Chief Operating Officer

**Interested candidates please email [email protected]. Thank you!

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:
We’re looking for a Chief Operating Officer to build and lead the operating engine behind OS BENEFiTS — a modern health benefits platform designed for the hospitality industry.
This role partners closely with the CEO, who owns high-level vision and long-term strategy, while the COO owns execution and day-to-day operational authority. That means a clear division of responsibility: you run the engine, and together you set the direction.

You’ll bring a bias toward building clear decision-making frameworks — think RACI-style accountability, defined ownership, and structured rollouts — so the team can move fast without stepping on each other. This is a role for someone who thrives in ambiguity, builds systems from scratch, and leads with both rigor and hospitality.

What You’ll Do:

1. Customer Experience & Retention
2. Design and oversee the full customer lifecycle (onboarding → engagement → renewal)
3. Establish a best-in-class, hospitality-driven experience model

4. Own retention, satisfaction, and long-term customer value

5. Insurance & Benefits Operations

6. Oversee day-to-day insurance operations, including plan administration, enrollments, and vendor coordination

7. Build scalable systems for onboarding, eligibility, and support

8. Partner with compliance to ensure operational accuracy and risk mitigation

9. Operational Infrastructure & Decision-Making

10. Build and optimize internal workflows, systems, and processes with clear ownership frameworks (e.g. RACI)

11. Develop KPIs across customer success, operations, and support

12. Establish and maintain a knowledge management system to capture institutional knowledge as the team scales

13. Ensure the business can scale efficiently with growth

14. AI & Technology Integration

15. Lead a structured 60-day initiative to embed AI across internal operations and product — starting with support email automation and high-repetition workflows

16. Build the roadmap for AI-assisted operations and partner with the technology team on implementation

17. Identify opportunities to leverage AI to improve member experience and reduce operational overhead

18. Cross-Functional Leadership

19. Serve as the bridge between Product, Engineering, Marketing, and Revenue

20. Translate customer insights into product and operational improvements

21. Partner with the CEO on strategic planning and execution

22. Team Building & Recruitment

23. Hire and lead the Operations and Customer Experience team

24. Actively participate in recruiting and candidate selection across functions as the company grows

25. Establish a strong culture rooted in hospitality, accountability, and continuous improvement

26. Coach and develop leaders across functions

What We’re Looking For:

• 8–12+ years of experience in operations, preferably in health tech, insurance, or a high-growth startup
• Proven experience building and scaling operational systems from early stage
• Strong understanding of customer experience and retention-driven businesses
• Comfort operating in ambiguity and building from scratch
• Deeply strategic but highly execution-oriented

Why OS BENEFiTS:

• Small team, lean operation—you’ll make an immediate impact
• Flexible hours and remote work
• A product and mission you can stand behind

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.