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Come Grow With Us

Proposal Writer

Springfield, Massachusetts; Boston, Massachusetts

Job ID: R16090

Thank you to our employees for voting us one of the top places to work in Massachusetts for five consecutive years!


A career with us means you’ll help our customers secure their future and protect the ones they love. It also means you’ll work alongside exceptional people and be empowered to reach your professional and personal goals. Our employees are at the foundation of what makes MassMutual a strong, stable, and ethical business.

Our culture embodies the idea that we all are stronger and better through our support for one another. By valuing people for who they are, how they think, and what they bring to the table, we’ve become a better, more innovative company.

We invite you to explore the possibilities.

What our employees say

Roger Crandall
Roger CrandallCEO
“Since our founding in 1851, mutuality has put our policyowners at the center of everything we do. At our core, we’re a company of people helping people in their time of need, and that spirit extends to the culture we’ve built at our company. Our employees support and rely on each other each day, collaborating to deliver the best solutions for our customers and help millions more secure their future and protect the ones they love.”

Job Description

Worksite Underwriting Formal Proposal Writer, Underwriting Department

Worksite Division, Fulltime, Hybrid - Boston or Springfield Office

The Opportunity

As the Worksite Underwriting Formal Proposal writer, you will assume a hybrid Project Management/Proposal Writing/Content Curation role on a consistent scale for mid-large scale opportunities. You will collaborate across lines with sales personnel, underwriting, subject matter experts and community facing teams across the organization to curate content and respond to RFP’s. Scope of work includes sales strategy collaboration, capture management, proposal development, submission, and follow-up. By highlighting our purpose and strategically positioning MM products and offerings, you will contribute to MM Worksite Division’s growth and success.

The Team

The Worksite Underwriting Team is comprised of a Voluntary Benefits underwriting Team, an executive DI underwriting team and a formal proposal team. This team will support library compilation, establish cross functional process and ensure completion and submission of RFP’s for all of these products, including the new supplemental health products. As the Worksite Division grows and develops, underwriting must remain agile, responsive and collaborative, in support of our growth goals. Communication in this role is key within the team and across boundaries.

The Impact:

  • Business Acumen: Researches, compiles, writes, edits, and proofreads proposals, bids, and other written documents, as requested by the sales and management, meeting due dates and deadlines as needed; validates contractual and documentation packages for quality, accuracy, persuasiveness, and compliance with company practices with strong attention to detail. Influences strategy development and uses independent judgment to complete moderately complex work, often requiring in-depth analysis of various requests contained in an RFP.

  • Communication: The WS Proposal Writer is primarily responsible for managing the response to public or private RFP’s/RFI’s, including written narratives and production necessary for external delivery.

  • Decision Making: Decisions are typically focused on methods, tactics and processes for completing strategic RFP response to potential and existing customers. This position understands department, segment and organizational strategy and operating objectives, including linkages to other areas. Regularly exercises discretion and judgment in prioritizing requests and interpreting and adapting procedures, processes, and techniques, and works under limited guidance due to previous experience/breadth and depth of knowledge.

  • Accountability: Identifies and recommends improvements of processes and information for bid and proposal packages; comprehends prospective client requirements; researches and drafts responses to formal Request For Proposal (RFP) questions enhancing the responses to meet or exceed the client’s requirements positioning Mass Mutual’s success.

  • Leading Others: Coordinates with subject matter experts within marketing and other divisions in the enhancement of proposals to increase win rate; in partnership with the Underwriters, communicates bid information to sales personnel; increases percentage of successful bids.

  • Agility: Integrates the various pieces of information gathered from all departments into a comprehensive presentation; creates and modifies graphics to convey ideas, methodologies, and approaches.

  • Maintains the internal archive of proposal documents, product information, correspondence, and other proposal information; organizes and maintains proposal and product data using print and electronic tools to ensure that current and accurate information is captured appropriately.

  • Provides research, administration, and coordination for all forms of proposal research; provides reports based on findings; locates statistical data and interprets in various formats to the team and/or management.

  • Resolves problems and answers questions from sales professionals pertaining to assigned proposals; works independently to analyze issues to determine best solutions; sets priorities, plans and organizes workload, and meets established deadlines

  • Responds to brokers and external partners with regards to benefit questions pertaining plans and requirements submitted within RFPS.

The Minimum Qualifications

  • 2+ years experience completing formal proposals, bids, or quotes

  • 5+ years insurance industry or equivalent financial services experience

  • 5+ years technical writing experience

The Ideal Qualifications

  • 5+ years group benefits/worksite insurance experience preferred

  • Excellent written and oral communication skills

  • Project management skills to coordinate responses and meet deadlines

  • Proficient with Microsoft products – excel, power point, word, project, etc.

  • Bachelor’s degree or equivalent experience

  • Demonstrated ability to craft compelling messages, impactful responses

  • Proficient in Adobe and Microsoft Excel

  • Strong written communication skills

  • Sales Support experience

  • Strong team player with collaboration mindset

  • Works well with ambiguity, takes initiative to research responses

  • Good communicator

  • Well organized, detail oriented in building RFP library

  • Requires limited guidance on everyday tasks with general direction on new assignments, takes ownership of day to day tasks, multi-tasking in a fast paced environment

What to Expect as Part of MassMutual and the Team

  • Regular meetings with the Underwriting/Proposal Team.

  • Focused one-on-one meetings with your manager

  • Access to mentorship opportunities

  • Networking opportunities including access to Asian, Hispanic/Latinx, African American, women, LGBTQ, veteran and disability-focused Business Resource Groups

  • Access to learning content on Degreed and other informational platforms

  • Your ethics and integrity will be valued by a company with a strong and stable ethical business with industry leading pay and benefits


MassMutual is an Equal Employment Opportunity employer Minority/Female/Sexual Orientation/Gender Identity/Individual with Disability/Protected Veteran. We welcome all persons to apply. Note: Veterans are welcome to apply, regardless of their discharge status.

If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.
EEO Statement(Opens in new window)

MassMutual will accept applications on an ongoing basis until such time as a candidate has been offered employment.

Salary Range: $76,200.00-$100,000.00

Hiring Process

  • Explore

    To get started, explore our open jobs by clicking 'search jobs' to find a position that aligns with your experience and skills. You may also consider joining our Talent Network to receive information on jobs that may interest you and stay up-to-date with the latest MassMutual news.

  • Apply

    To apply for a specific position, please click the “apply” button on that job posting to complete and submit your application. Your application will be reviewed by a recruiter which, due to the volume of applications received, may take some time as we carefully consider each application.

  • Screen

    After your application has been reviewed, if you meet the qualifications for the role, a recruiter will reach out to you to start a conversation.

  • Interview

    If you are invited for an interview, you will be scheduled to meet with the hiring manager and hiring team. Coordinating calendars for interview schedules can take time, so your patience and flexibility is appreciated.

  • Offer

    If you are extended an offer to join MassMutual and accept, your start will be contingent upon a satisfactory background check.

  • Hire

    If you accept the offer, we will be so excited to welcome you to the MassMutual community!

Recruitment Fraud Awareness

Job recruiter fraud is a scam by impostors posing as recruiters or representatives of a company promoting fake job opportunities to job seekers.

MassMutual will never ask job candidates to pay any kind of fee, make cash or check advancements, cash checks or make an investment in any product or service or provide information such as credit card numbers or banking PIN numbers as part of our hiring process.

If you are contacted by anyone asking for information outlined above it is likely fraudulent. If you have any concerns about the veracity of a request, please contact us directly to verify its legitimacy.

If you need an accommodation to complete the application process, please contact us and share the specifics of the assistance you need.

Award-Winning Culture

MassMutual is guided by a single purpose: We help people secure their future and protect the ones they love. As a company operated for the benefit of our members and participating policyowners, we are defined by mutuality and our vision to provide financial well-being for all Americans. It’s more than our company structure—it’s our way of life. We are a company of people protecting people. Our company exists because people are willing to share risk and resources and rely on each other when it counts.

We strive to embrace diversity in every sense, focusing on building a thriving community where everyone is valued, included, and feels that they belong.

At MassMutual, we Live Mutual.

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Benefits for the whole you (and your loved ones)

There’s more to your life than your job and there’s more to your aspirations than a paycheck. We take a holistic view of compensation and benefits that provides the flexibility to create a healthy balance in your life for work, family, and community. We offer the benefits you’d expect, like medical, dental, 401(k), and generous vacation time, but we also offer ones you might not expect, like three paid days for volunteering, a $1250 annual wellness wallet, and up to 320 hours of caregiver leave.

Explore some of our offerings below. Full benefits details can be found here

  • In addition to generous vacation time, paid holidays, and flexible holidays, MassMutual offers 'take care' time to take care of yourself or someone you love—whether for physical illness or mental health.
  • Medical and dental insurance
  • Life, disability short-term and long-term insurance
  • Well-being wallet: $1,250 per year for a wide range of qualifying wellness expenses
  • Well-being support: Mindfulness, nutrition, fitness
  • Personalized mental health solutions
  • Adoption and surrogacy reimbursement programs
  • Competitive salary and bonuses
  • 401(k): Up to 10% total benefit, consisting of a 5% company match and a 5% annual contribution
  • Educational assistance program
  • Childcare support
  • Financial counseling
  • Caregiver Leave (up to 320 hours)
  • Maternity Leave (a total of 18 weeks, 10 maternity + 8 parental)
  • Parental Leave (8 weeks for all parents, birth or adoption, continuous or intermittent)
  • Bereavement Leave: Up to 15 days to mourn the loss of a loved one, and you define 'loved one'
  • Matching Gift: 100% match on employees’ charitable contributions to non-profits up to $5,000
  • Volunteering: Three paid days for employees to volunteer with eligible nonprofits of their choice
  • Matching time: MassMutual Foundation awards dollars to organizations for which employees volunteer
  • Qualified Commuter Program through which eligible employees can pay qualified workplace commuting expenses with before-tax dollars
  • Commuter wallet option for employees based at Boston and NYC campuses

Why MassMutual?

Compliance Consultant
Service Management Consultant
Head of Experience Journey Mapping

How we work

MassMutual’s flexible workplace approach combines the importance of connecting in person and the flexibility of working remotely. Our hybrid model puts collaboration first with employees coming in at least three days per week to our spectacular campus settings and also enjoying the flexibility of remote Fridays, company-wide remote weeks, and a bank of flexible remote weeks to use throughout the year.



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Where we work

Springfield Office

1295 State Street,
Springfield, MA

Boston Office

10 Fan Pier Blvd,
Boston, MA

New York Office

2 Park Ave,
New York, NY


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