Sales Operations Manager – Medicare (Client Success Team)

CoverRight is an insurtech startup on a mission to make Medicare more accessible for the 60 million beneficiaries across the U.S. We help the 10,000 Americans aging into retirement each day navigate one of the most important and complex decisions they’ll make: choosing the right health insurance.

*** CoverRight's pace and intensity is not for everyone. *** Intelligence is table stakes. To thrive here, you need extreme speed, agency, adaptability, and a bias toward action. We move fast, take risks, and deeply care about each other and our customers. We have aggressive goals as we accelerate growth and are looking to bring on new team members who are able to move mountains to ‘get things done’.

We’re seeking a Sales Operations Manager to lead and scale our Client Success team of licensed Medicare agents and drive high-velocity performance.

What You’ll Do

• Lead, coach, and develop our licensed Medicare agent team to exceed enrollment and customer experience targets.
• Build a performance-focused culture grounded in discipline, integrity, and high accountability—leveraging leadership principles shaped by both sales experience and military background.
• Drive operational excellence across workflows, KPIs, staffing, and performance, especially through AEP/OEP.
• Partner with Growth, Product, and Compliance to boost conversion rates, lead quality, and agent productivity.
• Create and optimize training, performance management systems, and incentive structures.
• Operate with high ownership, urgency, and independence — expect to be “on call” — this is NOT a 9–5 role.

What We’re Looking For

• 5 years leading Medicare sales, Client Success, or licensed agent teams.
• High accountability. Military leadership experience strongly preferred.
• Strong, clear communicator with high EQ who knows when to apply both carrot and stick.
• Proven ability to drive performance, motivate diverse teams, and enforce high accountability.
• Disciplined, data-driven operator who thrives in high-growth, high-intensity environments.
• Someone who doesn’t wait for assignments — you internalize the mission and deliver results better, faster, and more creatively than expected.

Why Join CoverRight?

• Direct impact on improving healthcare outcomes for seniors.
• High-ownership leadership role in a fast-scaling insurtech company.
• A tight-knit, scrappy, mission-driven team that values speed, accountability, and getting things done.
• The opportunity to build and shape the future of our Client Success organization.

If you’re a disciplined, performance-driven leader who thrives in fast-paced environments and knows how to build exceptional teams, we’d love to talk.