Deputy Director/Chief Operations Officer, Heading Home, Inc.
Heading Home. Inc. - Charlestown, MA

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Organizational Description
Heading Home’s mission is to end homelessness in Greater Boston by providing a supported pathway to self-sufficiency that begins with a home, together with critical services such as life skills, financial literacy, and job training. Heading Home provides emergency, transitional and permanent housing, and support services, to low-income homeless and formerly homeless families and individuals in the communities of Boston, Cambridge, Somerville, Medford, Malden, Everett and Quincy. As our name reflects, a home provides the optimal foundation to get back on track; our programs focus heavily on getting people permanently housed as quickly as possible.

Position Summary
The Deputy Director\ Chief Operations Officer (COO) reports to the Executive Director and serves as an integral member of the senior management team. The COO is responsible for providing the leadership, management and vision necessary to ensure that service delivery, operational controls, administrative and reporting procedures, financial management strategy, and people systems are in place and sufficiently aligned to support Heading Home’s programmatic work and mission. The COO will promote the culture of mutual respect and collaboration between the operational and programmatic parts of the agency, necessary to effectively grow the organization while maintaining effective ongoing operations.

Essential Job Functions

  • Develop, and in conjunction with Executive Director and senior staff, implement an organization-wide annual administrative and program planning and budgeting process that aligns strategy and program goals with projected revenues and expenses
  • Ensure that all department activities are regularly aligned with each other and the agency mission and goals, and that effective and ongoing inter-departmental communication is instituted
  • With HR staff, promote an agency-wide culture of high performance and continuous improvement that fosters collaboration and values excellence, learning and a commitment to quality service delivery
  • With HR staff and internal training team, help design and implement practices including those for recruitment and hiring, orientation, training, performance management, and others designed to build and maintain a highly effective workforce holding a shared vision of the agency’s mission, vision, values and goals
  • With internal training team, regularly assess skills gaps and staff training needs and work with the Internal Training Manager to address these needs and promote a culture of continuous learning
  • Provide coaching and support to supervisors and managers around team-building, establishing and maintaining mutually respectful relationships with staff, and addressing employee relations and performance issues
  • In collaboration with the Executive Director and senior staff, develop and implement a system for collecting programmatic data for funder and internal use; Promote a shared sense of responsibility across the organization for accurate and timely reporting
  • Regularly analyze programmatic process and outcome data, especially as they relate to strategic goals; Report to and advise the Executive Director, senior staff and the Board of Directors
  • Regularly analyze financial reports and projections; Report to and advise the Executive Director, senior staff and Board of Directors
  • Ensure that all policies, procedures and benefits are communicated to and well understood by current and new employees
  • Design and implement a compensation structure for Heading Home staff; Conduct personnel, compensation and other analysis as needed

Information Systems and Operations Management Duties

  • Manage the deployment, monitoring, maintenance, development, upgrade, and support of all IT systems, including servers, PCs, operating systems, telephones, voice mail systems, software applications, and others
  • Work with program staff to develop strategies and plans to use technology to enhance client services and record keeping, and to improve user effectiveness
  • Develop standard operating procedures and best practices, including providing written protocols and guidance to staff; Ensure documentation is developed and maintained, including system and user manuals, license agreements, and documentation of modifications and upgrades
  • Develop and implement all IT policies and procedures including those for architecture, security, disaster recovery, standards, purchasing, and service provision

Additional duties
As required.


  • A Bachelor’s degree is required; A Master’s degree in business, human resources management, organizational management, social work and/or psychology, along with extensive administrative experience is preferred
  • Eight or more years of administrative and management experience, including budget management and oversight, preferably in a nonprofit or human services setting
  • At least five years of experience working in a senior leadership capacity
  • Significant experience working in a highly collaborative setting and the ability to foster such an environment built around mutual respect and shared commitment and vision
  • In-depth knowledge of general & nonprofit accounting principles and nonprofit reporting and audit requirements
  • In-depth knowledge of human resources practice and employment regulations
  • Experience with and/or working knowledge of information systems technology management
  • Working knowledge of government, foundation and other funding rules and reporting requirements
  • Experience and skill using accounting, spreadsheet and other computer applications
  • Ability to work with a wide range of people representing various backgrounds, levels of training, and career stages
  • Demonstrated success building high functioning teams and working collaboratively
  • Excellent communication skills with staff across programmatic, cultural and other differences
  • Sophisticated problem solving and analytical skills
  • Ability to juggle multiple tasks and responsibilities and to meet deadlines
  • Ability to work independently and, to function well as part of a team
  • Ability to work in a fast-paced, multi-cultural environment
  • Commitment to the work and mission of Heading Home

Application Process
This is a full-time position (40 hours per week) offering a competitive salary, commensurate with skill and experience, along with benefits.

This search is being conducted by Third Sector New England. Candidates should submit a resume and cover letter responding specifically to the stated position requirements, and include starting salary requirements. Only electronic applications will be considered. All submissions are confidential and will be acknowledged and reviewed as they are received.

About this company
Heading Home serves more than 2,000 homeless people in Greater Boston annually. Homelessness is a complex, growing societal problem and...