Inceptions of Plansight: How One Broker’s Frustration Sparked an Industry TransformationIn this episode of Benefits Broker Boost, host Adam Smith sits down with Steve Overton, founder of Plansight and a former employee benefits broker with over 25 years of experience. Steve shares the story behind Plansight’s creation that was born from his own frustration with the chaotic, manual RFP process that brokers faced every renewal season.
They dive into:

• The evolution of benefits technology from fax machines to AI-powered quoting tools
• How PlanSight helps brokers eliminate chaos, increase scalability, and collaborate seamlessly
• The challenges of change management and why larger brokerages are embracing automation faster
• How technology is reshaping the broker–employer relationship to drive better client outcomes
• Predictions for the next decade of employee benefits, from consolidation to AI-driven efficiency

Steve also reflects on the noble side of the industry, noting how brokers are helping families through life’s hardest moments and why he believes AI won’t replace brokers but will make them superheroes.
If you’ve ever struggled through Q4 renewals or wondered where benefits technology is headed next, this episode is a must-listen