Head of Group Retiree Solutions

Health Care Service Corporation

Chicago (IL)

On-site

USD 153,100 - 229,600

Full time

14 days+
Application generator

Don’t send a generic resume — generate a resume and cover letter tailored to this exact role.

Get past ATS filters

Job summary

Health Care Service Corporation (HCSC) seeks a Head of Group Retiree Sales to drive revenue growth and market share in the Medicare retirement space. This executive will lead a team of sales and account professionals and partner with product and compliance to deliver comprehensive group retirement solutions to large employers.

The role requires 8+ years in group health insurance sales or related fields, plus 6 years of leadership.

Qualifications

  • Bachelor degree required with 8+ years in group health insurance sales or related roles, or 12+ years of experience.
  • Active State Life and Health Insurance licenses or obtain license within 90 days.
  • 6 years of leadership or management experience.
  • Strong executive-level communication and contract negotiation skills.

Responsibilities

  • Define the overarching go-to-market strategy for the Medicare group retiree business.
  • Recruit, mentor, and lead a team of sales and account management professionals.
  • Lead complex presentations to corporate plan sponsors, labor unions, and large consultant firms.
  • Collaborate with operations, implementation, product development, and relationship management teams for onboarding and retention.
  • Monitor industry trends, regulatory changes (ERISA and DOL) to adapt sales strategies and inform offerings.
  • Work with commercial sales leaders and AE in market development.

Skills

Leadership
Public speaking
Negotiation
Strategic planning
Sales leadership
Executive communication
Budget management
Industry knowledge

Education

Bachelor's degree

Tools

Insurance licenses

Job description

At HCSC, our employees are the cornerstone of our business and the foundation to our success. We empower employees with curated development plans that foster growth and promote rewarding, fulfilling careers.

Join HCSC and be part of a purpose-driven company that will invest in your professional development.

The Head of Group Retiree Sales is a senior leadership role responsible for driving revenue growth and market share in the Medicare retirement space. This executive leader oversees sales strategies, manages a team of sales and account management professionals, and collaborates with product and compliance teams to deliver comprehensive group retirement solutions to large employers.

Job Responsibilities
  • Define the overarching go-to-market strategy, product positioning, and sales objectives for the Medicare group retiree business
  • Recruit, mentor, and lead a team of sales and account management professionals
  • Lead or oversee complex, high-value consultant and employer presentations to corporate plan sponsors, labor unions, and large consultant firms
  • Partner with operations, implementation, product development, and relationship management teams to ensure seamless client onboarding and long-term retention
  • Monitor industry trends, competitive landscapes, and regulatory changes (such as ERISA and DOL guidelines) to adapt sales strategies and inform product offerings
  • Work in collaboration with the commercial sales leaders and AE in market development
Job Qualifications
  • Bachelor Degree and 8 years of group health insurance account management, sales, broker, product development, underwriting, or benefit consulting experience OR 12 years of group health insurance account management, sales, broker, product development, underwriting, or benefit consulting experience
  • Requires active State Life and Health Insurance licenses or obtain license within 90 days of starting in the position
  • 6 years of leadership or management experience
  • Superior public speaking, executive-level communication, and contract negotiation skills
  • Demonstrated results in being able to think strategically, anticipate future consequences and trends, and incorporate them into both a short-term and long-term organizational plan
  • Strong influencing and negotiation skills, contracting and network savvy, business owner mindset and ability to successfully lead in an ambiguous and changing market
  • Proven track record of exceeding goals and a bottom-line orientation; evidence of the ability to consistently make good decisions through a combination of analysis, wisdom, experience, and judgment; high level of business acumen, including the ability to balance the delivery of programs against the realities of a budget; allocates resources and manages operating expenses while managing risk
  • Effective communicator to executive level staff and external audiences balanced with strong interpersonal skills

Compensation: $153,100.00 - $229,600.00

Exact compensation may vary based on skills, experience, and location

HCSC Employment Statement

We are an Equal Opportunity Employment employer dedicated to providing a welcoming environment where the unique differences of our employees are respected and valued.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or any other legally protected characteristics.

To learn more about available benefits, please click https://careers.hcsc.com/totalrewards

Get your free, confidential resume review.
or drag and drop your file here.
Similar jobs

Similar jobs worth comparing

Head of Group Retiree Solutions
Head of Group Retiree Solutions

Medicare • Chicago (IL)

On-site
USD 153,000 - 230,000
Total rewards
Head of Group Retirement Sales
Head of Group Retirement Sales

HCSC Group • Chicago (IL)

On-site
USD 153,100 - 229,600
Head of Group Retirement Sales
Head of Group Retirement Sales

Health Care Service Corp. • Chicago (IL)

On-site
USD 153,100 - 229,600
health and wellness benefits
401(k) savings plan
pension plan
+8
Medicare Group Retirement Sales Leader
Medicare Group Retirement Sales Leader

Health Care Service Corporation • Chicago (IL)

On-site
USD 153,000 - 230,000
Lead, Medicare Group Retiree Solutions
Lead, Medicare Group Retiree Solutions

Medicare • Chicago (IL)

On-site
USD 153,000 - 230,000
Total rewards
Sales Executive II
Sales Executive II

Health Care Service Corporation • Houston (TX)

On-site
USD 58,000 - 87,000
Director National Account Management - North Texas
Director National Account Management - North Texas

Health Care Service Corp. • Richardson (TX)

Hybrid
USD 131,000 - 197,000
Senior Manager, Medicare Product Solutions - Work From Home
Senior Manager, Medicare Product Solutions - Work From Home

HCSC Group • Nashville (TN), Northern (KY)

Hybrid
USD 102,000 - 184,000
Senior Manager, Medicare Product Solutions - Work From Home
Senior Manager, Medicare Product Solutions - Work From Home

Health Care Service Corp. • Nashville (TN)

Remote
USD 102,000 - 184,000
Health and wellness benefits
401(k) savings plan
Pension plan
+6
Director Small and Mid Market Sales - South Texas
Director Small and Mid Market Sales - South Texas

TX PLAN • Houston (TX)

Hybrid
USD 119,000 - 179,000
Health benefits