Manager Health Insurance Enrollment Jobs in Kentucky

We're building a world of health around every individual - shaping a more connected, convenient and compassionate health experience. At CVS Health®, you'll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger - helping to simplify health care one person, one family and one community at a time.

We are seeking a highly motivated Senior Project Manager - Health Insurance to support our Stop Loss business and lead critical cross-functional initiatives from planning through implementation. This role will be responsible for driving strategic and operational projects that support a multi-million-dollar portfolio of initiatives impacting underwriting, actuarial, finance, sales, account management, marketing, and product teams. The ideal candidate takes initiative, solves complex problems, and is comfortable making decisions with limited direction. This individual will be expected to quickly learn our systems, understand business processes, and advance existing projects while identifying opportunities for continuous improvement.

This position offers a unique opportunity for someone interested in expanding their career into Product Management, with anticipated growth into product-focused responsibilities within the next 12-18 months.

Key Responsibilities

• Lead and manage strategic and operational projects supporting the Stop Loss business from initiation through completion.
• Partner with stakeholders across underwriting, actuarial, finance, product, sales, account management, marketing, and operations to execute business priorities.
• Drive project plans, milestones, dependencies, risks, and deliverables to ensure successful outcomes.
• Learn and navigate healthcare insurance systems and processes, including projects involving Aetna platforms and workflows.
• Advance existing projects, remove roadblocks, and identify opportunities to improve processes and business results.
• Analyze issues, evaluate options, and make sound recommendations and decisions.
• Communicate project status, risks, and key decisions to leadership and stakeholders.
• Adapt priorities as business needs evolve and support the ebb and flow of initiatives across the Stop Loss organization.
• Contribute to strategic discussions and gradually assume product-oriented responsibilities as business needs evolve.

Required Qualifications

• 7+ years of professional experience in project management, program management, or related business leadership roles.
• Healthcare industry experience required, ideally within health insurance or employee benefits.
• Demonstrated success leading complex, cross-functional projects with multiple stakeholders.
• Strong problem-solving, critical thinking, and decision-making capabilities.
• Ability to take initiative, work independently, and drive progress in ambiguous situations.
• Excellent collaboration, relationship-building, and communication skills.
• Growth mindset with a demonstrated ability to learn new systems, processes, and business functions.
• Interest in growing into Product Management responsibilities over time.

Preferred Qualifications

• Experience in Stop Loss

Education

Bachelor's degree (Required) and specialized training/relevant professional qualification and experience

This role is located either in Hartford or remote in either Eastern or Central time zones. The role does not support sponsorship at this time.

Pay Range

The typical pay range for this role is:

$67,900.00 - $182,549.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company's equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full-time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well-being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 08/31/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.