Callan Harrington sits down with Nick Golubitsky, VP of Revenue Operations at GreenSlate, for a deep dive into how AI is actually being used in go-to-market today. Nick brings over 8 years of revenue operations experience across multiple insurtech companies and shares real campaigns and tools he's implementing right now. This conversation cuts through the AI hype to focus on practical applications that are driving results.

Nick walks through a live enterprise lead campaign using multiple AI tools, explains why conversational intelligence has become the gateway for sales teams to embrace AI, and how these tools are making sales reps more effective rather than replacing them. The discussion covers everything from automated lead qualification to proactive customer success initiatives powered by AI-generated insights.

This episode delivers tactical insights for anyone wondering how AI is actually being implemented in revenue operations and what's possible today versus what's coming in the next few months.

Key topics covered:

[00:00] Intro
[03:16] Salesforce Admin to Rev Ops Evolution
[06:41] AI and Rev Ops Partnership Era
[09:43] Competitor Campaign Using Multiple AI Tools
[13:09] Native Hubspot vs Category Leaders
[16:10] Prospecting Agent Research Capabilities
[20:37] Conversational Intelligence Gateway Drug
[23:05] AI Enhanced Sales Training Methods
[26:01] Data Collection Without Resource Overhead
[30:24] Insurance Tech Lessons from 5 Years Ago
[35:02] Proactive Value vs Generic Outreach
[36:48] Future of Rev Ops Role Evolution
[42:18] Confidence Advice for Starting Out

Connect with Nick on LinkedIn to learn more about his revenue operations strategies: https://www.linkedin.com/in/nickgolubitsky/

Subscribe for more tactical insights from insurance growth leaders, and let us know in the comments what AI tools you're experimenting with in your go-to-market operations.

Host Callan Harrington sits down with Ryan Hanley, President of Linqura and one of the insurance industry's most recognized voices, to break down the content strategy that built his personal brand over 20 years. Ryan shares how he went from nearly being fired by his father-in-law to becoming a sought-after speaker and industry leader through consistent content creation.

Ryan explains his unique approach to content development, filtering ideas through leadership topics and insurance applications to create wholly original takes. He reveals his current workflow using AI tools to streamline commenting and editing, allowing him to maintain consistent output across multiple platforms. The conversation dives deep into why Ryan believes personal branding is now mandatory for anyone in leadership positions, not optional, and how content serves as a trust-building mechanism that moves prospects closer to purchase before any sales conversation begins.

This episode delivers actionable insights for insurance professionals and business leaders looking to build their personal brand and leverage content marketing for career growth.

Key topics covered:

[00:00] Intro
[03:21] Why Ryan Started Creating Content for Insurance Agents
[06:07] Being a Misfit in Traditional Insurance Sales
[11:03] When Content Creation Started Working
[16:02] Ryan's Current Content Strategy and Process
[19:39] Video First Content Creation Approach
[20:08] Personal Brand vs Business Marketing Debate
[26:28] Content as Trust Building Before Sales Conversations
[31:25] Is Personal Branding Mandatory for Success
[36:58] Building Content From Scratch Today
[42:07] Starting with Commenting Before Creating Posts
[47:17] AI Hack for Automated Content Commenting
[49:55] What Ryan Would Do Differently Starting Over

Connect with Ryan Hanley on LinkedIn: https://www.linkedin.com/in/ryanhanley/

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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

Subscribe for more tactical insurance marketing strategies and growth campaigns that drive real results in the industry.

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/

Subscribe to The Insurance Growth Lab for more tactical growth strategies from insurance industry leaders. New episodes every week.

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:

• How That Worked began as a networking tool, and why it quickly became something more impactful
• How repeated founder advice led Callan to niche down into insurance, sparking major growth
• The lessons and momentum gained from getting tactical and going deep with guests
• What to expect from The Insurance Growth Lab, including a video-first format and industry focus
• How vulnerability and consistency shaped the long-term success of the show

Follow Callan on LinkedIn