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Director of Strategic Initiatives - Deputy Mayor for Education

POSITION: Director of Strategic Initiatives


OPEN:  January 2, 2020

CLOSE: Open until filled

SALARY RANGE/GRADE:    Excepted Service, Grade 8 Range: $100,3574 to $125,447


This position is located in the Office of the Deputy Mayor for Education (DME). The Director of Strategic Initiatives is a core member of the senior leadership team and a valued policy expert across the Education Cluster’s four priorities: early childhood, K-12 education, workforce & career readiness and strong enabling environments to support education and employment systems for all residents. 

The Director of Strategic Initiatives is the senior leader on the policy team responsible for leading, tracking and coordinating priority initiatives in the area of career readiness and workforce development. This individual will work with agency leaders and community stakeholders to strengthen pathways so every District resident can pursue meaningful family-sustaining work.  


The Director of Strategic Initiatives supervises and coaches a team of direct reports executing strategic projects. The position also has non-supervisory responsibilities related to convening and coordinating the work of other directors and staff to accomplish the Office’s strategic initiatives. The Director works closely with all DME agency partners to ensure the education cluster achieves the Mayor’s ambitious goals for workforce development and career readiness.  The Director also liaises with the Chief of Staff and Office of the City Administrator on issues related to DME and agency oversight.


Major Duties and Responsibilities:

The Director of Strategic Initiatives is an innovative thinker, planner and problem solver.  This individual finds solutions to complex problems and forges new pathways for DC’s for all residents to attain family-sustaining careers.  Successful candidates must demonstrate a commitment to educational equity, workforce development and have a proven track record for delivering meaningful, measurable results.  The Director’s specific responsibilities include: 


  • Identify steps needed to reach Office vision and goals under the Ready for Career strand,  including new projects or activities or steps to improve, connect or enhance existing projects or activities. 
  • Build and implement processes to track results, advance work, and resolve challenges that arise with policies and programs impacting the education or career readiness of our city’s residents.
  • Serve as a lead support for DME by encouraging a team-based environment among DME’s departments by building alliances, promoting open communication and collaborating to achieve joint objectives.
  • Communicate career and workforce policy trends both internally and externally through a variety of mediums including EdSights, reports, briefing memos and consultation on communications with the Director of Communications and Outreach and other DME senior leaders.
  • Build relationships with external and internal partners on behalf of the office in support of strategic initiatives. In particular, the Director of Strategic Initiatives will partner most directly with agency leaders at W.I.C (Workforce Investment Council) and DOES (Department of Employee Services). 
  • Maintain an effective working relationship with all levels of management officials and team members.  Build trust-based relationships and partnerships to deliver shared goals.
  • Supervise direct report(s) executing strategic initiatives; provide team-members with guidance, coaching and supervision to drive impact 
  • Serve as a key member of the Deputy Mayor’s senior management and advisory staff, and participate in recommending and formulating policies and strategies on career readiness and workforce development. 
  • Manage and oversee the completion of strategic career readiness policy projects.  Monitor comprehensive, long-range project plans showing the sequence of tasks, target dates and persons responsible. 
  • Conduct extensive research on best practices, policy issues and resources to guide and inform on the development of major projects in the area of career readiness and workforce development.  
  • Analyze data, identify problems, and recommend career and workforce priorities.  Assess, compile and review data in order to develop policies, procedures and/or systems for establishing, operating, and assessing the effectiveness of programmatic and administrative control systems such as those designed to achieve anti-deficiency requirements are met, streamline and simplify regulatory schemes, facilitate inspection, compliance and enforcement activities, etc.
  • Work with staff from relevant District agencies and external stakeholder groups to accomplish this work.  Project will change over time as implementation of the plan progresses.  
  • Attend meetings with or on behalf of the Deputy Mayor, where issues of significant administrative and managerial importance are discussed and decisions of significant administrative, managerial and programmatic impact are made.  Provide supporting information, and addresses issues and concerns raised by program managers. 
  • Advise and make recommendations to the Deputy Mayor concerning policy, legislative and/or regulatory issues impacting agencies in the Education Cluster.
  • Undertake responsibility for legal, legislative and policy analysis, and report on agency implementation.
  • Perform other related duties as assigned.


Other Significant Requirements

  • Mastery knowledge and experience with career readiness and workforce development issues, policy and effective programming at the local and national levels 
  • Mastery of project planning, performance management and change management within DME and cluster agencies.
  • Mastery knowledge of and skill in problem-solving, negotiation strategies and project management to conduct in-depth research and analysis.  Mastery knowledge of management principles, procedures and techniques of analysis and evaluation.
  • Track record of analyzing complex problems, identifying key issues, and simplifying the approach to solving them.
  • Strong influencing and negotiating skills, and excellence in giving constructive feedback.
  • Ability to work well in a team, especially when teams are drawn from across organizations and sectors.
  • Demonstrated ability as an analytical thinker, with ability to translate technical information to a lay audience; ability to use data and other evidence to make arguments and solve problems.
  • Ability to write high quality presentations and reports.
  • Demonstrated ability to think logically to sequence and plan delivery of public sector strategy
  • Knowledge of key federal, state, and local education, career and workforce policies.
  • Demonstrated experience in providing leadership, guidance and direction in a managerial/supervisory capacity, and in a team-based environment.
  • Strong organization and time-management skills. Ability to set goals and help others reach them by recommending improvements in complex programmatic, managerial and administrative processes; and to plan, organize and direct team work.
  • Superior oral and written communication skill sufficient to advise and consult with a variety of management officials, supervisors and others.  
  • Ability to establish and maintain an effective working relationship with all levels of management officials and team members.


Special Requirement

  • Graduate from an accredited college or university with a Bachelor’s degree in  public or business administration, education, public policy, or a closely related field, plus a minimum of five  (5) years of work related experience; OR an equivalent combination of education and/or experience which exhibits the ability to perform satisfactorily in the position.
  • Candidate must possess at least one (1) year of specialized experience equivalent to ES-07 grade level or the equivalent grade 13.  Specialized experience is experience which is directly related to the position and has equipped the individual with the knowledge, skills, and abilities to successfully perform the duties of the position. 
  • Advanced degree(s) preferred. 
  • Experience working in education leadership and management of strategic policy initiatives is desirable.



There is a legal requirement that each new appointee to the Excepted and Executive Service either: (1) be domiciled in the District of Columbia at the time of appointment; or (2) establish District domicile within one hundred eighty (180) days of appointment.  The law also requires that Excepted and Executive Service employees maintain District domicile during the period of the appointment.  Failure to maintain District domicile during the period of the appointment will result in forfeiture of employment.


For more information, please contact Steven Walker, Director, Mayor's Office of Talent and Appointments (MOTA) at 202-727-6101.

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