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 offers a full benefits program and opportunities for professional growth.
