Description

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.

Position Summary

The Drafting Supervisor leads a team responsible for the preparation, review, and maintenance of employee benefits documentation, including plan documents, summary grids, SOBs, amendments, and compliance-related materials. This role ensures accuracy, regulatory compliance, and timely delivery while driving consistency, process improvement, and strong collaboration with internal stakeholders such as Legal, Compliance, and Account Management teams.

Primary Job Responsibilities

• Lead, coach, and develop a team of benefits document drafters, including assigning work, prioritizing workloads, and conducting performance evaluations
• Oversee the drafting, revision, and maintenance of benefit plan documents, SOBs, and related communications
• Ensure compliance with applicable laws and regulations (e.g., ERISA, IRS, DOL, ACA), maintaining current knowledge of regulatory changes and incorporating updates as needed
• Partner with legal and compliance teams to interpret regulatory guidance and apply it to plan documentation
• Maintain and manage a comprehensive inventory of benefit documents, including tracking regulatory requirements, key deadlines, and document status (in-progress, completed, backlog), ensuring timely updates and compliance
• Establish and maintain drafting standards, templates, procedures, and quality control processes
• Identify workflow inefficiencies and implement process improvements to enhance accuracy, productivity, and turnaround times
• Collaborate with cross-functional teams (Implementation, Coding, Account Management and Legal) to meet client needs and resolve issues
• Oversee the use and optimization of document management systems, drafting tools, and version control practices
• Support adoption of automation and new technologies to improve efficiency and scalability

Required Qualifications

• 3+ years of experience in employee benefits, insurance, healthcare, or related documentation
• Familiarity with ePub, CCI, or similar structured content systems
• Proven experience drafting and managing benefit plan documents, SOBs, and amendments
• Strong working knowledge of ERISA, IRS, DOL, and ACA regulations
• Demonstrated ability to lead or mentor a team in a deadline-driven, high-volume environment
• Experience managing multiple projects, priorities, and timelines simultaneously
• Proficiency with document management systems, version control practices, and drafting tools
• Advanced skills in Microsoft Word (styles, templates, formatting controls)
• Strong analytical skills with the ability to interpret complex regulations and translate into clear documentation
• Excellent written communication and attention to detail
• Ability to collaborate effectively with cross-functional teams and stakeholders

Preferred Qualifications

• Prior supervisory or people management experience
• Experience in a TPA, health plan, carrier, or benefits administration organization
• Experience with workflow optimization, Lean, or process improvement methodologies
• Exposure to automation tools, macros, or AI-assisted document drafting
• Certification such as CEBS, PMP, or similar
• Experience working with complex plan designs (e.g., self-funded, multi-state plans)

Education

• High School

Anticipated Weekly Hours
40

Time Type
Full time

Pay Range

The typical pay range for this role is:

$43,888.00 - $93,574.00

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.

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: 06/30/2026

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