Agency Intelligence

Executive Sessions focus on the person behind the position, and that’s exactly what happens here. Jason Cass sits down with Keith Savino, Managing Partner at Trucordia, live at Accelerate. With over three decades in the business, Keith shares lessons from his journey through five agencies, the evolution of insurance tech from green screens to AI, and why servant leadership and collaboration still drive the industry forward. Key Topics: The insurance industry’s “inside baseball” pace and why it only feels slow from the stands. How community, collaboration, and consensus have fueled decades of industry progress. Mentorship and servant leadership lessons from Mike Stein and other early influences. Building success by putting others first and leading with purpose. From green screens to AI and Keith’s early days implementing technology in the late 1980s. The evolution of transactional filing and how it shaped modern agency efficiency. Predictions for 2030, including resp

In this Halloween-themed episode of Stuff About Money They Didn’t Teach You in School, host Erik Garcia, CFP®, ChFC®, BFA™ is joined by Dr. Matt Morris and first-time guest Stephanie Osborn for a fun and insightful conversation about fear, especially the fear of money. The trio starts by sharing their thoughts on scary movies (and why Erik can’t stand them) and explores some New Orleans lingo about what it really means to call someone “scary.” From there, they draw parallels between the things that spook us on screen, and the real-life anxieties people feel around money. As the discussion unfolds, they unpack why money can be so intimidating and how fear often leads to poor, or no financial decisions at all. The group explores the antidote to financial fear: identifying what’s truly important to you, Erik’s first pillar of financial security. Matt shares personal stories about how that focus has helped him overcome financial stress, while Erik and Stephanie offer practical strategies like setting small goa

The Executive Sessions: Ryan Westerman, President at AndDone Executive Sessions are all about humanizing the C-suite, and this one does just that. Jason sits down with Ryan Westerman, President at AndDone, to talk about his path from physics major to payments innovator, the lessons that shaped his leadership, and how AndDone is changing the way agents get paid. What starts as a career story unfolds into an honest look at communication, responsibility, and the human side of leading a growing company. Key Topics: Ryan’s journey from physics and public administration to leading a fintech company in insurance How a Pepsi bottling job sparked his entry into payment facilitation and technology innovation The birth of AndDone and its mission to simplify premium collection for agents Why Ryan believes technology and business models must evolve together Lessons from early mentors on communication, clarity, and explaining ideas that inspire buy-in The human side of executive lea

In this new episode of Insurance Shoptalk, join host Eric Stein and guest Jim Urseth, president of Reliable Premium Management (RPM), for a deep-dive into their pay-as-you-go solutions. RPM has many unique offerings, including a pay-as-you-go general liability program billed by payroll instead of the company’s revenue. Their pay-as-you-go offerings also include Workers’ Compensation programs, with superior options, flexibility, and benefits like easy implementation, a simplified audit experience, and pay-as-you-go insurance premiums to minimize the upfront costs of Workers’ Compensation. To learn more about RPM and their pay-as-you-go solutions, find them online at https://reliablepremium.com/. About Insurance Shoptalk: Join host Eric Stein on a journey through the dynamic world of commercial property and casualty insurance. With over 25 years of experience in the industry, Eric brings a wealth of knowledge and insights to every episode. Insurance Shoptalk is your premier destination for in-depth discu

When clarity meets compassion, leadership becomes legacy. Jason Cass sits down with Jason Sanders, COO and Senior Vice President at IPFS, for an Executive Session that uncovers how a people-first mindset can shape an entire organization. From starting in the mailroom to building one of the industry’s most respected leadership programs, Jason shares how structure, service, and culture drive both his success and IPFS’s future. Key Topics: Jason’s rise from the mailroom to COO at IPFS and what he learned at every level The creation of IPFS’s Leadership Development Program and its impact on culture Why clarity and transparency are essential traits of great leadership How mentorship shaped his philosophy that “clarity is kindness” The role of rhythm, discipline, and family in sustaining leadership energy Giving back through community service and serving on the Children’s Mercy Hospital board The vision for a more agile, future-ready IPFS that’s more than just premium fin

In this episode of Insurance Shoptalk, explore the world of human resources (and more!) with host Eric Stein and special guest host Ryan Floyd. Eric and Ryan talk with David Ainsworth and David Bell from Zynergia, a trusted HR partner that offers a variety of services, including payroll, benefit management, risk management, and more. They discuss Zynergia’s the coverage, features, and benefits of their unique programs, especially their PEO and Workers’ Compensation offerings. To learn more about Zynergia and their services, please find them online at https://zynergiahr.com/ About Insurance Shoptalk: Join host Eric Stein on a journey through the dynamic world of commercial property and casualty insurance. With over 25 years of experience in the industry, Eric brings a wealth of knowledge and insights to every episode. Insurance Shoptalk is your premier destination for in-depth discussions on the latest industry trends, technology impacts, interviews with leading experts, and much more. If you en

In this episode of Stuff About Money They Didn’t Teach You in School, Erik Garcia, CFP®, ChFC®, BFA™, and Xavier Angel, CFP®, ChFC®, CLTC, tackle one of the most important yet often overlooked financial topics: long-term care. The conversation kicks off with a laugh as Erik shares how Xavier nearly got himself kicked out of a professional study group for challenging the conventional wisdom around long term care insurance. That sets the stage for a lively discussion about why this issue matters so much, even if it is not the kind of thing people want to chat about at a cocktail party. Between sobering stats about rising care costs and Xavier’s candid story of his aunt currently in a long term care facility, this episode keeps things engaging while shining a light on a subject that is too often ignored. But ignoring the problem does not make it go away. With the average nursing home room now costing well into six figures annually, long term care planning is a reality everyone needs to address. Erik and Xavier

What shapes a leader who has spent decades at the highest levels of business? Jason sits down with Frank Friedman, CEO & President at IPFS, for an Executive Session that blends personal stories with industry insight. From mentors who made a difference to premium financing, payments innovation, and the future of insurance tech, this conversation highlights the human side of leadership. Key Topics: Early career mistakes that shaped Frank’s leadership style The mentors who stood behind him during pivotal moments Lessons from decades at Deloitte and a global COO role The pace of technology change, from the dot-com bubble to AI How IPFS and AndDone are innovating payments and financing Why consolidation and automation will define the next decade Frank’s perspective on AI’s impact on jobs and efficiency The books and history that inspire Frank’s worldview A defining 9/11 experience that reshaped Frank’s perspective on unity Reach out to: Frank Fried

What happens when a State Farm agent decides he’s not cut out for the captive world and instead builds a tech empire supporting $2B in premium? Jason Cass sits down with Austin Moorhead, Founder of Lava Automation to unpack that journey.  Key Topics: Austin’s leap from State Farm to automation and his “lightbulb moment” with Keap Growing from a side project into 350+ virtual assistants powering $2B in premium Balancing hard work, family, and redefining success in the agency tech space Why AI hype feels like past industrial shifts and what it really means for agencies How LAVA approaches SOC 2 certification and data security in the AI era Turbo Dial’s customizable VoIP and HubSpot’s growing role in larger agencies Why lead generation remains the great separator for top-performing agencies Optimizing websites for ChatGPT and AI-driven search, not just Google Fear, valuations, and why relationships still anchor the future of independent agents Reach out

In this episode of Front Cover: A Rough Notes Podcast on the Agency Intelligence Podcast Network, Jason Cass sits down with Jackson Rollo, President at Rollo Insurance, the agency featured on the October 2025 front cover of Rough Notes Magazine.  Key Topics: The honor of being featured on the Rough Notes Magazine front cover Carrying forward a family agency legacy while creating new impact Jackson’s journey from aspiring attorney to agency president The “God, Family, Country” framework shaping their culture Why investing in a Director of Culture transformed their agency Building unity through quarterly leadership book studies Lessons from Good to Great and embracing healthy debate Scaling from 60 to 275 employees while preserving culture AI as a tool for growth, not replacement, in the insurance industry Balancing rapid expansion with staying true to core values Reach out to: Jackson Rollo Jason Cass Visit Website: Rollo

We’re bringing back a powerful Executive Session with Ryan Hanley, who at the time of this recording was CMO at Linqura (and is now the company’s President). In this replay, Ryan opens up about his journey from small-town beginnings to industry leadership, sharing raw insights on humility, resilience, and the seasons of business leadership. He and Jason dig into AI’s role in reshaping insurance, why data accuracy and security can’t be overlooked, and the surprising parallels between leading a company and raising a family. Key Topics: Navigating the seasons of leadership and evolving roles as businesses grow. Why shedding your ego is essential to leveling up as an entrepreneur. How diverse career experiences create unmatched perspective and adaptability. The three human roles that remain in an AI-driven insurance future. Linqura’s mission is to make every agent a specialist with real-time insights and data. How parenting challenges mirror leadership—building resilience thr

What does marketing look like when it’s less about pushing products and more about building trust?  Jason sits down with Rushang Shah, Chief Marketing Officer at HawkSoft, for an Executive Session about trust-driven marketing, lessons from the early tech world, and how a purple cow became the company’s most recognizable symbol. Key Topics: Why HawkSoft views marketing as building trust, not promotion The family story behind HawkSoft’s 30-year growth journey How Rushang’s tech background shaped his approach to insurance The origins of HawkSoft’s “Purple Cow” and what it represents Why HawkSoft focuses on bleeding efficiency instead of bleeding edge Helping agencies balance tradition with new technology demands Marketing as education: why HubSpot inspired HawkSoft’s strategy Reach out to: Rushang Shah Jason Cass Visit Website: HawkSoft Agency Intelligence Produced by PodSquad.fm

In this episode of Stuff About Money They Didn’t Teach You in School, hosts Erik Garcia, CFP®, BFA™, ChFC®, and Xavier Angel, CFP®, ChFC®, CLTC, dive into what they call “backwards planning.” Erik shares a story about driving his daughter to college, where the destination was clear but the journey allowed for meaningful detours that still aligned with their ultimate goal. This idea of starting with the end in mind sets the stage for a conversation about how clarity in your future direction influences the decisions you make today. Together, Erik and Xavier explore why envisioning your future, whether that is retirement, your personal life, or your career, matters so much. They highlight fascinating research showing that people who see an older version of themselves are more likely to save for the future, underscoring the power of visualization in financial planning. Tune in to learn how backwards planning can help you make intentional choices now that lead to the life you want later. If you enjoy this episo

What happens when the next generation of InsurTech leaders blends efficiency with servant leadership? Jason Cass sits down with Toby Hung, Co-Founder & COO of 1Fort, to talk about AI-driven automation, the future of agency workflows, and why people, not just technology, remain at the center of insurance. Key Topics: Toby shares 1Fort’s vision as an all-in-one AI solution for commercial agencies Automating submissions and proposals with AI to save time and money Why productivity and efficiency are two sides of the same strategy Lessons on leadership, mentorship, and building with servant values The insurance talent shortage and what younger generations want from work How agencies can make insurance a career path for Gen Z and Millennials The role of culture, impact, and balance in retaining and growing great teams Reach out to: Toby Hung Jason Cass Visit Website: 1Fort Agency Intelligence Produced by PodSquad.fm

In this episode of Insurance Shoptalk, join host Eric Stein and guest Vladimir Vladimirov for an in-depth exploration of NowCerts and their cloud-based integration CRM and agency management system, Automate 365. In this episode, NowCerts system manager Vladimir talks though the many uses and benefits of Automate 365, including the system’s ability to assist P&C agents with task like online quoting, sales, marketing, customizable reporting, and workflow automations. To learn more about NowCerts, please visit www.nowcerts.com. You can also learn more about Automate 365 at www.automate365.com. About Insurance Shoptalk: Join host Eric Stein on a journey through the dynamic world of commercial property and casualty insurance. With over 25 years of experience in the industry, Eric brings a wealth of knowledge and insights to every episode. Insurance Shoptalk is your premier destination for in-depth discussions on the latest industry trends, technology impacts, interviews with leading experts, and much mo

Executive sessions are all about pulling back the curtain, and this one does just that. Sean Hawkins, Co-Founder and VP of Development at HawkSoft, joins Jason to share how a farm kid turned programmer helped build one of the industry’s most trusted systems. From navigating shiny tech trends to keeping data ownership and people first, Sean’s story shows why HawkSoft’s culture continues to stand out. Key Topics: Sean’s early programming roots and the origins of HawkSoft with his dad Why InsurTech “shiny objects” sometimes become core system features Balancing thousands of agency requests without losing product focus The importance of data ownership and HawkSoft’s people-first philosophy Security challenges with users, vendors, and virtual employees How Sean blends product leadership with being a developer at heart Life outside of work: woodworking, pickup basketball, and raising five kids Reach out to: Sean Hawkins Jason Cass Visit Website: Haw

Are you disgusted yet? Yes, disgusted! But, disgusted with your own personal sales results, more specifically. I mean, at the end of the day, nothing will get better until you become disgusted enough with the results you've been getting that you then implement change and do something different. It really is that simple. Building a $1,000,000 or more Book of Business through a signed Broker of Record Letters is really that simple. That hard, but also that simple. In today's episode, host Charles Specht will explain to you the "buckets" you should be most concerned about, and how to know what to change and by how much. Moreover, the next cohort of the "PERMISSION PRODUCER SCHOOL" will be starting on October 6, 2025. Find out more information by visiting: www.PermissionProducerSchool.com You won't want to miss out on this one! Key Topics: Why real change only comes after you’re disgusted with the status quo The “bucket” exercise to identify what’s holding back your sales success How wa

Ohio Workers’ Comp Just Changed – Here’s What Agents Need to Know: In this episode of Insurance Shoptalk, host Eric Stein talks with Bob Butts, Chief Risk Officer at Alternative Comp Solutions (ACS), about a major change in Ohio’s workers’ compensation market. For the first time, agents can now sell workers’ comp in Ohio and earn commission, thanks to Senate Bill 2011 and approval by the Ohio Bureau of Workers’ Compensation. Bob explains how ACS is leading the way with an Alternative Employer Organization (AEO) model that saves employers 10–30% on premiums, simplifies claims handling, and eliminates the need to switch payroll systems. The discussion covers the differences between AEOs and PEOs, how the pay-as-you-go approach helps employers with cash flow, and why this new model is such a big opportunity for insurance agents. About Insurance Shoptalk: Join host Eric Stein on a journey through the dynamic world of commercial property and casualty insurance. With over 25 years of experience in th

What happens when the heart of a company beats just as strongly as its technology? Jason sits down with Paul Hawkins, CEO at HawkSoft, for an in-person Executive Session at HawkSoft HQ. From family roots and servant leadership to AI, agency tech trends, and the story behind the Purple Cow, this conversation is as much about people as it is about platforms. Key Topics: Why HawkSoft hires 80% on culture and 20% on skill The role of family and faith in shaping HawkSoft’s leadership style Paul’s journey from dairy farm to software founder Technology shifts that moved from “peripheral” to core in agencies How AI and system integration are reshaping agency workflows Lessons on servant leadership and building other leaders Advice Paul would (and wouldn’t) give his younger self The story of HawkSoft’s Purple Cow movement Why people, not products, define a company’s success Building a workplace culture that wins awards year after year Reach out to:

What do engineering, entrepreneurship, and divinity have to do with each other? Apparently, more than you think. In this episode, Erik Garcia, CFP®, ChFC®, BFA™, sits down with Tulane professors Rob Lalka, who teaches entrepreneurship, and Matt Escarra, a professor of engineering, to talk about a course that challenges students to ask the big questions. They discuss technology, ethics, purpose, and yes, even money. Inspired by a curriculum from Yale Divinity School, the class invites students to wrestle with questions like: What is the good life? What should we hope for? And how do we shape a future worth building? Together, they explore how innovations like AI, gene editing, climate tech, and social media are not just technical challenges. They are deeply human ones. This conversation will make you think differently about how we define progress, what we value, and how we prepare the next generation of leaders. If you enjoy the episode, follow the show, share it with a friend, and keep asking the questions