Meet the team that’s modernizing the RFP process

Weston Lunsford
CEO
Weston brings years of experience as an operator, investor, and leader in the SaaS world.  Weston drives our vision and strategy, ensuring that Plansight remains at the forefront of innovation in the employee benefits space.
Chris Toyn
CFO
With his extensive experience in finance and accounting, Chris plays a critical role in driving our financial success and growth. His strategic insights and financial expertise enable us to make sound business decisions and optimize our operations for maximum efficiency.
Steve Overton
FOUNDER | CPO
Steve oversees all aspects of Plansight, with a particular focus on the software platform. Steve’s decades of experience in the employee benefits industry brings unrivaled insight to the product for both brokers and carriers.
David Sitterud
FOUNDER
Dave works hand-in-hand with our broker and carrier partners to ensure success on all sides. His work on both broker and carrier technologies gives our product and clients a leg up.
Nick Warner
EVP OF CLIENT SUCCESS
Nick leads our customer success team with a proven track record in onboarding and supporting clients successfully in the software world. With his expertise and dedication to our client’s success, Nick ensures that each client receives the best possible experience.
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6 min read

The Future of Brokerage: Why Brokers Must Think Differently in 2025

Based on Episode 1 of the Benefits Broker Boost Podcast with Adam Smith and Weston Lunsford.

Executive Summary

In this kickoff episode of The Benefits Broker Boost Podcast, Plansight's CEO Weston Lunsford and CMO Adam Smith discuss why brokers face more pressure than ever, and why this is also the most exciting time to be in the employee benefits space. From rising healthcare costs and client demands to the explosion of automation and AI, the industry is at a turning point.

The takeaway is clear: brokers who rethink their processes and adopt smarter tools like Plansight will position themselves as strategic partners, not just renewal processors.

The Problem: Too Much Pressure, Too Little Time

As Weston put it, "There's never been more pressure on benefit brokers than ever before."

Medical premiums are rising, employers expect greater value, and employees want comprehensive coverage at lower cost.

Most agencies still manage this complexity with outdated systems, spreadsheets, email chains, and manual data entry. This creates operational drag and leaves brokers reactive instead of strategic.

Weston explained it:

"Most brokers are operating on outdated technology that forces them to hire people just to manage repetitive manual work. Technology should handle that so people can focus on strategy, creativity, and relationships."

That mindset is what inspired Plansight to help brokers replace chaos with clarity through automation. You can see how it works in detail here.

The Turning Point: Modernizing How Brokers Work

Adam described the podcast's mission perfectly: "We want every episode to give brokers something practical they can apply to grow their business."

Each conversation is designed to share proven ideas that help brokers grow smarter, whether through marketing innovation, new tech adoption, or more efficient operations.

Weston built on that idea:

"Plansight eliminates manual work through technology. This podcast does the same thing, just through knowledge. Think of it as workflow automation for your mindset."

That philosophy fuels both Benefits Broker Boost and the Plansight platform. The goal is to help brokers modernize not just how they work, but how they think about their business.

The Shift: From Data Managers to Strategic Partners

The brokerage role is transforming fast. Rising costs, tighter margins, and client expectations are forcing agencies to be proactive rather than reactive.

Brokers who embrace automation and AI tools like PlansightAI will have the freedom to spend more time where it matters most, on strategy, creativity, and client outcomes.

Weston predicts,

"The role of the broker is evolving from a data manager to a strategic consultant. The ones who embrace that shift will grow faster and deliver more value."

That's why Plansight continues to innovate with features like renewal automation and built-in QA to reduce risk and save hours each renewal cycle.

What Top Agencies Are Doing Differently

The most successful agencies aren't "winging it." They've built disciplined, repeatable systems, especially around client engagement.

Top-performing firms:

  • Conduct post-renewal reviews to identify improvements
  • Host mid-year check-ins to monitor satisfaction
  • Begin planning renewals months before rates drop

These agencies turn renewals into a process that runs like clockwork, improving retention and valuation. Weston explained:

"They've turned renewal management into a process that runs like clockwork, and it shows up in their growth."

You can learn more about building scalable systems in a recent webinar Scaling Smarter with AI.

The Future: Technology That Frees Brokers to Think Bigger

The next five years will redefine brokerage. AI and automation are already transforming how brokers quote, market, and renew benefits.

Weston shared a clear vision:

"AI and automation are removing repetitive, low-value tasks. Brokers who embrace it will see their margins expand and their teams become more effective."

The ones who resist won't disappear, but they'll fall behind those using more intelligent workflows to scale. Plansight was built for this future, combining automation, accuracy, and intelligence into a single platform designed specifically for Brokers and General Agencies.

Final Thought: Stake Your Claim

To close the episode, Weston challenged brokers to define their unique value:

"Stake your claim. Define who you are, why you're different, and live up to it. Every decision should go back to that claim."

That's how brokers move from feeling stuck to standing out.

If you're ready to simplify renewals, reduce manual work, and build a more strategic business, now's the time to act.

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

Book a Demo

About Plansight

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. 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. Plansight is here to make sure they have the tools, insights, and support to shine. For brokers, Plansight is the only complete end-to-end renewal and marketing solution that transforms a manual, time-consuming RFP process into one that is fast, efficient, and more profitable.