Interested? Please email careers@osbenefits.co.Sales Manager
Title: Sales Manager Location: Remote, within the USClassification: Exempt, full-time
Working Hours: 40 hours/week, 9a-5pm in individual’s time zone (within the US)
Compensation: $55,000 Annual Salary with Commission + Benefits
About OS BENEFiTS:
OS BENEFiTS is the first affordable health insurance and wellness benefits marketplace made for the hospitality industry, by the hospitality industry.
About the Role:
OS BENEFiTS is entering a period of focused growth, and the Sales Manager will be at the center of it. This is a ground-floor sales leadership role: you’ll build and own our pipeline, develop relationships with hospitality operators across the country, and work hand-in-hand with our CEO and product team to bring our benefits marketplace to the workers who need it most. If you're motivated by the idea that a hospitality worker somewhere gets covered because of a deal you closed, and you want real ownership over how we build our sales function from the ground up, this role is for you.
What You’ll Do:- Own the full sales cycle from prospecting to close, targeting hospitality employers, operators, and associations
- Build and manage a pipeline of employer and association group clients across the restaurant, hotel, and hospitality sectors
- Develop and execute outbound sales strategies in partnership with the CEORepresent OS BENEFiTS at industry events, conferences, and community gatherings
- Collaborate with the product, operations and customer success teams to ensure smooth onboarding and client handoffs
- Track sales activity, pipeline health, and key metrics in CRM; report progress to leadership
- Identify partnership and referral opportunities that expand our reach within the hospitality ecosystem
- Provide market feedback that informs product development and go-to-market strategy
What We’re Looking For:- 3+ years of B2B sales experience, ideally in insurance, benefits, HR tech, or hospitality-adjacent industries
- Active insurance producer/broker license required on day one
- Demonstrated track record of hitting or exceeding quota in a consultative sales environment
- Deep familiarity with or genuine passion for the hospitality industry and its workforce
- Strong relationship-builder — comfortable with both independent operators and larger group accounts
- Self-starter who can operate without heavy infrastructure or a large support team
- Clear, compelling communicator: written, verbal, and in-person
- Experience working with CRM and project management tools (Insightly, HubSpot, Asana, Salesforce, or similar)
Comfort with remote, asynchronous work on a small, fast-moving teamAI-Curious: have a desire to use and adapt to AI.
Why OS BENEFiTS:- Small team, lean operation — you'll shape how we sell, not just execute a playbook already built for you
- Real flexibility: remote, and trusted to manage your own time
- A product and mission built to serve the hospitality workforce — the people who often get left out of "employee benefits" conversations
- Room to grow: as we scale, this role scales with you
Milestone-based bonus structure tied to company growthDISCLAIMERWe're committed to building a team as diverse as the workforce we serve, and we encourage candidates from all backgrounds — including those who don't check every box in the qualifications above — to apply.
OS BENEFiTS provides equal employment opportunity to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local laws.
