Head, Strategic Initiatives and Business

Head, Strategic Initiatives and Business Operations

New York

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.

Key Responsibilities

• 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.

Professional Qualifications

• 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.

Personal Characteristics

• 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.

Exact compensation may vary based on skills and experience.

Compensation Range

$250,000 - $275,000 USD

Success Academy Charter Schools is an equal opportunity employer and actively encourages applications from people of all backgrounds. Compensation is competitive and commensurate with experience. Success Academy offers a full benefits program and opportunities for professional growth.

We are an equal opportunity employer and value diversity at our organization. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We actively seek applications from people of all backgrounds to strengthen our community and the perspectives needed to flourish in a multicultural world. Success Academy offers a full benefits program and opportunities for professional growth.

Success Academy Charter Schools does not offer employment-based immigration sponsorship.