POSITION OVERVIEW

We are seeking a Field Sales Manager for a growing Medicare Agency! This company has 10+ years of industry experience. The role offers $50k/year with variable comp up to an additional $30-50k/year annually! This position will be in the field managing a team of 20-25 Medicare Agents in retail locations in PA/NJ.

Candidates with Insurance or Medicare experience are preferred but not required as there is extensive training!

The Medicare Field Sales Manager (FSM) is a critical frontline leadership role within our Field Marketing Organization (FMO). The FSM serves as the direct point of accountability for all sales activity, agent productivity, compliance, and channel performance across an assigned territory of 15–25 retail locations, partner storefronts, or employer group sites. This position bridges executive strategy and boots-on-the-ground execution — ensuring that licensed Medicare agents within the territory are fully certified, schedule-adherent, quota-driven, and delivering a best-in-class consumer experience during both Annual Enrollment Period (AEP) and non-AEP selling seasons.

CORE RESPONSIBILITIES

Territory Management & Location Oversight

• Conduct regular in-person visits to all 15–25 assigned locations on a structured rotation schedule, ensuring consistent brand presence, agent readiness, and location compliance at each site.
• Serve as the primary relationship owner for each location — maintaining strong partnerships with store management, site coordinators, and partner contacts to facilitate smooth daily operations.
• Conduct location audits to ensure agent workstations, marketing materials, enrollment technology (tablets, laptops, CRM access), and signage are in compliance with CMS and carrier standards.
• Coordinate with operations and logistics teams to resolve location-level issues including equipment, scheduling gaps, and enrollment platform access.
• Monitor location-level enrollment volume, lead flow, and consumer traffic trends, adjusting staffing and scheduling strategy accordingly.

Agent Recruiting & Hiring

• Own full-cycle recruiting for licensed Medicare producers within the territory — sourcing, screening, interviewing, and selecting candidates in partnership with the Talent Acquisition team.
• Conduct structured behavioral interviews and role-play assessments to evaluate candidates' Medicare product knowledge, sales aptitude, consumer engagement skills, and compliance awareness.
• Maintain a proactive hiring pipeline to ensure the territory is fully staffed ahead of AEP, SEP surges, and attrition events — targeting a zero-gap model for all assigned locations.
• Evaluate candidate licensure status (resident and non-resident), carrier certifications, and AHIP completion during the screening process.
• Collaborate with onboarding teams to expedite carrier appointments, background checks, and system provisioning for new hires.
• Provide hiring recommendations and headcount forecasts to the Regional VP on a weekly basis during peak recruiting cycles.

Training, Onboarding & Development

• Deliver structured onboarding programs for all new agents, covering Medicare product fundamentals, carrier-specific benefit structures, CMS marketing guidelines (Chapter 3), enrollment platform usage, and objection handling.
• Conduct ongoing field training through side-by-side observation, live call monitoring, and co-enrollment sessions — providing real-time coaching and documented feedback to agents at all performance levels.
• Facilitate regular team meetings, product refresher trainings, and carrier-sponsored education sessions to maintain product currency across the team.
• Develop and execute individualized performance improvement plans (PIPs) for agents who fall below baseline productivity metrics, with clear milestones and accountability checkpoints.
• Ensure 100% AHIP completion, carrier certification, and required continuing education (CE) compliance for all agents in the territory prior to selling season.
• Champion a culture of continuous improvement — leveraging data from CRM platforms, enrollment reports, and quality audits to identify coaching opportunities across the team.

Agent Compensation Structure (Direct Reports)

Each licensed Medicare agent under the Field Sales Manager’s supervision operates on the following compensation structure. The FSM is responsible for clearly communicating this model during recruiting, onboarding, and ongoing performance conversations, and for ensuring agents understand how their activity directly drives their take-home earnings.

● FSM Responsibility: The Field Sales Manager is expected to use the compensation model as both a recruiting tool and a performance motivator — clearly articulating the earning potential to candidates during hiring conversations and consistently reinforcing the link between daily enrollment activity and take-home pay during coaching sessions and team meetings.

Productivity & Performance Accountability

• Hold agents accountable to weekly and monthly enrollment targets, application submission rates, consumer touchpoint goals, and lead-to-close conversion benchmarks.
• Monitor and report on territory-level KPIs on a daily basis during AEP and weekly during non-AEP periods — escalating performance risks to the Regional VP with data-supported action plans.
• Conduct weekly 1:1 performance reviews with each agent in the territory, reviewing individual enrollment counts, schedule adherence, consumer satisfaction scores, and open leads.
• Enforce minimum activity standards including daily consumer engagements, appointment sets, enrollment submissions, and follow-up contacts per CRM protocol.
• Identify top performers and champion recognition, advancement, and retention strategies to reduce voluntary attrition across the territory.

Schedule Management & Shift Accountability

• Develop and manage location-level staffing schedules across all assigned sites — ensuring appropriate coverage during peak consumer hours, enrollment events, and high-traffic periods.
• Hold agents to strict shift adherence standards — monitoring clock-in/clock-out compliance, escalating unexcused absences, and documenting schedule violations per company policy.
• Manage and approve time-off requests, shift swaps, and schedule modifications in a manner that maintains minimum location coverage thresholds at all times.
• Coordinate surge staffing during AEP, SEP events, and carrier-sponsored enrollment drives — sourcing temporary coverage from the recruiting pipeline or existing float agents.
• Communicate schedule expectations clearly and consistently, ensuring agents have confirmed assignments no fewer than two weeks in advance.

Compliance & CMS Regulatory Adherence

• Ensure all agents within the territory operate in full compliance with CMS Medicare marketing guidelines (Chapter 3), carrier-specific compliance standards, and applicable state insurance regulations at all times.
• Conduct monthly compliance observations at each location — reviewing sales presentations, enrollment documentation, SOA (Scope of Appointment) handling, and consumer interaction protocols.
• Escalate any suspected compliance violations, unauthorized marketing activity, or consumer complaints to the Compliance team immediately upon identification.
• Ensure agents maintain all required licensure, carrier certifications, and E&O coverage, maintaining current records in the organization's agent management system.
• Stay current on CMS Final Rule updates, carrier benefit changes, and state-specific regulatory developments — disseminating relevant changes to the field team with appropriate urgency.

Reporting & Communication

• Submit weekly territory performance reports to the Regional VP, including enrollment volume, agent headcount, hiring pipeline status, compliance observations, and location-level issues.
• Maintain complete and current records in the CRM for all agents, locations, leads, and enrollment activity within the territory.
• Communicate proactively with carrier BD representatives, enrollment platform contacts, and FMO operations staff to resolve issues and surface opportunities.
• Represent the organization professionally at carrier meetings, partner events, community enrollment fairs, and trade events within the territory.

PREFERRED QUALIFICATIONS

• Prior experience managing a distributed team across multiple retail or partner locations simultaneously.
• Carrier appointments across two or more major Medicare Advantage plans (UHC, Humana, Aetna, Cigna, BCBS, WellCare, or equivalent) within the territory.
• Experience operating within an FMO, IMO, or MGA distribution structure.
• Bilingual preferred in high-demand markets (Spanish/English).
• Experience with Medicare field marketing events, community-based outreach, and retail enrollment programs.
• Bachelor's degree in Business, Healthcare Administration, Communications, or a related field preferred; equivalent experience accepted.

CORE COMPETENCIES

• Ability to lead, motivate, and hold accountable a geographically dispersed team of licensed producers without direct daily oversight. Field Leadership:
• Proven ability to identify, attract, and close high-quality sales talent in a competitive licensed producer market. Recruiting Instinct:
• Commitment to continuous agent development through observation, feedback, and structured improvement frameworks. Coaching & Development:
• Unwavering adherence to CMS and carrier standards, with the ability to instill a compliance-first culture across the team. Compliance Discipline:
• Ability to read, interpret, and act on enrollment data, agent productivity reports, and location-level performance dashboards. Data Fluency:
• Strong organizational skills to manage scheduling, site logistics, reporting, and pipeline simultaneously across a multi-location territory. Operational Rigor:
• Clear, direct, and professional in written and verbal communication with agents, carrier partners, store management, and senior leadership. Communication:
• Thrives in a fast-paced, deadline-driven AEP environment; proactively identifies and resolves issues before they escalate. Sense of Urgency:

Pay: From $50,000.00 per year

Benefits:

• Dental insurance
• Health insurance
• Paid time off
• Vision insurance

Application Question(s):

• Are you comfortable managing a field sales team where you are required to visit specific worksite locations on a daily basis?

Experience:

• Retail, Business to Business or Business to Consumer Sales: 2 years (Required)
• Management/Leadership: 2 years (Required)
• Medicare: 1 year (Preferred)

Willingness to travel:

• 75% (Preferred)

Work Location: On the road