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Director of Supportive Services

Groundworks Collaborative

Groundworks Collaborative was established in 2015 following the merger of two well-established organizations: the Brattleboro Area Drop-In Center and Morningside Shelter (having previously been in existence for 27 and 36 years respectively).  We work with people and systems creating solutions to end hunger and homelessness for all people in our region.  We envision a community in which all people have their basic needs met, including a safe and dignified place to call home.

Position Title: Director of Supportive Services 

Reports To: Executive Director

Position Classification: Full-Time, Exempt

Salary Range: $65,000 to $80,000, we are proud to offer benefits valued at $19,000/year.

Position Summary

The Director of Supportive Services oversees Groundworks’ supportive services, including two supportive housing sites, case management services, Coordinated Entry, and Healthworks, GWC’s embedded mental and physical health care provider program.  As a senior clinically-trained staff member, the Director of Supportive Services is responsible for delivering the highest quality services possible and collaborating with community partners to provide programmatic excellence.  This position also helps clients access and navigate community services, enables the seamless integration between Groundworks’ programs and services, and works to create a great place to work and volunteer.  This position has the creative opportunity to enhance services, build new collaborations, develop new initiatives, build staff members’ capacity, and set high service delivery standards to ensure that all Groundworks’ programs and services embody our philosophy of dignity and respect.  

The Director of Supportive Services supervises 7 staff members directly, and approximately 15 indirectly.  This position is responsible for ensuring quality programs, effective partnerships and for building a welcoming and collaborative team environment marked by nonjudgmental and compassionate care.  The Director of Supportive Services facilitates program planning, evaluation, and continuous improvement, monitors evolving community needs, and develops new services as needs emerge.  This position also ensures that Groundworks’ services comply with all governmental and private funding regulations.  As a member of the Executive Leadership Team (ELT), the Director of Supportive Services provides agency-wide leadership to ensure the overall success of Groundworks’ programs, workplace and impact.



  • Excellent communication and interpersonal skills that inspire a dynamic team environment.

  • Leads change and develops new systems using a creative and innovative lens.

  • Outstanding people leadership and supervisory skills including recruitment, onboarding, expectation and goal setting, feedback giving and coaching.

  • Delegates effectively, involves people in decisions that affect them and builds effective teams.

  • Manages complex operations and scheduling thoughtfully and strategically.

  • Embraces continuous learning in leadership, operations and program excellence. 

  • Flexible, willing to be hands-on and multitask in a fluid and fast-paced work environment.

  • Strong time management skills, prioritizes competing tasks and meets deadlines. 

  • Highly organized, plans effectively, pays attention to details and completes work accurately.

  • Remains calm under pressure, models effective stress management and self-care.

  • Analyzes problems/issues, gathers data and information, and finds effective solutions.

  • Exercises solid judgment and critical thinking.

  • Knowledge of budget planning and preparation, program evaluation and grants management.

  • Balances the needs of clients as a whole with individual client needs, with a steadfast commitment to fairness, consistency and consideration of individual circumstances. 

  • Exhibits empathy while maintaining professional boundaries.

  • Personal commitment to social justice, anti-racism and equity. 

  • Understands trauma-informed care and program design.

  • Insight into challenges associated with poverty, addiction and mental health.

  • Knowledgeable of area resources and systemic barriers; effectively navigates services.

  • Understands anti-oppression frameworks, mutual aid vs. charity in program design, harm reduction and the root causes of homelessness.

  • Working knowledge of Google Workspace, Microsoft Word, Excel, Outlook, or other software applications to retrieve data, create spreadsheets, and generate reports. 

Desired Qualifications

  • Masters in Social Work, or human services related field 

  • Five or more years of senior nonprofit, homeless services or housing experience 

  • Significant experience in supervising staff, team building and creating a great place to work.

  • Experience working with substance abuse, mental illness, individuals with trauma histories.

  • Track record in evaluating, enhancing and managing programs, systems building, planning, budgeting and grants and data management.

  • Significant experience working with low-income and diverse populations.

  • Experience in training and enhancing staff and volunteers’ skills in crisis intervention and a range of issues relating to mental health, substance abuse and homelessness.

  • Lived experience with poverty and/or housing or food insecurity.

  • Strong knowledge of community resources and experience in community engagement and navigating services. 

  • Passion for Groundworks’ mission, philosophy and nonjudgmental, compassionate approach.

  • Competency in using a computer. 


Program Excellence (20%) 

  • Ensure all Groundworks’ supportive servicessupportive housing at The Chalet and Great River Terrace (GRT), case management, Coordinated Entry, Healthworks, and the UVM Intern—achieve the highest level of excellence and service provision through continuous quality improvement.

  • Ensure high service standards and a compassionate, non-judgmental approach.  Train all staff in GWC’s philosophy, mission, values, theory of change, and standards of excellence.

  • Ensure that all day-to-day operations meet the needs of clients, staff and volunteers.  

  • Develop and enhance systems to promote efficiency and effectiveness.

  • Ensure facilities are clean, welcoming and comply with health, safety and funder requirements.

  • Update program policies, guidance, care standards, procedures, forms, etc.

  • Create annual program budgets and manage programs to those budgets. 

  • Enable the seamless integration of GWC’s programs; co-facilitate Operations Team meetings.

  • Assess evolving community needs; develop and implement new services in response to needs.

  • Develop clear goals, objectives and work plans that result in quality, responsive services; monitor progress regularly to ensure that goals and objectives are fulfilled.

  • Continuously monitor supportive services and provide feedback to staff.  Formally evaluate services quarterly; solicit client, staff and community feedback.

  • Identify improvement opportunities, lead change and adjust programs based on feedback

  • Report frequently on programmatic progress, challenges and improvements to ELT and board.

  • Oversee the accurate, complete and timely collection and entry of program data, enhance the efficiency of data management systems, and provide program data to funders as needed.

Community Partnerships and Collaborations (20%)

  • Partner with Windham & Windsor Housing Trust (W&WHT).  Communicate regularly about shared projects, facilitate weekly site meetings, support joint training activities, evaluate and adjust shared services, oversee MOUs.

  • Oversee Coordinated Entry (CE) program.  Ensure all assessment partners are fully trained and engaged in the CE process, oversee the Master List, and monitor prioritization of community resources such as The Chalet, GRT, Rapid Re-Housing, Shelter Plus Care, etc.

  • Represent Groundworks and the needs of its clients at the Housing Coalition, Consortium on Substance Use (COSU, and elsewhere throughout the community.

  • Advocate for community-wide systems and solutions to address evolving community needs.

  • Maintain current, robust knowledge of community resources, cultivate partnerships and collaborate with service providers, and effectively navigate community services for clients.

  • Promote community awareness of Groundworks’ shelters, housing and other services.

  • Serve as an ambassador by recruiting clients, donors, volunteers and staff to GWC.

Staff and Volunteer Engagement (20%)  

  • Ensure programs are fully staffed at all times through robust recruitment, hiring, onboarding, training and staff retention efforts.  

  • Anticipate staffing needs and maintain effective scheduling practices, including substitute/per diem staffing systems.  Provide direct staffing if needed.

  • Ensure that all staff initially receive robust onboarding and training.  Provide or ensure rigorous ongoing staff and volunteer trainings to enhance skills and performance.

  • Continuously monitor and enhance the on-call system.

  • Conduct weekly 1:1 meetings with direct reports.  Create priorities, development goals and work plans; observe staff, provide feedback, coaching, and technical assistance.

  • Foster direct reports’ leadership growth; evaluate performance annually.

  • Ensure supervisors set all staff and volunteers up for success through clear roles, at least bi-weekly 1:1 supervision, regular feedback, coaching, training and support. 

  • Ensure that all staff have development goals and that skills are assessed regularly.

  • Address employee concerns or grievances.  Ensure exit interviews for all departing staff. 

  • Grow volunteer participation in GWC’s programs through effective volunteer recruitment, engagement and retention. Support volunteers’ onboarding, training and supervision.

  • Monitor volunteers’ effectiveness, engagement and satisfaction.

Team and Culture Building (10%)

  • Create an exceptional workplace and a team culture of collaboration, ownership and leadership in order to attract, fully engage and retain staff members and volunteers. 

  • Uphold, model and maintain Groundworks’ values.  Foster dedication to Groundworks’ service mission and a culture of understanding, compassion and positive regard for clients.

  • Ensure staff embrace diversity, equity and inclusion; enable skill-building and understanding of anti-racist/anti-oppression frameworks, mutual aid vs. charity, and root causes of poverty.

  • Convene regular, participatory staff meetings that promote teamwork, ownership and collaborative problem-solving.

  • Train staff and volunteers in skillfully managing and deescalating crisis situations, and in nonjudgmental and compassionate approaches to working with vulnerable populations.

  • Ensure staff understand Groundworks’ goals, priorities, budget and financial status.

  • Model accountability in relation to individual, programmatic and organizational goals.

  • Help lead staff Wellness Committee and facilitate wellness-related programs and activities.

  • Submit stories capturing client and staff experiences for Groundworks’ communications.

Client Support (20%) 

  • Interact regularly with clients, build effective, trust-based relationships. 

  • Work directly with clients to help navigate resources and transition to stable housing.

  • Develop GWC’s capacity for providing direct services to clients experiencing a crisis.     

  • Manage and participate in on-call services, including evenings, weekends and holidays.

  • Provide skills consultation and/or access to clinical supervision for staff as needed.

  • Review all critical incident reports, ensure timely follow-up with staff and clients.

  • Help coordinate COVID-related efforts including safety protocols, internal testing system, tracking and monitoring cases, coordinating with state partners, providing staff updates, etc.

Agency-Wide Leadership (10%)

  • Serve on the executive leadership team; provide agency-wide strategic leadership, problem-solving, planning, coordination and communication.

  • Participate in and help facilitate effective leadership team meetings.

  • Model and uphold Groundworks’ values, policies and procedures; foster a great workplace.

  • Perform other duties as contributions to a collaborative and values-driven team.

How to Apply:

Please email a resume and cover letter to

Job Location:

Brattleboro, VT

Date Added: May 1, 2022

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