Senior Director, AI Strategy and Innovation

KIPP Foundation • New York, NY

1d • Remote

About The Position

The Senior Director, AI Strategy and Innovation develops and leads KIPP’s multi-year, network-wide AI strategy, aligned with One KIPP and the KIPP 2030 Plan. This role serves as the KIPP Foundation’s AI expert and advisor to regions, the Schools team, and Foundation leadership, while establishing the network’s approach to instructional AI and its decision-making structure.

The role leads AI pilots and their evaluation, including designing measurement systems, assessing evidence, and making data-grounded recommendations about whether to scale, continue, or stop tools. It applies a common framework to AI tools that considers efficacy, alignment to student outcomes, accessibility, equity and bias, implementation requirements, total cost of ownership, and student data privacy and security. The position partners with the Schools team, researchers, vendors, universities, and the Data and Technology team.

The Senior Director coordinates AI work across KIPP regions, maintains an inventory of tools and outcomes, advises regions, and brokers multi-region pilots. The role also builds relationships with funders and external partners, represents KIPP at relevant forums, maintains an AI ecosystem update for the CEO, prepares AI Working Group updates for the KIPP Foundation Board, and carries pilot learnings into national guidance and annual One KIPP planning. The position may be based remotely or at a KIPP Foundation office in New York City or Chicago, with travel of up to 10% (up to 20 days per year).

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, with credibility advising school leaders, system leaders, and senior executives.
• Experience teaching or leading in schools serving students like those KIPP serves, with the classroom judgment to assess whether tools work beyond demonstrations.
• Proven record 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.
• Demonstrated experience designing measurement or evaluation systems for programs or pilots, including work with research partners on comparison designs, subgroup breakouts, and data plans, and translating results into recommendations.
• Proven record 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, evidence of efficacy, accessibility, bias and equity risk, and student data privacy requirements, and to design systems that show whether tools work and for which students.
• Demonstrated ability to set goals, monitor progress, use quantitative and qualitative data, and adjust plans to achieve outcomes.
• Ability to lead complex work, develop agile project plans, manage stakeholder relationships, and build knowledge-management systems and cross-team processes.
• Strong communication, change-management, collaboration, and relationship-building skills, including translating complex information into clear, persuasive narratives for diverse audiences.
• Passion for and commitment to KIPP’s mission and core values.

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.
• Advise KIPP Foundation leadership, regions, and the Schools team on AI tools, uses, and risks; establish KIPP’s position on instructional AI and a network AI decision structure.
• Translate the AI strategy into clear guidance for regional, school, Foundation, and development audiences.
• Manage the AI pilot group, set its priorities, and establish standards of evidence for AI pilots across the Foundation and regions.
• Design and administer measurement systems for AI pilots; assess pilot quality in regions, collect and analyze evidence, and report whether tools work and for which students.
• Partner with the Schools team and external researchers to establish comparison designs, subgroup breakouts, and data plans before licenses are issued.
• Evaluate AI tools for efficacy, alignment to One KIPP anchor 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; 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; lead structured platform diligence with the Data and Technology team.
• Help Foundation teams use AI effectively and maintain a coherent position on internal AI use and classroom tools.
• Coordinate AI work across regions and maintain a current inventory of tools, costs, funding sources, early outcomes, lessons learned, and privacy considerations.
• Advise regions on how tools fit 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 the Development team to position KIPP to attract support for priority AI needs.
• Represent KIPP at conferences, convenings, and forums where AI tools, funding, and policy are discussed; provide a weekly ecosystem read 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 carry pilot learnings into national guidance and annual One KIPP planning.

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 employee medical, dental, and vision plan premiums and 75% coverage for employee-plus-family premiums.
• 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