Head of Group Retirement Sales

hcsc· Health Care Service Corp.
Apply Now ↗
🌍 Remote📍 4 Locations📍 IL - Chicago📍 TN - Nashville📍 TX - Richardson📍 Work From Home (HB)Full time💰 USD 153K–230K
Full timeRemoteHealth Care Service Corp.

About this role

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 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.

Frequently Asked Questions

What is the salary for the Head of Group Retirement Sales role at hcsc?
The listed salary for this Head of Group Retirement Sales position at hcsc is USD 153K–230K. This is a remote Full time role.
Is the Head of Group Retirement Sales job at hcsc remote?
Yes, this Head of Group Retirement Sales position at hcsc is remote, with team members based in 4 Locations, IL - Chicago, TN - Nashville, TX - Richardson, Work From Home (HB). You can work from home or anywhere in the supported regions.
Is the Head of Group Retirement Sales role at hcsc full-time or part-time?
This is listed as a Full time position. It is posted as a Head of Group Retirement Sales role in the Health Care Service Corp. department at hcsc.
Which team or department does the Head of Group Retirement Sales at hcsc belong to?
This Head of Group Retirement Sales position is part of the Health Care Service Corp. department at hcsc. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Head of Group Retirement Sales position at hcsc?
Click the "Apply Now" button on this page. You will be redirected to hcsc's official application portal hosted on workday where you can submit your application directly.
When was the Head of Group Retirement Sales job at hcsc posted?
This Head of Group Retirement Sales position at hcsc was posted on Jul 27, 2026. Apply as soon as possible — early applications are often reviewed first.
Head of Group Retirement Sales
hcsc · 💰 USD 153K–230K
Apply for this role ↗

You'll be redirected to hcsc's official application page on Workday.