Senior Director, AI Strategy and Innovation

KIPP • New York, NY

14h • $156,000 - $188,500 • Remote

About The Position

The Senior Director, AI Strategy and Innovation is the KIPP Foundation's expert on artificial intelligence. This leader develops and leads KIPP's multi-year, network-wide AI strategy and coordinates AI work across KIPP regions. The role leads the AI pilot group, designs and administers the system for measuring AI pilots, and serves as the final recommender on AI vendors, uses, and approaches for Foundation and regional work. The role brings evidence and recommendations to instructional AI decisions, while the Chief Schools Officer makes final decisions on AI work led by the Schools team.

Reporting to the Chief of Staff to the CEO in the Office of the CEO, the role serves on the CEO-chartered AI Working Group and works across the Foundation with the Schools, Data and Technology, Legal, and Development teams, as well as with regional leaders, funders, external research partners, and vendors. The position develops network guidance, evaluates AI tools for efficacy, accessibility, equity, implementation requirements, cost, and privacy, and translates pilot findings into recommendations and broader guidance. The role may be based remotely full-time or at a KIPP Foundation office in New York City or Chicago. Travel is 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 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 demo well.
• A proven 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.
• Demonstrated experience designing measurement or evaluation systems for programs or pilots that others continued to run.
• Experience working with research partners on comparison designs, subgroup analyses, and data plans, and translating results into clear recommendations.
• A proven record of negotiating and managing partnerships with vendors, research organizations, or universities.
• Working knowledge of student data privacy, FERPA, and operations across multiple state regulatory environments.
• Ability to evaluate AI products against instructional goals, efficacy evidence, accessibility, bias and equity risks, and student data privacy requirements, and to design measurement systems that show whether tools work and for which students.
• Demonstrated ability to set ambitious goals, monitor progress, use quantitative and qualitative data, and adjust plans to achieve outcomes.
• Ability to set a vision for complex work, implement agile project plans, navigate conflict, maintain stakeholder relationships, and establish knowledge-management systems and processes.
• Ability to define relevant metrics and ensure decisions and recommendations are data-informed.
• Strong communication, change-management, collaboration, diplomatic, relationship-building, and presentation skills, including the ability to translate complex information into persuasive narratives for diverse audiences.
• Passion and commitment to KIPP's mission and ability to uphold its 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, bring it through the AI Working Group, 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 on AI tools, uses, and risks.
• Own KIPP's position on instructional AI and its standards for evaluating tools; propose and maintain the network's AI decision structure.
• Translate the AI strategy into clear guidance for regional superintendents, development officers, school leaders, and other stakeholders.
• Manage the AI pilot group, establish its priorities, and set standards of evidence for AI pilots across the Foundation and regions.
• Design and administer the AI pilot measurement system; 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 analyses, and data plans before licenses are issued.
• Apply a common evaluation framework to AI tools, covering efficacy and alignment to One KIPP metrics; accessibility; bias and equity; implementation requirements and 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 instructional work for which the Chief Schools Officer makes the final decision.
• Make and present evidence-based recommendations to scale, continue, or stop pilots to the AI Working Group and senior leaders.
• Identify, negotiate, and steward partnerships with research and development partners, key vendors, and university researchers; structure agreements around KIPP's model and lead vendor diligence with the Data and Technology team.
• Help Foundation teams use AI more effectively and maintain a coherent position on internal AI use and classroom tools.
• Coordinate AI work across regions and maintain an 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 to promote shared learning and reduce duplicate spending.
• Build relationships with funders investing in AI in education and partner with the Development team to attract support for priority AI work and coordinate regional and national requests.
• Represent KIPP at relevant conferences, convenings, and forums; keep Foundation leaders current on the ecosystem through a weekly read to the CEO.
• Own the strategic narrative and evidence base used externally by the Development team, subject to the CEO's final approval, and 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 in years 3 and 4 and to 28 days in 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 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