Senior Paralegal Jobs in Springfield, MA (NOW HIRING)

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.

The Senior Paralegal will assist attorneys by providing primary legal support and serving as a subject matter expert in connection with the Trade Legal group.

The Senior Paralegal works with multiple internal partners/stakeholders to generate, red‑line, and prepare contract documents for attorney review with the goal of finalizing Caremark's negotiated agreements with pharmaceutical manufacturers. In this role you will work on a variety of document types and across many contracted relationships. You will also follow department guidelines for meeting deadlines and turnaround times and with the team to prioritize documents based on multiple considerations.

A candidate must have experience with contract preparation, support, drafting and document red‑lining in Microsoft Word, as well as, ideally, familiarity with the pharmacy benefit management space. The job requires high attention to detail, critical thinking skills and ability to manage multiple complex agreements simultaneously to identify, assess and elevate critical issues to attorneys. These contracts must accurately reflect Caremark's current business strategies and all current regulatory requirements.

• Preparing initial documents from template forms or creating originals (contracts, letters, settlements, etc.).
• Reviewing contracts received from internal departments and incorporating requested revisions with accuracy and ensuring standard contract language is captured.
• Working with, interpreting and understanding documents including red-lines.
• Reading comprehension.
• Ensuring version control of assigned contracts.
• Proper filing of contracts on the legal drives.
• Drafting new and alternative contract language, letters, prepare settlement agreement and other documents associated with contract documents.
• Gaining familiarity with template contract language and possessing the ability to write, draft, and suggest alternative language for the attorneys review.
• Attention to detail.
• Ability to be flexible and handle heavy contract workload/organize multiple priorities (prioritize documents).
• Excellent communication and time management skills.
• Working independently but also being a dedicated team member in order to assist with workloads of other paralegals on the team.
• Working with attorneys for guidance, direction and document approvals.
• Maintaining confidentiality.

3+ years of paralegal contract support or contract interpretation experience.

3+ years of experience with Microsoft Word and Excel.

Healthcare, PBM, or pharma experience.

Associates degree required or equivalent years of experience.

40

Full time

The typical pay range for this role is:

• $34.66 - $76.26

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.

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: 09/21/2026

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