Define and operationalize a multi-year sales strategy aligned to enterprise Medicare growth goals.
Own the end-to-end sales funnel, including lead intake, routing logic, prioritization, and conversion optimization.
Lead a large-scale sales organization, including both internal teams and external BPO partners.
Lead end-to-end planning and execution for Annual Enrollment Period (AEP) and Open Enrollment.
Partner closely with Marketing and Digital teams to align lead generation strategies with sales capacity and performance expectations.
Design and continuously improve the sales customer journey.
Lead the evolution of the sales technology stack, including CRM systems, analytics platforms, and AI-enabled tools.
Own financial outcomes for the career sales channel, including revenue growth, cost per acquisition, and overall efficiency.
Ensure strict adherence to CMS Medicare marketing guidelines, state regulations, and internal compliance standards.
Align career sales with digital, broker, and telesales channels to create a seamless and consistent consumer experience.

15+ years of leadership experience in managing a direct team that cold calls and drives self gen sales volume.
Proven ability to lead National or large-scale, high-volume sales organizations with measurable results.
Strong financial, operational, and analytical capabilities.
Experience in healthcare, Medicare, or other regulated industries preferred.
Proven ability to develop strategy, set and meet established targets and effectively manage programs.
Ability to synthesize complex information and communicate it to a wide variety of audiences including internal and external business partners.
Experience working with and supporting senior leadership to achieve strategic goals across the segment or enterprise-wide.
Critical thinking skills to connect disparate dots and overcome ambiguity.
Data-driven operator with advanced proficiency in CRM, funnel analytics, forecasting, and sales productivity tooling (AI-enabled call guidance a plus).
Exceptional people leadership: culture builder, change leader, and developer of high-performing teams.
Bachelor’s degree required; MBA or related advanced degree preferred.

Hybrid work; flexibility based on business needs and seasonal AEP demands.
Travel ~30% to partner locations, field markets, councils, and internal meetings.
Health insurance
401(k) matching
Paid time off
Professional development opportunities.
Work from a dedicated space lacking ongoing interruptions to protect member PHI / HIPAA information.

VP, National Field Career Sales

Key skills