Inside the Strategic Shift Coming to Insurance in 2026 with Callan Harrington

Host Callan Harrington breaks down why the insurance industry may be entering a new growth phase and shares a standout story from his Bold Penguin days that proves what’s possible when momentum shifts. With enterprise carrier spend up 27% and major players like Nationwide committing $1.5 billion to tech, all signs point to a market ready to get back on offense. In this episode, Callan unpacks what it really takes to capitalize on that kind of opportunity. He explains how the Bold Penguin team hit a nearly impossible sales goal during what most consider to be the “slowest” month of the year by throwing out their usual processes and going all-hands-on-deck. What started as chaos turned into one of the most successful campaigns of his career, teaching him that sometimes you need to do things that don't scale to capture major opportunities. Key topics covered: [00:00] Intro [01:20] Growth Period Signs Emerging [02:34] EverQuote Earnings Signal Carrier Spending [03:22] Nationwide's $1.5 Billion Tech Investment [04:02] Window of Aggressive Growth Opportunity [06:09] Bold Penguin's 200 Agency Challenge [07:28] Setting Stretch Goals vs Impossible Goals [08:30] Commercial Rating Platform Background [10:48] November December Sales Reality [11:24] All Hands Blitz Strategy [12:52] Team Rally Around Shared Goal [14:46] Hitting the 200 Agency Mark [16:17] Doing Things That Don't Scale [17:15] Repairing Carrier Agent Relationships [18:38] InsurTech Competition for Carrier Investment [19:55] Planning Bold 2026 Strategies Subscribe for more tactical insurance growth strategies and connect with Callan Harrington on LinkedIn to share your thoughts on this episode: https://www.linkedin.com/in/callanharrington