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 ofemployee 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
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.
CVS Health is an equal opportunity/affirmative action employer, including Disability/Protected Veteran — committed to diversity in the workplace.
CVS Health offers a world of promising job opportunities across a diverse range of careers in everything from corporate and pharmacy roles to retails positions. No matter where you work at CVS Health, your unique skills, talents and abilities are welcome and valued. We recognize and reward greatness and want our employees to know their work is making a difference in the lives of millions. Join us today. Together we can continue making innovative, high-quality health and pharmacy services safe, affordable and accessible – for all.