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In this episode of the Benefits Broker Boost Podcast, Adam Smith sits down with Steve Overton, a 25-year industry veteran turned CPO and Founder, to discuss the radical evolution of the benefits space. The conversation centers on how Plansight has transitioned from a collection of individual features to a fully integrated ecosystem that eliminates the "data entry clerk" role for brokers.
By leveraging cutting-edge AI and guided workflows, Plansight is enabling agencies of all sizes to reclaim their time. Whether it is a boutique shop in Virginia or a top-five national firm, the goal is the same: scaling smarter with AI to focus on high-value consulting rather than manual spreadsheets.
For years, the industry struggled with fragmented tools that required manual "stitching" by the broker. Steve reflects on how Plansight has changed over the last two years to solve this. "We built all these features that people needed, but sometimes it was difficult for them to know how they all connected," Steve explains.
The solution was a shift to what teams love about Plansight: the introduction of dedicated, guided paths. Steve notes that they have "really thoughtfully put together how the workflow happens, taking out the bottlenecks, the pieces that are very time-consuming, streamlining those pieces". This evolution ensures that even a team member only three months into the industry can navigate mission-critical processes without getting lost.
The most significant technological shift discussed is the integration of AI to handle the industry’s oldest headache: data entry. Steve points out that the ability to extract data from quote documents is "significantly cutting the time down from what people had to do".
However, the "magic" of Plansight is not just the AI's complexity, but its simplicity for the user. Steve emphasizes that the technology should feel invisible: "We just inject it into their workflow... they understand exactly what our software is doing, and helping them make easy decisions". By choosing the right AI, brokers can move away from being "numbers bots" and return to being strategic consultants.
One unique aspect of the Plansight ecosystem is how it facilitates a "brain trust" between large national brokerages and small boutique agencies. Adam notes that small shops are often excited to use the same workflows as the giants they compete against.
This feedback loop goes both ways. Steve explains that "even the small little suggestions that come from the small boutique brokers... it's something that large agencies can use or not. But all those things get shared". This collaborative approach to our latest updates, inspired by you, ensures the platform remains highly configurable and "unrecognizable" compared to its form just a few years ago.
The ultimate value proposition of Plansight is time. Adam challenges brokers to consider how they will spend the hours saved per RFP and per renewal. Whether it is adding additional lines like Life and AD&D, focusing on the future of broker growth, or simply spending more time with family, the benefit is in the choice.
Steve shares a powerful example of a power user, Whitney, who managed 178 groups single-handedly using the platform. "Plansight is going to save you time. The benefit that you get from Plansight depends on what you decide to do with that time," Adam concludes.
Success in the modern benefits landscape requires a departure from old, manual playbooks. By embracing a blueprint for winning that prioritizes simplicity and technological efficiency, brokers can focus on the relationships that matter most. As Steve puts it, the goal is an easy workflow that gets people from "A to Z really, really quickly".
If you haven’t seen Plansight in action and you want to, book a discovery call with us.
At the end of the day, Plansight is more than just software. It is a partner built with brokerages and their benefits teams in mind. Plansight is the only end-to-end benefits marketing platform that uses AI and automation to ensure every renewal and RFP is consistent, accurate, and fast.
From SmartSheetingAI™ to RFP automation to side-by-side comparisons to the intelligence of PlansightAI, everything we create is designed to lighten the load, reduce risk, and elevate your client relationships. Your team is your greatest asset, and Plansight is here to make sure they have the tools, insights, and support to shine.
Plansight works alongside leading General Agencies to help brokers move faster, stay compliant, and deliver a better client experience. You can explore our trusted GA partners here.
For brokers, Plansight transforms a manual, time-consuming RFP process into one that is faster, more efficient, and more profitable, without sacrificing accuracy or control.
