Senior Director, AI Strategy and Innovation

KIPP • New York, NY

6h • $156,000 - $188,500 • Remote

About The Position

The Senior Director, AI Strategy and Innovation will develop and lead KIPP’s multi-year, network-wide AI strategy, aligned to 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 on AI tools, applications, and risks. The position owns KIPP’s instructional AI position and the network’s evaluation standard, establishes how AI recommendations and decisions move through the organization, and translates the strategy for school, regional, Foundation, and funding audiences.

The Senior Director manages the AI pilot group and establishes priorities and standards of evidence for pilots across the Foundation and regions. The role designs and administers pilot measurement, assesses pilot quality in regions, analyzes evidence, and reports whether tools work and for which students. In partnership with the Schools team and external researchers, the Senior Director establishes comparison designs, subgroup analysis, and data plans before licenses are issued. Each AI tool is evaluated for efficacy, alignment to network metrics, accessibility, bias and equity risk, implementation needs, total cost of ownership, and student data privacy and security.

The role makes recommendations on AI vendors, uses, and approaches for Foundation and regional work, including scale, continue, or stop recommendations based on pilot evidence. It identifies and manages partnerships with research and development partners, vendors, and university researchers, and coordinates platform diligence with the Data and Technology team. The Senior Director also helps Foundation teams use AI effectively and maintains a coherent position on internal AI use and classroom tools.

Across regions, the position maintains an inventory of AI tools, costs, funding sources, outcomes, lessons, and privacy considerations; advises regions while respecting their authority; and brokers multi-region pilots with common evaluation designs. The role builds relationships with AI education funders alongside the Development team, represents KIPP in relevant external forums, provides the CEO with a weekly ecosystem update, owns the strategic narrative and evidence base used externally (subject to the CEO’s final approval), prepares AI Working Group updates for the KIPP Foundation Board, and carries pilot learnings into national guidance and annual One KIPP planning.

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

Requirements

• Demonstrated passion for and commitment to KIPP’s mission and ability to uphold its core values.
• A record of setting ambitious goals and achieving them consistently, developing teammates, identifying relevant quantitative and qualitative data, and monitoring progress and outcomes.
• Ability to set a clear vision for complex work, develop and implement agile project plans, navigate conflict, maintain stakeholder relationships, and establish knowledge-management systems.
• Ability to align goals and project plans with organizational priorities, build and codify cross-team processes, and use data to improve processes.
• Ability to define relevant metrics and ensure actions, decisions, and recommendations are data-driven.
• Ability to make a compelling case for change, tailor communications to different audiences, and champion change across teams.
• Strong interpersonal, diplomatic, relationship-building, collaboration, and communication skills, including the ability to translate complex information into persuasive narratives.
• Deep, current expertise in AI tools and a working understanding of their capabilities and limitations.
• Ability to evaluate AI products against instructional goals, efficacy evidence, accessibility, bias and equity risk, and student data privacy requirements, and to design measurement systems that assess whether tools work and for which students.
• 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 classroom judgment to assess whether a tool works beyond its demonstration.
• Proven experience 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, working with research partners on comparison designs, subgroup breakouts, and data plans, and translating results into recommendations.
• Proven 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.

Nice To Haves

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

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 KIPP Foundation, regions, the Schools team, and Foundation leadership.
• Own KIPP’s position on instructional AI and maintain the network’s standard and decision structure for evaluating AI tools and recommendations.
• Communicate the AI strategy clearly to regional, school, Foundation, and development audiences.
• Manage the AI pilot group, establishing priorities and evidence standards for pilots across the Foundation and regions.
• Design and administer the AI pilot measurement system; assess pilot quality, collect and analyze evidence, and report whether tools work and for which students.
• Partner with the Schools team and external researchers on comparison designs, subgroup breakouts, and data plans before licenses are issued.
• Apply a common evaluation framework covering efficacy, alignment to One KIPP anchor metrics, accessibility, bias and equity, 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; for Schools team instructional pilots, the Chief Schools Officer makes the final decision.
• Present evidence-based scale, continue, or stop recommendations to the AI Working Group and senior leaders.
• Identify, negotiate, and manage partnerships with research and development partners, selected vendors, and university researchers; coordinate 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 KIPP regions and maintain an inventory of tools, costs, funding sources, early outcomes, lessons learned, and privacy considerations.
• Advise regions on how AI 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 division of labor.
• Build relationships with funders investing in AI in education and work with the Development team to position KIPP for philanthropic support while coordinating regional and national requests.
• Represent KIPP at relevant conferences, convenings, and forums, and provide the CEO with a weekly update on the AI ecosystem.
• 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.
• Carry lessons from pilots 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 to 28 days for years 5 and beyond.
• 100% paid parental leave.
• 100% coverage of the employee medical, dental, and vision premium, 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