OS Benefits

Name

OS Benefits

Legal name

Royal & Pelham Inc.

Website

https://osbenefits.co

Company type

Private

Founded year

2022

Operating status

Operating

Headcount range

1–10 employees

Short description

OS Benefits is a membership-based health insurance and wellness benefits marketplace for independent US hospitality businesses, pooling SMBs to negotiate pre-negotiated ACA-compliant plans and 25+ wellness perks via the OSB Dashboard.

Ownership category

akta.pro rank

Product category

Employee Benefits & Health Insurance

NAICS

Pharmacy Benefit Management and Other Third Party Administration of Insurance and Pension Funds (524292), Health and Welfare Funds (52512)

SIC

Insurance Agents, Brokers & Service (6411), Accident & Health Insurance (6321)

akta.pro primary industry

Benefits Administration (BPACAPAC)

akta.pro secondary industries

Eligibility, Enrollment & Benefits Administration (HLAEALAH), Benefits Administration & Enrollment Support (BPAAAIAB), Association & PEO Group Health Plans (AHP/PEO-Sponsored) (FSAIAFAH)

Keywords

• Health insurance marketplace
• Wellness benefits platform
• Hospitality employee benefits
• Group health coverage
• Benefits administration software

Headquarters

HQ city

New Orleans

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Operations, Technology or R&D, Marketing or Sales, Infrastructure

Revenue model

1. OSB Membership Fees: Annual or monthly membership fees for access to wellness benefits marketplace and OSB Association. Pricing scales by team size from 1-10 employees ($63/month) up to 101+ employees (enterprise pricing). Annual billing provides 10% savings.
2. Health Insurance Premiums: Per-person monthly premiums for ACA-compliant health insurance plans. Four tiers available: Essential ($214), Advantage ($414), Premium ($524), Max ($664). Employers choose contribution levels. Optional dental and vision add-ons available.
3. Teladoc Mental Health Add-on: Optional $10 per employee per month (PEPM) for unlimited virtual therapy through Teladoc partnership. Available as add-on to any OSB Membership with or without health insurance.

Pricing tiers

Go-to-market motion2 records

Distribution channels4 records

Marketing channels7 records

Core offering

OS Benefits operates a membership-based health insurance and wellness benefits marketplace built specifically for the US hospitality industry. Through the OSB Association, it pools independent hospitality businesses to collectively purchase ACA-compliant health insurance plans (EPO and PPO tiers) and access 25+ wellness benefits (mental health, fitness, childcare, culinary tools, continuing education) managed via a HIPAA-compliant dashboard that integrates with major payroll systems.

Product overview

OS Benefits is a health insurance and wellness benefits marketplace designed specifically for the hospitality industry. The platform operates through the OSB Association membership model, providing a unified system that combines ACA-compliant health insurance plans (Essential EPO, Advantage PPO, Premium PPO, and Max PPO) with over 25 wellness benefit categories including mental health support via Teladoc, crisis services, preventive care, family planning, fitness partnerships (ClassPass), childcare (UrbanSitter), continuing education (General Assembly), and culinary tools (Coutelier). All offerings are managed through a centralized HIPAA-compliant dashboard that integrates with major payroll systems. The architecture is modular, allowing employers to select health insurance plans with optional dental and vision add-ons, while wellness benefits are included at no additional cost for all team members regardless of insurance enrollment.

Differentiator

Problem solved

Functional benefit

Products and services

• Essential EPO Plan ACA-compliant EPO health insurance plan with $0 deductible, $1,850 out-of-pocket max, $25 in-person primary care copays, unlimited virtual visits, and hospitalization coverage. Starting at $214 per person per month, designed for independent hospitality employers.
• Advantage PPO Plan ACA-compliant PPO health insurance plan with $2,500 deductible, $9,100 out-of-pocket max, $15 copays, and hospitalization coverage. Starting at $414 per person per month, sold to independent hospitality employers.
• Premium PPO Plan ACA-compliant PPO health insurance plan with $0 deductible, $9,100 out-of-pocket max, $15 copays, full hospitalization and pregnancy coverage. Starting at $524 per person per month for hospitality employers.
• Max PPO Plan Top-tier ACA-compliant PPO health insurance plan with $0 deductible, $9,100 out-of-pocket max, $15 copays, full hospitalization, pregnancy, and prescription coverage. Starting at $664 per person per month.
• OSB Wellness Benefits Marketplace A bundled wellness benefits marketplace offering 25+ categories including mental health support, preventive care, family planning, fitness, childcare, culinary tools, and continuing education, available free to all team members with OSB Membership.
• Teladoc Mental Health Support Optional add-on providing unlimited virtual therapy and mental health care through Teladoc for $10 per employee per month, available with or without OSB health insurance enrollment.
• Dental Plan Add-On Voluntary dental insurance add-on available to all OSB health insurance plans for a nominal fee, sold to hospitality employers.
• Vision Plan Add-On Voluntary vision insurance add-on available to all OSB health insurance plans for a nominal fee, sold to hospitality employers.
• OSB Member Dashboard Centralized HIPAA-compliant platform for employers and employees to manage health insurance, wellness perks, enrollment, and benefits administration, with native integrations to payroll systems including Paycor, Paylocity, Paychex, Proliant, and Rippling.

Quantifiable outcome

• Wellness benefits are free for all team members included with OSB Membership
• +3 more outcomes

Named customers9 records

Segments1 record

Ideal customer profiles2 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration5 records

Feature3 records

Partnerships

Nine partnerships are on record, tiered core, supporting and flagship.

• TeladoccoreTechnology or IntegrationTeladoc provides unlimited virtual mental health care including therapy, crisis support, and self-guided tools. Available through OSB Association membership for $10 PEPM. Teladoc has over 20 years of virtual care experience and serves 100 million members through 40,000+ providers.
• Southern Smoke FoundationcoreStrategic or Co-development PartnerPartnership provides free therapy sessions with licensed professionals who understand hospitality challenges. Currently available in California, Illinois, Louisiana, Maine, Massachusetts, New York, South Carolina, Tennessee, Texas, Virginia, and Washington D.C.
• ClassPasssupportingGTM or Marketing PartnerFitness and wellness class discounts through ClassPass. Part of the 25+ wellness benefits offered to OSB members.
• CouteliersupportingGTM or Marketing PartnerCulinary tools and supplies discounts. Part of the culinary apparel and tools benefits for hospitality workers.
• General AssemblysupportingGTM or Marketing PartnerProfessional development and education opportunities. Part of continuing education benefits for OSB members.
• UrbanSittersupportingGTM or Marketing PartnerChildcare discounts and family planning support. Part of family support benefits for hospitality workers.
• Crisis Text LinecoreTechnology or Integration24/7 text-based mental health support and crisis intervention services. Available to all OSB members.
• SesamesupportingGTM or Marketing PartnerHealthcare discounts and access through Sesame platform. Part of wellness benefits marketplace.
• Oyster SundayflagshipStrategic or Co-development PartnerParent company and operator of OS Benefits. Brings expertise from Union Square Hospitality Group, Momofuku, The Dinex Group, Instacart, Dig, Blue Hill Stone Barns, Rethink Food, Wagstaff Worldwide, and Nordic Food Lab. Created OS Benefits to provide affordable benefits access to independent hospitality businesses.

Scale indicators6 records

Recent moves4 records

Expansion highlights5 records

Direct peers

• Justworks: PEO that administers payroll, benefits, and compliance for SMBs across verticals. Comparable to OS Benefits because both sell health insurance and benefits administration as the primary value proposition to small employers, but Justworks is broader in vertical scope and far more scaled.
• PeopleKeep: ICHRA and small-group benefits administration platform purpose-built for employers with fewer than 50 employees. Closely comparable to OS Benefits' model of packaged, easy-to-buy benefits for small employers, though without the hospitality vertical focus or association buying pool.
• Take Command Health: ICHRA administrator and small-business health benefits platform. Comparable to OS Benefits in delivering simplified, technology-led health benefits to small employers, with overlapping positioning on ACA compliance and pre-negotiated plan design.

Broad incumbents

• Gusto: HR, payroll, and benefits platform serving very small businesses nationwide. Overlaps with OS Benefits on benefits administration and insurance brokerage for SMBs, but operates at much greater scale and across all industries.
• TriNet: PEO providing HR, benefits, payroll, and risk solutions primarily to small and mid-size businesses. Overlaps with OS Benefits on health and welfare benefits administration for SMB employers, but serves multiple verticals at much larger scale.
• ADP TotalSource: Incumbent PEO from ADP serving SMBs with co-employment, benefits administration, and HR outsourcing. Comparable to OS Benefits in the core benefits-administration value proposition, though vastly broader in vertical and product scope.
• Paychex PEO: PEO/HR outsourcing arm of Paychex delivering benefits, payroll, and HR to small and mid-size employers. Comparable to OS Benefits on benefits administration for SMBs, with deeper payroll infrastructure and broader industry coverage.
• Aflac: Leading worksite and voluntary benefits carrier distributed through employers and brokers. Comparable to OS Benefits in the worksite/employee-paid voluntary benefits layer (e.g., the Teladoc mental-health add-on at $10 PEPM), but Aflac is a carrier, not a broker/marketplace.

Emerging players

• Thatch: Modern ICHRA and health benefits platform aimed at small businesses and startups. Comparable in target buyer and product surface (health benefits administration for SMBs), but earlier-stage and not vertical-specialized like OS Benefits.

Regional players

• Toast: Restaurant POS and operating system with an expanding fintech and insurance marketplace (Toast Capital, Toast Insurance) for the same independent hospitality buyer that OS Benefits targets. Comparable because both monetize independent restaurants and have begun offering benefits and insurance-adjacent products, though Toast's primary surface is POS rather than benefits administration.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/osbenefits
• Instagraminstagram.com/osbenefits

Compliance2 records

Revenue estimate

Valuation estimate

Number of profiles

Funding overview

Funding rounds2 records

Investors2 records

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about OS Benefits