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Retiree Jobs in Massachusetts (NOW HIRING)

Benefits Specialist

Holyoke, MA · On-site

$105 - $130/hr

Drive annual open enrollment for active and retiree populations--project planning, system readiness/testing, vendor coordination, and employee-ready communications * Lead special projects as assigned ...

Drive annual open enrollment for active and retiree populations-project planning, system readiness/testing, vendor coordination, and employee-ready communications * Lead special projects as assigned ...

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Showing results 1-20

Retiree information

See Massachusetts salary details

$10

$18

$25

How much do retiree jobs pay per hour?

As of Sep 5, 2026, the average hourly pay for retiree in Massachusetts is $18.52, according to ZipRecruiter salary data. Most workers in this role earn between $16.30 and $21.25 per hour, depending on experience, location, and employer.

What is a retiree?

Retirees are individuals who have permanently left the workforce, typically after reaching a certain age or fulfilling years of service that allow them to claim retirement benefits. They may receive income from pensions, Social Security, savings, or investments. Many retirees use this period to pursue hobbies, travel, volunteer work, or spend more time with family and friends. Retirement marks a significant life transition that often involves adjusting to new routines and managing finances without employment income.

What are the key skills and qualifications needed to thrive as a retiree, and why are they important?

This role is not a professional occupation and does not require specific job skills, qualifications, or technical tools. Retirees may benefit from personal financial management skills and familiarity with retirement planning resources. Adaptability, self-motivation, and social engagement are valuable soft skills for adjusting to post-career life. These qualities help retirees maintain their well-being, pursue new interests, and enjoy a fulfilling retirement.

What part-time or consulting opportunities are commonly available for retirees looking to stay engaged in the workforce?

Many retirees opt to remain active professionally by pursuing part-time or consulting roles in areas where they have significant experience. These opportunities can range from mentoring, project-based consulting, seasonal work, or advisory positions, often allowing for flexible hours and remote options. Employers value the expertise and reliability retirees bring, and such roles often provide both continued income and the satisfaction of contributing to their field. Networking, professional associations, and specialized job boards can be great starting points for retirees seeking these positions.

What is the difference between Retiree vs Volunteer?

AspectRetireeVolunteer
CredentialsNo specific credentials requiredNo credentials typically required
Work EnvironmentVaries; often leisure or part-timeCommunity settings, nonprofits, hospitals
Employer/IndustryPersonal choice, no employerNonprofit organizations, charities
Search/Comparison IntentUnderstanding post-retirement optionsFinding volunteer opportunities

Retirees are individuals who have stopped working after reaching retirement age, often seeking leisure or part-time activities. Volunteers, on the other hand, actively contribute their time to organizations without pay, often in community or nonprofit settings. While both roles involve time outside of traditional employment, retirees focus on personal leisure or part-time work, whereas volunteers aim to support causes and communities.

What is the best job for a retiree?

Retirees often find suitable jobs in areas such as part-time retail, consulting, tutoring, or administrative roles, which typically offer flexible hours and less physical demand. These jobs often require minimal training or certifications and can be tailored to individual interests and skills.

What are the most commonly searched types of Retiree jobs in Massachusetts?

The most popular types of Retiree jobs in Massachusetts are:

What job categories do people searching Retiree jobs in Massachusetts look for?

The top searched job categories for Retiree jobs in Massachusetts are:

What cities in Massachusetts are hiring for Retiree jobs?

Cities in Massachusetts with the most Retiree job openings:

Infographic showing various Retiree job openings in Massachusetts as of August 2026, with employment types broken down into 75% Full Time, 23% Part Time, and 2% Contract. Highlights an 97% Physical, and 3% Remote job distribution, with an average salary of $38,526 per year, or $18.5 per hour.

Sr. Manager, Group Retiree Solutions - Strategic Initiatives Lead

CVS Health

Wellesley, MA • On-site

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 4 days ago


Key responsibilities

  • Serve as the GRS Open Enrollment COE leader, overseeing annual Open Enrollment performance, operational execution, and team leadership.

  • Develop, implement, and execute end-to-end planning, training, and delivery of GRS Open Enrollment operational activities and workflows.

  • Partner with cross-functional teams and stakeholders to enhance Open Enrollment processes, track performance, and report results.


CVS Health rating

5.8

Company rating: 5.8 out of 10

Based on 4,364 frontline employees who took The Breakroom Quiz

92nd of 113 rated pharmacies


Job 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 ourselvesaccountable 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.

Aetna Group Retiree Solutions (GRS) is a core component of the HCB Medicare Organization. Our vision is to develop an industry-leading group retiree health care business by delivering unrivaled value to our plan sponsors and their members. We aspire to provide personalized, member-centric care that treats retirees like human beings during a sensitive chapter in their lives. We work as a strategic partner that is uniquely committed to helping our clients reach their benefit goals. Innovation, accountability, and teamwork, with an emphasis on structure and process, drive us to deliver unparalleled results.

TheGroup Retiree Solutions - Strategic Initiatives Project Leadwill be responsible for:

  • Serving as the GRS Open Enrollment COE leader, accountable for annual Open Enrollment performance, operational execution, and team leadership.

  • Developing, implementing, and executing end-to-end planning, training, and delivery of GRS Open Enrollment operational activities framework (which includes cross-functional workflows and best practices).

  • Proactively partnering with several teams, including Account Management, Direct to Consumer Marketing, Medicare Service Operations (MSO) and various business partners to build upon and enhance our Open Enrollment processes and workflows in support of new/existing business.

  • Developing annual Open Enrollment Activity Roadmap, performance dashboards and managing, tracking and reporting results against OE Activity budgets.

  • Establishing key partnerships and collaborating with stakeholders and business partners to advance various GRS goals.

  • Leading and implementing the SBI Scorecard tracking / performance monitoring process to ensure operational objectives and other strategic business initiatives are tracked / measured (i.e., performance dashboards).

  • Managing coinciding project/initiative budgets, plans and expenses.

  • Proactively evaluating project activities, building contingency plans, executing corrective actions, and monitoring issue resolution to mitigate risks such as scope and/or budget variances.

  • Developing and presenting information on our services, capabilities and performance results to internal/external customers, constituents, and business partners to drive the decision-making process and support business operations.

  • Identifying gaps and recommending enhancements related to new and/or existing services and workflows based on broad view of the organization.

  • Collaborating with teammates and business partners to drive and influence process improvements/enhancements and implement new ideas that support optimal member experience and improve overall team efficiency.

  • Additional cross-functional duties as needed to ensure departmental and business unit goals are met.

This individual is a critical member of the GRS Strategic Business Initiatives team and is integral in delivering on our commitment to ensure we are tracking and reporting overall performance results across our open enrollment strategy / performance and various other enablement activities.

The ideal candidate is a motivated, self-starter, strategic thinker who can execute against business goals with agility and in a collaborative manner and possesses an enterprise mindset, excellent analytical, interpersonal, written, and verbal communication skills.

Required Qualifications

  • 5+ years of demonstrated leadership

  • 8+ years of project management experience

  • 10+ years of total business experience

  • Healthcare experience and/or general Medicare business acumen

  • Demonstrated ability to effectively coordinate, lead and oversee multiple projects simultaneously, with a track record of successfully executing on established goals and objectives

  • Demonstrating strong business acumen as well as systems knowledge and can perform reasonability checks as needed

  • Proven ability to deliver and communicate results in complex, fast-paced environments

  • Advanced skills in MS Office (Excel, PPT, etc.)

Preferred Qualifications

  • Leadership experience

  • 8+ years of data interpretation and analysis experience

  • Problem-solver and independent strategic thinker, with track record of meeting key business goals

  • Experience in building effective networks of internal and external contacts

  • Track record of creating consensus for change and implementing process improvement strategies

Education

Bachelor's degree required or equivalent experience.

Knowledge, Skills and Abilities

  • 15+ years of business-related experience

  • Well-rounded business acumen with excellent analytical and project management skills

  • Ability to travel up to 5%

Pay Range

The typical pay range for this role is:

$82,940.00 - $199,144.00


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. This position also includes an award target in the company's equity award program.

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 fulltime position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial wellbeing 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: 09/30/2026

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


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