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Head of Worksite Underwriting - Remote

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Employer Provided Salary: $180,000-$225,000 Annually
Salary data is provided by the employer. Please note this is not a guarantee of compensation.

Reporting to the Head of Worksite, the Head of Underwriting is responsible for developing and executing a underwriting strategy to drive revenue, manage risk and grow our voluntary insurance and executive disability product market share. Working in partnership with the Heads of Distribution Strategy, National Sales and Product, drive alignment across the organization, to create effective and competitive underwriting packages across our product lines that meet our distribution channels' needs.

This role will provide leadership and oversight for hiring, developing, motivating, retaining and managing underwriters across all products including evaluating capacity plans to ensure we hit market response times.

The role requires deep knowledge of the markets we serve to provide competitive, timely, quality offers; set a strategic path of continuous and iterative improvements for Underwriting, aligned with the overall business strategy by proactively partnering with key partners in distribution, product and corporate actuarial. Individual will provide the Head of Worksite and peers with market feedback and dependencies critical to the broader organization's success.


Seasoned leader who will help MassMutual grow its business profitability and through multiple channels. Align underwriting directly with financial plans for current and future years. Build an underwriting/risk policies that are visible for the organization to understand and follow. 

Partner with distribution and product to continually bring trends and feedback to leadership team and ideas on how we improve our capabilities. 

Be responsible for new offers and focus on retaining existing business profitably.

Represent MassMutual as a thought leader at conferences, industry conferences and meetings, etc.

Manage and understand financial levers of the worksite business; in particular develop and manage underwriting and quote activity and results in a deep data driven way. Provide insights to organization on data trends, vs the market and competition. 

Lead with data - provide timely leading and lagging indicators, results and analysis to all levels of the organization.

Represent Worksite Underwriting as part of the Worksite Sr. Leadership team, addressing sales and distribution needs and concerns, while contributing as a general manager responsible for delivering on any and all key business metrics committed to by the Worksite business.

Provide market insights on competitive new products and markets, and any changes required to achieve business results.

Be a strong role model for implementation and sustainment of MMWay business system. Foster an atmosphere and culture of continuous improvement where problems are embraced and explored through open and candid discussion and effective problem solving, with an enduring focus on process, not people. Streamline processes, improve customer satisfaction, create efficiencies, and grow employee engagement.

Key Responsibilities:

  • Strategic Focus:  

    • Understand market competitive levers, advisor dynamics to bring win/loss and other pertinent data to help drive UW strategy and execution and support overall sales growth while maintaining profitability. 

    • Ensure leading and lagging indicators are transparent to the key stakeholders in the organization. 

    • Build and drive new capabilities to ensure we are competitive in the market

    • Partner with head of distribution strategy to interact with field committees to best position Worksite in the market

    • Work closely with product to ensure profitability measures are met, reviewed, understood by the leadership team and have a line of sight into overall sales and persistency measures

  • Production & Quality:  

    • Daily (and active) production level management of UW professionals. 

    • Be “a step ahead” to understand and inform the Worksite Leadership Team of demand / capacity gaps. 

    • Hire and develop staff for performance, manage capacity effectively to drive output and sales expectations. 

    • Actively manage the bottom 10% to also change culture.

  • Customer Advocacy:

    • Build communication, clarity, trust and transparency to make UW's “offer makers” with our distribution partners. 

    • Eliminate friction and drive customer delight (profitably).

  • Learning & Development:  

    • Move each of the UWs to active seekers of knowledge. We need a culture of market competitiveness and customer advocacy to ensure alignment to strategy and delivery of goals.


  • 15+ years managing UW teams in a fast-paced environment

  • Deep Experience in Voluntary or Group benefits industry with solid quality results and ability to manage and navigate case and advisor complexities

  • Demonstrated behaviors that excel in the MM competency framework. Especially Inclusion, Communication, Leading Others, Agility and Resilience.

  • Maintain and iterate a balanced scorecard (performance metrics; customer advocacy; Team first; development focused) for each UW. Performance manage to it

  • Collaborate and serve as strategic advisor to key stakeholders and for the Worksite business

  • Experience communicating and working with technology, product owners and Customer Care professionals – including Insurance Advisors/Brokers

  • Limited travel

  • Ideally Springfield, or Boston, MA based



Salary Range: $180,000 to $225,000 plus annual bonus and long-term incentives

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.

Offers of employment are contingent on the completion of satisfactory references, background investigation, and (if applicable) any federal securities law requirements/FINRA regulations (including fingerprinting) and/or passing of a drug screening.

At MassMutual, we focus on ensuring fair, equitable pay by providing competitive salaries, along with incentive and bonus opportunities for all employees. Your total compensation package includes either a bonus target or in a sales-focused role a Variable Incentive Compensation component. For more information about our extensive benefits offerings please check out our Total Rewards at a Glance.

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What are MassMutual Perks + Benefits

MassMutual Benefits Overview

At MassMutual, employees have the opportunity to earn a competitive salary and bonus, enroll in an
array of benefits, and participate in programs and services that support healthy lifestyles, assist them
in building financial security for themselves and their families and help them live well-balanced lives.

Volunteer in local community
Every action supporting a common cause is meaningful, and our employees make a difference in their own communities through our Matching Gift, Matching Time and Volunteer Time Off Programs.
Partners with nonprofits
Every year, MassMutual and the MassMutual Foundation invest more than $20 million focused on advancing economic opportunity.
Open door policy
OKR operational model
Team based strategic planning
Open office floor plan
Employee resource groups
Employee-led culture committees
Hybrid work model
In-person all-hands meetings
Employees can either attend the in-person all-hands meeting, watch live via Zoom, or watch the recording. All employees are invited to submit questions.
Employee awards
Flexible work schedule
Flexible work arrangements, including telecommuting, are available in many departments across the company.
Remote work program
In addition to two remote days per week, MassMutual offers employees four full remote weeks of their choice per year.
Documented equal pay policy
Dedicated diversity and inclusion staff
Highly diverse management team
More than half of our Board of Directors are comprised of women and people of color, making it one of the most diverse groups in the industry.
Mandated unconscious bias training
Diversity manifesto
Diversity employee resource groups
Hiring practices that promote diversity
Diversity recruitment program
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
A health care flexible spending account (FSA) allows employees to save money on a before-tax basis for eligible medical, dental and vision expenses, subject to IRS limits.
Disability insurance
For details on short term and long term disability insurance please visit
Dental insurance
Basic Dental covers preventive and basic restorative care; Major Dental covers all that Basic covers, plus restorations and orthodontia (limits apply).
Vision insurance
Health insurance
To learn more about our Health and Welfare Benefits please visit:
Life insurance
For more information about our Life Insurance Benefits please visit:
Pet insurance
Wellness programs
Team workouts
Mental health benefits
Transgender health care benefits
Wellness days
Abortion travel benefits
Our general medical travel benefit covers abortion-related travel.
Financial & Retirement
In addition to our 401(k), MassMutual a cash balance plan that provides an account-based pension benefit based on accruals of pay credits and interest credits.
401(K) matching
Performance bonus
Charitable contribution matching
Every action supporting a common cause is meaningful, and our employees make a difference in their own communities through our Matching Gift and Matching Time Programs.
Pay transparency
Child Care & Parental Leave Benefits
Childcare benefits
Dependent care flexible spending account to allow you to set aside before tax dollars to pay for certain eligible child care expenses.
Generous parental leave
Leave for birth mothers of 18 weeks of fully paid leave. Non-birth mothers, fathers and adoptive parents eight weeks of fully paid parental leave.
Family medical leave
Caregiver leave: Up to two weeks paid leave to care for a loved one. Bereavement Leave: 15 days of paid time off to grieve the loss of a loved one with the employee defining who the loved one is.
Adoption Assistance
Company sponsored family events
MassMutual offers many opportunities for family events, from group volunteer experiences and chances to attend Red Sox games to business resource group-sponsored outings like annual pride parades.
Fertility benefits
Vacation & Time Off Benefits
Generous PTO
Paid holidays: 9 fixed and 1 floating. Vacation: starts at 19 vacation and personal days per calendar year, with increases at 5-year service intervals.
Paid volunteer time
Three days of paid time off is available to employees annually to give back to their communities, by sharing their time and talent with a cause close to their heart.
Paid holidays
Paid sick days
Occasional illness: up to 5 days per calendar year.
Flexible time off
Floating holidays
Bereavement leave benefits
Hardship benefits
320 hours of caregiver leave to take of loved ones when it matters most.
Office Perks
Commuter benefits
Free daily meals
Free snacks and drinks
Some meals provided
Onsite office parking
Recreational clubs
Relocation assistance
Fitness stipend
Home-office stipend for remote employees
MassMutual's wellness wallet is a stipend available to all employees, and can be used for myriad wellness-related purchases, including home-office purchases.
Meditation space
Mother's room
Onsite gym
Professional Development Benefits
Job training & conferences
Tuition reimbursement
Lunch and learns
Promote from within
Mentorship program
Continuing education stipend
Continuing education available during work hours
Online course subscriptions available
Customized development tracks
Paid industry certifications
Personal development training
Virtual coaching services

Additional Perks + Benefits

To learn more about our comprehensive benefits please visit:

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