Senior Director Of Strategy Jobs (NOW HIRING)

Position Type:

Administration and Professionals

Date Posted:

2026-05-05Location:Administration or As Assigned

ABOUT CLEVELAND METROPOLITAN SCHOOL DISTRICT

The Cleveland Metropolitan School District (CMSD) is Ohio's third-largest public school system, serving more than 35,000 students.

CMSD strives to ensure that every child receives a high-quality education, regardless of the provider. To that end, CMSD lets families choose which District schools their children attend, with options that include STEM, the arts, single-gender education, International Baccalaureate, Montessori, and early college.

Our schools have autonomy over human and financial resources in exchange for accountability for performance. The principal has primary responsibility and accountability for establishing their school as a high-quality, high-expectation academic center focusing on personalized instruction, professional support for teachers, and school-wide practices that lead to measurable results.

CMSD ensures that students have access to technology and training to prepare them for the future. The District provides a free laptop or tablet for every student and connects every family that needs internet access. Graduating seniors leave commencement with not only a diploma but also a laptop.

In our pursuit of a more fair, just, and good system of education, we strive to ensure that all of our learners, both scholars and educators, to be challenged with academically and intellectually complex tasks that are worthy of their efforts and provide them opportunities to demonstrate their best work.

BUILDING BRIGHTER FUTURES

The Cleveland Board of Education adopted the Building Brighter Futures (BBF) initiative on December 9, 2025. Building Brighter Futures is a strategic and data-driven plan shaped by more than a year of community engagement, information analysis, and thoughtful deliberation. The goal of this plan is to strengthen enrollment and ensure scholars attend a newer school building that offers more educational opportunities, including algebra in the eighth grade, more sports and extracurricular activities, and college credits and college and career pathways in high school. BBF is ensuring academic excellence so every CMSD scholar can thrive.
THE OPPORTUNITY:

Location: Administration or As Assigned
Reports to: Chief of Staff
FLSA Status: Exempt
Salary Band: 8
Compensation: $ 77,158.00 - $ 104,164.00
**Internal applicants must submit a current resume as part of the application process.
The Director of Strategy Implementation supports the Chief of Staff in ensuring that CMSD's Strategic Plan is implemented and sustained through disciplined, system level planning, monitoring, and performance review. Reporting to the Division of People & Strategy, this role serves as a strategic integrator-facilitating recurring cycles through which goals, guardrails, and initiatives are set, cascaded, implemented, and monitored.
In implementing strategic initiatives, the Director coordinates contributors, structures the work, and surfaces evidence and tradeoffs to strengthen decision-making, accountability, and ways of working, all in service of supporting District leaders in their pursuit of system goals.

DUTIES AND RESPONSIBILITIES:

System-Level Planning & Cadence

• Own the facilitation and calendaring of CMSD's recurring system-level planning, progress monitoring, and performance management cycles.

• Facilitate the annual planning cycle to set and confirm CEO Measures, strategic initiatives, and key deliverables (typically January-March).

• Facilitate the process of cascading system goals to teams and individuals (e.g., aligned scorecards), in partnership with Talent and Research, Evaluation & Accountability (REA).

Progress Monitoring & Follow-Through

• Coordinate system-level monitoring of progress against goals, guardrails, and strategic initiatives.

• Coordinate and synthesize tracking of updates from CMSD teams on their progress to strategic performance goals

• Partner with the Executive Director of REA to manage the development and maintenance of monitoring infrastructure in coordination with functional teams.

• Synthesize and carry forward outputs of monitoring activities (progress, risks, patterns) to drive follow-through and inform subsequent monitoring cycles.

Cross-Functional Implementation Enablement

• Convene and facilitate cross-functional teams delivering high-leverage strategic initiatives, particularly within or adjacent to People & Strategy.

• Ensure clarity of roles, timelines, deliverables, and interdependencies, and promote disciplined follow-through.

• Facilitate proactive, collaborative discussions by helping teams anticipate the path forward, surfacing insights about any gaps, risks, and opportunities

• Support course correction and continuous improvement through structured reflection and review.

Integration & Content Stewardship

• Coordinate integration across strategic planning, progress monitoring, and talent management systems.

• Support alignment of system priorities with team and individual goals, without owning functional performance systems.

• Serve as steward of core district strategy artifacts, ensuring they remain current, coherent, and accessible.

Leadership Enablement

• Enable ELT, SLT, and Division leadership through agenda design, facilitation, synthesis, and follow-up aligned to system-level cycles.

• Facilitate Division of People & Strategy leadership meetings and collaboration structures to support continuity and forward planning.

Essential Competencies & Ways of Working

• Disciplined System Operator - Runs complex, recurring planning and monitoring cycles with rigor and reliability.

• Strategic Integrator - Connects strategy, people, processes, and performance across functions without overstepping ownership.

• Skilled Facilitator - Effectively convenes senior leaders, navigates ambiguity, and frames evidence and tradeoffs.

• Technologically Fluent - Leverages CMSD's modern workplace tools (e.g., SharePoint, Smartsheet, Teams, Copilot).

• Discerning Delegator - Relies appropriately on the expertise of Talent, REA, and functional leaders.

Qualifications:

• Bachelor's Degree required, master's degree preferred

• Minimum five (5) years of experience managing projects in a fast-paced environment with a strong track record of executing to plan

• Strong organizational skills; ability to prioritize and successfully manage multiple priorities and deadlines

• Demonstrated cultural competency and experience working effectively across organizational structures and lines of cultural difference to achieve results

• Strong collaboration and influencing skills

• Excellent communication skills (verbal, written, presentation, interpersonal) with all types/levels of audience

• Valid Driver's license, reliable transportation, and auto insurance

WORKING CONDITIONS/PHYSICAL DEMANDS

The characteristics listed below are representative of the work environment typically encountered by an individual while performing the essential duties of this position. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential duties.

• Expected to move, walk, and stand consistently in an office environment, and occasionally lift up to 15 pounds

• While performing the duties of this job, the employee is regularly required to stand, walk, and sit; use hands to finger, handle, or feel; and reach with hands and arms

• The employee is frequently required to talk and/or hear.

• Specific vision abilities required by this job include close vision, color vision, depth perception, and the ability to adjust focus.

• While performing the duties of this job, the employee is exposed to a normal office environment.

• Local travel may be required for training/meetings.

NOTE: The above-stated duties are intended to outline those functions typically performed by individuals assigned to this classification. This description of duties is not intended to be all-inclusive or to limit the discretionary authority of management to assign other tasks of a similar nature or level of responsibility.

Education

To Apply

EEO Statement

We believe that equity and inclusion at CMSD is an essential call to action, a catalyst to ensure value and appreciation among all our employees, so we may be fair and welcoming now and in the future. CMSD provides equal opportunities for employment, retention and advancement of all personnel by administering all terms and conditions of employment regardless of race, color,ethnicity, ancestry, national origin, sex, disability orgeneticinformation, age, citizenship status, military status, sexual orientation or expression, socio-economic status, title, other dimensions of identity, or any other characteristic protected by law.