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
40Time Type
Full timePay Range
The typical pay range for this role is:
$43,888.00 - $93,574.00This 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.
Additional details about available benefits are provided during the application process and on Benefits Moments.
Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.
Skills Required
- 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
CVS Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about CVS Health and has not been reviewed or approved by CVS Health.
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Healthcare Strength — Healthcare coverage is positioned as comprehensive for benefits-eligible colleagues, including medical, dental, and vision with free preventive care and access to virtual care and select no-cost MinuteClinic services. Mental health support is also highlighted with no-cost confidential counseling sessions per issue.
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Retirement Support — Retirement benefits include a 401(k) with a dollar-for-dollar match up to 5% after meeting service and hours requirements. Ownership programs are also offered through an employee stock purchase plan with a stated purchase discount.
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Pay Growth & Progression — A companywide minimum wage floor establishes a baseline that is framed as a positive starting point in some roles and markets. Unionized or high-cost areas are described as having clearer wage scales and step-ups that can materially lift pay over time.
CVS Health Insights
What We Do
CVS Health is the leading health solutions company that delivers care in ways no one else can. We reach people in more ways and improve the health of communities across America through our local presence, digital channels and our nearly 300,000 dedicated colleagues – including more than 40,000 physicians, pharmacists, nurses and nurse practitioners. Wherever and whenever people need us, we help them with their health – whether that’s managing chronic diseases, staying compliant with their medications, or accessing affordable health and wellness services in the most convenient ways. We help people navigate the health care system – and their personal health care – by improving access, lowering costs and being a trusted partner for every meaningful moment of health. And we do it all with heart, each and every day.
