Leader - Business Transformation

About the Role

The role is designed to help senior leaders solve the organization's hardest, most ambiguous operating problems — and to build the organization's own muscle for doing this work. At its core, this is a role about sharp thinking and sharper facilitation: the ability to walk into a room of busy, skeptical school and network leaders, drive them to the real root cause of a hard problem, and leave them aligned on what to do next. You'll lead a team of strategy and operations practitioners and own the organizational effectiveness strategy and pipeline — but your primary instruments are diagnosis, facilitation, and the ability to communicate root causes and solutions in a way that moves executive leadership to act.

Structured decision-making and problem-solving frameworks are part of the toolkit, not the point of the job. We're looking for someone who can flex and adapt those frameworks to fit a fast-moving, people-intensive, mission-driven school system — not someone applying a rigid, one-size-fits-all playbook.

Who thrives in this role?

People who've spent their career getting a room full of skeptical, busy leaders to diagnose what's actually broken and what to do about it — whether that muscle was built in management consulting, corporate strategy, internal operations, organizational design, or leading transformation inside a school system, hospital, or other complex, mission-driven organization. You're energized by ambiguous, human problems more than by cleanly executing a known methodology.

Key Responsibilities

• Facilitate to Root Cause: Lead diagnosis of workflow impediments and organizational friction across the business — especially where the problem itself isn't yet well-defined — and facilitate senior stakeholders toward clear, actionable root causes.
• Influence Executive Leadership: Distill complex, ambiguous problems into a clear narrative and communicate root causes and solution options in a way that builds conviction and drives decisions at the executive level.
• Drive Change Through Structured Problem-Solving: Lead focused problem-solving sessions that apply rigorous analytical and decision-making frameworks to drive process improvement and cross-functional alignment.
• Own the Operations Optimization Roadmap: Develop the organizational effectiveness roadmap in partnership with senior leadership, aligned to business priorities, annual targets, and strategic plan objectives.
• Build the Organization's Problem-Solving Muscle: Promote and evolve a practical set of strategic and analytical tools — with the judgment to know which approach fits which situation, and when to set the playbook aside.
• Partner on Strategy Execution: Be an active partner in strategic transformation and performance management initiatives alongside business leadership.
• Develop Talent: Own and continuously improve the team's training program; coach and evaluate practitioners toward advanced proficiency.

Qualifications

• Executive facilitation and influence: Demonstrated ability to facilitate senior stakeholders — including C-suite/Board-level audiences — through ambiguous, high-stakes problem-solving to a clear root cause and a compelling, actionable path forward. This is the single most important skill for this role.
• Comfort with ambiguity: Track record of shaping and scoping problems that don't arrive pre-defined, rather than only executing a known methodology against a known workflow.
• 8+ years leading strategic problem-solving, organizational transformation, or operational improvement in complex, fast-moving, or mission-driven organizations. This might come from management consulting, corporate strategy, organizational design, or internal ops/strategy roles at complex service organizations — or from operations-heavy contexts such as healthcare, education, or government. Your problem-solving and facilitation ability matters more than your specific methodological pedigree.
• Coaching and talent development: Demonstrated ability to build and develop high-performing, cross-functional problem-solving teams.
• Experimentation mindset: Able to help teams take and manage risk, and drive experimentation to facilitate learning.
• Change leadership: Demonstrated ability to lead an organization through significant change without losing momentum, and to inspire continuous focus on key drivers — ideally within a decentralized, people-first, or mission-driven organization.
• Analytical acumen: Working fluency in structured decision-making and problem-solving frameworks, with the judgment to apply the right approach to the right situation rather than a single methodology by default.
• Prior experience in consulting or in-house strategy team is preferred.
• Bachelor's degree in Business, Education, Public Policy, Engineering, or another relevant field — or equivalent demonstrated experience.

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/monthcellphonestipend(600/year), pre-tax commuter benefits, backup family care, and performance-based earning incentives.

This is a hybrid position based in our NYC Financial District office, requiring on-site work Tuesday through Thursday and remote work on Monday and Friday.