Zorro

A New York startup is quietly retiring the group health plan.

It is open-enrollment season at a mid-sized employer, and for once nobody is dreading it. There is no binder of identical plan options, no shrug from HR, no annual ritual of picking the least-bad PPO. Instead, each employee opens a screen, types in their doctor and their prescriptions, and watches an AI sort through dozens of individual plans to find the one that actually fits. That screen belongs to Zorro.

Zorro runs on a simple, slightly subversive idea: that the company should not be the one choosing your health insurance. The employer sets a budget. The employee gets an allowance. Everyone picks the plan they would have picked anyway, if only someone had handed them the keys. It sounds obvious. In American health benefits, obvious is in short supply.

Three people at the table, all unhappy, all stuck.

The traditional group health plan is a marvel of mutual dissatisfaction. Employers watch premiums climb every year and have almost no levers to pull except cutting coverage or eating the cost. Employees get handed a plan chosen by committee, designed for the statistical average, fitting almost nobody in particular. And brokers - the people who are supposed to fix this - have been selling the same product with the same tools for decades.

The fix has technically existed since 2020. It is called an ICHRA, the Individual Coverage Health Reimbursement Arrangement, which lets employers reimburse workers with pre-tax dollars for insurance they buy themselves. A genuinely good idea wrapped in a genuinely terrible acronym, which may explain why it sat mostly unused. The plumbing was missing. Nobody had built the software to make it painless.

Two investors who got tired of waiting for someone else to build it.

Guy Ezekiel and Maya Perl met at Pitango, one of Israel's largest venture funds, where they spent their days as HealthTech investors looking for the company that would fix employer benefits. They kept not finding it. So in 2022 they did the slightly reckless thing investors rarely do: they left the comfortable side of the table and started building the company themselves.

Ezekiel took the CEO seat. Perl became Chief Customer Officer - a telling choice of title, since Zorro's whole premise rests on whether ordinary employees can actually navigate the individual insurance market without panicking. The bet was that data science could do the navigating, and that human empathy, not just algorithms, would keep people from feeling abandoned at the moment they needed coverage most.

A company on two clocks

Zorro was built across two cities at once: a New York headquarters near the customers and the carriers, and an R&D team in Tel Aviv near the engineering talent. The company came out of stealth in March 2023 with an $11.5 million seed round co-led by Pitango and 10D - the very fund the founders had just left, now writing them a check.

One platform, three people, each handed a different superpower.

Zorro's software does something deceptively hard: it serves the employer, the employee, and the broker without making any of them feel like an afterthought. The employer sets a contribution budget and gets predictability, compliance, and engagement analytics. The broker gets real-time quoting and contribution modeling, plus the ability to put a group plan and an ICHRA option side by side. And the employee gets the part that matters most at the moment of truth.

The decision engine

When an employee enrolls, Zorro's AI asks the questions a good broker would: Who are your doctors? What medications do you take? What can you afford if something goes wrong? Then it searches across dozens of individual-market plans and verifies that the coverage actually includes the doctors and prescriptions that person named. The headline number Zorro likes to cite: more than 75% of employees pick a plan straight from the AI's recommendation, no human in the loop.

The numbers, before the narrative gets ahead of them.

Skepticism is the correct response to any benefits company promising to cut costs and add choice at the same time, since those two usually trade against each other. Zorro's claim is that ICHRA breaks the trade-off: by letting people self-select into plans priced for individuals, the math works for both sides. The early evidence is encouraging, if still early.

Then there is the single case study Zorro keeps in its pocket: Rush Memorial Hospital, which reported $2.25 million in annual healthcare cost savings after moving to Zorro. A hospital, of all places, fixing its own benefits bill. If the people who run healthcare can save money on healthcare, the argument writes itself.

Health and wealth, on the same balance sheet.

Zorro's ambition runs past insurance. Ezekiel talks about a "health-to-wealth journey," the idea that the way Americans pay for, save for, and plan around healthcare should sit alongside the rest of their financial life rather than in a separate, confusing silo. One early framing was even bolder: to become something like the Wells Fargo of healthcare and financial services. Bold, and the kind of line that ages either very well or very badly.

For now the company is staying close to the thing it does well - making individual coverage selection painless - and adding payment processing and financial-planning tools around it. The $20 million Series A is earmarked for exactly that: scaling operations, building out customer infrastructure, and pushing the AI further. The investors clearly think the trade-off is real. So, increasingly, do the brokers.

Back to the screen, one year later.

Return to that open-enrollment screen. The employee who typed in their doctor and their prescriptions now has a plan that covers both, chosen in minutes, paid for with the employer's allowance, and roughly 20% cheaper than the group plan it replaced. HR did not dread it. The broker made a sale they could be proud of. The employer got a number it can actually predict.

That is the whole pitch, and it is not complicated: give people the budget, give them a good guide, and let them choose. Group health insurance spent decades insisting that choice and savings could not coexist. Zorro is one of the companies betting that the only reason they couldn't was that nobody had built the software yet. The screen is open. The binder is gone.