Senior Director - AI Strategy and Innovation

Job Description

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, the plan that will carry the network into the next generation of teaching, learning, and operations, and coordinates AI work across KIPP regions. The role leads the AI pilot group, designs and runs the system that measures whether AI pilots are working, and serves as the final recommender on AI vendors, uses, and approaches for both Foundation and regional work. With a network that serves nearly 210,000 students and alumni, KIPP has the reach to shape how AI serves students nationally, especially those at the margins. 

Reporting to the Chief of Staff to the CEO in the Office of the CEO, this leader serves on the CEO-chartered AI Working Group and works across the Foundation as a peer to the Schools, Data and Technology, Legal, and Development teams, and with regional leaders, funders, and external research and vendor partners. The Schools team oversees instructional pilots and the Chief Schools Officer makes final decisions on the AI work the Schools team leads; this role brings the evidence and the recommendation those decisions rest on. The strongest candidates are deeply steeped in AI, bring substantial school-based experience and the credibility to advise school and system leaders, and can tell a tool that works in a classroom from a tool that demos well. 

Responsibilities 

Network AI Strategy and Leadership 

• Develop and lead KIPP's multi-year, network-wide AI strategy, aligned to One KIPP and the KIPP 2030 Plan, that positions the network for the next generation of teaching, learning, and operations; bring it through the AI Working Group and keep it current as the field moves. 

• Serve as the AI expert for the entire KIPP Foundation and the go-to advisor for regions, the Schools team, and Foundation leadership on AI tools, uses, and risks. 

• Own KIPP's position on instructional AI and the standard the network uses to judge whether a tool serves its students; propose and maintain the network's AI decision structure, making clear how recommendations reach decision-makers and how decisions flow to Foundation teams and regions. 

• Translate the strategy so it travels: a regional superintendent can repeat it in a sentence, a development officer can put it in front of a funder, and a school leader recognizes it in the guidance they receive. 

AI Pilot Leadership and Measurement 

• Manage the AI pilot group, setting its priorities and the standard of evidence for AI pilots across the Foundation and regions. 

• Design and administer the measurement system for AI pilots: go to regions to assess pilot quality, collect, and analyze evidence, and produce a report on each pilot that states clearly whether the tool is working and for which students. 

• Partner with the Schools team, which oversees instructional pilots, and with external researchers to set the comparison design, subgroup breakouts, and data plan before licenses are issued. 

• Apply a common evaluation framework to every AI tool under consideration, covering efficacy and alignment to One KIPP anchor metrics; accessibility for multilingual learners, students with IEPs, and students arriving below grade level; bias and equity risk; implementation requirements and total cost of ownership; and student data privacy and security, with the Data and Technology team setting technical, privacy, and security requirements. 

AI Recommendations and Partnerships 

• Serve as the final recommender on AI vendors, uses, and approaches for both Foundation and regional work, including work led by the Schools team, where the Chief Schools Officer makes the final decision. 

• Make scale, continue, or stop recommendations grounded in pilot data, and present them to the AI Working Group and senior leaders with the evidence behind them. 

• Identify, negotiate, and steward partnerships with research and development partners, a small set of key vendors, and university researchers; structure agreements so partners build to KIPP's model, and lead structured diligence with the Data and Technology team on any platform under consideration. 

• Help Foundation teams use AI more effectively in their own work, keeping the principles for the Foundation's internal AI use and the standard for classroom tools in one coherent position. 

Network Coordination Across Regions 

• Coordinate AI work across KIPP regions, maintaining a current inventory of tools, cost, funding source, early outcomes, lessons learned, and privacy considerations through regional AI leads and touchpoints such as RAMP, so the Foundation can answer a question about network AI use the week it is asked. 

• Advise regions on how tools fit KIPP's approach and what evidence the network needs to recommend them, respecting regional leaders' authority over their own schools. 

• Broker multi-region pilots with a shared challenge, a common evaluation design, and a clear division of labor, so the network learns once instead of many times and reduces duplicate spending. 

Funding, Ecosystem, and External Voice 

• Build KIPP's relationships with funders investing in AI in education and, with the Development team, position KIPP to attract the philanthropic dollars and support its priority AI work needs, coordinating regional and national requests so KIPP does not compete with itself. 

• Represent KIPP at the conferences, convenings, and forums where AI tools, funding, and policy take shape, and keep Foundation leaders current on the ecosystem through a weekly read to the CEO. 

• Own the strategic narrative and evidence base the Development team carries externally, with the CEO holding final say on what goes out, and prepare the AI Working Group's updates to the KIPP Foundation Board. 

• Carry what pilots teach into national guidance and the annual One KIPP planning cycle. 

Qualifications

Skills and Mindsets 

• Mission and Student Focus: Demonstrates passion and commitment to KIPP’s mission and possesses the desire and ability to uphold KIPP’s core values (Focus on Excellent Results, Collective Impact, and Courageous Action)  

• Self Management: Demonstrated record of setting ambitious goals and achieving them with consistency. Invests in developing teammates' skills and mindsets to address gaps in achieving team growth; determines what quantitative and qualitative data are most relevant to their goals and supports the team in creating and monitoring systems for collecting, reviewing, and acting upon data to drive outcomes; able to monitor progress, communicating status to the right stakeholders and adjusting plans and use of time to ensure systems are yielding desired outcomes. 

• Work Management: Sets a clear vision for new or complex bodies of work. Develops and implements agile project plans, navigating difficult situations or conflicts while maintaining effective relationships with all stakeholders; creates and ensures systems are in place for knowledge management. 

• Process Management: Able to build and align goals and project plans with organization priorities; leverages relevant organizational processes and systems to execute work; can build and maintain knowledge management systems; effectively develops and codifies cross-team processes relevant to their team's work that improve work quality and efficiency; uses data to drive process improvements in support of organizational priorities. 

• Data-Driven Actions and Decisions: Efficiently defines the right metrics to evaluate work and ensures critical team actions, decisions, and recommendations are driven by data; effectively works with team to resolve issues around data to ensure sound data-informed decisions. 

• Communication and Change Management: Effectively articulates case for change through clear and compelling presentations and translates this into actionable plans. Effectively tailors communications and engagement approach for different audiences to deepen investment and drive actions and behavior change that would lead to org-wide goals. Acts as a champion for change with cross-team stakeholders. 

• Collaboration: Has the interpersonal, diplomatic, relationship building, and communications skills needed to develop successful working relationships with diverse constituents to deliver results. Evolves and adapts plans and approach with diverse stakeholders to drive results. Possesses excellent communication skills with aptitude for translating complex information into clear and persuasive narratives that convince others by identifying benefits for all. 

• AI Expertise and Evaluation: Brings deep, current expertise in AI tools and a working understanding of what these systems can and cannot do. Able to evaluate AI products against instructional goals, evidence of efficacy, accessibility, bias and equity risk, and student data privacy requirements, and to design measurement systems that show whether a tool is working and for which students. 

Experience and Qualifications 

• 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, advanced degree preferred. 

• Deep, current expertise in AI and its uses in education, with the credibility to advise school leaders, system leaders, and senior executives on what these tools can and cannot do. 

• Experience teaching or leading in schools serving students like those KIPP serves, with the classroom judgment to tell a tool that works from a tool that demos well. 

• 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, including working with research partners on comparison designs, subgroup breakouts, and data plans, and turning results into clear recommendations. 

• Proven record of negotiating and managing partnerships with vendors, research organizations, or universities, with working knowledge of student data privacy, FERPA, and operating across multiple state regulatory environments. 

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

Additional Information

Work Conditions 

• Basic Travel Expectations: Up to 10% (up to 20 days per year) 

• Full time, Exempt 

Location 

It is preferred, but not mandatory for this role to be based out of a KIPP Foundation office. This role has the option of working from a remote office full-time. KIPP Foundation offices are in NYC and Chicago. 

Compensation and Benefits 

In compliance with local law, we are disclosing the compensation, or a range thereof, for roles in locations where legally required. Actual salaries will vary based on several factors, including but not limited to external market data, internal equity, and relevant experience. The salary range for this position is $156,000-$188,500. In addition, KIPP Foundation provides a variety of benefits to employees, including:  

• 25 holidays for + 18 days additional flexible PTO days (flexible PTO increases to 23 days for years 3 and 4 and to 28 days for years 5+). 

• 100% paid parental leave 

• 100% coverage of the premium for employee and 75% for employee + family’s medical/dental/vision plans. 

• Wellness benefits such as fitness reimbursements, discounted tickets to theme parks/attractions, backup care support for children and adults/elders, and our employee assistance program 

• Finance Security benefits include such as a 401K retirement plan with 4% match, employer-sponsored legal plans, life/disability insurance, and flexible spending accounts