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From Legacy to Leverage: How the Next Generation Is Reshaping the Agency Playbook

Family agencies have been the backbone of the insurance industry for decades. But as a new generation steps into these businesses, they’re not just continuing the legacy, they’re rewriting the playbook. In the debut episode of Sembley Sessions, Joe Ems sits down with Alex Janes of Maverick Risk (Minnesota) and Dean Bowen of Stable Rock (New York) to explore what it’s like to be a second-generation insurance professional in an era defined by AI, insurtech, and rapid change.

Unconventional paths into insurance

Neither Alex nor Dean followed a straight line into the industry. Dean spent years in blue-collar work, general contracting, brewing, aluminum can manufacturing, before joining his father’s agency at 23. That hands-on experience turned out to be a superpower: he can speak credibly to contractors, manufacturers, and trades workers because he’s been in their shoes.

Alex was studying computer science and programming before stepping into his mother’s agency. What started as a temporary desk job to build his resume became a career once he realized that writing an insurance policy scratches the same itch as writing code, both demand precision from top to bottom, or you end up with bugs.

The takeaway: the more “unrelated” your background, the more valuable your fresh perspective can be.

Earning your name, not inheriting it

All three hosts agreed that being the owner’s kid is a double-edged sword. There’s an implicit expectation to prove you belong, that you’re more than just a name on the door. Dean described having to clear a higher credibility bar, while Alex talked about channeling that pressure into a “prove everybody wrong” mentality.

But there’s an upside too. Clients often have an existing relationship with the parent, which opens doors. And the legacy itself, the pride of contributing to something a parent built, becomes a powerful source of motivation that goes deeper than a paycheck.

Becoming the unofficial IT department

Both Alex and Dean naturally fell into the role of in-house tech advisor for their agencies. Dean identified “shiny object syndrome”, agencies signing contracts for exciting-sounding tools that never get adopted, and took ownership of evaluating whether tools were actually being used and whether vendor support was responsive enough to matter.

Alex, drawing on his programming background, focused on process efficiency. He audited workflows, questioned why things were done certain ways, and ran internal training sessions to bridge the gap between powerful software and the staff who needed to use it daily.

Their shared insight: the problem is rarely the software itself, it’s the gap between what a tool can do and whether anyone has been trained to actually use it.

Driving implementation and staff buy-in

Getting veteran staff to adopt new technology isn’t about mandating change, it’s about making the case that it genuinely improves their day. Alex described running webinars for his team showing exactly how tools like Sembley eliminate hours of manual ACORD form entry. Dean focused on being a living example: if he’s using a tool every day and it’s helping him, that carries more weight than any sales pitch from a vendor.

Both emphasized that resistance usually isn’t hostility toward tech, it’s a natural comfort with familiar processes built over decades. The key is shifting the conversation from “we’re bringing in new software” to “here’s how this frees up your time so you can focus on clients instead of paperwork.”

An AI-realist perspective

In a landscape flooded with AI hype, Alex and Dean struck a notably grounded tone. Dean positioned himself as the agency’s “AI realist,” noting that growing up watching AI evolve, from basic chatbots to today’s tools, gives their generation an intuitive sense for what’s genuine capability versus marketing noise.

Alex drew on his CS background to make a clear distinction: AI should automate the tasks nobody enjoys (email drafting, form population, data entry) without replacing the critical thinking, relationship-building, and risk analysis that define an agent’s real value. Their shared philosophy:

  • It’s not about replacement, it’s about empowerment
  • Cut out the “button pressing” so agents can spend more time advising clients
  • Be aggressive in exploring AI tools, but know where to draw the line
  • The best AI posture is neither 100% buy-in nor 0%, it’s the informed middle ground

Looking ahead: the next 5-10 years

Dean sees the future in hyper-tailored AI, not more powerful general models, but tools custom-trained on an agency’s own data, iterated over years, becoming uniquely capable for that specific operation. He also expressed optimism about the independent agency channel holding its ground against aggregation.

Alex took the long view. At 21, he’s energized by the sheer runway ahead, decades to shape not just his agency but the industry itself. He sees today’s younger professionals eventually becoming the ones speaking at the conferences they’re currently attending as note-takers.

Both agreed: the perception of insurance as an “old man’s game” is cracking. More informational content, more young producers, and more tech-forward agencies are pulling the industry toward a future that’s more transparent, more efficient, and more accessible.

Key takeaways

  1. Diverse backgrounds are an asset, not a liability. Blue-collar experience, programming skills, or any non-insurance background brings perspectives that career lifers may never consider.
  2. Legacy is a motivator, not a burden. Contributing to something a parent built adds purpose that goes beyond the daily grind.
  3. Tech adoption is a people problem, not a software problem. The best tools fail without training, support, and a clear answer to “how does this make my job better?”
  4. AI works best as a force multiplier. Automate the tedious, preserve the human, and stay skeptical of anyone promising it can do everything.
  5. The runway is long. Young professionals entering insurance today have decades to shape the industry, and the earlier you start, the more influence you’ll have.

Sembley Sessions is a conversation series spotlighting the people and ideas shaping the future of insurance. Have a topic or guest suggestion? Reach out to team@sembley.com.