A Rewards Program That Doesn’t Trip the Rebate Laws

Stuart Winchester is a lifelong New Yorker with a genuine, self-described obsession with the subway system — he tracks every ride in a spreadsheet, keeps a real-time LED subway map in his home office, and collects vintage transit posters. It’s a fitting detail for a founder whose company, Marble, is built around the idea that a well-designed system (in this case, an insurance rewards program) should feel effortless to the person using it, however much complexity sits underneath.

Before founding Marble, Stuart built and ran the insurance vertical at Better.com — now the company’s second-largest business line after mortgage — and before that, ran the flagship New York campus for coding bootcamp General Assembly. He’s also, by his own account, come full circle: his father is a lifelong insurance professional who started at Lloyd’s of London at 18 and still works in the industry today. Watching his English-major son detour through a coding bootcamp and land back in insurance has been, Stuart said, one of the great joys of his father’s career.

About Stuart Winchester

Stuart Winchester is CEO and Founder of Marble, a digital wallet for insurance built to be a consumer’s central hub for their policies — comparable, in his framing, to Mint for budgeting or Robinhood for stocks — layered with the industry’s first true rewards program.

Building Rewards Without Tripping State Rebate Laws

Marble’s core insight, per Stuart, isn’t that insurance is broken — it’s that legacy carriers have poured investment into distribution technology and, especially with climate change, risk assessment, while consumer-facing tools have consistently been left for later. Marble’s answer is a rewards layer modeled loosely on how credit card companies skim a share of interchange and return it to cardholders as rewards — except applied, for the first time, to insurance.

Getting there took roughly a year of legal work with McDermott Will & Emery and Cooley to design an approach that stays inside the boundaries of state rebate laws — no soliciting business, no cross-selling, and rewards tied strictly to risk-based or financial-wellness actions rather than the purchase itself. Stuart noted, with some satisfaction, that the NAIC has since proposed model legislation explicitly consistent with Marble’s approach, which he sees as strengthening the company’s regulatory position further.

In practice, a Marble user connects their insurance information into the app, can refer friends, and — in features rolling out over the following quarters — earns rewards for actions like installing a flood monitor, completing a home inventory, or switching to paperless billing, funded by a pool carriers contribute from the discounts, lead fees, and expense-ratio gains those actions actually generate for them.

Who Pays, and Who Gets Excited

Marble’s paying customers are insurance carriers; policyholders use the product for free. Internally, Stuart said marketing leaders and retention teams (chief retention officers, CRM leads) are consistently the most engaged champions, since a rewards program speaks directly to their mandate the same way airline miles or credit card rewards do. Innovation teams engage too, though they tend to have a harder time handing the relationship off to the business units that would actually operationalize it. A newer, “half a category” of interest, per Stuart, has come from large carriers exploring the same mechanic to incentivize independent and captive agents — validating that a continuing education course was completed, or a policy was bound, and triggering rewards dynamically in response, rather than building a generic points-and-leaderboard gamification layer for its own sake.

At the time of this recording, Marble was preparing to launch with a top-15 legacy carrier whose CMO, per Stuart, brought real conviction to the partnership — targeting a 9-to-1 return on investment on the rewards budget itself, through improved expense ratios and risk mitigation.

Early Traction, and an Honest Take on Facebook Ads

Marble launched its web app in April of the recording’s year, and had grown to roughly 4,000 users in four months, covering millions of dollars of premium inside the digital wallet, with about $45,000 in rewards pushed out to users. Stuart’s favorite signal wasn’t the raw numbers — it was that users had started describing Marble in conversation the way they’d describe a fintech app like Chime or Robinhood, which is exactly the category Marble is trying to earn a place in.

He was candid, and unapologetic, about the channel driving most of that growth: Facebook ads — cheap, efficient, and consistently improving for Marble’s specific audience, despite being an unfashionable answer among venture capitalists who prefer defensible, enterprise-value-building spend over consumer acquisition budgets. He acknowledged the tension directly: it’s genuinely harder for a VC to justify writing a check where a large share of it becomes ad spend rather than product-building, which is part of why B2B SaaS has become an easier sell for many investors — but he pushed back gently on the idea that consumer products are therefore a lesser opportunity, noting simply that consumers still want new things, and someone still has to market to them.

Getting Into Insurance, the Hard Way

Stuart’s own path into insurance ran through Better.com’s revenue operations team, where market feedback pointed toward the need for more lifetime value beyond a single mortgage transaction. Homeowners insurance stood out as the natural adjacency — Hippo was raising capital at the time, and Lemonade was headquartered nearby in SoHo — and Better made a deliberate decision to build an owned agency rather than route business through lead fees, prioritizing a consistent customer experience over the simpler economics of referral. That meant Stuart needed his own insurance license, which at the time required in-person coursework in New York — three weeks of classes near Penn Station, a bombed practice exam the night before, and, by his account, the last all-nighter he’s pulled in his life to pass on the first try.

From there, Stuart’s on-ramp into the broader insurtech community ran through the NAIC conference in Boston and, shortly after, InsureTech Connect — where he met the teams at Hippo and Lemonade, insurtech Young Alfred, and investors at IA Capital.

Advice: Start a Blog, or Get a Cat

For his closing recommendation, Stuart pointed to a personal project he’d taken up during the pandemic: finally building out a personal website, informed by his earlier career as a bootcamp career coach who always told graduating students to keep a public home for their writing and projects. He’s using it to publish commentary on insurance, transit, and whatever else comes to mind — self-deprecatingly describing himself as “a failed English major” finally getting his writing fix. His backup recommendation, only half in jest: get a cat, or get married — he did both during the pandemic.

Key Takeaways

• Marble spent roughly a year working with McDermott Will & Emery and Cooley to design a rewards program that stays inside state rebate law boundaries — tying rewards to risk-based and financial-wellness actions rather than the purchase itself, an approach the NAIC has since echoed in proposed model legislation
• Carriers pay for Marble; policyholders use it free — the clearest internal champions are marketing and retention leaders, with a newer wave of interest from carriers wanting the same validated-action rewards mechanic applied to agent incentives
• Stuart’s unfashionable but effective growth channel has been Facebook ads — a deliberate contrast to the enterprise-value story that makes B2B SaaS easier for many VCs to underwrite, and a reminder that consumer insurance products still need real, unglamorous marketing spend
• Better.com’s decision to build homeowners insurance as an owned agency rather than a lead-fee referral business was a deliberate customer-experience choice, not just an economic one — and it’s what put Stuart through in-person licensing requirements in New York
• Marble’s first major carrier launch was targeting a 9-to-1 return on its rewards budget, driven by expense-ratio improvement and risk mitigation rather than raw customer acquisition