Insurance Leadership Podcast

This podcast is designed to help insurance leaders improve their leadership skills and learn from the best in the industry. We pull in experienced leaders to tackle topics from employee engagement and management to creating vision that will elevate your organization. We believe that when we raise the bar for our leaders that our industry will thrive. At The Insurance Leadership Podcast, we provide you with resources that can be implemented in your business.

A Year of Change 11/06/2025

A Year of Change Markets moved fast, technology moved faster, and leadership had to keep pace. In this roundtable conversation, Casey Combest, Ryan Eaton, and Ben Markland reflect on the defining trends that shaped 2025—from digital transformation and carrier exits to AI innovation and developing the next generation of talent. The trio shares how brokers and carriers are adapting to a more data-driven, technology-forward marketplace while staying rooted in relationships, mentorship, and integrity. Whether you’re leading a team, managing partnerships, or navigating the changing insurance landscape, this episode highlights how adaptability, creativity, and human connection remain the keys to success. /episode/index/show/insuranceleadershippodcast/id/38820975

Millionaire Milestones 10/02/2025

Millionaire Milestones What if the key to financial freedom isn’t just about earning more—but preparing for the moment you won’t love your job anymore? In this episode, host Casey Combest sits down with Sam Dogen, better known as the Financial Samurai, to talk about his new book Millionaire Milestones: Simple Steps to Seven Figures. Sam shares practical strategies on forecasting your misery, managing inconsistent income, celebrating wins without losing focus, and investing with perspective in uncertain markets. Whether you’re a sales professional juggling commission, a leader steering a team through change, or someone planning for long-term independence, this conversation is packed with lessons to help you build wealth and lead with confidence. /episode/index/show/insuranceleadershippodcast/id/38276100

Vision Benefits in the Digital Age 09/04/2025

Vision Benefits in the Digital Age In this episode, Ben Markland sits down with Terry Ward, Senior VP of Sales at United Vision Plan, live from the ICMG Conference in Tampa, Florida. With over 40 years of experience in the vision benefits industry, Terry shares his journey and how technology, consumer expectations, and transparency are reshaping the way benefits are delivered. From the evolution of vision care to the rise of digital platforms, Terry offers a fresh perspective on leadership, adaptability, and meeting today’s industry challenges head-on. /episode/index/show/insuranceleadershippodcast/id/38033900

From Entrepreneur to Insurance Leader 08/07/2025

From Entrepreneur to Insurance Leader In this episode, Ben Markland talks with Dustin Moseley, Head of Distribution & Partnerships at Guardian Life, about his journey from entrepreneurship to the insurance industry. Dustin shares insights on building strategic partnerships, trends in the gig economy, and opportunities in the retiree market. He also discusses the importance of perseverance, staying informed, and how to navigate today’s evolving insurance landscape. Tune in for valuable advice and industry insights. /episode/index/show/insuranceleadershippodcast/id/37087210

From ER to Advocacy 07/03/2025

From ER to Advocacy What happens when someone with firsthand experience in both clinical chaos and corporate healthcare decides to challenge the status quo? In this episode of the Insurance Leadership Podcast, host Ryan Eaton sits down with Tiffany Rider—health policy expert, NFL cheerleader alum, ER clinician, and founder of 20+ ventures—to explore her unconventional journey from rural Louisiana to national healthcare reform advocate. Tiffany opens up about the defining moments that shaped her mission to empower patients, expose inefficiencies in the system, and bring transparency to the broker-employer relationship. From misaligned incentives to the promise of direct primary care, this conversation is a must-listen for brokers, business leaders, and anyone seeking practical ways to drive real change in healthcare. /episode/index/show/insuranceleadershippodcast/id/37216515

CEO & Founder of Thatch 06/05/2025

CEO & Founder of Thatch Welcome back to the Insurance Leadership Podcast! Chris Ellis, CEO and Founder of Thatch, joins co-host Ben Markland for a powerful conversation recorded live at the ICMI Conference in Tampa. From his early days in cancer research at MIT to launching a company built to empower brokers, Chris shares how a deep understanding of healthcare and a passion for solving real problems led him to create one of the most promising platforms in the benefits space. /episode/index/show/insuranceleadershippodcast/id/36767250

From News Desk to Distribution 05/01/2025

From News Desk to Distribution Welcome back to the Insurance Leadership Podcast! Alisha Pequeno, Head of Distribution and Broker Partnerships at Zurich North America, joins co-host Ben Markland to share leadership lessons from the carrier side. She discusses building strong partnerships, leading with authenticity, and creating a culture that drives growth. Tune in for practical insights to help you lead, adapt, and build lasting success. /episode/index/show/insuranceleadershippodcast/id/36278000

Reinventing Leadership After the Uniform 04/03/2025

Reinventing Leadership After the Uniform Welcome back to the Insurance Leadership Podcast! What happens when the uniform comes off—but the mission isn’t over? Army veteran and entrepreneur Adam Peters joins co-host Casey Combest to talk life after service, rebuilding identity, and leading with authenticity. From combat zones to boardrooms, Adam shares how discipline, vulnerability, and purpose helped him launch Stronghold—a thriving community supporting veterans in transition. This episode is packed with leadership insights for anyone navigating change, redefining success, or learning to lead from who they truly are. /episode/index/show/insuranceleadershippodcast/id/35884435

Leadership and Longevity 03/06/2025

Leadership and Longevity Welcome back to the Insurance Leadership Podcast! In this engaging episode of the Insurance Leadership Podcast, co-host Ben Markland welcomes Warren Laird, a seasoned leader in the insurance and vision care industry. With nearly three decades at VSP Vision Care, Warren shares invaluable insights on leadership, company loyalty, and fostering a workplace culture that stands the test of time. We explore the key lessons he’s learned throughout his career and how they apply to today’s ever-evolving business landscape. /episode/index/show/insuranceleadershippodcast/id/35525295

Simplifying Benefits 02/06/2025

Simplifying Benefits Welcome back to the Insurance Leadership Podcast! In this episode, Co-host Casey Combest opens today’s episode with Luke Aslesen, Founder of INFRMD, a leader in revolutionizing how employees engage with their benefits. Luke shares his fresh approach to simplifying complex insurance concepts and discusses innovative programs like Benefits Boot Camp, designed to transform employee education in the industry. /episode/index/show/insuranceleadershippodcast/id/35155175

New Year, New Voices: Bold Moves for 2025 01/02/2025

New Year, New Voices: Bold Moves for 2025 In this special episode, Ryan shares heartfelt gratitude for the team that made it all possible and introduces two new co-hosts: Casey Combest and Ben Markland. Both bring a wealth of knowledge and fresh energy, poised to add even greater depth to the ILP. Listeners will hear about exciting updates for the new season, including a revamped format with dynamic Q&A sessions, an impressive lineup of guest speakers, and an enhanced focus on audience interaction. /episode/index/show/insuranceleadershippodcast/id/34555965

Wrapping UP 2024 Highlights and Gratitude 12/05/2024

Wrapping UP 2024 Highlights and Gratitude Join us as we reflect on an incredible year of growth and insights. From leadership lessons with a former Secret Service leader to game-changing innovations in AI and industry expertise, 2024 was transformative. Celebrate the milestones, gratitude, and inspiration as we look ahead to a bright future! /episode/index/show/insuranceleadershippodcast/id/34247275

Small Agency, Big Impact 11/07/2024

Small Agency, Big Impact Welcome back to the Insurance Leadership Podcast! In this episode, host Ryan Eaton sits down with Mark Lampen, founder of Health Insurance Specialists, a Missouri-based general agency known for its exceptional service and specialized approach. Mark shares his journey from starting in insurance right out of college to building a successful small agency focused on quality over quantity. He discusses the benefits of specialization, the importance of relationship building, and how staying hands-on with brokers and clients has helped him thrive in an industry filled with larger competitors. Join us to hear Mark’s insights on the unique strengths that small agencies bring to the insurance world! /episode/index/show/insuranceleadershippodcast/id/33817242

Bigger Isn’t Always Better 10/03/2024

Bigger Isn’t Always Better Welcome back to the Insurance Leadership Podcast! In this episode, Ryan Eaton talks with Mikel Cook, owner of The Cook Group Inc., about his 25-year journey in the insurance industry. Mikel discusses his transition from Blue Cross Blue Shield to founding his own general agency in Dallas, Texas, and reflects on 15 years as a general agent, highlighting the challenges and successes of running a small GA in a market dominated by larger corporations. /episode/index/show/insuranceleadershippodcast/id/33276582

Building For The Future 09/05/2024

Building For The Future Welcome back to the Insurance Leadership Podcast! I'm Ryan Eaton, and today we have an outstanding guest. Joining us is Suril Kantaria, Co-founder of , a visionary leader who's made waves in both insurance and tech. From his days as student body president at Dartmouth to founding and scaling Savvy, and even contributing at Twitter under Elon Musk, Suril has consistently pushed the boundaries of what's possible. /episode/index/show/insuranceleadershippodcast/id/32757207

From Secret Service to Insurance 08/01/2024

From Secret Service to Insurance Welcome to another engaging episode of the Insurance Leadership Podcast, hosted by Ryan Eaton. In this episode, we chat with Richard Lett, CEO of LeClair Group, who has an intriguing background that spans from serving in the British Secret Service to leading an FMO in the insurance industry. Tune in to uncover Richard’s unique journey and gain insights on leadership, risk management, and the importance of relationships in business. /episode/index/show/insuranceleadershippodcast/id/32256172

Adapting to Change 07/03/2024

Adapting to Change In Episode 40 of the Insurance Leadership Podcast, Ryan Eaton welcomes Brendan McLoughlin, President and Chief Marketing Officer at e123. Brendan shares his extensive experience in the healthcare industry, innovative approaches to distribution, and the impact of technology and AI on business processes. /episode/index/show/insuranceleadershippodcast/id/31926372

Unleashing the Power of Distribution 06/06/2024

Unleashing the Power of Distribution This episode features a chat with industry veteran Tom Dimmer, who has 37 years of experience and Vice President Business Development with Renaissance Life and Health. Tom shares his extensive knowledge of distribution, focusing on how to effectively get carriers, plans, and rates on various platforms and exchanges. The conversation spans a wide range of topics, from the intricacies of individual and group markets to the importance of adapting to different distribution channels. /episode/index/show/insuranceleadershippodcast/id/31521777

Revolutionizing Insurance 05/02/2024

Revolutionizing Insurance In this Insurance Leadership Podcast episode, host, Ryan Eaton and Chad Hogan discuss Quotit's transformative impact on carriers and the insurance landscape. Chad shares Quotit's role in streamlining enrollment processes and highlights technology's importance in insurance. They explore AI-driven analytics, automation for brokers, and improved data exchange standards. Discover how Quotit is reshaping the industry for a more efficient and consumer-centric experience. Tune in at . /episode/index/show/insuranceleadershippodcast/id/31036338

Excellence in Product Development 04/04/2024

Excellence in Product Development Our latest Insurance Leadership Podcast embarks on an illuminating journey through the intricate landscape of insurance product development. A treasure trove of insights from industry trailblazers on pivotal topics like distribution strategies, visionary leadership, and product development can be found in the second of five mini-series episodes. Join host Ryan Eaton as he explores the minds of two distinguished guests: Marc Flood, Senior Vice President, Business Development at Crum & Forster and Bryan Krul, Vice President of Growth and Strategy at Crum & Forster. Tune in for valuable takeaways on strategic adaptation and more. To learn more about leadership skills visit us at www.insuranceleadershippodcast.com /episode/index/show/insuranceleadershippodcast/id/30638393

Charting A Course For Success 03/07/2024

Charting A Course For Success Welcome to the Insurance Leadership Podcast, where industry leaders navigate challenges and embrace innovation for growth. Join host Ryan Eaton in a conversation with Kyle Dietz, Senior VP of Sales for Healthcare.com, as they explore leadership insights and industry trends. Tune in for valuable takeaways on strategic adaptation and more. /episode/index/show/insuranceleadershippodcast/id/30185353

Generations of Leadership 02/01/2024

Generations of Leadership Join us in this insightful episode as we explore into the unique leadership dynamics between a father and son in the health insurance industry. Rick Eaton, the Chief Operating Officer, and his son, Ryan Eaton, the Head of Broker Services Division and Chief Marketing Officer, share their experiences navigating family relationships while holding key positions in the company. /episode/index/show/insuranceleadershippodcast/id/29739868

Year-End Recap: Revisiting Highlights 01/04/2024

Year-End Recap: Revisiting Highlights In this month's installment, host Ryan Eaton revisits the standout moments from each guest speaker's episode throughout the year. Each speaker offered a unique perspective on thought leadership in the dynamically evolving insurance industry, covering a spectrum of topics from acquisitions to technology. As we look back at these insightful snippets, we eagerly anticipate a more inspiring year ahead in 2024. /episode/index/show/insuranceleadershippodcast/id/29323843

In The Leader’s Chair: Q & A With Ryan Eaton (Part 2) 12/07/2023

In The Leader’s Chair: Q & A With Ryan Eaton (Part 2) On today's Insurance Leadership Podcast, we discussed Part 2 of the episode 'Ryan Eaton In the Leader's Chair' with host Casey Combest. As we continued our conversation with Ryan, we gained invaluable insight into key leadership strategies within the insurance industry. /episode/index/show/insuranceleadershippodcast/id/28679473

In The Leader’s Chair: Q & A with Ryan Eaton (Part 1) 11/02/2023

In The Leader’s Chair: Q & A with Ryan Eaton (Part 1) In this episode, join Ryan Eaton as he becomes both the host and guest. Casey Combest, producer for the Insurance Leadership Podcast, sits down with Ryan for this special episode. Listen to Ryan and Casey as they discuss the intricacies of leadership, personal development, secrets of effective communication, team engagement, and the art of decision-making. Check out our website at for bonus content. /episode/index/show/insuranceleadershippodcast/id/28472759

ACA Enrollment Platforms 10/05/2023

ACA Enrollment Platforms In this episode, Ryan and Chad explore the invaluable benefits that Quotit brings to carriers in the insurance landscape. Chad Hogan, with his wealth of experience, walks us through the efficiency of electronic enrollment. He sheds light on how Quotit has streamlined the enrollment process for both consumers and agents. As the president of Quotit, Chad delves into crucial aspects such as pricing models, implementation strategies, and the significance of building strong partnerships in the insurance ecosystem. The conversation is a deep dive into Quotit's innovative approach, emphasizing the delivery of clean data and a seamless experience for agents and consumers alike. Tune in as Chad Hogan shares his expertise and unveils Quotit's approach to enrollment that is reshaping the insurance industry. For more episodes visit us at www.insuranceleadershippodcast.com /episode/index/show/insuranceleadershippodcast/id/28208789

Voluntary Disruption 09/07/2023

Voluntary Disruption Welcome to the Insurance Leadership Podcast, hosted by Ryan Eaton. In this week's episode of the Insurance Leadership Podcast, we are joined by Eric Silverman, a prominent figure and catalyst for change in the realm of enhanced employee-funded benefits. Eric's expertise and innovative approach have significantly impacted the insurance industry. He provides a fresh perspective on employer benefits and marketing strategies that will challenge conventional thinking. During the podcast, Eric engages in a conversation with Ryan about his journey into the insurance industry, which began after his college graduation. This experience has played a pivotal role in shaping the life he leads today. He delves into his unique business model, which he developed in response to identified gaps within the insurance market. Eric also emphasizes his philosophy on renaming voluntary benefits to better convey their value to employees. Additionally, he sheds light on the crucial elements of effective marketing for insurance products. This episode promises a wealth of insights that will reshape your understanding of insurance and benefits. Don't miss this opportunity to gain valuable knowledge from Eric Silverman's perspective on the Insurance Leadership /episode/index/show/insuranceleadershippodcast/id/27892326

Lead You 08/03/2023

Lead You Welcome to the Insurance Leadership Podcast, hosted by Ryan Eaton. Today's episode showcases Bobby Harrington, a renowned author, and CEO of Rubicon COA. Harrington shares valuable insights on leadership, drawing from his diverse background in college football, the Marines, and years of corporate leadership in Fortune 500 companies. His latest book, "Lead You," places a strong emphasis on the importance of self-leadership. Through personal experiences such as surviving in the Philippines and working with college athletes, Harrington illustrates how these diverse experiences contribute to personal growth as a leader. He emphasizes the power of practicing and refining skills through self-leadership while acknowledging that certain leadership traits are inherent. Throughout the conversation, Harrington sheds light on the demanding nature of leadership and emphasizes the significant role that self-leadership plays in attaining success. /episode/index/show/insuranceleadershippodcast/id/27457629

Morgan White Group’s New InPocket Plan 07/06/2023

Morgan White Group’s New InPocket Plan We extend a warm welcome to our esteemed guest speakers, David White and Rick Holmes, as they grace the platform of the Insurance Leadership Podcast, hosted by Ryan Eaton. Together, they embark on an enlightening discussion centered around the groundbreaking InPocket Plan Health Insurance Supplement by Morgan White Group. In their enlightening dialogue, Holmes and White shed light on a critical issue plaguing countless individuals: the struggle to afford essential healthcare due to exorbitant out-of-pocket costs and burdensome deductibles. Drawing attention to a staggering statistic revealing that more than 60% of Americans have less than a thousand dollars in their bank accounts, they emphasize the pressing need for a solution. /episode/index/show/insuranceleadershippodcast/id/27359160

Navigating Volatile Markets 06/01/2023

Navigating Volatile Markets In this episode, we are thrilled to have Sam Dogen, author of Buy This Not That and a seasoned professional with a background in investment banking and Wall Street. Today, Sam shares his expertise with Ryan Eaton, as they delve into the intricacies of business management, personal finance, and the current state of the economy. With a focus on practical tips and strategies, they discuss how to navigate the challenges of a volatile market and position oneself for success both personally and professionally. Whether you are a business leader, entrepreneur, or simply looking to improve your financial literacy, this episode offers valuable insights and principles to live by. So, sit back, relax, and tune in to the Insurance Leadership Podcast. /episode/index/show/insuranceleadershippodcast/id/26990526

Insurance Leadership Podcast

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