Head of Outbound Sales (Remote)

Sales Manager

Sales Manager

Location: Remote, within the US

Classification: Exempt, full-time

OS BENEFiTS is the first affordable health insurance and wellness benefits marketplace made for the hospitality industry, by the hospitality industry.

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.

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; Identify partnership and referral opportunities that expand our reach within the hospitality ecosystem

3+ years of B2B sales experience, ideally in insurance, benefits, HR tech, or hospitality-adjacent industries

Demonstrated track record of hitting or exceeding quota in a consultative sales environment

Strong relationship-builder — comfortable with both independent operators and larger group accounts

Experience working with CRM and project management tools (Insightly, HubSpot, Asana, Salesforce, or similar)

Comfort with remote, asynchronous work on a small, fast-moving team

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

Milestone-based bonus structure tied to company growth

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.