Head of Group Retiree Solutions

Medicare

Chicago (IL)

On-site

USD 153,000 - 230,000

Full time

14 days+
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Job summary

HCSC is seeking a senior sales and account leadership role focused on the Medicare group retiree business. You will define the go-to-market strategy, recruit and mentor a high-performing team, and lead presentations to corporate sponsors and large consulting firms.

You will collaborate with operations, product development, and relationship management to ensure seamless onboarding and long-term client retention, while tracking industry trends and regulatory changes to adapt offerings.

Qualifications

  • Bachelor degree required with extensive experience in group health insurance account management or related fields.
  • Active Life and Health Insurance licenses or ability to obtain within 90 days of starting.
  • Proven leadership with ability to manage and mentor teams.
  • Strong public speaking, executive communication, and contract negotiation skills.

Responsibilities

  • Define 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 complex consultant and employer presentations to sponsors, unions, and large firms.
  • Collaborate with operations, implementation, product development, and relationship management for onboarding and retention.
  • Monitor industry trends and regulatory changes to adapt sales strategies and offerings.
  • Work with commercial leaders and AE in market development.

Skills

Public speaking
Executive communication
Negotiation
Strategic thinking
Influencing
Leadership
Budget awareness

Education

Bachelor Degree
12+ years industry experience

Tools

Life & Health 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.

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
Required 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

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