As the old saying goes, insurance is bought not sold. U.S. businesses alone spend hundreds of billions on it each year, yet the details go unnoticed. Coverage is understood as “the cost of doing business” while many companies go without the protection they actually need. In a market that still runs on emails and PDFs, customers have nonetheless come to expect that their premiums will increase every year. And business owners also accept, or simply don’t know, that commissions—often as high as 30%—incentivize brokers to sell them expensive policies that too often don’t actually mitigate the risks they face.

The very largest companies, such as the Fortune 2000, have in-house risk managers to oversee insurance. But most other businesses must rely on traditional brokers. These legacy providers’ high costs and manual operations prevent personalized assessments from specialists who deeply understand a business’s operations, while perverse incentives align the brokers’ interests with insurers’, not customers’. Rather than delivering the best client experience, insurance producers are focused primarily on growing their book of business; as a result, customers are simultaneously overcharged and underinsured.

With AI, however, all of that can change.

WithCoverage co-founders JD Ross and Max Brenner are supercharging risk management by pairing industry experts with technology. JD and Max believe comprehensive risk audits shouldn’t be reserved for the world’s biggest companies—they think that’s how insurance should work for everyone. WithCoverage’s AI audit engine helps their team analyze a business’s policies and operations to spot what brokers miss, so they can deliver a line-by-line breakdown of potential savings and risks on a customer’s first call. Meanwhile, countless emails and PDFs are replaced by a simple, digital platform and a unified team. Hidden commissions are replaced by transparent fees. One convert told us, “I had no intention of changing brokers, but they blew us away.” 

When we at Sequoia talked to the teams that use WithCoverage, we heard the same effusive customer love again and again. “The best claims call we’ve ever had.” “Your team will actually thank you.” “Instead of taking you golfing, they will actually save you money on insurance.” And then there were the bottom lines: saving customers up to 30% on their total insurance budget, representing up to seven figures.

The customers aren’t the only ones suddenly paying more attention to insurance. JD and Max understand that building applied AI is about capturing nuance—automating countless tiny decisions, in the right order, to deliver for their customers—and that is exactly how WorkCoverage operates. Product and Engineering teams sit side-by-side with risk specialists, working together to design what customers truly need. For anyone interested in breaking the scaling laws of a massive market, it is the perfect place to be.

Even better, WithCoverage is led by two exceptional founders. While at Washington University, JD founded and scaled two businesses, joined the fintech company Addepar as its fifth employee when he was just 19, and still graduated in three years. A few years later, he and Keith Rabois (our co-lead in WithCoverage’s Series B) joined forces with Eric and Ian to co-found Opendoor. Max, meanwhile, scaled Compound to its first $1B in AUM as part of the founding team. Applying software to financial advice reshaped his view of why legacy advisory businesses stagnate—and where they can be rebuilt from first principles. After leaving, he was intent on starting a generational business. When a friend introduced JD and Max over lunch, they knew immediately that they wanted to work together. They are true outliers, and they have the velocity and grit to go the distance.

Hundreds of companies across sectors have already switched to WithCoverage, and word is spreading fast. JD, Max, and the team are quickly expanding into new verticals, from construction to aerospace—and in response to customer demand, plan to grow beyond insurance, as well. We at Sequoia are proud to be by their side as they work to fully modernize risk management and to bring insurance on-side for businesses.