounting how his passion for ethical hacking develop…

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Revolutionizing Property Insurance Claims with Elnor Rozenrot 30:26

3M ago30:26

30:26

In this episode of Founder Journey, host Jeff Shi sits down with Elnor Rozenrot, a seasoned entrepreneur with deep experience in corporate leadership and venture capital. Elnor shares his unconventional path to entrepreneurship, driven by his passion for innovation and disruption. He reflects on his time leading innovation at LG Electronics and his…

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Revolutionizing Insurance Ratings: A Deep Dive with Joseph Petrelli 36:11

3M ago36:11

36:11

Welcome to another insightful episode of Founders Journey, where host Jeff is joined by Joseph Petrelli, the founder and CEO of DemoTech. In this engaging conversation, Joseph reflects on his remarkable career in the insurance industry, starting in 1969, and how a Reader's Digest book ignited his passion for actuarial science. From his early days a…

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Transforming Financial Advisory with AI Innovations by Sam Robinson 32:50

3M ago32:50

32:50

Welcome to this episode of Industry Voice with Jeff! Today, Jeff is joined by Sam Robinson, co-founder of an innovative financial advisory company that’s transforming the industry through AI. Sam’s journey into financial services began after a deeply personal experience—the cancellation of his father’s insurance policy in 2015—motivating him to ste…

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Journey of Building a Cutting-Edge insurtech Platform with David Watson 33:27

3M ago33:27

33:27

Welcome to this episode of Founders Journey! Join us as David Watson shares his inspiring entrepreneurial path in the world of insurtech. David recounts his journey from working at Chick-fil-A to founding Blue Lake Insurance and developing the innovative platform Risk Advisor. His story illustrates the dedication and vision required to succeed in t…

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The Founder’s Journey: AI, Fraud Prevention, and Insurance with Sunil Madhu 38:36

3M ago38:36

38:36

Welcome to another exciting episode of Founders Journey! In this episode, host Jeff sits down with Sunil Madhu, a seasoned entrepreneur and founder of six successful companies, including the $5 billion giant, Socure. Sunil shares his incredible journey from systems architect to startup founder, with a focus on IT risk and security, and how these ex…

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The Evolution of Bamboo Insurance in the Industry with Taylor Mobley 31:35

3M ago31:35

31:35

Welcome to this episode of Founder's Journey! Join us as Taylor Mobley, the CFO of Bamboo Insurance, shares insights into the company's innovative strategies and evolution in the insurance market since 2020. With a rich background in public accounting and experience at Ernst Young and Kemper, Mobley discusses how Bamboo prioritizes technology and o…

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Building Benekiva and the Future of Insurance Solutions with Bobbie Shrivastav 38:19

3M ago38:19

38:19

In this episode of Founder's Journey, Bobbie Shrivastav shares her remarkable transition from technologist to a prominent founder in the insurtech space. Starting in 2015 with her first startup, Doxmore, Bobbie was inspired to digitize documents after experiencing the inefficiencies of paperwork during her maternity leave. Her journey led to the cr…

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How Oak Street Funding Drives Insurance Success with Scott Stars 27:19

3M ago27:19

27:19

Welcome to another insightful episode of Insurance VC, PE, and M&A with Jeff, where we delve into the complexities of insurance lending with Scott Stars, a key figure at Oak Street Funding. Scott discusses his transition from a successful career at HSBC to his current leadership role in the specialized world of insurance loans. This episode offers …

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Understanding Insurance Deal Complexity and Ecosystems with Grant Griffin 46:02

3M ago46:02

46:02

Welcome to another insightful episode of Insurance VC, PE, and M&A. Today, host Jeff sits down with Grant Griffin, Vice President of Investment Banking at Sherman Company, to delve into his transition from retail insurance to leading M&A efforts in the insurance sector. Grant shares his expertise in navigating the intricacies of insurance mergers a…

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Building Insurtech Communities & Investing in Innovation with Tony Lew 35:42

3M ago35:42

35:42

In this episode of Founders Journey, host Jeff Shi sits down with Tony Lew, co-founder of insurtech New York, to discuss his journey from software engineering to building one of the most influential insurtech communities. Tony shares how he and his partner David Gritz started insurtech New York, their challenges in pivoting through the COVID-19 pan…

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Lessons in Persistence from Wade Millward’s Insurance Franchise Success 46:15

4M ago46:15

46:15

Welcome to this exciting episode of Founders Journey, where host Jeff interviews Wade Millward, a pioneering entrepreneur in the insurance industry. Wade recounts how he and Jeff first connected at an insurtech event in New Mexico three years ago, bonding over their shared passion for innovation. Wade's story starts as a third-generation insurance …

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ITC Vegas Reflection: Building Talent Pipelines with Laurissa Berk 11:32

4M ago11:32

11:32

In this episode of Post-ITC Reflection, we sit down with Laurissa Berk, Director of Global and Experiential Education at the University of Connecticut. Laurissa shares insights into how UConn is bridging the gap between academia and industry, particularly within the insurtech space. She discusses the university’s approach to fostering talent pipeli…

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Building a Life Saving Device and a CRM Empire with Beau Bratton 36:44

4M ago36:44

36:44

Welcome to this episode of Founders Journey, where Jeff dives into an inspiring conversation with Beau Bratton, a pioneering entrepreneur in CRM solutions. From his Santa Barbara roots to building a game-changing CRM tool in the insurance industry, Beau’s journey is one of resilience, innovation, and adaptability. He shares how his early telemarket…

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ITC Vegas Reflection: Event Takeaways & Industry Trends with Jon Spaugy 20:57

4M ago20:57

20:57

In this episode of Post-ITC Reflection, we sit down with Jon Spaugy to unpack his experience at ITC Vegas. Jon, a seasoned industry professional and event organizer, shares his first-time experience attending the conference as a registered participant. He reflects on the sheer scale of the event, key takeaways on networking, and how ITC fosters con…

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Building a Global Insurance Recruiting Empire with Nick Hoadley 40:31

4M ago40:31

40:31

In this episode of Industry Voice, host Jeff welcomes Nick Hoadley, founder of Insurance Search and host of the Insurance Coffeehouse Podcast. Nick shares his journey from law to insurance broking, and how his experiences led him to build a successful executive search firm specializing in the insurance and Insurtech industries. He dives into the ev…