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Position Profile

Executive Director

City with Dwellings

Winston-Salem, NC

UPDATED 5/20/2021


City with Dwellings: A Community First Initiative works to end the crisis of homelessness in Winston-Salem and Forsyth County by building a supportive, consistent community with individuals experiencing homelessness.

City with Dwellings (CwD) is a low-barrier agency, honoring the inherent dignity of each person and respecting the unique challenges homeless individuals must overcome in their daily lives. CWD spends the needed time and capital to establish relationships of trust and accountability with the individuals we serve, as well as with the wider community in Winston-Salem. This relational approach enables us to effectively organize a coordinated response to assist persons experiencing homelessness and reduce recidivism.

CwD currently operates four integrated programs focused on our mission of building community and ending homelessness: Community First Center, Winter Overflow Emergency Shelter, The HEARRT Project, and Street Outreach. At our Community First Center, we provide the people and occasion for community to form, and the one-on-one support as people work to navigate the complex system of critical resources. The Winter Overflow Emergency Shelter brings our entire community together to directly meet the need that exists when there are not enough beds in our Continuum of Care system for the persons seeking shelter during the coldest months of the year. The HEARRT Project combines housing with wrap-around, Peer-led services as an immediate intervention for highly vulnerable and chronically homeless persons in our community. Our Street Outreach team seeks to develop a direct relationship with each person living outside of housing or shelter, partners with health care professionals and others to bring critical resources directly to their site, and assists with transitions toward housing, healthcare, and re-entering social spaces.

Since its inception in 2012 as a response to a critical need, CwD has continually worked with our partners and volunteers to collaborate around addressing the gaps that exist for the most vulnerable in our city. We organize and equip our community for this ongoing challenge. We are committed to the education and empowerment of the unhoused AND housed people of CWD, by which we create a community of advocates. We believe in changing the narrative of the role of the entire community in addressing issues of the common good.

We are excited to begin the search for our first Executive Director.


As CwD’s first Executive Director, this role requires a compassionate leader, growth-oriented visionary, and innovative problem solver. A nonprofit professional with a collaborative focus and strong experience working with a Board, the Executive Director will represent CwD’s collective voice in the community, serving as an encouraging partner, identifying and leveraging opportunities, and leading fundraising and advocacy efforts.

The Executive Director will act with integrity and convey their passion for the mission throughout their work. As a key individual in the organization, the Executive Director will sustain and enhance the work and embrace the values of CwD.


The Executive Director serves as the key strategic, operational, and development leader of City with Dwellings. In collaboration with the board, the Executive Director leads the development and execution of a strategic plan. The Executive Director is responsible for the overall leadership of operations, including fund development, board engagement, communications, financial oversight, personnel management, and compliance. The Executive Director responsibly manages program development, advocacy, and community relations by partnering with the existing strong staff, board committees, and volunteers who are deeply invested in these areas.


Candidates must be able to demonstrate a progressive record of leadership and accomplishment relative to the following:

Leadership, Strategic Planning, and Operations: Work with the staff and board to ensure CwD’s mission is achieved through strategic planning and plan execution.

  • Provide motivational leadership and actively engage, energize, and empower staff. Ensure a positive, collaborative, and opportunistic team environment.
  • Hire, onboard, lead, develop, and retain qualified and competent staff.
  • Review, update, and develop operational, personnel, and volunteer policies, manuals, and materials for board approval.
  • In partnership with the board, guide CwD’s strategic plan. Align all endeavors to ensure CwD can successfully fulfill its mission.
  • Createthe systems needed to ensure all programs are impactful, cost-effective, and achieve their purpose.
  • Seek input from a variety of sources; be open to diverse points of view; actively listen to board, staff, volunteers, partners, and the community.
  • Stay current on the changing landscape, trends, challenges, and best practices.

Fund Development and Financial Performance: Develop resources sufficient to ensure the financial health of the organization and programming.

  • Establish resource development goals with the board; develop a strong and diversified fundraising strategy.
  • Cultivate potential and existing funding sources. Seek appropriate grant opportunities; apply for grants; comply with and report as required for grants received.
  • Manage donor and prospect engagement, development, and acknowledgements.
  • Develop annual budgets in conjunction with the board; manage operations within approved budgets.
  • Produce monthly financial reports for review by the Treasurer and board.
  • Create and adhere to internal financial controls.
  • Oversee financial and accounting operations. Develop and maintain sound financial policies, procedures, and practices.

Community Relations and Communications: Serve as CwD’s primary spokesperson to partnering agencies, the media, and the community.

  • Sit on the Continuum of Care (CoC) Operating Cabinet as CwD’s representative.
  • Develop and maintain strong relations with other CoC agencies, the City, the media, donors, and the community.
  • Work in collaboration with other agencies to achieve the distinct mission of CwD.
  • Oversee the execution of a communications plan for all CWD stakeholders.
  • Maintain and steward CwD’s reputation and goal of being a “low-barrier” organization, and our CoC as being “housing first.”
  • Promote awareness and education about people who are experiencing homelessness/

Programs, Advocacy, and Education: Create the conditions for the board, staff, and volunteers to develop programming that meets CwD’s mission.

  • Assist staff and volunteers at the CFC in program generation, development, and implementation.
  • Partner with organizations to develop potential solutions to homelessness; promote solutions that address the intersectional issues which impact someone’s homelessness and helps reduce recidivism.
  • Maintain a working knowledge of significant developments and trends in Winston-Salem and Forsyth County related to the homeless population, agencies addressing homelessness, and local policy changes.
  • Work with the Education and Advocacy Committee to educate the wider community on the multi-faceted crisis of homelessness and assist community members in becoming advocates who can champion solutions to homelessness in Winston-Salem.


The Executive Director will be committed to the organization's mission and have proven leadership experience. Other qualifications include:

  • Exhibit an understanding of the culture and circumstances of individuals experiencing homelessness and generational poverty.
  • Demonstrated experience in fundraising, program management, budget management, and administration.
  • Strong collaborative leadership skills to provide good team management.
  • Strong communication skills and presentation skills.
  • Strong organizational skills, including planning, delegating, program and project development, and time management skills.
  • Ability to share the mission and value of the current work of the organization to staff, board, donors, and community stakeholders.
  • Ability to engage diverse cultures and community partners.
  • At least five years of professional leadership experience, preferably with a non-profit.
  • Minimum of a four-year college degree; certification in non-profit management is a plus.

The target hiring salary for this position is $65,000 to $75,000. No additional benefits are offered at this time. CwD recognizes that the position and compensation will grow as the organization and funding grow.


Please send cover letter, resume, and contact information for three to five references (including a past or present supervisor and/or Board member, a direct report, and a volunteer working directly with you) to: Only applications received through this address will be considered.

Applications will be reviewed and considered as they are received, on a rolling basis.