.svg)
In this Benefits Broker Boost episode, Plansight CMO Adam Smith sits down with Landon Fielding, the founder and CEO of Brite, to discuss the friction points that define the modern insurance landscape. After spending nearly a decade as a broker, Landon realized that traditional benefits education was failing both employers and employees. The conversation explores how shifting from static paper guides to dynamic digital environments allows brokers to move from data entry to strategy.
By prioritizing engagement and scaling smarter with AI, agencies can bridge the gap between complex plan design and employee understanding. This episode reinforces that the industry's future belongs to those who treat authenticity and creative disruption as core competencies.
Landon recounts a pivotal experience from 2019 where a client pointed out that, despite spending $60,000 on custom benefit guides, employees were ignoring the presentation to play on their phones. “I hate to say it, but let’s see how many of these booklets end up in the garbage can,” the HR director told him. As it turned out, two-thirds of the expensive materials were trashed immediately, leaving the HR team flooded with basic questions.
This highlighted a massive innovation gap in the industry. As Adam notes, “To get in there and present that and have the employees not even like take a second to learn about what you’ve put together for them is probably a pretty big slap in the face”. The realization was clear: the industry needed to move beyond the spreadsheet and into a digital-first approach.
A core philosophy at Brite is that the broker is responsible for “zero-to-one” engagement, simply getting an employee to look at their benefits. To achieve this, the product focuses on the “TLDR” (Too Long; Didn’t Read) approach, providing essential information in under ten minutes.
Landon emphasizes that brokers must stop building products based solely on outdated HR requests and start breaking old playbooks. “You’ve got to get creative with how you engage people. You’ve got six different generations in the workforce now,” he explains. By choosing the right AI and decision support tools, brokers can ensure employees feel confident in their selections without the friction of creating new accounts or logins.
Another turning point in Brite’s growth came when the company was accepted into Y Combinator, one of the most well-known startup accelerators in the world.
The program has helped launch companies like Airbnb, Stripe, and DoorDash, and its network carries enormous credibility with investors and customers alike.
For Brite, the experience did more than accelerate fundraising. It validated the problem Landon had been trying to solve.
Before the program, many potential customers were hesitant to adopt a new technology in such a high-risk industry. After the acceptance, the reaction changed almost overnight. Conversations that had stalled suddenly moved forward.
The lesson for founders and consultants alike is simple: if you deeply understand the problem you are solving, you are already ahead of most competitors.
Unlike many software categories, the benefits industry rarely adopts new technology overnight. Brokers operate in an environment where introducing friction into a client relationship can quickly backfire.
Because of that reality, Brite’s growth did not come from rapid scaling or aggressive expansion. Instead, it followed a slower but durable pattern: build trust with early partners, deliver value consistently, and expand through strong relationships.
That approach reflects a broader truth in the broker ecosystem. Reputation travels quickly in this industry, and one negative experience can ripple across multiple firms.
By prioritizing relationships over short-term revenue, Brite focused on going deeper with a smaller group of partners before expanding outward. Over time, that strategy helped the platform reach more than 3 million employees who learned about their benefits through Brite.
Growth in the benefits space is notoriously difficult due to the high risk of client friction. Landon attributes Brite’s success to prioritizing relationships over short-term revenue. This mirrors Plansight's philosophy of building a trusted benefits platform through continuous feedback loops.
“We know if you mess one relationship up, the industry is... everyone knows each other,” Landon warns. Success comes from going deeper with core customers rather than just going wider. This service-to-sales journey requires brokers to prove they can handle the most complex groups to earn the right to manage the rest of the book.
Growth in the benefits space is notoriously difficult due to the high risk of client friction. Landon attributes Brite’s success to prioritizing relationships over short-term revenue. This mirrors Plansight's philosophy of building a trusted benefits platform through continuous feedback loops.
“We know if you mess one relationship up, the industry is... everyone knows each other,” Landon warns. Success comes from going deeper with core customers rather than just going wider. This service-to-sales journey requires brokers to prove they can handle the most complex groups to earn the right to manage the rest of the book.
The conversation also explored how the definition of “great benefits” is changing. While employers often focus on the strength of their health plan, employees frequently place more value on benefits that improve their daily lives.
Core insurance coverage still matters, but it is rarely the feature that drives excitement or retention.
Instead, employees remember benefits that remove small stress points from their routine. That might include wellness stipends, flexible spending perks, commuter benefits, or lifestyle allowances that help employees manage everyday expenses.
The takeaway for brokers and HR leaders is that benefits strategy is no longer just about protecting employees from worst-case scenarios. Increasingly, it is about creating an experience that supports employees in the moments they encounter every day.
When those experiences align with employee priorities, benefits become a powerful tool for both recruitment and retention.
Looking toward 2026, the consultant's role will be defined by how they manage and connect information. Landon predicts that AI will be instrumental in from fax machines to AI workflows, but only if the foundational data is structured correctly.
“If you don’t have structured data to be able to access that information and provide benchmarking and resources and insights and visibility… It’s going to be very interesting who rises up and who crashes,” Landon concludes. By 2026, the manual “numbers bot” role will be obsolete, replaced by consultants who use integrated technology to provide high-level strategic value.
The benefits industry is entering a period of rapid transformation. As new technology unlocks faster access to information, the role of the consultant is shifting from manual analysis to strategic guidance.
But that transformation depends on one critical factor: data structure.
Brokers who invest in structured data, connected systems, and modern engagement tools will be positioned to lead the next era of benefits consulting. Those who ignore these changes may quickly find themselves struggling to keep pace with a more connected and data-driven industry.
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.
