Sales Manager

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