Health Care Service Corporation

Head of Group Retirement Sales

Health Care Service Corporation$153K — $229K *
Finance & Insurance
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree plus 8+ years in group health insurance or 12+ years of relevant experience
  • Active State Life and Health Insurance license or ability to obtain within 90 days
  • 6+ years of leadership or management experience
  • Superior public speaking and executive-level communication skills
  • Strong negotiation skills with a proven track record of achieving results

Responsibilities

  • Define and implement go-to-market strategies for Medicare group retiree business
  • Recruit, mentor, and lead a sales and account management team
  • Deliver high-value presentations to corporate plan sponsors and unions
  • Collaborate with operational and product development teams for client onboarding
  • Monitor industry trends and regulatory changes to adapt sales strategies

Benefits

  • Health and wellness benefits
  • 401(k) savings plan
  • Pension plan
  • Paid time off and parental leave
  • Disability insurance and life insurance options
  • Tuition reimbursement
  • Employee assistance program
  • Paid holidays
Full Job Description
Job Summary

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

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.

Are you being referred to one of our roles? If so, ask your connection at HCSC about our Employee Referral process!

Pay Transparency Statement:

At Health Care Service Corporation, you will be part of an organization committed to offering meaningful benefits to our employees to support their life outside of work. From health and wellness benefits, 401(k) savings plan, pension plan, paid time off, paid parental leave, disability insurance, supplemental life insurance, employee assistance program, paid holidays, tuition reimbursement, plus other incentives, we offer a robust total rewards package for employees. Learn more about our benefit offerings by visiting https://careers.hcsc.com/totalrewards.

The compensation offered will vary depending on your job-related skills, education, knowledge, and experience. This role aligns with an annual incentive bonus plan subject to the terms and the conditions of the plan.

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.

Base Pay Range
$153,100.00 - $229,600.00

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

About Health Care Service Corporation

Health Care Service Corporation (HCSC) is the largest customer-owned health insurer in the United States. HCSC offers a wide variety of health insurance products and related services, through its operating divisions and subsidiaries in Illinois, Montana, New Mexico, Oklahoma and Texas. HCSC's headquarters is located in Chicago, Illinois.
Learn more about Health Care Service Corporation
Size
24,000 employees
Industry
Founded
1936

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