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This is a summary of an episode of Pioneers, an educational podcast on AI led by our founder. Join 3,600+ business leaders and AI enthusiasts and be the first to know when new episodes go live. Subscribe to our newsletter here.
TL;DR:
- Brokers adopting AI aren’t just cutting costs, they’re scaling sales and automating their “secret sauce” to reach more clients efficiently.
- Legacy agencies that resist AI face extinction, while those that adopt it become “risk concierges” operating at superhuman scale.
- The real opportunity lies in serving underserved SMBs with digital-first, transparent insurance marketplaces like Agent3.
- GenAI enables faster, more contextual decision-making, compressing underwriting timelines from weeks to minutes.
- Trust, education, and personalization, not price, will define the winners as the industry shifts to AI-powered brokerage.
Before we dive into the key takeaways from this episode, be sure to catch the full episode here:
Meet Cheynna - Managing Partner at Massie Risk
Cheynna Massie is reshaping commercial insurance from the inside out. As Managing Partner and CFO of Massie Risk, a third-generation Bay Area brokerage, and Founder of Agent3, an AI-native insurance platform, she’s bringing automation and intelligence to one of the industry’s most traditional sectors.
Her background in finance and investment banking gives her a unique edge in understanding mid-market economics and how technology can drive top-line growth.
“AI can be this great enabler of top-line growth... it’s not just an operational efficiency play.” — Ankur Patel
At Massie Risk, she oversees operations that blend human expertise with AI-powered insight; at Agent3, she’s building a marketplace that connects SMBs with top-rated carriers through transparent, AI-driven workflows.
A self-described “contrarian” in insurance, Cheynna believes the future belongs to hybrid models where brokers act as risk concierges, scaling human empathy with machine intelligence to deliver faster, fairer coverage.
From Legacy Brokerage to AI-Native Vision
Cheynna Massie began her career in finance before taking over Massie Risk, her family’s third-generation brokerage. But her “aha moment” came when she realized how generative AI could revolutionize insurance.
“I was blown away in five minutes by the amount of research I could do,” she recalls, comparing it to the days when brokers relied on expensive, outdated lead lists.
That insight led her to found Agent3, an AI-native commercial insurance platform connecting SMBs with top-rated carriers.
“It’s beautiful to fix the margins in the back office, but the profit bottleneck is really our brokers.” — Cheynna Massie
For Cheynna, AI is not just an efficiency play. It is a way to scale expertise and capture each broker’s “secret sales sauce” in code.
Why Traditional Agencies Risk Extinction
Cheynna warns that agencies resisting AI could fade from relevance.
“I do see a semi-extinction path for agencies that don’t adopt some of these technologies,” she says. The future broker, she believes, will become a “risk concierge” who uses AI as a co-pilot to serve clients faster and smarter. “You don’t have to have a sales agent out there, an AI agent selling to your customers, but I think you become more of a price taker for acquisitions,” she explains.
Her vision balances automation with humanity: “People don’t want to talk to a human until they want to talk to a human. You better have a human.”
To survive, traditional firms must modernize their workflows while preserving the personal trust that defines the industry.
Automating the Unstructured: Commercial vs. Retail Insurance
Retail insurance is largely standardized, but commercial lines remain messy and complex. “Retail is a homogeneous risk,” says Cheynna.
“Commercial insurance comes with a lot of messy unstructured data.” Each business has a unique risk profile, from a restaurant to a roofer or software company, making it difficult to automate. But that is changing fast.
“My whole thesis centers around this automation migration that’s about to happen in insurance,” she explains. Generative AI can now reason over variability and handle “the heavy-hitting issues” that traditional RPA could not.
“Decision AI distills expertise and workflow knowledge of industry veterans,” says Cheynna, enabling faster, more consistent underwriting. What once took weeks can now be completed in minutes, turning specialized human judgment into scalable, auditable logic.
Agent3 and the New Marketplace Model
At Agent3, Cheynna is building what she calls an orchestration layer between SMBs and carriers. “We’re building a marketplace where businesses have the opportunity to access the best policies and coverages,” she explains.
The timing could not be better. “We have this infrastructure alignment happening right now,” she says, pointing to the “carrier API revolution,” the rise of GenAI reasoning, and “an SMB digital expectation shift” where “85% of SMBs prefer a digital-first interaction in insurance.”
With these conditions, Agent3 can automate underwriting for smaller accounts that most brokers ignore. “We can now provide white-glove service to everyone,” says Cheynna, “without broker fees or that feeling of ‘is my broker doing the right thing by me?’”
The Human Element Still Matters
Even as automation transforms insurance, Cheynna insists that trust and education remain at the heart of the business.
“It’s not price. As organizations scale, it’s a trust and relationship game. And it’s an education game.” — Cheynna Massie
“As organizations scale, it’s a trust and relationship game.” Most small businesses, she notes, “fail a basic insurance quiz” and rely on brokers to guide them. “Part of that is hand-holding the client through helping them understand exactly why they need certain coverages,” she explains. That personal connection builds credibility even in an AI-driven world.
The best brokers, she believes, will combine specialized knowledge with transparent, AI-powered tools that make coverage faster, fairer, and easier to understand.
