Organization: Heading Home

Location: Boston, MA

Express Interest

About Heading Home      

For four decades, Heading Home has provided emergency, transitional, and permanent housing and support services to low-income, homeless, and formerly homeless families and individuals in the Boston, Cambridge, Somerville, Medford, Malden, Everett, Quincy, Chelsea and Revere communities.

Heading Home’s mission is to end homelessness in Greater Boston by providing a supported pathway to self-sufficiency that begins with a home and is strengthened with critical services such as life skills, financial literacy, and job training. As homelessness is a complex societal issue, Heading Home’s programs provide the flexibility to meet the unique needs of each client, managed by a well-trained, experienced, and compassionate case management staff throughout all stages of the transition from homelessness into permanent, affordable housing. Through close collaboration with its training partners, Heading Home utilizes state-of-the-art case management tools. The wide array of comprehensive services provides the framework for enhancing the economic mobility opportunities for Heading Home clients. These services include housing search, life skills training, education and employment services, financial literacy, and asset development. In addition, through Heading Home’s large network of community partners, case managers facilitate complementary services such as access to child care, medical and mental health providers, outside counseling, and other important resources.

Heading Home is a dynamic place to work and prides itself on being a learning organization. This means utilizing best practices in the field of service delivery with the populations it serves. Heading Home works in close collaboration with other service providers and training resources to ensure that its staff, through interactive learning, evidenced-based approaches, and a strengths-based model, is poised to achieve the best possible outcomes.

For more information, please visit

The Opportunity

Heading Home seeks an experienced and passionate Chief Executive Officer (CEO) to lead the organization and build upon its strong reputation as a key leader in solving the crisis of homelessness in Greater Boston.

A dynamic and thoughtful leader, the CEO will ensure the organization’s continued success by providing exceptional vision and leadership. This individual will also possess the fundraising and administrative skills necessary to leverage the expertise and commitment of the Heading Home staff, Board of Directors, and partners to establish a clear strategic direction for deepening the organization’s impact and reach.

Heading Home’s CEO will serve as the primary ambassador for the organization, playing a significant external role as the organization’s “chief relationship builder” with funders, partners, and other constituents. S/he will advocate and interface with agencies at the federal, state, and local levels to ensure and expand Heading Home’s role as a preferred provider of services in the communities it serves.

Ideal candidates will bring experience leading a growing organization or program, exceptional relationship building and communications skills, a genuine personal commitment to serving those in need, and the ability to develop and implement an effective strategic vision for a large and complex organization.

This is a full-time position located in Boston, MA.

The CEO’s responsibilities include, but are not limited to, the following:

Strategic Leadership and Vision

  • Lead the Board and staff in shaping strategic priorities for programs, overseeing the implementation of related action plans
  • Provide direction to the Board and staff to enhance both human and financial resources and ensure continued growth and success

Financial, Operational and People Management

  • Effectively manage Heading Home’s annual budget, update Board on all significant financial developments, and work with the Board and senior staff to ensure that business practices and plans meet all financial goals
  • Understand and optimize our revenue and program opportunities with our primary funders (HUD, various housing authorities, etc.)
  • Work closely with the CFO to closely monitor the financial status of the organization and ensure that sound financial controls are both in place and properly observed; ensure a budgeting process that provides both accountability and program creativity
  • Work with the Chief Operating Officer and Chief Financial Officer to ensure that day-to-day operations and programs are effectively administered
  • Evaluate the financial impact of ongoing programs and new initiatives
  • Build and maintain effective and trusting relationships with Heading Home’s senior management team and staff, encouraging and empowering them to maximize productivity, ensure professional excellence, and promote teamwork
  • Recruit and retain the highest quality professionals to ensure that state-of-the-art programs and services are available to Heading Home clients
  • Continue to provide appropriate training and professional development opportunities to promote the growth and retention of existing staff

Fundraising and External Relations

  • Serve as an articulate, persuasive, and effective spokesperson for Heading Home by effectively representing its mission, goals, and services to the Board, staff, and both current and prospective supporters and partners
  • Maintain strong relationships with our primary funders (HUD, various housing authorities, etc.) and position Heading Home to optimize its revenue and program opportunities with these groups.
  • Work with the Director of Development and Board of Directors in the design and implementation of fundraising strategies, including cultivation and direct fund solicitation of key individuals, foundations, and corporate donors
  • Develop and strengthen partnerships with key stakeholders and constituencies, including funding organizations, individual donors, governmental agencies, and other nonprofit organizations
  • Advance Heading Home’s public profile by developing new and innovative approaches to increase community awareness of its services

Board Relations

  • Partner closely with the Board of Directors to drive strategic vision, leverage its experience and expertise, and thoughtfully grow the Board as the organization moves forward
  • Serve as an advisor, keeping the Board informed with appropriate information to support its policy-making responsibility
  • Design and implement clear expectations in partnership with the Board for its contributions to the governance and success of the organization

Candidate Profile:

The ideal candidate will bring the following skills, experiences, and characteristics:

Skills and Experiences

  • Strategic organizational leader with at least 10 years of professional experience, including prior success in managing a team, program, or initiative through a period of growth
  • Strong track record of financial and operational management experience, with the ability to lead and motivate teams
  • Record of effective fundraising and external relations, with exposure to a variety of revenue streams (e.g. government contracts, individual, institutional, and events) and an ability and enthusiasm to build relationships and secure new sources of funding
  • Ability to serve as a compelling and credible spokesperson for Heading Home in interactions with both internal and external stakeholders
  • Experience partnering successfully with a Board of Directors to set and drive the strategic vision and growth of an organization
  • Track record of developing innovative solutions coupled with the ability to operationalize them across a wide range of stakeholders
  • Experience working with low-income populations, and knowledge of services related to housing and homelessness

Personal Qualities

  • Passionate, empathetic champion for the mission and vision of Heading Home
  • Collaborative approach to leadership, including exceptional listening and communication skills and a focus on creative solutions
  • Ability to build support for new ideas and initiatives across a range of stakeholders with multiple points of view
  • Ability to thrive in a culture that is dynamic, mission-driven, and client-centric
  • Compassion and understanding of the needs of Heading Home’s clients
  • Commitment to diversity, equity, and inclusion in organizational culture


Compensation will be competitive and commensurate with experience and accomplishments.


Molly Brennan and Alena Guerra of Koya Leadership Partners have been exclusively retained for this search. To express your interest in this role, please submit your materials here. All inquiries and discussions will be considered strictly confidential.

Heading Home is committed to providing equal employment opportunities to all individuals without regard to race, color, religion, sex, national origin, ancestry, age, disability, marital status, sexual orientation, or any other characteristic protected by law.

About Koya Leadership Partners:

Koya Leadership Partners is a national retained executive search and human capital consulting firm that works exclusively with nonprofits and social enterprises. We deliver measurable results, finding exceptionally talented people who truly fit the unique culture of our client organizations and ensuring that organizations have the resources and strategies to support them. For more information about Koya Leadership Partners, visit