Interested candidates, please reach out to [email protected].
Title: Sales Manager
Location: Remote, within the US
Classification: Exempt, full-time
Working Hours: 40 hours/week, 9a-5pm in the individual’s time zone (within US)
Compensation: $65,000 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 CEO
- Represent 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 Managements tools (Insightly, HubSpot, Asana, Salesforce, or similar)
- Comfort with remote, asynchronous work on a small, fast-moving team
- AI-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 growth
DISCLAIMER
We'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.
Skills Required
- 3+ years of B2B sales experience
- Experience in insurance, benefits, HR tech, or hospitality-adjacent industries
- Active insurance producer or 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-building skills with independent operators and larger group accounts
- Self-starter able to operate without heavy infrastructure or large support team
- Clear, compelling written, verbal, and in-person communication skills
- Experience with CRM and project management tools (Insightly, HubSpot, Asana, Salesforce, or similar)
- Comfort with remote, asynchronous work on a small, fast-moving team; AI-curious mindset
What We Do
Affordable, ACA-compliant health insurance plans with low co-pays, competitive monthly premiums, and nationwide coverage for services like preventative care, accidental and many other services. Many of our insurance plans have no deductible and members have the option to add dental and vision coverage for a nominal fee.
Why Work With Us
Our team consists of experienced specialists from across the hospitality industry who have built their careers under industry-leading brands. By pooling these resources for our clients, we create a mutually beneficial economy of scale, but also draw from the learnings of operators across the country, optimizing our services and best practices.
