COBRA Operations Supervisor

Location: Preference for candidates located in Denver, CO or Minneapolis, MN metropolitan areas; remote candidates will also be considered.

Employment Type: Full-time, Exempt

Who We Are

At ThrivePass, we’re on a mission to help employees and businesses Thrive - because benefits should be more than just checkboxes. Through personalized benefits technology, data-driven insights, and meaningful experiences, we empower companies to support their teams in ways that truly matter.

We don’t just talk about culture - we build it. Everything we do is rooted in our CARE values:

Courageous – We embrace new challenges and fresh ideas.

Accountable – We show up as our true selves and value transparency.

Resourceful – We find creative solutions and make things happen.

Engaged – We hold ourselves accountable and take pride in our work.

At ThrivePass, performance isn’t just about hitting goals - it’s about how you show up. We invest in our employees’ growth and encourage bold thinking, collaboration, and continuous learning. Join us in shaping the future of employee benefits!

What You’ll Do

The COBRA Operations Supervisor is responsible for leading, developing, and supporting a high-performing COBRA Operations team while ensuring exceptional customer service, operational excellence, and compliance. This role partners closely with the COBRA Operations Manager and Director of TPA Services to drive team performance, optimize processes, and deliver consistent, high-quality support to clients.

The ideal candidate is a people-first leader who enjoys coaching employees, solving complex operational challenges, and continuously improving the customer experience.

Team Leadership & Talent Development

Lead, coach, mentor, and develop a high-performing COBRA Operations team through regular feedback, performance management, and career development.

Partner with People & Culture to recruit, interview, onboard, and proactively build a pipeline of qualified talent to support current and future staffing needs.

Foster a culture of accountability, continuous learning, collaboration, and operational excellence.

Operational Excellence

Oversee daily COBRA operations, including workload management, scheduling, service levels, and team performance.

Monitor KPIs, customer satisfaction, and operational metrics, implementing action plans to improve results.

Maintain and enhance standard operating procedures, training materials, and compliance with COBRA regulations.

Customer Support & Escalations

Serve as the primary escalation point for complex customer issues and ensure timely, effective resolution.

Act as a subject matter expert on COBRA regulations, operational processes, and customer support best practices.

Collaborate with Product, Operations, Data Services, Finance, and other internal teams to deliver exceptional client outcomes.

Continuous Improvement

Identify opportunities to improve operational efficiency, customer experience, and team effectiveness.

Analyze trends, customer feedback, and regulatory changes to recommend and implement process improvements.

Lead or support strategic initiatives and special projects that advance departmental and organizational goals.

What You Bring

We're looking for a leader who enjoys developing people, improving operations, and delivering exceptional client experiences. The ideal candidate will demonstrate:

A people-first leadership style with a passion for coaching, mentoring, and developing high-performing teams.

Strong critical thinking and problem-solving skills with the ability to make sound decisions in a fast-paced environment.

A customer-focused mindset that balances operational excellence with exceptional service.

Strong organizational skills with the ability to prioritize competing demands and adapt to changing business needs.

Excellent communication and collaboration skills that foster strong partnerships across teams.

A continuous improvement mindset with a desire to streamline processes, develop talent, and drive operational results.

Must Haves

3+ years of COBRA administration or employee benefits operations experience.

2+ years of leadership experience, including coaching, mentoring, performance management, and employee development.

Experience leading customer support or operations teams.

Experience recruiting, interviewing, onboarding, and proactively building a pipeline of qualified talent.

Experience using metrics and KPIs to manage team performance and drive operational improvements.

Nice to Have

Experience with benefits administration, COBRA, or HR technology platforms.

Experience developing KPIs, dashboards, and operational reporting to drive team performance.

Experience leading process improvement, workflow optimization, or system implementation initiatives.

Familiarity with compliance requirements related to employee benefits administration.

Why You’ll Love Working Here

Hiring Range: $60,000 - $75,000

A culture that values courageousness, authenticity, resourcefulness, and excellence (we don’t just say it - we live it).

Opportunities to grow, learn, and level up your skills.

A team that genuinely enjoys working together and celebrating wins.

Competitive benefits package including medical, dental, vision, 401(k) with match, and paid parental leave.

An inclusive and welcoming environment for all. ThrivePass is committed to fostering a workplace where everyone feels valued and respected. We do not and shall not discriminate based on race, color, religion (creed), gender, gender expression, age, national origin (ancestry), disability, marital status, sexual orientation, or military status in any of our activities or operations.

Join Us!

If this role sounds like your next great adventure, we’d love to hear from you. Apply today and let’s build something amazing together!