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CoverRight · 4 weeks ago

Sales Operations Manager – Medicare (Insurance)

New York, NY

Full-time

Onsite

Senior Level

5+ years exp

CoverRight is an insurtech startup focused on making Medicare accessible for millions of beneficiaries in the U.S. They are seeking a Sales Operations Manager to lead their Client Success team of licensed Medicare agents and drive high-velocity performance and operational excellence.

FinTechHealth CareInsuranceInsurTechMedicalRetirement

Responsibilities

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

Qualification

Medicare sales leadershipClient Success managementPerformance management systemsData-driven operationsHigh accountabilityTeam motivationCommunicationAdaptability

Required

5+ years leading Medicare sales, Client Success, or licensed agent teams

High accountability

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

Preferred

Military leadership experience strongly preferred

Company

CoverRight

CoverRight is the trusted co-pilot for older adults to navigate health and finance options.

Founded in 2021

Brooklyn, New York, USA

2-10 employees

https://coverright.com/

Funding

Current Stage

Early Stage

Total Funding

$8.13M

Key Investors

Carthona Capital

2025-08-11Series Unknown· $5.93M

2024-07-01Series Unknown

2022-12-12Undisclosed· $2.2M

Leadership Team

Richard Chan

Founder & CEO

Akash M.

Business Development & Partnerships Consultant

Recent News

SEC Filings

UNITED STATES SECURITIES AND EXCHANGE COMMISSION

2025-08-14

Governor Kathy Hochul

Governor Hochul Announces Winners for Tenth Annual 43North Startup Competition

2025-02-27

CoverRight and Asset Insure, Inc. Partner to Deliver Enhanced Medicare Services to Clients

2024-03-02

Company data provided by crunchbase