Medicare Sales Manager - Territory Lead (Senior Role)

About Us

Silvur is modernizing what retirement decision-making in America looks like. We partner with financial institutions to deliver world-class tools and educational resources to their account holders—including personalized content, calculators, and connections to healthcare and financial services—to support the critical decisions their members make in their 50s, 60s, and through retirement.

Our white-labeled online platform is available to millions of credit union members and has been named to the Forbes Fintech 50 Most Innovative Companies. We’ve been featured in The New York Times, Fortune, CNBC, and Yahoo! Finance, and are backed by leading VCs like Anthemis and strategic investors including Curql, Reseda Group, Idaho Central Credit Union, Maps, WESECU, and Mission Federal Credit Union.

We believe health and wealth are inseparable in retirement—and we’re reimagining how credit union members are educated and supported during their Medicare journey. The introduction of our full-service, concierge Medicare agency, Silvur Insurance, in 2024 allows us to extend our services to provide members with much-needed one-on-one guidance led by licensed insurance agents. Our education-first model ensures trust, clarity, and personalized care.

About the Role

The Medicare Sales Manager – Territory Lead is responsible for driving Medicare sales performance while leading, coaching, and enabling a team of Medicare agents within an assigned territory.

This role is a player-coach leader who balances direct sales leadership with operational ownership. The Sales Manager is responsible for helping agents achieve enrollment goals while also building the tools, processes, and reporting needed to scale the Medicare sales organization.

The ideal candidate thrives in lean, fast-moving environments and has experience working with smaller teams with limited resources, where leaders are expected to take ownership and build infrastructure that enables growth. This includes developing reporting dashboards, job aids, training materials, operational templates, and process improvements.

In addition to managing agent performance, Sales Managers serve as subject matter experts (SMEs) in key operational areas and lead cross-functional initiatives that support agent development, partner onboarding, and organizational growth.

We are looking for leaders who enjoy building and scaling sales organizations—not simply managing established ones.

Key Responsibilities

Sales Leadership & Execution

• Own Medicare sales performance across the territory (appointments, conversions, enrollments, retention)
• Lead and coach agents across virtual and in-person channels
• Step in to sell during peak demand or coverage gaps
• Ensure consistent execution of the sales process and high-quality member experience
  

Build & Scale Sales Systems (Core to Role)

• Design and build sales reporting, dashboards, and KPI frameworks
• Develop and standardize sales processes, workflows, and operating rhythms
• Create job aids, templates, and training resources to drive consistency and scale
• Identify inefficiencies and implement process improvements across the sales org
• Partner with operations, marketing, and technology to improve systems and automation

Coaching, Talent & Team Development

• Coach agents on consultative sales, compliance, and performance improvement
• Support recruiting, hiring, onboarding, and ramp of new agents
• Drive accountability to performance standards and KPIs
  

Medicare & Operational Expertise

• Serve as a subject matter expert on Medicare products, compliance, and carrier processes
• Support agent certification, contracting, and ongoing readiness
  

Territory Growth & Partner Execution

• Support onboarding and success of credit union partners
• Drive member engagement through events, webinars, and branch activity
• Ensure operational readiness for new market and partner launches
  

Organizational Leadership

• Lead cross-functional initiatives and special projects (process, tools, launches)
• Act as an escalation point for complex agent or operational issues
• Own key SME areas (e.g., analytics, onboarding, training, recruiting) that support broader organizational scale

Travel

• Up to 50% travel may be required to support agents, credit union branches, and member engagement events within the territory.
• Occasional overnight travel should be expected.
• Must live in Mid-Atlantic / Northeast Regions. Driving distance to airport less than 1 hour and/or (direct flights to Boston, NY, Baltimore)

What Success Looks Like

• Consistent achievement of territory enrollment and revenue targets
• Clear, scalable sales processes adopted across the team
• Strong agent performance, productivity, and retention
• Operational systems (reporting, tools, training) that enable growth beyond the current team

Requirements

Required

• 5+ years of Medicare sales experience with a track record of driving enrollment growth
• 2+ years leading or coaching Medicare agents
• Demonstrated experience building sales processes, reporting, or operational systems
  Active health insurance license
• Strong knowledge of Medicare products, compliance, and carrier processes
• Must live in Mid-Atlantic / Northeast Regions. Driving distance to airport less than 1 hour and/or (direct flights to Boston, NY, Baltimore)
  
  

Preferred

• Experience in lean or high-growth environments where leaders build infrastructure
• Experience with CRM systems, dashboards, and sales analytics
• Experience supporting new market or partner launches

Benefits

Compensation & Benefits

You will be an employee of Silvur Insurance Services. Employees receive a total compensation package including base salary, policy incentive commission, options, health benefits (healthcare, vision, and dental), paid time off + holidays, and 401k with employer contribution. You may choose the technology you need to help you excel in your role. You will work in a flexible environment with an impact-driven, high-growth team that is changing the future of retirement healthcare. 

Salary: $90,000 - 120,000 base pay, depending on experience

Silvur Technology Services is an equal opportunity employer. We’re committed to building a team that reflects the diverse communities we serve and creating a workplace where everyone feels valued and included.