Training and Organizational Development Specialist

Heading Home's mission is to prevent and end homelessness. Through personalized support and shelter, as well as larger advocacy and affordable housing work, we provide stability and foster the independence every family and individual needs to thrive. 

Founded in 1974, Heading Home is a leading provider of housing and support services for low and extremely low-income individuals and families currently or formerly experiencing homelessness in Eastern Massachusetts. For over 50 years, we have successfully helped thousands of people end their homelessness.

As an agency, our services are diverse; we provide emergency, transitional, permanent and affordable housing, and support services, to low-income individuals and families.

We are proud to share that for 17 years running, 90% of Heading Home's clients retained permanent housing. Last year, 97% of Heading Home clients remained housed after one year.

Job Title: Training and Organizational Development Specialist
Reports To: Chief Administrative and Information Officer
Location: Boston, MA 02115
Position Type: Full Time; Non-Exempt

Hourly Salary: $28 - $33

Overview:

The Training and Organizational Development Specialist supports the design, coordination, and delivery of learning programs that build staff and volunteer capability across the organization. Reporting to the Chief Administrative and Information Officer, the Coordinator manages the day-to-day logistics of training initiatives, administers the learning management system (LMS), tracks compliance training, and helps assess learning needs across departments. This role is ideal for an organized, people-focused professional who is passionate about employee development and mission-driven work.

The ideal candidate is an engaging and organized learning professional who can translate organizational and program needs into practical, accessible, and effective training experiences. This role requires strong facilitation, communication, project-management, and relationship-building skills, as well as the ability to work collaboratively across departments.

Responsibilities / Essential Job Functions:

Program Coordination and Delivery

• Coordinate scheduling, logistics, materials, and communications for in-person, virtual, and hybrid training sessions, workshops, and onboarding programs.
• Support the design and rollout of new hire orientation and onboarding, ensuring a consistent and welcoming experience for staff and volunteers.
• Assist in developing training content, job aids, e-learning modules, and facilitator guides in collaboration with subject matter experts.
• Source and liaise with external trainers, vendors, and facilitators as needed, including managing contracts and invoices within budget.

Learning Systems and Administration

• Administer the learning management system: enroll users, upload content, troubleshoot issues, and generate reports.
• Maintain accurate training records, certifications, and compliance documentation (e.g., safety, harassment prevention, data privacy, and grant-required training).
• Monitor completion rates for mandatory training and follow up with staff and managers to ensure compliance deadlines are met.

Needs Assessment and Evaluation

• Support annual learning needs assessments through surveys, focus groups, and consultations with department leads.
• Collect and analyze training feedback and evaluation data; prepare summary reports and recommendations for the CAIO.
• Track L&D metrics (participation, completion, satisfaction, budget utilization) and contribute to reporting for leadership, the board, and funders as required.

Culture and Engagement

• Promote learning opportunities through internal communications, newsletters, and the intranet.
• Support career development initiatives such as mentoring programs, lunch-and-learns, and leadership development cohorts.
• Champion accessible, inclusive learning practices that reflect the organization’s commitment to diversity, equity, and inclusion.

Equal Employment Opportunity Statement

Heading Home, Inc. is an Equal Employment Opportunity (EEO) employer and welcomes all qualified applicants. Applicants will receive fair and impartial consideration without regard to race, sex, color, national origin, age, disability, veteran status, genetic data, gender identity, sexual orientation, religion or other legally protected status, or any other classification protected by federal, state, or local law.

Work Environment (should include noise level, physical demands such as bending, sitting, lifting) Example: 

Cubicle space within large office building; prolonged sitting at a desk and working on a computer, OR, requires equal amounts of sitting and standing, must be able to climb stairs. Office is open to the public and visitors only by appointment. Position requires a minimum of four days onsite. Office is climate controlled with heat and air conditioning.

Salary : $28 - $33