Pine Street InnVerified Source

Director of Benefits, Wellness, and HRIS

Partially · Boston, Massachusetts
Posted August 12, 2026
payroll

Overview

You will own benefits, wellness, and HRIS operations at Pine Street Inn, a mission-driven nonprofit serving nearly 2,000 individuals daily in Boston. Reporting to the VP of People and Culture, you lead the benefits team, manage outsourced benefits administration, and oversee the HRIS transition from paper to electronic. You align wellness programs with organizational goals, ensuring compliance and competitive plans within budget. This role stands out for its hybrid schedule, meaningful mission, and opportunity to modernize HR systems.

What You'll Do8

  • 1Design and execute the benefits administration strategy, including health, retirement, and wellness plans, using Workday and ADP.
  • 2Lead the migration of employee records from paper to digital, implementing HRIS features to support data-driven decisions.
  • 3Supervise the benefits team, coaching staff and coordinating with finance to optimize ROI on systems like Applicant Tracking and payroll.
  • 4Build vendor relationships with insurers, brokers, and consultants to negotiate benefits packages and resolve issues.
  • 5Drive wellness program alignment, promoting initiatives that reduce absenteeism and support employee engagement.
  • 6Ensure compliance with federal and state regulations, auditing records and updating policies as needed.
  • 7Facilitate benefits open enrollment and communicate changes to employees clearly and empathetically.
  • 8Collaborate with HR and finance to streamline benefits processes, eliminating redundancies and improving accuracy.

Requirements8

  • 15+ years of progressive HR and benefits administration experience, with a focus on complex benefits programs.
  • 2Associate's degree or PHR/SHRM-CP certification, with Bachelor's or Master's preferred.
  • 3Experience supervising staff and leading projects, including HRIS implementations.
  • 4Strong analytical skills to manage data, budgets, and vendor performance.
  • 5Excellent communication and facilitation skills for difficult conversations and presentations.
  • 6Proven ability to handle sensitive employee information with discretion.
  • 7Demonstrated experience in change management and building partnerships with managers.
  • 8Experience in human services or nonprofit environments, supporting underserved populations, is preferred.

Salary Insight

Salary not disclosed in listing

Location

Typepartially
LocationBoston, Massachusetts

Required Skills

workdayadphrisbenefits administrationphr
Share:

Similar open positions

Explore active roles that match your skills and interests.

Midatlantic Employers' Association

9h agoPhiladelphia, Pennsylvaniapayroll

Human Resources Coordinator, HRIS & Payroll Support

Own the employee lifecycle at Self Help Movement, a mission-driven behavioral health nonprofit serving 120+ team members. You will keep HRIS records pristine, run payroll audits, and guide new hires through onboarding. Working beside the HR Director, you will handle benefits questions, compliance training, and audits. This full-time on-site role offers hands-on exposure to every HR function, from recruiting to benefits, with ADP Workforce Now as your daily tool. You will make a direct social impact while building a strong HR foundation.

Competitive salary
MS OfficeADP Workforce NowHRIS+5 more

AIMED Human Services

11h agoPittsburgh, Pennsylvaniapayroll

Human Resources Director - AIMED Human Services

AIMED Human Services seeks a Human Resources Director to lead employee benefits and personnel records. This role involves managing open enrollment unemployment claims workers compensation and payroll. The ideal candidate is efficient personable and skilled in diverse communication environments.

Competitive salary
SHRM certificationBambooHRADP+3 more

GRACIOUS HOME ADULT DAY HEALTH CARE

14h agoBoston, Massachusettscontract

HR Generalist, Adult Day Health Care

You will own the full employee lifecycle for a team of healthcare professionals, from onboarding to offboarding, at a growing adult day health center in Boston. You'll work directly with leadership to shape HR policies and drive retention. This contract role puts you at the heart of a mission-driven environment where your HR expertise directly supports quality care. HR Generalist experience in healthcare is a plus.

25K–25K
microsoft officeapplicant tracking systemshr databases+2 more
Win Brands - FatCats & Costa Vida

Win Brands - FatCats & Costa Vida

13h agoSalt Lake City, Utahcontract

Manager of Benefits and HCM Administration

Lead strategic initiatives supporting benefits and HR systems at Win Brands - FatCats & Costa Vida. Oversee HR administrative functions and employee benefits programs across multiple locations. Align system processes with organizational goals while fostering a high-performance culture.

Competitive salary
pythonawsreact+2 more

Pine Street Inn

5h agoBoston, Massachusettspayroll

Employee Engagement Partner Pine Street Inn

The Employee Engagement Partner at Pine Street Inn leads initiatives to improve employee experience and engagement. This role serves as a liaison between department leaders and HR teams while supporting HR functions. It involves facilitating cooperative relationships across programs and modeling PSI values.

80K–96K
hr generalist experienceemployee relationsperformance management+2 more

Homeowner's Rehab, Inc.

14h agoBoston, Massachusettspayroll

Staff Accountant, Nonprofit & Payroll

Own full-cycle accounting for three 501(c)(3) nonprofits with a $25M portfolio of affordable housing. Report directly to the Controller and manage cash, Accounts Payable, Payroll, and month-end close. Join a collaborative team of 5 in a hybrid schedule (3 days in Cambridge office, 2 remote). This role stands out for its exposure to audit preparation and related-party reconciliations across entities.

65K–75K
AccountingAccounts PayablePayroll+8 more