Benefits Specialist (Boston HQ) - Boston Massachusetts

Company: WinnCompanies LLC
Location: Boston, Massachusetts
Posted On: 05/10/2025

WinnCompanies is looking for a detail-oriented and proactive Benefits Specialist to join our corporate team located in Boston, MA and play a key role in the administration of our employee benefits programs.The ideal candidate will have 3-5 years of experience in benefits administration, a solid understanding of leave-of-absence policies, and a strong desire to help employees navigate their benefits options.In this role, you will be responsible for supporting new-hire orientations, responding to employee and manager benefits inquiries, managing leave-of-absence requests, interpreting FMLA, State Leave, and ADA regulations, and assisting with 401(k) plan administration. You will stay up-to-date on industry trends and regulatory changes, ensuring compliance while working with vendors and third-party administrators to resolve any issues efficiently.This position adheres to a Monday through Friday work week from 8:30AM to 5:00PM. You'll benefit from a blend of collaboration in our Boston headquarters four days per week (Monday through Thursday) and flexibility of one remote day per week (Friday).Responsibilities

• New-Hire Orientation Support: Assist in delivering new-hire orientations, ensuring smooth and accurate onboarding of benefits programs.
• Benefits Inquiries: Respond promptly to questions from employees and managers regarding benefits plan provisions, enrollments, status changes, and general inquiries.
• Leave-of-Absence & Disability Administration: Manage all leave-of-absence requests and disability paperwork, including medical, personal, disability, and FMLA leave, ensuring timely and accurate processing.
• FMLA & ADA Interpretation: Effectively interpret and communicate the implications of FMLA and ADA as they relate to leave-of-absence and disability matters.
• 401(k) Inquiries & Administration: Address inquiries related to 401(k) enrollments, plan changes, contribution amounts, and oversee the annual catch-up contribution process.
• Regulatory Compliance: Maintain a strong knowledge of relevant benefits regulations and industry trends, ensuring all benefits programs comply with legal requirements.
• Vendor & Third-Party Liaison: Work closely with vendors and third-party administrators to ensure effective benefits administration and swift resolution of any issues.
• Employee Support: Act as the primary point of contact for team members, helping them navigate benefits paperwork, meet deadlines, ensure compliance, and address concerns.
• Benefits Training & Presentations: Develop and deliver benefit-related training and presentations, ensuring employees fully understand and effectively utilize their benefits options.Requirements
  • Education: Associate's degree, preferably in human resources or another related field.
  • Experience: 3-5 years of experience in benefits administration, with a focus on leave-of-absence management, FMLA, ADA, and 401(k) plans.
  • Knowledge: Strong understanding of benefits programs, including health, welfare, and retirement benefits.
  • Proficiency in FMLA and ADA regulations.
  • Experience with oversight of workers' compensation administration.
  • Skills: Excellent communication, organizational, and interpersonal skills with the ability to manage multiple priorities efficiently.
  • Compliance-Focus: Strong attention to detail and an in-depth understanding of benefits compliance requirements.
  • Ability to handle data with confidentiality.
  • Technical Skills: proficiency with V-Look Ups and Pivot Tables using Microsoft Excel. Strong experience with computer systems, particularly Microsoft Office applications.Preferred Qualifications
    • Bachelor's degree, preferably in human resources or another related field.
    • Experience with Ceridian Dayforce HRIS benefits administration software.
    • Knowledge of healthcare trends.
    • Bilingual in English and Spanish.#LI-BB1Our Benefits:Permanent 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 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 .Salary will vary based on job responsibilities and scope, geographic location, candidate's relevant experience, and other factors.Current Winn employees should apply through .
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