Managing Director - JayDot, LLC

JayDot, LLC seeks a Managing Director as a values-driven and entrepreneurial leader to provide executive leadership for the company’s operations, programs, and external relations.

About JayDot

Jaydot is a mission-based social enterprise focused on creating affordable housing solutions for people in the Washington, DC area, particularly those who have experienced homelessness. Its mission is to create innovative, high-quality housing solutions that address the needs of those impacted by social inequity. Jaydot operates from the belief that housing is a human right, homelessness is a solvable problem, and an equitable, human-centered, trauma-informed system can be created in which housing solutions are readily adapted to meet the needs of the people served.

In close collaboration with the company’s owner and Principal, the Managing Director will play a critical role in leading the company: centering Jaydot’s compassionate team culture, strengthening operations, mentoring and growing the expertise of staff, deepening partnerships, and positioning Jaydot for continued growth and impact.

The Managing Director will be responsible for a $3 million budget, with a diverse revenue mix from both government and fee-for-service contracts. They report to and work closely with the Principal and supervise the Director of Programs and Director of Operations, with overall responsibility for a current team of 22 full-time staff members.

Strategic Leadership

• Partner with the Principal to shape and implement a forward-looking strategy aligned with Jaydot’s mission, values, and community needs.
• Refine company goals and key performance indicators.
• Oversee Jaydot’s financial health, including goal setting, budgeting, and forecasting.
• Lead, develop, mentor, and retain a high-performing team that values communication, respect, humility, and dignity for all people.
• Identify, evaluate, and pursue new contracts to expand Jaydot’s community impact.

Finance and Operations

• Supervise and support the Director of Operations in carrying out the day-to-day operations, including HR, financial management, and legal and regulatory compliance.
• Direct long-range financial analysis, review trends, and engage the Principal in discussions about financial planning.
• Guide budgeting and ensure DC government contracts and reports meet requirements.
• Maintain policies, procedures, and technology.
• Ensure compliance with all legal, financial, and contractual obligations.

Programs

• Supervise and support the Director of Programs in overseeing PSH and Resident Services teams to ensure high-quality service delivery and program outcomes.
• Provide guidance and leadership in resolving programmatic challenges.
• Collaborate with program leadership to strengthen systems, policies, and practices.
• Monitor program performance and impact, using data and feedback to inform continuous improvement and decision-making.
• Partner with the Principal to identify and assess new programmatic opportunities.

External Relations

• Cultivate and manage relationships with nonprofit partners, developers, DC agencies, and residents to ensure effective service delivery and collaborative housing solutions.
• Elevate Jaydot’s visibility as a trusted program service delivery leader.
• Liaise with government agencies and housing system partners.
• Represent Jaydot in coalitions, public forums, and industry partnerships.

Experience, Skills, and Qualities

While we understand that no single candidate can possess every qualification listed below, the following are priority areas.

• 7 years of progressive leadership experience within nonprofit, public sector, or small business settings.
• A mission-driven mindset, with a passion for ending homelessness.
• Demonstrated entrepreneurial mindset with the ability to take initiative and solve problems.
• Excellent business acumen, including experience with budgeting, financial management, human resources, contracts, and legal compliance.
• A significant supervisory record, including coaching leaders, developing high-performing teams, and setting an inclusive, positive workplace culture.
• A successful record implementing strategy and setting goal frameworks.
• Experience building and maintaining long-term relationships with a diverse range of audiences (e.g., residents, agency leaders, community partners).
• Experience developing and maintaining systems, standard operating procedures, management processes, and office policies.
• A high level of emotional intelligence, integrity, cultural sensitivity, and interpersonal skills.
• Polished and persuasive written and verbal communication skills.
• Demonstrated understanding of structural racism and its impact on communities of color.

Considered a plus:

• Experience with housing and social services.
• A history of working on programs that serve low-income populations.

Location

Jaydot has several offices throughout Washington, DC. The Managing Director will have their own office at one of the sites from which Jaydot operates. A limited portion of the Managing Director's time can be spent working remotely, as approved by the Principal.

Compensation

The budgeted salary is $120,000 - $125,000, with a generous benefits package that includes employer-matched retirement savings, health, dental, and vision insurance, and paid time off. Jaydot is committed to an equitable wage scale that fosters a sense of shared purpose among employees; therefore has a policy of a maximum scale of 3:1 from highest to lowest paid staff.

Application Process

Jaydot has retained Good Insight, a national executive search firm serving nonprofits, to conduct this search. See the full executive profile and application information at www.good-insight.org/careers. Resume reviews begin immediately. For best consideration, apply by early December, 2025. Early applications are encouraged due to the pace of the search.

Equal Opportunity Employer

Jaydot is an equal opportunity employer.