About Success Academy

Success Academy's dual mission is to build world-class schools that empower children to thrive in college and in life, and to advocate for policies that expand access to educational opportunity. We are growing rapidly in New York and expanding to Florida.

Role Overview

The Vice President of School Operations owns the strategy, operating model, and performance of School Operations across ~60 schools and ~300 Operations staff. Leading through a team of Regional Operations Managers (ROMs), this leader ensures every school has the talent, systems, resources, and accountability structures to deliver exceptional outcomes for scholars, families, and staff.

The role demands a rare combination of strategy and organizational design, multi-site operational expertise, business acumen, and exceptional people leadership. The Vice President inherits significant reach and a strong foundation, with a mandate to elevate the ROM team, reduce variation across schools, and build management systems that support continued growth.

This is a school-based role. Approximately 60% of this leader's time is spent in schools — observing operations firsthand, coaching leaders, and diagnosing performance where the work actually happens. Candidates should expect regular travel across the network.

Leadership of Regional Operations Managers

• Lead, develop, and hold accountable a high-performing ROM team, establishing expectations, decision rights, operating rhythms, and performance measures.
• Coach leaders of leaders to diagnose performance, develop talent, and deliver sustained results across their school portfolios.
• Differentiate coaching and intervention based on leader readiness and performance risk; make rigorous talent decisions with clarity and fairness.
• Build succession plans and a strong internal pipeline for Regional Manager.
• Ensure leaders own and solve problems rather than depending on senior intervention.

Strategy, Organizational Design, and Change

• Design and continuously improve the School Operations operating model — roles, structures, decision rights, regional support, and accountability systems.
• Advise the executive leadership on the operational implications of enterprise priorities, including where School Operations can accelerate goals or create risk.
• Use root-cause analysis to distinguish whether a performance challenge originates in strategy, systems, design, leadership capability, execution, or clarity.
• Lead change from diagnosis through implementation and measurement, anticipating resistance and unintended consequences.
• Actively seek opportunities to simplify, automate, and improve School Operations through AI and technology — reducing administrative burden on school-based staff so their time goes to scholars and families.
• Build the capabilities required to support growth without compromising quality.

Operational Excellence and Risk

• Establish network-wide operational standards and accountability measures across safety, compliance, facilities, enrollment, family experience, financial management, and technology.
• Serve as senior escalation point for significant operational, safety, compliance, and reputational risks.
• Use regional and school-level insight to strengthen the broader operating model.

Cross-Functional and Executive Leadership

• Build trusted partnerships across Schooling, Enrollment, Facilities, Technology, Finance, People, Family Engagement, and Supply Chain — influencing without relying on formal authority.
• Ensure cross-functional initiatives reflect implementation realities in schools and can be executed at scale; clarify ownership, resources, timelines, and accountability across teams.
• Translate financial, operational, and talent information into clear recommendations, and communicate difficult tradeoffs with discretion and respect.

Talent and Financial Stewardship

• Define the leadership competencies and performance standards required across School Operations, and create pathways for high-potential staff to advance.
• Identify systemic talent risks and partner with People leadership on workforce planning.
• Provide senior oversight of budgets, staffing models, and major investments; partner with Finance on forecasting, reporting, and resource allocation.
• Identify efficiency opportunities that don't compromise scholar experience, safety, or school quality.

Knowledge, Skills, and Experience

• 10+ years of progressive leadership experience in operations, education, consulting, military, hospitality, retail, healthcare, government, or another complex multi-site environment.
• 7+ years in multi-site operations, performance management, continuous improvement, and operational risk — including leading senior leaders responsible for large, distributed teams.
• Direct experience leading organizational redesign — restructuring roles, reporting lines, decision rights, and management systems in a large organization, and carrying that change through adoption rather than stopping at the design.
• A track record of building new teams from the ground up — defining the function, hiring the leaders, setting standards and operating rhythms, and scaling the team to sustained performance.
• Demonstrated use of AI and technology to simplify operations — identifying manual, low-value work and replacing it with better tools, automation, or redesigned process, and driving adoption across a distributed team.
• Expertise in lean methodologies, data-informed decision-making, and change management, with a record of quickly assessing ambiguous situations and identifying the highest-leverage path forward.
• Proven ability to influence executive leadership and drive adoption through leaders in a large, distributed system.
• Exceptional people leadership: senior talent assessment, coaching, succession planning, and difficult talent decisions.
• Strong business and financial acumen, and excellent executive communication.
• Willingness and desire to spend approximately 60% of working time in schools across the network.
• Deep commitment to educational equity and Success Academy's dual mission.

Compensation, Benefits & Perks

At Success Academy, we invest boldly in our Network team with a comprehensive package designed to support your health, financial future, and overall well-being:

• Day-One Health & Wellness: Medical, dental, and vision coverage starting your first day (SA covers 82% of our core medical plan), plus a free One Medical membership and confidential mental health support via EAP/Talkspace.
• Financial Security: 403(b) retirement plan with a 3% employer match, up to $2,400/year in employer HSA contributions, employer-paid life/disability insurance, and Public Service Loan Forgiveness (PSLF) eligibility.
• Time to Recharge: Generous paid time off, paid holidays, and paid parental leave.
• Perks & Stipends: A $50/month cellphone stipend ($600/year), pre-tax commuter benefits, backup family care, and performance-based earning incentives.