FAQS

Benefits can be complicated.

We’re here to help.

We are happy you asked — OS BENEFiTS is the first health insurance and wellness benefits platform built for the hospitality industry, by the hospitality industry. We use collective bargaining power to give small businesses access to affordable, ACA-compliant health plans and wellness perks designed with your teams in mind.

If you’re a hospitality business in the U.S. you’re eligible to join. Whether you run a single café or multiple locations, we’ll meet you where you are.

An OSB Membership gives you and your team access to affordable health insurance, dental and vision plans, talk therapy, and a full suite of wellness benefits. Through our community partner network, your employees can enjoy everything from mental health support to fitness, family planning, and lifestyle perks.

• Affordable health insurance with nationwide coverage
• 25+ wellness benefits (mental health, family planning, childcare, etc.)
• A custom OSB Dashboard to manage it all
• Ongoing education, events, and industry insights

Did we mention the wellness benefits are free for all team members with your OSB Membership? Yep—it’s true. Every single employee gets access, whether they enroll in health insurance or not. We designed our membership to empower hospitality businesses of all sizes to offer comprehensive, pre-negotiated benefits that care for the whole health of their people.

Membership starts at $63/month for small teams and scales with your business size. Health insurance premiums begin at $249/month per employee. You can pay monthly or save 10% with annual billing.

Your OSB Membership unlocks access wellness perks designed to support your team’s physical, mental, and everyday well-being. All our benefits are discounted (20-80% off) or free. Every single employee gets these benefits, whether or not they’re enrolled in a health insurance plan.

The best part? These wellness benefits are included for all team members at no additional cost—because caring for your people shouldn’t stop at insurance. Here’s a look at what’s included:

Mental Health Support | 24/7 text-based crisis support and free therapy sessions via our partnership with Southern Smoke Foundation.

Physical Wellness & Preventive Care | Discounted fitness classes, gym memberships, and training programs as well as access to preventive care products like at-home health tests, nicotine gum, and emergency contraception.

Family & Lifestyle Support | Reduced rates on childcare, eldercare, pet care, and fertility resources.

Professional Development | Workshops, training, and industry-specific education to help your team grow in and out of the workplace

Culinary Tools & Apparel | Discounts on pro-grade culinary gear, apparel, and supplies from best-in-class brands

And more | Exclusive perks from our network of hospitality-focused partners to help your team thrive inside and outside of work

We offer ACA-compliant plans designed for hospitality teams:

• Essential Plan EPO Plan – preventive care + unlimited virtual visits ($249/month)
• Advantage, Premium & Max PPO Plans – robust coverage for hospitalizations, maternity, and Rx (starting at $424/month)
• Optional dental & vision add-ons

Unlike other plans, we’re built specifically for hospitality. Our plans and offerings meet our needs and our budgets. Our collective model means lower premiums, no huge deductibles, and perks your team will actually use—like unlimited virtual primary care, mental health resources and crisis support.

Rates vary slightly in New York, California, and Connecticut but only by about $15-$50 PEPM. All to say, a little different but in the same ballpark. We’ll give you a state-specific quote when you reach out.

Any full-time employee, which is defined as any employee who works over 30 hours per week. Plans also offer optional coverage for eligible dependents (those 26 years old and younger) and spouses.

For part-time employees, all of our plans—including the Essential plan—are great for part-time workers with no minimum hours required.

No minimum for our Essential plan. For PPO plans, you’ll need at least 5 enrolled employees.

Nope. You choose who’s eligible—full-time, part-time, or salaried—and we’ll help you set up the right class structure and contribution levels.

Yes, we offer comprehensive dental and vision plans that the employee can choose to add-on to their coverage.

The Affordable Care Act (ACA), is also known as Obamacare, helps all Americans access affordable health insurance. There are several requirements for a health insurance plan to be considered ACA-compliant with things like guaranteed issue during open enrollment (aka pre-existing conditions are not a factor) and coverage for ten essential benefits (e.g. hospitalization, preventative care, maternity & newborn care, etc).

There are some differences between individual / small group (less than 50 full-time employees) and large group (more than 50 full-time employees) plans to be considered ACA compliant, but all plans offered by OSB are ACA-compliant.

Understanding which ACA health plan is right for you can be overwhelming, but we’re here to help.

You can join the OSB Association today (just takes minutes to onboard). If you are interested in health insurance, it takes about 45 days (give or take) from sign-up to coverage start. We’ll walk you through every step so nothing gets missed.

Yes. We know benefits can feel tricky. That’s why Pearl—our support team—guides you and your employees every step of the way, from setup to questions about coverage.

Absolutely! Your OSB Membership unlocks wellness-only benefits for your full team. This includes over 25+ wellness benefits like virtual therapy, childcare support, and discounts on fitness, even if you don’t offer insurance.

Yes! You have two choices:

Teledoc: With your OSB Membership, you can offer your team mental health support—even if you don’t provide health insurance. If you want to add Teledoc to your membership for $10 PEPM, every team member gets free and unlimited virtual therapy through Teladoc, where they can talk to licensed therapists or psychiatrists by phone or video, anytime, anywhere.

Behind You: Also, thanks to our partnership with the Southern Smoke Foundation, your employees also have access to free therapy sessions with licensed professionals who understand the unique challenges of working in hospitality. This is currently rolled out in particular states so we will keep you updated.

It’s all included in your membership because we believe caring for mental health should be as easy as caring for physical health.

We’ve made it easy—just fill out [this form] and our team will send a custom quote for your team size and location.

Oyster Sunday has always been devoted to supporting independent hospitality businesses. After speaking with operators across the country, we found that many of them were struggling to navigate the needs of their teams and their margins at the same time.

That’s why we set out to create a practical way for small businesses to meaningfully and affordably support the health and happiness of their teams.

It’s not just a natural extension of our mission — it’s a tangible way to support the community we serve.

When you think of OS, think of us as Operational Support for independent hospitality businesses. (Or as the friendly champion for little guys everywhere.)

With years of combined experience at Union Square Hospitality Group, Momofuku, The Dinex Group, Instacart, Dig, Blue Hill Stone Barns, Rethink Food, Wagstaff Worldwide, and Nordic Food Lab, Oyster Sunday’s team knows what makes a hospitality business truly extraordinary.

Now we’re bringing the expertise, resources and negotiating power of these major hospitality groups to independent restaurants and hospitality businesses across the country. And we’re just getting started.