Senior Director, AI Strategy and Innovation

KIPP Foundation • New York, NY

10d • Remote

About The Position

The Senior Director, AI Strategy and Innovation is the KIPP Foundation’s expert on artificial intelligence and leads the development and implementation of a multi-year, network-wide AI strategy for teaching, learning, and operations. The role coordinates AI work across KIPP regions, leads the AI pilot group, designs and administers systems for evaluating pilots, and makes recommendations on AI vendors, uses, and approaches for Foundation and regional work. The position reports to the Chief of Staff to the CEO in the Office of the CEO and serves on the CEO-chartered AI Working Group. It works across the Foundation, with regional leaders, funders, and external research and vendor partners. For instructional work led by the Schools team, the Chief Schools Officer makes final decisions, with this role providing evidence and recommendations.

The role establishes evaluation standards and decision processes for AI, assesses pilot quality and outcomes, and provides clear recommendations on whether tools should be scaled, continued, or stopped. It coordinates common evaluation designs across regions, maintains an inventory of network AI use, builds research and vendor partnerships, and supports teams and regions in applying AI responsibly. It also develops KIPP’s external AI narrative and evidence base, supports fundraising and external engagement, prepares AI Working Group updates for the KIPP Foundation Board, and carries lessons from pilots into national guidance and annual planning.

The role is full-time and exempt, with travel expectations of up to 10% (up to 20 days per year). The position may be based remotely full-time; being based at a KIPP Foundation office in New York City or Chicago is preferred but not required.

Requirements

• 7–10+ years of professional experience, including 5+ years in K–12 education, with progressive leadership responsibility in complex, mission-driven organizations.
• Bachelor’s degree or equivalent experience.
• Deep, current expertise in AI and its uses in education, including the ability to advise school leaders, system leaders, and senior executives on AI capabilities and limitations.
• Experience teaching or leading in schools serving students like those KIPP serves, with classroom judgment to distinguish effective tools from tools that merely demonstrate well.
• A record of leading strategy or major initiatives across a school system, charter management organization, or multi-region network, including aligning senior leaders and teams without direct authority.
• Experience designing measurement or evaluation systems for programs or pilots that others continued to run, including work with research partners on comparison designs, subgroup breakouts, and data plans, and translating results into recommendations.
• Experience negotiating and managing partnerships with vendors, research organizations, or universities.
• Working knowledge of student data privacy, FERPA, and operating across multiple state regulatory environments.
• Ability to evaluate AI products against instructional goals, efficacy evidence, accessibility, bias and equity risk, and student data privacy requirements, and to design systems that determine whether tools work and for which students.
• Demonstrated ability to set ambitious goals, monitor progress, use relevant quantitative and qualitative data, and adjust plans to achieve outcomes.
• Ability to set a clear vision for complex work, develop agile project plans, navigate conflict, maintain stakeholder relationships, and establish knowledge-management systems.
• Ability to align goals and project plans with organizational priorities, codify cross-team processes, and use data to improve processes.
• Strong communication and change-management skills, including presenting a compelling case for change and tailoring communication to diverse audiences.
• Strong collaboration, diplomacy, relationship-building, and communication skills, including translating complex information into clear and persuasive narratives.
• Commitment to KIPP’s mission and values: Excellent Results for Students, Collective Impact, and Courageous Action.

Nice To Haves

• Advanced degree.
• Experience building relationships with funders or securing philanthropic support.
• Experience with budget ownership and vendor contract management.

Responsibilities

• Develop and lead KIPP’s multi-year, network-wide AI strategy, aligned to One KIPP and the KIPP 2030 Plan, and keep it current as the field evolves.
• Serve as the AI expert and advisor for the Foundation, regions, Schools team, and Foundation leadership on AI tools, uses, and risks.
• Own KIPP’s position on instructional AI and maintain the network’s standards and decision structure for evaluating and deciding on AI tools.
• Translate the AI strategy for regional, school, development, and Foundation audiences.
• Manage the AI pilot group, set priorities, and establish evidence standards for pilots across the Foundation and regions.
• Design and administer the AI pilot measurement system, including assessing pilot quality in regions, collecting and analyzing evidence, and reporting whether tools work and for which students.
• Partner with the Schools team and external researchers to establish comparison designs, subgroup analyses, and data plans before licenses are issued.
• Apply a common evaluation framework that covers efficacy, alignment to One KIPP metrics, accessibility, bias and equity risks, implementation requirements, total cost of ownership, and student data privacy and security.
• Serve as the final recommender on AI vendors, uses, and approaches for Foundation and regional work, including work led by the Schools team.
• Make evidence-based scale, continue, or stop recommendations and present them to the AI Working Group and senior leaders.
• Identify, negotiate, and steward partnerships with research and development partners, vendors, and university researchers; structure agreements around KIPP’s model.
• Lead structured diligence with the Data and Technology team on platforms under consideration.
• Help Foundation teams use AI effectively and maintain a coherent position on internal AI use and classroom tools.
• Coordinate regional AI work and maintain an inventory of tools, costs, funding sources, early outcomes, lessons, and privacy considerations.
• Advise regions on how tools align with KIPP’s approach and what evidence is needed, while respecting regional leaders’ authority over their schools.
• Broker multi-region pilots with shared challenges, common evaluation designs, and clear divisions of labor.
• Build relationships with funders investing in AI in education and work with Development to position KIPP to attract philanthropic support for priority AI work.
• Represent KIPP at relevant conferences, convenings, and forums, and provide Foundation leaders with a weekly ecosystem update to the CEO.
• Own the strategic narrative and evidence base used externally by the Development team, subject to the CEO’s final approval.
• Prepare AI Working Group updates for the KIPP Foundation Board and incorporate pilot findings into national guidance and the annual One KIPP planning cycle.

Benefits

• 25 holidays and 18 additional flexible PTO days; flexible PTO increases to 23 days for years 3 and 4 and 28 days for years 5 and beyond.
• 100% paid parental leave.
• 100% coverage of the premium for employee medical, dental, and vision plans, and 75% coverage for employee-plus-family plans.
• Wellness benefits, including fitness reimbursements, discounted tickets to theme parks and attractions, backup care support for children and adults or elders, and an employee assistance program.
• 401(k) retirement plan with a 4% employer match.
• Employer-sponsored legal plans.
• Life and disability insurance.
• Flexible spending accounts.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior