The global commercial insurance market is on the cusp of a digital revolution, with digital premium … More
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According to McKinsey, the global commercial insurance market is on the cusp of a digital revolution, with digital premium penetration expected to double by 2030. But for America’s 31 million small businesses, most with under five employees, that revolution can’t come soon enough.
Inflation has driven up premiums. Many insurers still demand annual lump-sum payments. And navigating coverage can feel like decoding legalese without a translator. But that’s changing.
To understand how, I spoke with three executives at the forefront of this transformation. Samantha Roady, CEO of Simply Business, a digital insurance marketplace focused on micro-small businesses. Doug Mohr, VP of Industry Relations at Vertafore, one of the largest insurance technology companies powering independent agents, carriers and MGAs. Daryle Stafford, President & CEO of Veracity Insurance Solutions, an MGA combining high-risk program underwriting with full product development.
What follows is an inside look at where innovation is happening, what gaps still remain, and how technology might just save the future of small business insurance.
Video: Samantha Roady, CEO of Simply Business
Simplicity Is the New Competitive Edge
Across all three conversations, one theme dominated: streamlining the insurance journey from quote to claim is now mission-critical.
Roady’s firm, Simply Business, has built a marketplace of 18 carriers across six major product lines. Instead of cold calls or clunky PDFs, micro-business owners can get multiple quotes, compare coverages, buy online, and download their certificates, often in less than 10 minutes.
“That, in and of itself, is a big innovation,” she said. “Most aren’t aware they can buy insurance online.”
Stafford, whose MGA focuses on automation and program underwriting, agreed. “Everything right now is focused on simplicity,” he said. “From quoting to bundling to renewals, every part of the experience has to evolve.”
Mohr, from Vertafore, sees it from the platform side. “The Amazon experience has raised the bar, because today’s policyholders expect fast, easy service, and self-service tools like automated payments help independent agents deliver.”
Video: Doug Mohr, VP of Industry Relations at Vertafore
Carriers Are Warming Up to Digital but Not Fast Enough
One blocker to digital transformation has historically been the carriers themselves. Many haven’t invested in the technology needed to plug into digital brokers or MGAs.
“That’s changing,” Roady noted. “More are investing in digital distribution. Some are even co-creating products with us specifically for new entrepreneurs and solopreneurs.”
But challenges persist.
Stafford highlighted how even when MGAs develop great digital front-ends, the back end, especially for E&S (excess and surplus) lines, can still feel stuck 15 years behind. Regulatory red tape often prevents digitizing processes like premium finance or renewals.
Mohr confirmed that even large insurers are struggling to modernize. “We’re connecting our agents with platforms and partners to help bridge the gap,” he said, pointing to Vertafore’s “Orange Partner” network of 55 vetted fintech and insurtech vendors.
Video: Daryle Stafford, President & CEO of Veracity Insurance Solutions
Premiums Are Rising, and Tech Is Stepping In
One of the hottest pain points is affordability. Inflation has driven up premiums, especially for small businesses in E&S markets, and many simply can’t afford to pay a year’s premium upfront.
“That’s the elephant in the room,” Stafford admitted. “We’re working on financing options, especially for E&S policies where traditional monthly payments aren’t available.”
Veracity is actively partnering with premium finance companies to offer automated financing at the point of quote. “We’re even seeing E&S markets letting us do monthly payments with no down payment,” he said. “That’s unheard of.”
Mohr sees the same shift. “The prediction is that premium finance will grow into an 80 billion dollar market by 2028. It’s being driven by two things: rising premiums and small businesses needing cashflow flexibility.” Vertafore has partnered with fintechs like IPFS, ePayPolicy, and Ascend to give independent agents the tools to offer clients both pay in full and financing options. “What we’re hearing from agents is that flexibility at the point of payment can make or break the deal,” Mohr said.
Vertafore has partnered with fintechs like IPFS, ePayPolicy, and Ascend to give agents the tools to offer both pay in full and financing options. “What we’re hearing from agents is that flexibility at the point of payment can make or break the deal,” Mohr said.
Roady’s marketplace leans more on installment payments than third-party finance. “For our customers, who often pay under 1,000 dollars per year, installment pay is enough,” she said. “But the pressure is real.”
Generative AI Has Entered the Chat
When asked about the role of Gen AI, Roady lit up. “It’s huge. We’ve built an insurance advisor that helps guide first-time business owners in a conversational way. They tell us what they do, and we recommend coverages.”
She added that Simply Business is also working on a tool where users can upload their existing policies and receive guidance on whether their coverage is appropriate.
Who Owns the Customer Journey?
One surprising tension in the industry is over who owns the customer journey: agents, MGAs, carriers, or tech platforms?
Stafford believes MGAs like Veracity can play a bigger role. “We’re not just writing risk. We’re building the platform, the bundle, and the journey,” he said. “That gives us leverage to drive better experiences.”
Mohr has a more holistic take. “We’re not in the business of picking winners. We help everyone, agents, carriers, MGAs, connect the dots.”
Roady took a clearer stance: “We’re a broker. That gives us neutrality. Our job is to give customers choice.”
But all agreed that seamless integration, especially around payments and financing, is key to delivering on the promise of digital.
What Still Needs Fixing?
Despite clear progress, all three leaders pointed to glaring gaps still waiting to be solved:
Legacy Regulations: “Regulatory constraints are holding us back,” Stafford said. “Things like wet signatures and snail mail for premium finance are killing conversion rates.”
Tech Fragmentation: “Agents have a lot of options when it comes to which fintech and insurtech partner to trust,” Mohr noted. “They are looking for more guidance on finding the right partner and the right tool for their business.”
Education: “Most new business owners don’t even know they can buy online,” Roady added. “That’s still a massive awareness gap.”
The Race Is On
It’s clear that innovation in small business insurance is no longer optional. It’s urgent. Rising premiums, regulatory friction, and customer demand for digital experiences are colliding.
And with billions in premium finance, embedded insurance, and AI-driven platforms on the table, the winners will be those who deliver simplicity, flexibility, and trust at scale.
As Stafford put it, “This is just scratching the surface. There’s so much more to do.”
For more like this on Forbes, check out How Innovation Is Transforming Small Business Insurance and Selling Financial Services Online? Forget SEO, Introducing GEO.
