Head, Strategic Initiatives and Business

Success Academy is seeking a highly motivated and experienced Director of Strategic Initiatives & Business Operations to serve as a key partner and force multiplier to senior leadership in the Enterprise Services division. This role sits at the intersection of strategy and execution. You will drive high-priority, cross-functional initiatives spanning growth, expansion, continuous improvement, and AI — creating significant leverage for your executive partner and helping Enterprise Services deliver on Success Academy’s ambition to scale world-class schools and reimagine public education.

The ideal candidate combines strategic rigor with operational horsepower: someone who thinks like a strategist, executes like an operator, and influences like a senior leader. You are comfortable navigating ambiguity, building systems from scratch, and moving complex work forward quickly across functions — without waiting for perfect conditions. This individual will play a critical role in shaping how Enterprise Services plans, prioritizes, and delivers at a rapidly growing, mission-driven organization already operating at substantial scale.
 

• Large-Scale Initiative Execution

  • Own and drive the execution of high-priority, cross-functional initiatives across the organization from conception through completion — including growth and expansion projects, enterprise process redesign, technology-enabled operational improvements, and special projects assigned by leadership.

  • Represent Enterprise Services and its executive leader in cross-functional initiatives when they cannot be directly involved; build alignment and drive decisions to closure across departments.

  • Develop project plans, define scope, set milestones, coordinate cross-functional resources, and communicate effectively with stakeholders at all levels — from junior employees to ELT and Board.

  • Proactively identify blockers, resolve cross-functional misalignment, and ensure commitments are tracked and delivered on time.

• Operating Excellence, Cadence & Communication

  • Streamline operational processes to enhance efficiency, reduce “operational debt,” and support scalable, codified workflows (in the spirit of continuous improvement / Kaizen).

  • Prepare and synthesize information for executive meetings, ensuring leadership is well-briefed on priorities, risks, progress, and decisions required.

  • Serve as a connective point across the organization — ensuring information flows, priorities stay aligned, and the right people are in the room at the right time.

  • Track initiative performance and enterprise goal progress; leverage data and metrics to surface insights, drive corrective action, and support evidence-based decisions.

• Strategic Partnership & Enterprise Priorities

  • Translate strategic priorities for the executive leader in Enterprise Services into actionable plans with clear owners, milestones, and measurable outcomes.

  • Support the department planning cycle, including goal setting, budgeting, business reviews, and alignment with the network’s operating cadence.

  • Serve as a trusted thought partner and sounding board on complex, ambiguous problems — breaking issues down, framing options, and recommending a path forward.

• Bachelor’s degree in Business, Economics, Technology, or a related field; MBA preferred.

• Minimum of 10–12 years of progressive experience in strategy, business operations, management consulting, program management, or Chief of Staff roles, with at least 3 years in a leadership capacity.

• Demonstrated success leading complex, cross-functional initiatives involving multiple senior stakeholders in high-growth organizations.

• Strong analytical and problem-solving skills; ability to synthesize disparate inputs into clear recommendations and executive-ready materials.

• Exceptional project and program management skills, with a track record of driving change in fast-paced, dynamic environments.

• Outstanding communication, interpersonal, and presentation skills — with the ability to influence, negotiate, and build trust with senior leaders across functions, even without direct authority.

• Experience supporting or participating in annual planning, goal setting, operating cadences, or board-level reporting preferred.
   

• Highest integrity and ethics

• Intellectually curious and able to think deeply and qualitatively about business problems, breaking down issues and presenting solutions.

• Holds themself and others to very high standards of excellence. 

• Takes pride in taking a high degree of ownership.

• Positive, cooperative attitude.  Collaborative with a track record of building strong relationships. 

• Entrepreneurial with unrelenting drive and comfortable operating in ambiguity.

• Ability to roll up sleeves and be hands-on in a fast-paced, dynamic environment.

• Analytical and metrics-driven, regularly leveraging data to support business decisions.

• Open, secure, and humble, with demonstrated resilience.

• Passion for education and a commitment to the mission of Success Academy.