Callan Harrington returns from ITC Vegas with a critical observation that every insurtech needs to hear. Despite increased capital flowing into the market and genuine excitement around new technology, decision makers are completely lost trying to figure out what these companies actually do. When everyone claims to be "the AI company for insurance," the messaging becomes indistinguishable noise.
Callan breaks down why this positioning crisis is happening and reveals the massive opportunity it creates for companies willing to get specific. He shares real examples from the conference floor, including how consultants are now stepping in as curators to help overwhelmed buyers navigate the sea of similar-sounding AI solutions. The episode covers tactical strategies for standing out, from owning specific use cases to building strategic partnerships that can unlock much larger deals.
This solo episode delivers actionable insights for any insurtech struggling to differentiate in an increasingly crowded market.
Key topics covered:
[00:00] Intro
[01:42] People are lost in insurtech
[02:33] How we got here
[04:20] AI companies trying to own everything
[05:45] VC perspective on AI differentiation
[07:07] Insurance's massive technology spending
[08:19] Having AI is now table stakes
[09:05] Decision maker fatigue and confusion
[10:00] Consultants filling the curation role
[11:09] Missing out on consultant relationships
[13:28] What insurtech companies can do
[14:43] Getting more specific with use cases
[16:18] Huge opportunity for better positioning
[17:56] Lean into partnership-led growth
[18:45] Most exciting ITC despite confusion
[19:51] Big opportunity for positioning winners
Connect with Callan Harrington on LinkedIn for more insurance growth insights: https://www.linkedin.com/in/callanharrington
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Callan Harrington sits down with Margeaux Giles, CEO of IRYS Insurtech, to break down their year-long rebranding process that transformed both their external presence and internal culture. Margeaux shares why rebranding felt necessary after 3 years of rapid startup growth and how the process became much deeper than choosing new colors and logos.
The conversation reveals the unexpected internal benefits of rebranding, from aligning employees on the company mission to dramatically improving content quality.
Margeaux walks through their discovery process, the challenges of getting executive team consensus, and how they developed their rallying cry, "step out of line", that now drives company culture. She also discusses the practical timeline challenges, the decision to keep their company name, and their strategic launch approach that treated the rebrand as a quarter-long marketing initiative.
Whether you're considering a rebrand or simply want to understand how it impacts company culture, this episode provides tactical insights from a CEO who just completed the process with measurable results.
Key topics covered:
[00:00] Intro
[03:42] Professional services vs SaaS company differences
[06:21] Hard pivot leadership style challenges
[08:03] Why IRYS needed a rebrand after 3 years
[11:53] Brand discovery process and internal alignment
[15:14] Finding the company's rebel archetype
[17:08] Making final brand decisions through consensus
[19:03] Internal culture impact of brand discovery
[21:40] Step out of line rally cry development
[24:10] Keeping the IRYS name during rebrand
[27:20] Content quality improvement after rebrand
[32:16] Authentic content vs AI-generated posts
[34:59] What she would do differently
[37:19] Perfect timing for rebranding doesn't exist
Connect with Margeaux Giles on LinkedIn: https://www.linkedin.com/in/margogiles/
Learn more about IRYS at https://iryscloud.com/
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Callan Harrington sits down with Alex Harris, co-founder of Fiat Growth and Fiat Ventures, to unpack how great partnerships actually drive growth. Alex shares the story of bringing together two major players in insurance, Lemonade and Bestow, and transforming that collaboration into a revenue engine, not just a press release.
He explains how journey mapping, trigger-based campaigns, and data-driven targeting helped unlock meaningful customer adoption. Along the way, Alex opens up about his viral marketing roots and what the future of partnerships looks like in an AI-driven world.
Key topics covered:
[00:00] Intro
[03:42] Viral video breakthrough
[08:20] Full circle moment with Chime
[14:19] Building Fiat Growth
[17:56] Partnership strategy for Lemonade and Bestow
[24:43] Driving real revenue from partnerships
[26:02] Customer journey mapping for success
[28:29] Life cycle marketing tactics and triggers
[32:51] AI tools transforming services business
[35:02] Target pregnancy prediction data story
[37:34] Embracing AI without losing human connection
[39:37] Events becoming more important than ever
[40:22] Advice to younger self
Connect with Alex Harris on LinkedIn: https://www.linkedin.com/in/alexharrisjdmba/
Learn more about Fiat Growth: https://www.fiatgrowth.com/
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Callan Harrington breaks down the evolving go-to-market landscape for insurtech companies, sharing insights from his presentation at InsureTech New York's Education Day. As founder of Flashgrowth, Callan examines what's stayed the same from 2024 and what's rapidly changing in 2025 as AI transforms sales and marketing strategies.
Callan covers critical benchmarks for scaling revenue from zero to 1 million, 1 to 10 million, and beyond 10 million in annual recurring revenue. He explains when to hire your first sales reps and VP of Sales, and when the timing is right to scale. The discussion includes essential metrics like customer retention rates, quota attainment benchmarks, and the importance of crossing the chasm from early adopters to early majority customers.
Key topics covered:
[00:00] Intro
[03:24] Zero to 1 Million Sales Benchmarks
[05:05] When to Hire First Sales Reps
[06:54] 1 to 10 Million Growth Stage
[08:01] Hiring Your First VP of Sales
[11:23] Scaling Past 10 Million Revenue
[12:25] Golden Rule of Quota Attainment
[14:05] Ideal Customer Profile Requirements
[14:59] Crossing the Chasm Strategy
[18:00] AI's Impact on Go-to-Market
[19:45] Cold Calling Death Myths
[21:13] Partnership Led Growth Rise
[22:25] Revenue Leaders Need AI Skills
[24:06] Things Are Moving Faster
[25:38] Expert Status Requirements
[27:04] Go-to-Market Headcount Predictions
[28:40] Relationships as Future Currency
Subscribe for more tactical insurance growth strategies that cut through the noise and focus on what actually works.
Host Callan Harrington sits down with Chris Kessler, Chief Product and Platform Officer at Bold Penguin, for an in-depth look at enterprise solution selling. Chris brings a unique background in strategy consulting that has directly shaped how Bold Penguin consistently lands household names as enterprise clients in the insurance space.
The conversation centers on Chris's detailed solutioning process, which goes far beyond typical sales approaches. He walks through his methodology of engaging with the right stakeholders, conducting strategic whiteboard sessions, and building comprehensive roadmaps that blend core product with custom services.
He covers everything from identifying P&L owners with long-term mandates to navigating brutal procurement processes in the insurance industry.
Key topics covered:
[00:00] Intro
[01:49] Solution in Enterprise Sales
[03:42] How Chris Fell Into Insurance
[08:15] Strategy Consulting to Corporate Strategy
[13:38] Solution Process Deep Dive
[16:00] Finding the Right Decision Makers
[18:48] In-Person Strategy Sessions Matter
[20:00] Whiteboarding Current State Process
[24:28] Charging for Discovery Work
[27:17] Building the Future State Roadmap
[32:48] Procurement Doesn't Get Easier
[36:15] Implementing Consulting Skills at Bold Penguin
[39:07] Recognizing a Real Opportunity
[42:24] Career Advice for Your Younger Self
Connect with Chris Kessler on LinkedIn: https://www.linkedin.com/in/kesslerchris/
Learn more about Bold Penguin: https://www.boldpenguin.com/
Subscribe for more tactical growth insights from insurance industry leaders, and leave a review if this episode helped you think differently about your acquisition strategy.
Callan Harrington sits down with Ido Deutsch, VP of Growth at Agentero, to break down one of the most successful (and shocking) paid media strategies for acquiring insurance agencies. Ido shares how he built a predictable and affordable machine generating leads via Facebook.
He breaks down the mindset that led him to bet on paid social, the experimentation framework behind his campaigns, and why chasing “more leads” is the wrong strategy.
For insurance companies looking to diversify beyond traditional outbound methods, this episode provides a proven roadmap for paid social success in a notoriously difficult B2B market.
Key topics covered:
[00:00] Intro
[03:32] First Tech Company Origin Story
[05:40] Building Solutions From Personal Pain Points
[08:22] When to Build vs Buy Decisions
[10:26] Understanding Your Audience is Everything
[13:44] Insurance Experience Advantage in Sales
[17:07] Career Pivot From Soccer to Tech
[20:12] Builder Mentality and Risk Taking
[22:46] Experimentation Framework for Growth
[25:26] Facebook Lead Generation Strategy Launch
[29:09] $30 Cost Per Lead Results
[32:34] Why Facebook Works for Insurance Agents
[33:17] Analytics and Optimization Process
[35:52] Revenue Leaders Should Own Marketing Funnel
[43:47] Ido’s Growth Journey at Agentero
[46:43] Advice to Younger Self
Connect with Ido Deutsch on LinkedIn: https://www.linkedin.com/in/ido-deutsch/
Learn more about Agentero: https://agentero.com/
Subscribe for more tactical growth insights from insurance industry leaders, and leave a review if this episode helped you think differently about your acquisition strategy.
Callan Harrington sits down with Amber Wuollet, Director of Product & Lifecycle Marketing at Cowbell, to explore how thoughtful marketing can change the trajectory of an insurance product. After years of lackluster performance, Amber’s team uncovered insights that helped a struggling policy hit its 12-month sales goal in just 6 months, without changing a single feature.
The conversation also touches on Amber’s career journey, including lessons from a launch that collided with COVID shutdowns and the practical steps she uses to uncover what really drives growth.
Key topics covered:
[00:00] Intro
[02:38] Epic marketing fail during Covid
[10:32] Early career ambition at 14
[13:37] How 10 years in underwriting shaped marketing perspective
[22:48] Product launch research strategy
[26:29] Complete positioning overhaul eliminates complexity
[28:01] 12-month goal achieved in 6 months
[32:47] 30 customer interviews reveal key insights
[35:33] Right-sized launch strategy for niche product
[37:53] Product unchanged but messaging transformed results
[43:34] Product marketing definition and role
[49:28] Lifecycle marketing beyond product launch
[53:09] Advice for younger self
This episode delivers practical insights on customer research methodology, positioning strategy, and how to execute product relaunches that drive real business results.
Callan Harrington, Founder of Flashgrowth and host of That Worked, reflects on the journey of his podcast as he records its final episode before shifting to The Insurance Growth Lab. In this solo episode, he dives into the origins of the show, what it became, and why now is the right time to focus fully on the insurance space. With stories, founder-inspired lessons, and a glimpse into what’s next, Callan shares the evolution of the podcast.
In this episode, you’ll learn:
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Matt Farrell is the COO at Niobium Microsystems, a trusted hardware design company developing high-performance microelectronic components to enable the secure collection, processing, and distribution of critical data.
Matt is a multi-time founder and early-stage executive. Before the startup world, Matt was a coach for the University of Dayton Men’s basketball team and later the Assistant Athletic Director at the University of Dayton.
In this episode, you’ll learn:
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In this episode of That Worked, co-hosts Callan Harrington and Sullivan Finlay dive into content strategy, delegation, and maximizing creative output. Sullivan shares how structured planning has transformed his workflow, the power of visual content boards, and why repurposing content is essential for expanding reach without reinventing the wheel. They also break down the 10-80-10 rule of delegation, an approach to outsourcing that helps creators and entrepreneurs focus on high-impact work. Plus, they dive into the role of relationships in business growth and discuss the balance between creative control and efficiency.
In this episode, you’ll learn:
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In this episode of That Worked, host Callan Harrington and comedian/content creator Sullivan Finlay explore how improv can transform leadership, the evolving landscape of AI-driven content creation, and why outsourcing is essential for scaling creative work. Sully shares improv techniques—such as adaptability and active listening—that boost effectiveness both on stage and in the workplace, while Callan emphasizes the growing importance of human-driven insights in an AI-saturated environment. Together, they unpack how AI-generated search results are reshaping content discovery, highlight the practical benefits of delegation to reclaim valuable time, and offer candid observations about the world of LinkedIn thought leadership.
In this episode, you’ll learn:
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In this episode of That Worked, host Callan Harrington and comedian/content creator Sullivan Finlay dive into the rapidly evolving role of AI in entertainment, content creation, and brand collaborations. They explore the ethical dilemmas of AI-generated personas, the impact of deep research tools on competitive analysis, and how AI is reshaping creative industries. Sullivan shares his perspective on balancing creative integrity with AI-driven scalability, the challenges of licensing digital likenesses, and why in-person entertainment might become even more valuable in an AI-saturated world. Callan and Sullivan also discuss their upcoming live comedy show, Corporate Takeover, and the creative process behind bringing corporate satire to the stage.
In this episode, you’ll learn:
Follow Sullivan Finlay on TikTok and Instagram
Follow Callan on LinkedIn
Callan Harrington, Founder of FlashGrowth and host of That Worked, takes a deep dive into the strategic decision to niche his business into the insurance space. In this solo episode, he breaks down the fears, challenges, and long-term benefits of narrowing focus in business. If you’ve ever hesitated to specialize, this episode is packed with insights on how niching down can unlock exponential growth opportunities.
In this episode, you’ll learn:
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In this episode of That Worked, host Callan Harrington and co-host Sullivan Finlay, a writer, comedian, and content creator, dive into the challenges and opportunities of building a career in the evolving digital landscape. They explore the vulnerability of content creation, why niching down can accelerate business growth, and how relationship-building plays a crucial role in expanding creative opportunities. Sullivan shares his insights on adapting to industry shifts, while Callan discusses adding instant value in business and the importance of strategic positioning. Together, they offer actionable advice on future-proofing careers and navigating an ever-changing digital world.
In this episode, you’ll learn:
Follow Sullivan Finlay on TikTok and Instagram
Follow Callan on LinkedIn
Sriya is the Co-Founder of Persana AI. Persana AI is a Y-Combinator-backed AI tool designed to enhance sales through hyper-personalization, seamless integration, and united workflows.
Prior to Persana AI, Sriya was a Product Manager at LinkedIn.
In this episode, you’ll learn:
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Connect
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Scott Knowles is the Co-Founder and CEO of Deep Vector, a web-based software platform that transforms unstructured documents into actionable insights with speed and precision.
Prior to Deep Vector, Scott was the Founder and CEO of Modgic, a software company that provided workers' compensation and mod analysis tools for the commercial insurance industry and was successfully acquired by Zywave in 2021.
In this episode, you’ll learn:
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Dan Snyder is the CEO & Co-Founder of Lower, a multi-channel home lender he helped build and grow over the last decade into the 28th largest lender in the country. Lower operates both an online direct to consumer business, and offline retail business with over 150 offices across the country.
Lower raised the largest Series A in the State of Ohio ($100M) from fintech investors Accel and Sofi. Dan has also been named in the Smart 50 Class of 2022, 40 Under 40, Future
50 Class of 2021, and the #4 CEO by Glassdoor.
In this episode, you’ll learn:
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Tom Grote is the CEO of Agape Automation, a food-tech innovation company that creates the automated Smart Kitchens of the future.
Prior to Agape Automation, Tom was the COO of Donatos Pizza for over 17 years, a family-owned pizza company with more than 150 locations in six states.
In this episode, you’ll learn:
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Dan Manges is the Co-Founder of RWX. RWX develops software engineering tools that optimize build and test performance, reliability, and developer experience. Its flagship product, Mint, is a generation newer Continuous Integration platform that gives engineers unparalleled capabilities to optimize their builds.
Dan was previously the CTO of Root, a technology-powered car insurance carrier, which he co-founded in 2015 and took public via an IPO in 2020. Before Root, Dan was the CTO of Braintree, where he built a payments platform that PayPal acquired in 2013 for $800M.
In this episode, you’ll learn:
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Matthew Achak is the Co-Founder and Managing Partner of Non-Linear Venture Partners, where he consults and invests in early-stage start-ups.
Prior to Non-Linear Venture Partners, Matt Co-Founded FCR, the leading provider of outsourced live agent support services for tech companies. FCR was acquired by TTEC in 2019.
In this episode, you’ll learn:
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