Podcast
The Insurance Growth Lab
Hosted by Callan Harrington · EN
Host Callan Harrington dives into the strategies, decisions, and lessons that have shaped the careers of top marketing and growth leaders in the insurance industry. From bold moves to costly mistakes, each episode uncovers real-world insights that listeners can apply to accelerate growth in their own businesses.
30episodes
Episodes
Newest firstAll episodes
How Rollo Insurance 5X'd in 5 Years Without a Niche or Outside Capital
1w ago00:42:14Tap to summarizeCallan Harrington sits down with Jackson Rollo, President of Rollo Insurance, to explore how he became president at 24 and led the agency through 5x growth over 5 years without private equity backing.Jackson explains Rollo's unique philosophy of being a local generalist rather than pursuing industry niches, focusing on relationships and community connections over product specialization. He details their systematic approach to scaling culture across 250 teammates in 50 locations nationwide, including the creation of the Rollo Rules and integration processes for acquisitions. The conversation covers practical strategies for driving cultural adoption remotely and how they maintain their family business values while achieving venture-backed growth rates.Discover how relationship-first thinking and local community focus can drive exceptional growth in the insurance industry.Key topics covered:[00:00] Intro[02:17] Top producer credibility drives leadership success[04:02] Converting sales expertise into teachable processes[07:59] Local generalist strategy over niche specialization[11:03] Building trust through personal connections[13:27] Scaling local relationships across multiple states[17:12] Culture integration for new acquisitions[22:28] Handling cultural misalignment in acquisitions[25:59] Defining culture through beliefs values standards[29:26] Driving adoption of Rollo Rules nationwide[33:53] Right people doing right way growth formula[38:13] Learning from mistakes with mentorship guidance[40:20] 10 year vision staying true to core valuesConnect with Jackson Rollo: https://www.linkedin.com/in/jacksonrolloSubscribe to The Insurance Growth Lab for more tactical insights from top insurance industry leaders, and don't forget to leave a review if this episode was valuable to you.
Transcribe →How Brokers Can Become True Risk Advisors with Aclaimant President David Wald
2w ago00:40:52Tap to summarizeCallan Harrington sits down with David Wald, President and Co-Founder of Aclaimant, to explore what it truly means to become a risk advisor in today's insurance market. David shares the unexpected origin story of Aclaimant and its growth trajectory to tracking billions of dollars in claims annually and serving thousands of companies.The conversation dives into the practical aspects of becoming a true risk advisor rather than just a rate-shopping broker. David outlines the three key components that separate real risk advisors from those who just talk about it. He also shares his insights on the importance of leveraging professional networks, the transition from founder to president, and why listening to industry veterans can accelerate business growth.This episode provides actionable insights for brokers looking to evolve their service model and technology entrepreneurs entering the insurance space.Key topics covered:[00:00] Intro[01:01] Father-in-law's app idea sparks startup[04:11] Three early customers say yes immediately[07:58] What being a risk advisor really means[11:00] Quarter million premium threshold for advisory services[12:32] Three parts of successful risk advisory[17:54] Geographic density versus vertical specialization[22:46] Leveraging asymmetric relationship advantages[25:48] Network building creates business opportunities[30:34] Hiring Kathy Burns as CEO transition[34:47] Organizational maturity through experienced leadership[37:33] Listen more to industry wisdomConnect with David Wald on LinkedIn: https://www.linkedin.com/in/davidawaldSubscribe for more tactical insurance growth insights and strategies from industry leaders who are driving real results.
Transcribe →Chris Paradiso's Retention System Every Insurance Agency Needs
3w ago00:43:41Tap to summarizeHost Callan Harrington sits down with Chris Paradiso, owner of Paradiso Financial and Insurance Services, to dive into the retention strategies that form the foundation of real agency growth. Chris shares how his 50+ employee agency learned the hard way that retention is everything when their numbers dropped nearly 10% after getting lazy with client communication during COVID.Chris breaks down his systematic approach to client retention, from the 60-day renewal process to the three-attempt phone call strategy for top clients. The conversation covers practical tactics like same-call resolution, Net Promoter Score follow-ups, and why Chris believes emails are for information but phone calls are for communication.This episode delivers actionable insights for any agency owner looking to build sustainable growth through stronger client relationships and proven retention systems.Key topics covered:[00:00] Intro[01:00] Marine Corps Boot Camp Experience[03:46] Conquering Fear Through Challenges[07:37] Real Growth Starts with Retention[08:15] Vegas Agency Retention Disaster[10:45] Phone Calls Drive Retention Success[13:53] Calling Every Single Client[18:14] Single A Clients Become Triple A's[20:30] Growth Formula with Retention Math[21:00] Soft Market Premium Challenges[23:55] Coverage First Price Second Strategy[26:02] Recording and Auditing Phone Calls[28:44] Segmented Client Touch Points[30:21] 60 Day Renewal Process[32:17] Net Promoter Score Follow Up[34:01] Dunkin Donuts Gift Card Hack[37:36] Same Call Resolution Strategy[39:17] First Step Retention Coaching Advice[41:40] Investing in the Best TrainingConnect with Chris Paradiso on LinkedIn: https://www.linkedin.com/in/christopherparadisoSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.
Transcribe →How Lyndon Block Built 7 Insurance Brokerages Through Community Building
May 700:40:46Tap to summarizeCallan Harrington sits down with Lyndon Block, President & CEO of Block's Agencies, Prairie Insurance, Mello Insurance, and Rosthern Agencies, to explore his unconventional path to building 7 insurance brokerages across Saskatchewan. Lyndon shares how a chance encounter with marketing expert Chris Paradiso at a conference sparked a relentless pursuit of digital marketing mastery that changed everything. After being called out for doing "nothing" with his marketing efforts, Lyndon's persistence led to a life-changing mentorship in Connecticut, where he learned the fundamentals of digital growth.The conversation reveals Lyndon's dual strategy of building both a self-funded digital insurance platform and acquiring struggling small-town agencies. He explains why distressed assets in rural communities represent hidden opportunities and how his boots-on-the-ground approach builds the trust necessary to turn around declining agencies.This episode offers practical insights for anyone looking to grow through acquisition or build authentic community connections in their business.Key topics covered:[00:00] Intro[02:09] Wake up call from insurance marketing guru[03:32] Flying to Connecticut for free training[05:55] Persistence as a competitive advantage[08:00] Self funding a digital insurance agency[09:27] Gary Vaynerchuk's cannibalization strategy[11:19] Building API bridges for online insurance[12:02] Old school door knocking for lead generation[14:17] Two minute tenant insurance buying process[16:37] Small town community strategy explained[18:58] Why buy struggling insurance agencies[21:33] Small town loyalty creates sticky clients[25:02] Turning around distressed agencies[28:40] Being present at hockey games and pancake breakfasts[31:17] Using comedy to generate insurance business[34:44] Digital versus community agencies coexisting[36:56] Never say no to opportunitiesConnect with Lyndon Block on LinkedIn: https://www.linkedin.com/in/lyndonblock/Subscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.
Transcribe →How Curtis Barton Built ALKEME into a $2B Insurance Powerhouse
Apr 3000:44:32Tap to summarizeCurtis Barton didn't take the traditional path to building a large platform agency. He convinced six agency owners to merge their businesses, raise private equity capital together, and build something that had never been done in the industry. ALKEME is now ranked 21st on the Insurance Journal top 100, with over $2 billion in premiums written, $122 million in EBITDA, and 83 acquisitions completed.Callan Harrington sits down with Curtis to break down how ALKEME was built from the ground up, why they moved every agency onto a single integrated system before anyone was talking about it, and how they use AI today to turn account managers from reactive paper pushers into proactive mini-salespeople. This episode is a blueprint for any agency owner thinking about what it actually takes to scale past a lifestyle business and build something that lasts.Key topics covered:[00:00] Intro[01:18] Skiing teaches business adaptation skills[04:24] Why leaders must explain change[06:48] Building agency from zero revenue[09:02] Lifestyle business versus generational wealth[11:00] Constant reinvestment beats traditional playbooks[12:36] Eight agencies merge into platform[17:19] Roadblocks to starting agency platforms[22:23] Pick niche then hyper niche[25:18] Organic growth fuels acquisition capacity[28:58] AI automates workflow from inbox[32:16] Blind scoring acquisition targets[36:22] Scale beats growth every time[40:07] Maturity means leading with intelligence[44:49] Building forever company not exitConnect with Curtis Barton on LinkedIn: https://www.linkedin.com/in/curtisbartonSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.
Transcribe →Breaking Down Modern Claims Operations with Snapsheet President Andy Cohen
Apr 2300:39:23Tap to summarizeCallan Harrington sits down with Andy Cohen, President and COO of Snapsheet, to dive into why claims operations represent the biggest opportunity left in insurance, and what it actually looks like when carriers get it right. Andy brings perspective from both the carrier side and Snapsheet's work with over 180 carriers, including 16 of the top 20 P&C carriers. Andy covers why loss adjustment expenses have barely moved even as premiums have surged, what modern claims operations actually look like when they're working, and what brokers and agents should be asking their carrier partners to hold them accountable on performance.This episode provides actionable insights for anyone looking to understand how claims technology can drive better outcomes and competitive advantage in today's insurance market.Key topics covered:[00:00] Intro[01:15] Change Management Takes 3 Years at Carriers[03:02] AI Moving Fast in Insurance[06:16] Snapsheet's 180 Carrier Network[08:10] Claims Tech Overnight Success 14 Years Later[10:59] Brokers Haven't Paid Attention to Claims[15:28] Agents Can Vote With Their Feet[18:03] Questions Agents Should Ask Carriers[21:07] Best Practices from Top Carriers[24:08] Key Questions About Loss Adjustment Expense[26:28] Modern Claims Process Breakdown[30:40] Where Agents Insert Themselves[32:49] The Next 10 Years of Claims[36:03] Modernization vs True Transformation[38:31] Claims as Competitive AdvantageConnect with Andy Cohen on LinkedIn: https://www.linkedin.com/in/andrewjustincohenSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.
Transcribe →What Top Insurance Producers Do Differently with Paul VanderMarck
Apr 1600:37:46Tap to summarizeHost Callan Harrington sits down with Paul VanderMarck, Chief Technology and Innovation Officer at SageSure, to explore what the best insurance producers actually do differently, and why a softening market is about to make that question impossible to ignore.Paul shares how top producers navigate the shift from a supply-constrained hard market to one where competition on price is back, and carriers are getting aggressive. He walks through a real example of how an admitted policy with full replacement cost coverage is a fundamentally different product than a surplus lines policy with a roof payment schedule, and why the agents who can explain that difference are also the most insulated from AI reshaping distribution.This episode is a must-listen for any producer or carrier executive trying to understand where distribution is headed and what it actually takes to win in a softening market.Key topics covered:[00:00] Intro[01:09] Mountain bike sales lesson for insurance[04:19] Why insurance isn't really a commodity[06:42] What top producers actually do differently[09:17] True advisory selling versus order taking[12:27] Technology supporting producer education[16:34] Hard market survival strategies for agents[19:39] Soft market competition and pricing tactics[22:55] AI deployment in insurance operations[25:28] AI threat to insurance distribution channels[28:37] Future of AI in customer acquisition[31:26] Leveraging AI for producer training acceleration[35:27] Insurance as life partnership visionConnect with Paul VanderMarck on LinkedIn: https://www.linkedin.com/in/pvandermarckSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.
Transcribe →Kyle Nakatsuji on What the Future of AI in Insurance Actually Looks Like
Apr 200:39:18Tap to summarizeHost Callan Harrington sits down with Kyle Nakatsuji, CEO and Founder of Clearcover and Dearborn Labs, to explore how AI is reshaping insurance from the ground up. Kyle shares his unconventional path from persistent business school dropout to insurance entrepreneur who raised over $500 million and built technology capable of processing claims in 7 minutes.The conversation dives into Kyle's decision to launch Dearborn Labs, essentially bringing a decade of hard-won AI deployment lessons to carriers and agencies who can't afford to wait. Kyle explains why the recent leap in reasoning capabilities from frontier models like Claude Opus 4.6 represents a genuine inflection point, not just incremental progress. He outlines a future where agents interact with AI orchestrators rather than navigating fifteen carrier portals, with context rather than software becoming the true competitive currency in insurance.Kyle's insights on the K-shaped economy emerging from AI adoption offer a clear roadmap for insurance professionals ready to embrace the technology revolution transforming their industry.Key topics covered:[00:00] Intro[03:42] Business school persistence pays off[06:13] Competing against billion dollar ad spends[07:07] Seven minute claim payout achievement[08:15] Why launch Dearborn Labs now[10:27] AI breakthrough moment arrives[12:23] Agent experience transformation begins[15:11] API for AI agents explained[20:11] Who builds the connection layer[24:18] K shaped AI adoption reality[28:34] Start simple with AI tools[31:06] Technology curve never flattens[32:18] Discovery process for carriers[35:58] Building hammers versus finding nails[37:17] Advice to younger selfConnect with Kyle Nakatsuji on LinkedIn: https://www.linkedin.com/in/kylenakatsujiSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.
Transcribe →How Matt Naimoli Built a Referral Network with 1300 Custom Bobbleheads
Mar 2600:41:18Tap to summarizeMatt Naimoli went from college baseball player to building one of the fastest-growing insurance agencies in America using an unconventional $10,000 bobblehead campaign. What started as a networking attempt became a systematic referral machine generating 500 warm leads monthly with a 75% closing ratio.In this episode, Callan Harrington sits with Matt to break down the exact process behind the campaign that helped his agency capture 7% of all new home sales in Massachusetts. He reveals how they identified centers of influence, created systematic follow-up processes, and built relationships with 100+ referral partners who consistently sent high-quality leads.Matt also shares insights from his current role helping agency owners maximize their business value for acquisition. He explains what buyers actually pay premiums for, why growth matters more than book composition, and how to position your agency in today's market.Whether you're starting an agency or looking to scale, this episode provides a blueprint for building sustainable referral systems that compound over time.Key topics covered:[00:00] Intro[01:17] Baseball to Insurance Career Journey[04:24] Sales Stereotypes vs Reality[06:11] From Liberty Mutual to Agency Success[07:05] The Office Inspired Bobhead Campaign[10:11] Identifying Centers of Influence Strategy[12:08] Building Systematic Networking Processes[16:26] Written Process for Relationship Building[19:47] Modern Bobhead Campaign Revival[23:23] What Drives Agency Valuation Today[27:42] Scale Growth and Leadership Matter Most[32:29] Advice for Next Generation Agency Owners[34:41] How Carriers Can Support Growth[38:39] Long Term Reputation Over ShortcutsConnect with Matt Naimoli on LinkedIn: https://www.linkedin.com/in/mattnaimoliSubscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.
Transcribe →Jim Waterwash's Playbook for Retaining Clients After an Agency Acquisition
Mar 2000:32:38Tap to summarizeHost Callan Harrington sits down with Jim Waterwash, Partner at INSocial Risk Advisors, to get into the details behind their 90%+ retention rate across 5 agency acquisitions, as well as the hard lessons that got them there.Jim traces the arc from running a fully digital agency selling 100% over the phone, to building a traditional operation with 20+ employees, $20M+ in premium, and a repeatable acquisition playbook. The insight that changed everything: the challenge of retaining a client you've never met is the same whether they came through an online lead or a book of business you just purchased.The conversation gets specific on how they identify cross-sell opportunities (they have actual coverage thresholds), how their pod-based service model works in practice, and why trying to build standard operating procedures collaboratively with acquired teams instead of arriving with them already built is big mistake.This episode offers actionable insights for agency owners considering acquisition strategies or looking to improve retention rates across diverse client bases.Key topics covered:[00:00] Intro[01:05] First Policy Double Charge Disaster[03:54] From Digital Leads to Traditional Agency[05:24] Why Digital Strategy Stopped Working[06:40] Acquisition Retention Similarity Insight[08:50] Great Insurance Minds Foundation[10:10] Book Integration Process Walkthrough[11:14] Change Management and Cultural Buyins[12:11] Cross Selling Acquired Books[14:03] Pod Based Service Model[16:51] Early Acquisition Road Bumps[19:42] Standard Operating Procedures Missing[22:17] Proving Systems Before Implementing[24:44] Craft Brewery Cash Deal[27:09] Cultural Alignment During Courtship[29:59] Carrier Support for Acquisitions[31:37] Keep Going AdviceConnect with Jim Waterwash on LinkedIn for more marketing insights and strategies: https://www.linkedin.com/in/jwaterwash/Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.
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