Head – Technology Project and Portfolio Management

About the Role

Reporting directly to the CTO, the Head of Technology Project and Portfolio Management runs the operating rhythm of the Technology department and acts as the CTO’s proxy with executive stakeholders. You will own demand intake, portfolio management, and executive reporting; oversee the department’s enterprise-wide programs; and manage the Tech Management cost center. Leading a team of program managers and partnering closely with the CTO’s leadership team, Finance, and School Operations leaders, you will make sure the right work gets in the door, the right people know where it stands, and decisions get made and followed through.

Key Responsibilities

• Demand Intake & Portfolio Management: Own the department’s intake process, from triage through executive approval. Maintain a clear view of the portfolio and recommend staffing and investment tradeoffs to the CTO.
• Roadmapping & Backlog Management: Establish a consistent approach to roadmaps and backlogs across technology teams and drive its adoption across the department’s leadership. Build and maintain a technology-wide roadmap that connects team plans to organizational priorities.
• Program Portfolio Leadership: Oversee the department’s enterprise-wide programs, ensuring each has clear scope, schedule, budget, and resourcing; resolve cross-program dependencies and conflicts; and set the risk and change management approach that drives adoption.
• Operating Rhythm & Executive Reporting: Run the department’s operating rhythm, including the biweekly sprint cycle, the weekly Tech Management staff meeting, and department all-hands. Own executive reporting, from the biweekly Technology Sprint Report to the CTO’s weekly update to the COO.
• Executive Stakeholder Management: Serve as the CTO’s proxy with executive stakeholders across the network, owning escalations, driving the CTO’s decisions to completion, and tracking leadership team commitments through to delivery.
• Budget & Vendor Governance: Own management of the CTO's Tech Management cost center, including annual budget planning, forecasting, actuals review with Finance, purchase approvals, and vendor contract reviews.
• People & Team Leadership: Manage and develop two program managers, establishing the PMO’s standards, methodology, and governance and coaching the team to apply them.

Qualifications

• 10+ years of experience in program or portfolio management, PMO leadership, or a chief of staff role, with at least 5 years managing people.
• Proven track record running an operating cadence for a senior executive, from agendas and executive updates to decision tracking and follow-through.
• Experience owning a department budget and partnering with Finance on forecasting, actuals, and procurement.
• Hands-on experience with work-management tools (monday.com or similar), including building boards and automations.

Competencies

• Executive Communication: Writes concise, outcome-first updates with specific dates and a mitigation or ask for every risk.
• Judgment & Influence: Knows what leadership needs to see, brings recommendations rather than open questions, and drives adoption of new practices across senior peers without direct authority.
• Relentless Follow-Through: Tracks commitments across many owners and keeps work moving until it's done.
• Discretion: Handles highly confidential information with professionalism and sound judgment.

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.

Compensation Range 250000 - 280000 USD