Digital Demands Reshape The Small Business Insurance Market

According to Deloitte’s 2025 Insurance Industry Outlook , more than 60% of small business owners consider digital experiences a top priority when selecting insurance providers. Yet most say the sector still lags behind when it comes to convenience, transparency, and personalization. As premiums rise and employee expectations evolve, insurers and financiers alike are racing to simplify offerings, automate service, and close what MetLife calls the “employee confusion gap.”

To explore what innovation actually looks like on the ground, I spoke with Bradd Chignoli, who leads the regional business and workforce engagement organization at MetLife, and Ben Rubin, EVP and Market Head for Premium Finance and Capital Markets at Wintrust Financial Corporation.

Video: Bradd Chignoli, EVP, Head of U.S Group Benefits Regional Business & Workforce Engagement at MetLife

Simplification as Strategy

Bradd Chignoli’s team at MetLife supports more than 35,000 small business clients across the United States, focusing on group benefits like life, dental, vision, and supplemental insurance. For him, innovation starts with simplification.

“We began scaling our new end-to-end platform at the end of 2023,” Chignoli said. “It’s built specifically for small employers, from quote to claim, with 24/7 access to portals that let business owners and employees make changes, view claims, and pay bills without friction.”

Chignoli pointed to the importance of fast onboarding as a key differentiator, noting that more than 90% of new plans are implemented in less than a week. “Ease and simplicity are everything,” he added. “Especially when small employers lack robust HR teams to help them administer these increasingly complex benefits.”

Video: Benjamin Rubin EVP & Market Head Premium Finance and Capital Markets at Wintrust

From Quote to Claim in Clicks

Ben Rubin’s role at Wintrust focuses on premium finance, a less visible but essential piece of the insurance ecosystem. His teams help small and midsize businesses finance the cost of annual insurance premiums by spreading payments over time, creating liquidity for businesses that may be juggling multiple policies across different carriers.

“Premium financing lets businesses align cash outflows with a 12-month policy term,” Rubin explained. “Especially with the rise of excess and surplus lines, which often require full payment up front, the demand has grown substantially in recent years.”

Despite being in a mature market, Rubin sees continued room for efficiency. “We integrate directly with agency management systems, so when a broker binds a policy, they can generate a premium finance agreement at the push of a button.”

Bridging the Employee Confusion Gap

At MetLife, the innovation isn’t just operational, it’s educational. Chignoli emphasized what the company calls the “benefits confusion gap,” a disconnect between the benefits offered and an employees’ complete understanding of their benefits and how to use them.

“MetLife’s 2025 Employee Benefit Trends Study found a decline in employee holistic health and productivity, particularly among small business workers,” he said. “Employees are financially stressed, less engaged, and less able to take advantage of benefits.”

To counter this, MetLife has invested in tools that help employees connect benefit offerings to their family’s real needs. “It’s not about selling more coverage,” Chignoli said. “It’s about helping people understand what these benefits actually do and when to use them. That increases satisfaction and retention.”

Technology as a Differentiator

Both leaders stressed that technology is no longer optional, it’s the price of admission. For Rubin, innovation hinges on integration.

“We’ve invested in a vast API library so we can plug into brokers, MGAs, carriers, and even insuretech platforms,” Rubin said. “We want to be in their workflow, not outside of it. That’s how we scale without sacrificing service.”

Rubin also sees opportunity in automating the back-end processes that slow down underwriting and approvals. “A lot of time is still spent manually validating policy information across stakeholders,” he noted. “That’s a pain point the whole industry shares, and whoever solves it will have a serious advantage.”

Affordability Through Bundling

Given rising medical and insurance costs, small employers are also looking for creative ways to control spend without sacrificing coverage. Chignoli sees bundling as a key lever.

“When employers combine both core and voluntary benefits, things like hospital indemnity or legal protection, we can help them build packages that are more affordable and better aligned with employee needs,” he said. “It’s not about cutting back. It’s about offering choice.”

He added that voluntary benefits often improve employees’ perception of the overall benefits package, even when employers shift more cost responsibility to the employee. “Offering more, even if it’s opt-in, helps employees feel supported.”

Pricing That Balances Risk and Scale

Rubin explained that Wintrust’s pricing model is based on standardized programs negotiated with brokers, with flexibility for bespoke deals in special cases.

“We look at down payment, number of installments, and risk exposure,” he said. “The goal is to keep it efficient and cost-effective for everyone, brokers, borrowers, and us. And we monitor macroeconomic trends to tighten terms in higher-risk sectors if needed.”

Despite thin margins, Rubin said the model works because of high volume and low default rates. “These aren’t loans to grow a business, they’re to manage required costs. Defaults are predictably low.”

The Roadblocks Ahead

When asked about barriers to growth, both executives cited technology as both the biggest hurdle and the biggest opportunity.

Chignoli sees the need to keep pace with evolving customer expectations. “Small business owners expect digital-first, seamless experiences now,” he said. “We need to deliver that with the same quality and speed as their favorite consumer apps.”

Rubin added that staying relevant also means adapting to new intermediaries. “There are more players in the chain now, insuretechs, embedded providers, and we need to integrate with all of them. If we can’t plug in, we can’t compete.”

Despite its complexity, the small business insurance sector is slowly becoming more accessible, responsive, and efficient. Leaders like Chignoli and Rubin are proving that legacy players can modernize, not by chasing trends, but by solving real problems at scale.

As Rubin put it, “The market may be mature, but innovation is alive and well. You just have to look beneath the surface.”

For more like this on Forbes, check out How Technology Is Reinventing Small Business Insurance and How Innovation Is Transforming Small Business Insurance.