Plan Sponsor Support Drafting Supervisor (International)

CVS Health•Hartford, CT

7d•$43,888 - $93,574•Onsite

About The Position

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.

Requirements

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

Nice To Haves

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)

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