Managing Director of Housing Support Services

Posted by
Pine Street Inn
Boston, MA
Published 17 days ago

SCHEDULE:40 hours, Monday-Friday 8:00am - 430pm. Additional evening and weekend hours as needed. Available for on call rotations nights/weekends.


Pine Street Inn provides comprehensive support services to tenants across its Hosing portfolio; the Managing Director of Housing Support Services oversees the Housing Support Services which is comprised of Case Management and Residential Service teams. The Managing Director of Housing Support Services reports directly to the Director of Housing Programs and focuses on the client interventions and staff development of the Housing Support Services programs.

The Managing Director will provide leadership, clinical oversight, and overall operational management to the Support Services program. The Managing Director will coordinate directives across teams to ensure the provision of cohesive and consistent services across the portfolio. The incumbent will establish compliance with both internal and external policies covering the programs. The Managing Director is also a key player in the creation as well as the achievement of program goals. The Managing Director will ensure Associate Directors and their respective teams adhere to evidence based practices (Trauma Informed Care, Comprehensive Case Management, Motivational Interviewing) and ethical and legal obligations of Pine Street Inn as a Housing Provider. The Managing Director of Housing Support Services will work closely with the Director of Housing Operations & Property Management the Administrators of Property Management, and the Coordinator of Housing Stabilization, to coordinate interventions necessary to sustain tenancies, prioritizing the use of clinical service interventions and, if necessary legal counsel. The Managing Director will also serve as the point-of-contact for high-level neighbor relations and response.

The Managing Director of Housing Support Services will be self-motivated, possess exceptional communication skills, capable of coordinating service provision, program procedures, and implementing program developmental plans. The position requires a great deal of tack, diplomacy, and creative problem solving in order to maintain a positive working relationship with internal and external partners.



  • Bachelor’s degree in related field (Social Work, Psychology, etc.)


  • Minimum of ten (10) years experience working in homeless services or behavioral health services; including progressive supervisory and management responsibilities
  • Skilled in the provision of trauma-informed care, motivational interviewing and harm reduction approaches
  • Experience integrating best practices into day-to-day operations as well as staff training, consultation, and supervision
  • Demonstrated history of leading and managing the provision of supportive services for a vulnerable population, preferably in homeless services, behavioral health services or residential support service field
  • Executive disposition and the demonstrated ability to work well with senior leadership and program managers and officials both within, and outside, of the PSI Housing Department; must also be able to effective work with peers, subordinates and internal and external partners.
  • Successful track record of facilitating change management initiatives, particularly with respect to service and program enhancements benefiting both program participants and staff.
  • Superior planning and organizational skills.
  • Proficiency in Microsoft Office (Word, Excel, Outlook, PowerPoint) and ability to learn new software (e.g., SmartSheet, SharePoint).
  • A positive approach to change
  • Experience in and ability to maintain confidential records and information
  • Demonstrated ability to successfully work in a goal-orientated team environment
  • Enthusiasm for the mission of the Inn and a positive sense of humor


  • Ability to access different building locations and program sites
  • Ability to sit for long periods of time and use computer, calculator, fax, copier and other office equipment
  • Flexibility to work or be available according to program demands


  • Highly developed organizational skills, excellent verbal/written communication skills required
  • Analyze and synthesize information to understand issues, identify options, and support sound decision making.
  • Experienced in critical thinking and problem-solving. Integrates information from diverse sources, often involving large amounts of information. Thinks several steps ahead in deciding on best course of action, anticipating likely outcomes. Ability to partner with both internal and externa stakeholders to develop and implement strategies
  • Ability to establish and retain boundaries with both tenants and staff
  • Adept at crisis intervention which includes both oversight of interventions for individual in crisis (suicidality, etc), but also responding to critical incidents effecting a property (such as a fire, flood, safety violation)
  • Demonstrated integrity, flexibility, professional judgment, and collaborative approach to work. Works in a conscientious and consistent manner. Demonstrates concern for thoroughness and accuracy.


  • LICSW or other licensure
  • Bi-lingual in either Spanish or Haitian Creole
  • Strong commitment to the affordable housing and/or Housing First and Harm Reduction approach


  • Promote movement towards tenant stability and greater independent living and, where appropriate, transition to alternative Housing.
  • Oversee all management and clinical processes of the program to ensure the safety of tenants and staff and to ensure the appropriateness of tenant care.
  • Ensure that a system is in place for service plan development, designation of Phases of Care, and entry of case notes.
  • Ensure that support services staff are adequately trained and supported in HMIS and ECR systems. 
  • Responsible for maintaining compliance of tenant support service records, with continual quality assurance regarding data collection reporting, and clinical/administrative documentation.
  • Work closely with the Property Management Department and subordinates on the following:
  • Maintain good working relationships with landlords and property managers
  • Assisting tenants to meet lease and occupancy agreements
  • Tenant orientation and legal/eviction proceedings.
  • Ensure high quality, on-going communication across all supervisory structures and relevant working partnerships within Housing Support Services, through regular supervision, monthly team meetings, case conferences, quarterly division meetings, and expanding house and portfolio cluster meetings where appropriate.
  • Ensure the critical debriefing of staff and tenants where appropriate.
  • Attract, develop, coach, and retain high-performance team members. Provide opportunities for staff development through participation in internal and external trainings.
  • Collaborate with Human Resources to ensure staff has the support and training tools they need to perform their job duties.
  • Curate relationships with, and integration of, specialized clinical staff in the Housing Stabilization team, through coordination with the Director of Housing Stabilization.
  • Implement evidence based practices in program design, training, and supervision to senior support services staff.
  • Participate in program development and the design of new program services. This includes, but is not limited to, involvement in supporting grant writing and fundraising activities to promote program development.
  • Responsible for the development of good working relationships with referral sources that ensure that targets of services to formerly homeless persons are met, where needed.
  • Accepts supervision and guidance and actively participates in efforts to improve quality of performance.
  • Demonstrate and support organizational efforts around diversity, equity and inclusion.
  • Other duties as assigned in order to meet the needs of the organization during the COVID-19 pandemic or other public health or weather emergency


SCHEDULE:40 hours, Monday-Friday 8:00am - 430pm. Additional evening and weekend hours as needed. Available for on call rotations nights/weekends.


Pine Street Inn provides comprehensive support services to tenants across…

Details at a Glance

  • Time Commitment
    Full Time Schedule
  • Education
    4-Year Degree Required
  • Professional Level
USD $90,000 - USD $94,000
/ year


155 Geneva Ave, Boston, MA 02121, USA

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