Director of Strategy Implementation

Cleveland Metropolitan School District

18h•Onsite

About The Position

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.

Requirements

Bachelor’s Degree required
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

Nice To Haves

Master’s degree preferred

Responsibilities

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).
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.
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.
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.
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.