Deputy Chief, Strategic Initiatives

Position Overview

The Office of the Chief of Staff works to maximize DCPS’ collective impact through ensuring strategic and data-based decisions, building upon DCPS successes through meaningful hiring and retention strategies, and effectively navigating citywide government partnerships. 

Divisions/Teams 

• Office of Employee Services (OES) supports the work of all school-based and Central Office staff to recruit, hire, retain, and train high-quality employees in the areas of benefits and compensation, Employee Experience, HR Systems Development, Strategic Staffing, Instructional Talent Acquisition and Retention. 

• Intergovernmental Affairs advances DCPS’ legislative agenda, clearly communicates with political leadership, assists elected officials with constituent services related to DCPS, and builds the knowledge and capacity of internal colleagues to understand and navigate political and legislative developments. 

• Strategic Initiatives supports collaboration, alignment, and coherence across DCPS through systems and structures focused on the strategic plan, performance management, and annual planning. 

Strategic Initiatives supports collaboration, alignment, and coherence across DCPS through systems and structures focused on the strategic plan, performance management, and annual planning. 

The Deputy Chief, Strategic Initiatives oversees the implementation of the DCPS Strategic Plan and related performance management systems, ensuring alignment across district priorities and initiatives. Serving as a key partner to the Chief of Staff and district leadership, the role drives strategic planning, organizational readiness, continuous improvement, and cross-functional execution to improve outcomes for students and strengthen district performance. 

This position has been designated as Security Sensitive. Pursuant to section 410 of Chapter 4 of the D.C. Personnel Regulations; in addition to the general suitability screening, individuals applying for or occupying security sensitive positions are subject to the following checks and tests: Criminal background check; Sex Offender Registry check; Traffic record check (as applicable); Consumer credit check (as applicable); Reasonable suspicion drug and alcohol test; and Post-accident or incident drug and alcohol test.

If you are hired into this position at an annual salary of one hundred fifty thousand dollars ($150,000) or more, DC government regulations require that you must establish residency in the District of Columbia within one hundred eighty (180) days of the effective date of the appointment and continue to maintain residency within the District of Columbia throughout the duration of the appointment.

The Deputy Chief, Strategic Initiatives will report to the Chief of Staff.

Essential Duties and Responsibilities

The below statements are intended to describe the general nature and scope of work being performed by this position. This is not a complete listing of all responsibilities, duties, and/or skills required. Other duties may be assigned.

• Leads the implementation and continuous improvement of the DCPS Strategic Plan by establishing systems, processes, and structures that drive alignment, accountability, and measurable progress toward district priorities.
• Acts as a key connector across district initiatives, supporting executive leadership in aligning priorities, removing barriers, and supporting organizational performance. 
• Oversees district performance management processes, including strategic plan monitoring, performance evaluations, and other systems designed to assess progress and improve organizational effectiveness. 
• Oversees compliance with district and citywide reporting requirements, ensuring accurate, timely, and high-quality submissions. 
• Leads enterprise-wide planning and readiness efforts, including the School Opening Readiness process, to ensure organizational preparedness and successful execution of key priorities.
• Builds strong relationships with senior leaders and key stakeholders to promote collaboration, shared ownership, and results. 
• Facilitates leadership meetings, strategic planning sessions, and learning opportunities that strengthen organizational capacity and continuous improvement. 
• Collaborates responses to interagency requests and constituent concerns, ensuring timely, collaborative, and solution-oriented engagement. 
• Leads special projects and initiatives on behalf of the Chief of Staff and Chancellor, managing complex workstreams that advance organizational priorities and improve systems, service delivery, and outcomes for students.

Qualifications

• Bachelor's degree and eight to twelve years of related work experience.
• Master's degree strongly preferred.
• Previous exposure to or experience in the education sector a plus.
• Demonstrated success leading complex, cross-functional initiatives and driving results through effective project management, stakeholder engagement, and execution.
• Strong analytical, problem-solving, and organizational skills, with the ability to manage multiple priorities, navigate complex challenges, and deliver high-quality work in a fast-paced environment.
• Proven ability to build productive relationships with senior leaders, stakeholders, and cross-functional teams to advance organizational priorities.
• High degree of accuracy, attention to detail, accountability, and professional judgment.
• Proficiency with Microsoft Office Suite, including Excel, Word, Outlook, PowerPoint, and Teams; experience with reporting and data analysis tools preferred.

DCPS Values

• STUDENTS FIRST: We recognize students as whole children and put their needs first in everything we do.
• COURAGE: We have the audacity to learn from our successes and failures, to try new things, and to lead the nation as a proof point of PK-12 success.
• EQUITY: We work proactively to eliminate opportunity gaps by interrupting institutional bias and investing in effective strategies to ensure every student succeeds.
• EXCELLENCE: We work with integrity and hold ourselves accountable for exemplary outcomes, service, and interactions.
• TEAMWORK: We recognize that our greatest asset is our collective vision and ability to work collaboratively and authentically.
• JOY: We enjoy our collective work and will enthusiastically celebrate our success and each other.

We are an equal opportunity employer and are committed to creating an inclusive, accessible workplace. We welcome and encourage applications from individuals with disabilities. Accommodation and/or application assistance is available upon request at all stages of the application and employment process. To request accommodation, please contact [email protected].