Senior Benefits Manager (Boston HQ)

Senior Benefits Manager – Lead, Empower and Make an Impact

Join our team as a Senior Benefits Manager, where you'll play a key role in guiding employees through life's changes and ensuring they feel supported every step of the way. This is an opportunity to lead a talented team, oversee complex benefit programs and make a meaningful impact on the employee experience across a diverse, multi-state workforce.

• Lead and develop the benefits team while actively managing day-to-day operations.
• Oversee all aspects of benefits and 401(k) administration, ensuring compliance and operational excellence.
• Review and validate data to maintain accuracy across multiple systems and programs.
• Partner with internal stakeholders to optimize processes and improve the employee experience.
• Deliver clear, compassionate communication to employees about their benefit options and life event changes.
• Manage budget and fiscal responsibilities and drive data-informed decisions.
• Ensure compliance with all health and welfare plan requirements (medical, dental, vision, etc.).

• 5–8 years of benefits experience (open to strong candidates with less).
• Proven people management and leadership experience.
• Strong background in leave administration and multi-state program management.
• Exceptional attention to detail and data accuracy.
• Excellent communication, organization, and problem-solving skills.
• Passion for delivering exceptional employee support and service.
• Dayforce experience is highly preferred.

• Bachelor's degree in Business Administration.
• Strong skillset with budget and fiscal responsibilities.
• Past experience with people management and having direct reports.
• Prior experience administering benefits.
• Multi-state experience.
• Proficient knowledge with leave administration.

Our Benefits:

Regular full-time US employees are eligible to participate in the following benefits:

- Generous time off policies (including 11 paid holidays (12 for MA employees); Generous Accrued Time Off increasing with years of service; Generous paid sick time; Annual day of service; Floating Holiday)

- 401(k) plan options with a company match

- Various Comprehensive Medical, Dental, & Vision plan options

- Flexible Spending Account, Dependent Care Flexible Spending Account, Health Savings Account options with HSA annual employer contribution

- Long Term Disability and voluntary Short Term Disability; Basic Term Life Insurance and AD&D; optional supplemental life insurance

- Health Expense Reimbursement program (including gym memberships, equipment, and subscriptions)

- Tuition Reimbursement program and continuous training and development opportunities

- Wellbeing program (group challenges, seminars, opportunities to earn points to reduce medical premiums), Employee Assistance Program, & Commuter and Parking Reimbursement options

- Employee Corporate Discount Programs (Verizon Wireless, Home Depot Pro, Staples, and more!)

- Flexible and/or Hybrid schedules are available for certain roles

- Employee Relief Program supporting employees with unexpected hardships that place undue financial stress on them and their families

- To learn more, visit winnbenefits.com

Why WinnCompanies?

A job you can be proud of: WinnCompanies is a nationally recognized leader in apartment community management and development. Our team members are committed to helping people in the communities we serve and making a positive difference in their lives. 

A job that challenges you: Our employees are responsible for our growth and success, and we challenge our team members to always be their best in our fast-paced, dynamic and rewarding workplace. 

A job you can learn from: We offer multi-faceted leadership and learning opportunities to support our team members’ career growth and professional development.

A team that cares: We value teamwork, innovation, diversity and mutual respect. Through our recognition and rewards programs, we’re committed to celebrating and uplifting our team members.

About Us:

WinnCompanies is a mission-driven, national business focused on building and operating top quality affordable housing communities for individuals and families of all incomes, including members of the U.S. Armed Forces and their families. Our people are the source of our success – 4,300+ team members working together to create the best possible living communities in 27 states, Washington, D.C., and Puerto Rico.

Whether your skills are in operations, maintenance, leasing, compliance, marketing, IT, HR, accounting or finance, there’s a role for you at WinnCompanies. Your passion for excellence can help us make a positive impact in the lives of real people every day.

If you are a California Resident, please see our Notice of Collection here.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.

Current Winn employees should apply through this internal link.