Why We Invested

OS BENEFiTS: Health Coverage for the Deskless Workforce

October 12, 2026

The Artemis Fund believes technology can create prosperity for all. With offices in New York, Texas, Massachusetts, and Nevada, Artemis leads seed rounds for companies creating resilient families, individuals, and businesses across the US. 
A line cook works a full week on her feet and picks up a second job bartending on weekends to make ends meet. If she gets sick, she has no health coverage, and going untreated means her income is at risk. She earns just enough to no longer qualify for Medicaid, but not enough to absorb a $30,000 medical bill if something goes wrong. The ACA marketplace is an option, but a comparable Bronze plan costs two to five times what a larger employer would pay for the same coverage. The restaurant that employs her wants to offer health insurance, but the group plans built for small businesses assume steady headcount, full-time hours, and margins the restaurant doesn't have.
There are 80M+ deskless workers in the US, the majority of whom lack access to affordable, effective benefits. OS BENEFiTS is tackling this, starting with the 16M+ employees, including hourly, part-time and seasonal staff, across the $800B hospitality industry.
OS BENEFiTS (OSB) is health insurance purpose built for a flexible, fractional workforce, including hourly, part-time and seasonal staff. Restaurants, bars, cafes, and hotels struggle to offer affordable, comprehensive coverage to their fractional workforces, so OS BENEFiTS built it for them. By allowing businesses to pool risk at an association level, the company gives owners access to pre-negotiated health plans, along with wellness perks like therapy, telehealth, and dental and vision coverage, at a price that actually fits a restaurant's margins. This enables operators to care for their teams, without sacrificing their bottom line.

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Founder and CEO Elizabeth Tilton built her career inside the hospitality industry, starting in the back of house in New Orleans before moving into brand and partnerships roles at Momofuku and W&P, and launching her own hospitality company, Oyster Sunday, in 2019. Oyster Sunday has become a customer acquisition channel and a direct line into the operator relationships that inform OS BENEFiTS' product.
The Opportunity
We believe that as technology changes, work will too (more fractional, part-time W2s, 1099s, etc.). For example, office and administrative support is projected to lose 752,100 jobs as AI-powered automation spreads, and the deskless workforce is expected to grow. The financial tools that make care accessible will have to become more flexible and purpose-built for the deskless workforce.
Accessibility is declining. Rising minimum wages have pushed many restaurant workers above the Medicaid income ceiling of $20,782 a year without giving them a realistic path to employer coverage in its place. ACA marketplace premiums in key markets run 2-5x higher than OS Benefits' equivalent plans, at comparable or worse coverage levels.
In hospitality, food preparation and serving occupations have a 22% uninsured rate, the third highest of any occupation group in the country. Fewer than 30% of restaurant workers receive employer-sponsored health insurance.
The problem extends well beyond restaurants: construction has a 27.8% uninsured rate across roughly 8 million workers, with similar gaps in retail and entertainment.
The Solution
OS BENEFiTS gives deskless workers access to comprehensive and affordable coverage. Employers join the OS Benefits Association, which pools risk across small employers who would not qualify for group coverage on their own. Participation floors are as low as one life for minimum essential coverage, and five lives for a major medical PPO plan. Members get access to ACA-compliant medical, dental, and vision plans built specifically for restaurants, hotels, and food and beverage businesses, starting at $214/month.
A single dashboard handles enrollment, onboarding, and benefits administration. Members also unlock 20+ wellness perks, from mental health support to continuing education to culinary tools discounts. OS BENEFiTS is built for portability, so even as employees move between hospitality roles, the product moves with them. OS BENEFiTS built this model from the ground up to fit how the deskless workforce actually works.
The Impact
Health insurance is one of the strongest financial safety nets a person can have, and most hospitality workers go without it. A single uninsured emergency can mean medical debt, missed rent, or a health issue left untreated until it becomes a crisis. OS BENEFiTS closes that gap, giving hospitality workers real, usable coverage instead of high-deductible plans that often fail when they're needed most. For operators, that same coverage becomes a retention tool in an industry where turnover costs 3-6x an employee's hourly wage. OS BENEFiTS is building the infrastructure to bring health coverage to every independent restaurant in the country, and eventually to every deskless worker beyond it.
We believe once in a generation companies will be built by unexpected founders. If that sounds like you, pitch us here!

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