Head, Technology Project and Portfolio Management

Success Academy Charter Schools•New York, NY

5h•$250,000 - $280,000•Hybrid

About The Position

The Head of Technology Project and Portfolio Management reports directly to the CTO and runs the operating rhythm of Success Academy’s Technology department, serving as the CTO’s proxy with executive stakeholders. The role owns demand intake, portfolio management, executive reporting, enterprise-wide technology programs, and the Tech Management cost center. It leads two program managers and partners closely with the CTO’s leadership team, Finance, and School Operations leaders to guide priorities, resourcing, and decision-making.

Requirements

10+ years of experience in program or portfolio management, PMO leadership, or a chief of staff role.
At least 5 years of people-management experience.
A proven track record running an operating cadence for a senior executive, including agendas, executive updates, 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 such as monday.com or similar, including building boards and automations.
Ability to write concise, outcome-first updates with specific dates and a mitigation or ask for every risk.
Sound judgment and influence, including identifying what leadership needs to see, making recommendations, and driving adoption among senior peers without direct authority.
Strong follow-through in tracking commitments across many owners and keeping work moving through completion.
Professionalism and sound judgment when handling highly confidential information.

Responsibilities

Own the Technology department’s demand-intake process, from triage through executive approval, maintain visibility into the portfolio, and recommend staffing and investment tradeoffs to the CTO.
Establish a consistent roadmap and backlog approach across technology teams, drive adoption among department leaders, and maintain a department-wide roadmap tied to organizational priorities.
Oversee enterprise-wide programs, ensuring clear scope, schedules, budgets, and resourcing; resolve cross-program dependencies and conflicts; and establish risk and change management approaches that support adoption.
Run the department’s operating rhythm, including the biweekly sprint cycle, weekly Tech Management staff meeting, and department all-hands.
Own executive reporting, including the biweekly Technology Sprint Report and the CTO’s weekly update to the COO.
Serve as the CTO’s proxy with executive stakeholders across the network, own escalations, drive the CTO’s decisions to completion, and track leadership-team commitments through delivery.
Manage the CTO’s Tech Management cost center, including annual budget planning, forecasting, actuals review with Finance, purchase approvals, and vendor contract reviews.
Manage and develop two program managers, establishing PMO standards, methodology, and governance and coaching the team in their application.

Benefits

Medical, dental, and vision coverage starting on the first day; Success Academy covers 82% of its core medical plan.
Free One Medical membership and confidential mental health support through EAP/Talkspace.
403(b) retirement plan with a 3% employer match.
Up to $2,400 per year in employer HSA contributions.
Employer-paid life and disability insurance.
Public Service Loan Forgiveness (PSLF) eligibility.
Generous paid time off and paid holidays.
Paid parental leave.
$50 per month cellphone stipend.
Pre-tax commuter benefits.
Backup family care.
Performance-based earning incentives.
Opportunities for professional growth.