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Position Profile

Executive Director

City with Dwellings

Winston-Salem, NC


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 and nimble agency, honoring the inherent dignity of each person and respecting the unique challenges homeless individuals must overcome in their daily lives. Building relationships of trust and accountability with individuals we serve and engaging the wider community in our work enables City with Dwellings to effectively facilitate a coordinated response to help house individuals and reduce recidivism.

At City with Dwellings’ Community First Center (CFC) we offer community and one-on-one support to individuals experiencing homelessness as they work to navigate a complex system of supportive resources. Our innovative programming engages individuals as they work towards health and stability.

CwD currently operates four integrated programs focused on building community to end the crisis of homelessness: Community First Center, Winter Overflow Emergency Shelter, The HEARRT Project, and Street Outreach. We engage with the individual experiencing homelessness to fully understand the unique circumstances they must overcome to successfully access resources. This person-centered approach builds trust and creates meaningful community with homeless individuals.

Founded in 2012 as a collaborative response to a critical need, CwD has worked with our partners and volunteers to create a coordinated model of support and care for the most vulnerable in our city. Over the years, countless volunteers and partners have been invited into the greater story of ending homelessness in WS. Supported through education and empowered as advocates, the people of CwD, housed and un-housed, are changing the narrative of what community can be in WS. 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 support, financial management, personnel and volunteer management, programs, advocacy, community relations and communications, and compliance.


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

Leadership and Strategic Planning: Work with the board and staff 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.
  • In partnership with the board, develop, implement, and periodically assess CwD’s strategic plan. Align all endeavors to ensure CwD can successfully fulfill its mission.
  • Commit to the continued development and management of a professional and efficient organization; recommend timelines and resources needed; establish effective decision-making processes.
  • 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 approved programming; plan for resource development; manage operations to approved plans.

  • 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 goals.
  • Produce accurate and timely monthly financial reports for review by the Treasurer and board.
  • Understand income statements, balance statements, statements of functional expense, 990s, audits, and compliance with standards. Create and adhere to financial controls.
  • Oversee and manage financial and accounting operations. Develop and maintain sound financial policies, procedures, and practices.

Community Relations and Communications: Sit on the Continuum of Care (CoC) as CwD’s representative and serve as CwD’s primary spokesperson to partnering agencies, the media, and the community.

  • Develop and maintain strong relations with other CoC agencies, the City, the media, donors, and the community. Work in coalition with other agencies to achieve the mission of CwD.
  • Develop and execute a communications plan for all stakeholders.
  • Maintain and steward CwD’s reputation and goal of being a low-barrier entry organization.

Programs, Advocacy, and Education: Create the conditions for the board, staff, and volunteers to develop programming that meets CwD’s mission. Promote awareness of and education about people who are experiencing homelessness, and advocate for solutions to homelessness in Winston-Salem.

  • Create the systems needed to ensure all programs are impactful, cost-effective, and achieve their purpose.
  • Partner with organizations to develop potential solutions to homelessness; promote solutions that help house individuals and reduce recidivism.
  • Increase awareness of the work CwD is doing to assist individuals who are experiencing homelessness; educate the community on the challenges homeless individuals face and potential solutions.
  • 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.

Staff Management and Operations: Oversee and implement effective resources and processes to help ensure the success of the organization.

  • Hire, onboard, lead, motivate, develop, and retain qualified and competent staff.
  • Provide a productive, positive, team-oriented environment for staff and volunteers.
  • Develop operational, personnel, and volunteer policies, manuals, and materials for board approval.
  • Manage the facility lease and procure appropriate insurance. Approve hardware and software procurement for donors, collaborating, storage, finances, communications, and records,
  • Comply with all laws and regulations.

Board Relationship and Duties: Work with the board to fulfill CwD’s mission.

  • Report to and cultivate a strong, transparent working relationship with the board and ensure open, accurate, and timely communication.
  • Recommend and execute strategies that ensure sound practices and governance.


The Executive Director will be thoroughly committed to the Coalition’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 skills.
  • Demonstrated ability to fairly, impartially, and effectively lead and collaborate with staff.
  • Strong collaborative leadership skills to provide good team management and to increase visibility and partnerships within the community.
  • Strong communication skills with above average public speaking and presentation skills.
  • Strong organizational skills, including planning, delegating, program and project development, and time management skills.
  • Ability to convey the mission and value of the current work of the organization to staff, board, donors, and community stakeholders.
  • Ability to understand, communicate with, and successfully engage across diverse cultures and community partners.
  • Ability to provide clear and timely communication, responding quickly to others, keeping the board and staff up to date.
  • 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 $60,000 to $70,000 at this time, with recognition that the position 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 accepted until February 28, 2021.