From Frustration to Innovation: The Origin Story of Plansight

Executive Summary

In this episode of The Benefits Broker Boost Podcast, Plansight Founder and Chief Product Officer Steve Overton sat down with Adam Smith, our Chief Marketing Officer, to talk about how frustration with the traditional renewal process led to one of the most transformative platforms in the benefits space.

What started as a broker’s pain point has become a mission: giving agencies a more innovative, faster, and more scalable way to manage renewals. In this conversation, Steve shares why the industry was ready for change, how Plansight helps brokers stay ahead, and what’s next for those who embrace technology in 2025 and beyond.

The Problem: A Process Built on Chaos

Every broker knows the feeling:

Spreadsheets scattered across folders. Endless email chains. Data entry that steals hours from your day.

For decades, renewals and quoting were manual, disconnected, and error-prone. Each agency reinvented the process every year, and every new team member brought their own system. The result? Inconsistency, burnout, and risk.

As Steve put it:

“I was banging my head against the wall. Why was it so chaotic? Why couldn’t we get quotes back faster, manage renewals better, and actually feel in control of the process?”

That question sparked the beginning of Plansight.

The Turning Point: From Pain to Purpose

Instead of settling for inefficiency, Steve went looking for answers. He spoke with peers, carrier reps, and clients only to hear the same story again and again.

Everyone was frustrated. Everyone wanted better tools. No one was building them.

That was the moment he realized the opportunity wasn’t just to fix his own workflow, it was to modernize how the entire industry operates.

Plansight was built to bring structure to chaos, automate what should have been automated years ago, and help brokers focus on what they do best: serving clients and building relationships.

The Solution: Building a Smarter Way to Work

Plansight helps brokers and general agencies streamline their renewal process through intelligent automation. The platform eliminates repetitive manual work while improving accuracy, transparency, and control.

1. Centralized Workflows‍

All client data, plans, and renewals live in one clean workspace. Brokers can quote, compare, and present without juggling files or duplicate entries.

2. AI-Powered Accuracy

PlansightAI automatically reads, structures, and verifies carrier data, reducing human error and giving brokers confidence in every number they present.

3. Seamless Collaboration

Teams can communicate directly with carriers, track RFP responses, and update presentations in real time, no spreadsheets required.

4. Consistent, Client-Ready Deliverables

With built-in presentation tools, brokers can deliver polished, branded outputs that prove the value of their work and strengthen client trust.

As Steve explained, “It’s not about replacing people. It’s about giving them the time and tools to be better at what they already do.”

What This Means for Brokers Right Now

The pressure on brokers has never been higher. Rising healthcare costs, more demanding clients, and tighter timelines make manual processes unsustainable.

Firms that cling to outdated tools will face:

• Longer renewal cycles that cut into profitability
• Higher error risk as teams rush through manual entry
• Reduced competitiveness against firms that automate

Those who embrace automation now will:

• Move faster with fewer resources
• Deliver more accurate, data-backed proposals
• Strengthen client relationships through transparency and strategy

Looking Ahead: A Smarter, Scalable Future

Steve’s vision for the future of brokerage is clear:

AI will become the backbone of every renewal process. Brokers who learn to harness it, not fear it, will scale their business without adding headcount.

Plansight continues to evolve with that goal in mind, creating a single, intelligent ecosystem for brokers and GAs to quote, market, and renew efficiently.

Final Thought: Innovation Born from Empathy

Every advancement at Plansight starts the same way, with a broker’s pain point.

That’s why Steve’s story resonates so profoundly with the industry. He didn’t build technology from the outside in; he built it from experience, frustration, and a desire to make things better for everyone in the benefits space.

If you’re ready to see how Plansight can help your team simplify renewals, reduce manual work, and scale smarter, now’s the time to start.

👉 Schedule a 30-minute discovery call to see how your next renewal season could look with Plansight.

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