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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Director of Benefits, Wellness, & HRIS - **Company:** Pine Street Inn - **Location:** Boston, MA, United States (Remote available) - **Experience:** Expert - **Salary:** $120,000.0 - $140,000.0 - **Contract:** Permanent contract - **Skills:** Human Resources Information System (HRIS), HR Software, Data Management - **Published:** August 9, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=39af223b889cea50 ## About the Role * Highly developed organizational and communication skills, including strong written communication skills * Must have superior judgement, and be able to handle sensitive or confidential information with discretion * Ability to motivate others * Demonstrate solid critical thinking skills and the ability to independently problem solve * Ability to organize and manage a heavy and complex workload * Must be able to develop effective relationships with various external partners to include insurers, brokers, consultants, software companies. * Excellent analytical interpersonal and written communication skills * Ability to facilitate, mediate or drive difficult conversations * Must be able to adapt to competing or changing priorities * Maintain commitment and passion to complete job responsibilities * High degree of discretion and confidentiality with respect to sensitive personnel or employee personal matters * Associate's Degree or a minimum of 5 years' experience in HR Benefits or certification, in human resources, business administration or related field * Bachelor's Degree or Master's degree in human resources or a related field * Human Resources Professional Certification (PHR, SHRM-CP) or Certified Employee Benefits Specialist or similar professional certification * Minimum of five years of progressively responsible human resources and/or benefit administration experience; or equivalent combination of skills and experience * Experience researching and implementing streamlined HRIS platforms * Strong planning and organizational skills; superior interpersonal, verbal and written communications skills * Successful experience supporting a human/social service, academic department or business unit * Significant experience in all facets of benefits administration * Strong systems experience and ability oversee and ensure accuracy and timeliness in electronic data management * Demonstrated experience building strong partnerships with managers to deliver expert HR guidance * Demonstrated experience leading work groups and project management * Experience streamlining HR data such that it contributes to data driven decision making and evolves from paper to electronic processing. PREFERRED: * Experience working in an HR department supporting programs servicing homeless or individuals suffering from complex disabilities and facing significant barriers to housing * Experience supervising administrative or junior level professional staff * Experience in change management or supporting an organization in evolution to enhance performance and driving individual and organizational performance improvement ## Description Reporting directly to the Vice President of People and Culture, the Director of Benefits, Wellness and HRIS is responsible for all the oversight and management of the employee benefits and wellness programs and the electronic (HRIS) and paper recordkeeping, of all employees and trainees. The Director will provide leadership and oversight in the development, execution and administration to the organization with a focus on customer services and delivering high-quality benefits and wellness programs to its employees. The Director will support, coach and provide general supervision to the Benefits department staff and will ensure that the benefits program is operating effectively and efficiently in support of HR department needs and in coordination with the finance department. Finally, the Director will ensure the agency is getting the best ROI on its systems including those for benefits administration, applicant tracking, employee file maintenance and payroll (in partnership with finance). While upholding the mission to the Inn's guests, tenants, trainees, and clients and modeling the Inn's Values of Accountability, Respect, Teamwork and Community; the Director of Benefits, Wellness and HRIS is responsible for ensuring that the Inn maintains an employee benefits program in compliance to all regulatory obligations, as well as offering the most competitive plan within resourcing limitations. The Director will support wellness strategy and program alignment with organizational goals. 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