Senior Director, Strategic Initiatives

Senior Director, Strategic Initiatives

Senior Director, Strategic Initiatives 150 150 CityWorksDC CityWorksDC
CityWorks DC
February 22, 2021



CityWorks DC is an entrepreneurial nonprofit venture sponsored by CityBridge Education. CityWorks DC’s mission is to reshape education-to-employment pathways in Washington, DC by mobilizing key stakeholders and resources in order to dramatically increase the number of young people who secure the family-sustaining jobs available in our growing regional economy. Our vision is that all young people in DC have the “social mobility trifecta”: 1) valuable certifications and credentials, 2) paid, relevant work experience, and 3) a supportive professional network. To provide this trifecta to all students, especially those who are marginalized and historically overlooked, CityWorks focuses its work on redesigning how young people experience high school, postsecondary, and early employment.

To accomplish this bold vision, CityWorks DC’s theory of change has two complementary strands: 1) launch a targeted set of innovative programs that work directly with young people and 2) lead systems-level initiatives that create the conditions for CityWorks programs and others to thrive and spark citywide reform across K12, postsecondary, and employment.

Founded in 2019 by Jennifer Niles and Furman Haynes, the CityWorks team is small and mighty with seven full-time staff members, one full-time contractor, and a number of expert consultants. CityWorks DC has ambitious plans to grow the current programs and initiatives rapidly, as well as consider new projects as appropriate. The work is funded by local, regional, and national foundations.


The Senior Director for Strategic Initiatives will be responsible for the implementation and management of existing systems-level initiatives and development of additional projects as needed. Our systems-level work, which is currently led by the President & CEO, includes three workstreams:

  1. Employers for Equity is a new employer-led initiative housed at the Federal City Council focused on driving the development of a local, equitable talent pipeline. The initiative will use convenings, policy papers, and best-practice sharing to accomplish three goals: 1) uniting employer voice, 2) expanding work-based learning, and 3) recognizing exemplary employers. The Senior Director will work with senior leadership at the Federal City Council and CityWorks’ President & CEO to further develop the project, set the strategy, and operationalize all aspects of this nascent initiative.
  2. CEMETS (Center on Economics and Management of Education and Training Systems) is a virtual 6-month Swiss institute housed at a Swiss research university in which teams from all over the world learn about the design of high-performing education and training systems and develop a reform plan for their local context. The Senior Director will help operationalize the set of recommendations that come out of the 2020-2021 Institute. This initiative is a complex change management process with a diverse set of stakeholders and requires managing the execution of multiple jointly-owned projects.
  3. Early Career Outcomes Project is a joint project of CityBridge Education, CityWorks DC, and Bain & Company to learn more about the early career outcomes of DC youth who attended DC public and public charter high schools. The project will include a survey that will provide a snapshot of DC public school alumni’s current wages, occupations, and other relevant factors. The Senior Director will help manage the project and execute the spring convening that will help push the mindsets of DC education and government leaders about the need to shift away from a narrow focus on college completion to think more holistically about early career outcomes.  Going forward, CityWorks DC expects to develop and implement additional projects with other partners, such as the DC Policy Center, to build a body of research and recommendations.

In all aspects of the work, the Senior Director of Strategic Initiatives will be responsible for building and strengthening relationships with critical formal and informal partners across the city. Reporting to the President & CEO, the Senior Director will collaborate with the other senior CityWorks DC leaders to set the strategic direction for the organization, ensuring the growth and success of initiatives that will transform the education-to-employment pipeline in the region. The Senior Director will also serve as a spokesperson for CityWorks DC across a range of settings and stakeholder groups and support CityWorks DC’s efforts to raise funds for this impactful work.

The ideal candidate will be a social entrepreneur who brings a) deep expertise in education, training and workforce policy and/or systems and b) extensive experience in working with diverse stakeholders to create systems-change in Washington, DC. Given that CityWorks DC is in its early growth phase of development as an organization, a successful candidate will thrive in a fast-paced and entrepreneurial environment, be comfortable with ambiguity and ideation, and will be willing to provide leadership and direction as well as step in and roll up their sleeves. This person also will have a track record of success in managing complex projects, building strong partnerships, and delivering on impactful goals. They will be an exceptional communicator and relationship manager, bringing the ability to build connections with stakeholders at all levels of an organization. Finally, they will also be comfortable managing a variety of initiatives on tight timelines with a drive for continuous improvement.


  • Leadership
    • Lead, manage, and execute all aspects of CityWorks DC’s systems-level initiatives from implementation through evaluation
    • Develop and manage strategic partnerships and build trust with key stakeholders and community members in order to accelerate the impact of systems-level initiatives
    • Work collaboratively with CityWorks DC senior leaders and staff to further CityWorks DC’s vision and mission, including supporting multi-year strategic planning efforts
    • Serve as a compelling internal and external spokesperson for CityWorks DC’s mission and vision and support the CEO with local and national fundraising efforts, as needed
    • Identify, develop, and launch new citywide initiatives as appropriate
  • Coalition Building and Systems Change
    • In partnership with the President & CEO, lead a citywide change management process that mobilizes leaders from key stakeholder groups to make high-priority changes to policies and practices to build a local, equitable talent pipeline
    • Identify and prioritize new policies and practices for K-12, postsecondary, and early employment to enact so that DC students, especially those from marginalized communities, achieve the social mobility trifecta (see above)
    • Build deep and trusting partnerships with key stakeholders and decision-makers in business (employers and business groups), education (K-12 and postsecondary), government (local and federal, as needed), and social services (especially work-based learning and wrap-around supports)
  • Project Management
    • Develop key goals and project plans with the CityWorks DC leadership and consultants, translating long-term goals into short-term initiatives that drive measurable impact
    • Prioritize, plan, and organize key processes for systems-level initiatives
    • Manage consultants and future staff members supporting system-level initiatives
    • Provide timely, clear communications to related parties
  • Continuous Improvement and Learning
    • Use a data-driven approach to inform decision-making and engage in cycles of feedback and improvement
    • Stay up-to-date on local, regional, national, and international research and innovative programming to inform CityWorks DC’s programs and initiatives


  • Deep commitment to achieving racial equity and the shared belief in the promise inherent in all young people, including a passion for service, student success, and the ability to connect with students from historically marginalized communities
  • Success as an entrepreneur or intrapreneur in imagining, creating, and implementing new initiatives in complex environments
  • Extensive experience in and knowledge of Washington, DC, including the business, education, government, and workforce landscapes
  • Demonstrated experience and expertise in policy development and/or implementation at the local, regional, state, and/or Federal level
  • Demonstrated experience in change management, including mobilizing external stakeholders towards a common goal
  • Demonstrated experience thriving in a fast-paced, demanding, and dynamic organization
  • Demonstrated ability to develop a project from its inception to successful completion
  • Demonstrated experience managing a team and executing against ambitious performance goals
  • Superior verbal and written communication skills to effectively lead relationships with stakeholders at all levels and expertise in creating and delivering compelling presentations
  • 12+ years of relevant experience in education (K-12 and/or postsecondary), workforce, and/or talent development
  • Demonstrated experience managing annual budgets
  • Demonstrated success in supporting fundraising efforts

How To Apply


This is a full-time position based in Washington, DC. The starting salary for this role is between $140,000–$170,000 with benefits, including healthcare, vision, dental, and 401(k) with employer matching. To apply, please submit a resume and a cover letter detailing your interest in joining CityWorks DC, your relevant experience, and your success in executing complex projects in a fast-paced environment. Applications will be reviewed on a rolling basis.


CityWorks DC’s goal is to build an inclusive work environment where everyone feels equally valued and respected. We understand the importance of bringing together a team with different perspectives, backgrounds, and life experiences, and we prioritize learning and reflection within our team. We encourage people from underrepresented backgrounds to apply.

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