Senior Director, AI Strategy, Innovation

This is a fully remote position, open to applicants in New York.

📋 Description

• Develop and oversee KIPP's comprehensive, multi-year AI strategy that aligns with One KIPP and the KIPP 2030 Plan.

• Act as the AI expert and consultant for KIPP Foundation leadership, regional teams, the Schools team, and Foundation teams.

• Maintain KIPP's stance on instructional AI and ensure the network's AI decision-making framework is upheld.

• Communicate AI strategy to regional superintendents, development officers, and school leaders.

• Manage the AI pilot group, setting priorities and standards for evidence collection.

• Design and implement measurement systems for AI pilot projects.

• Evaluate pilot quality in regions, gather and analyze data, and create reports on pilot effectiveness and student subgroups.

• Collaborate with the Schools team and external researchers on comparative designs, subgroup analysis, and data strategies.

• Utilize a unified evaluation framework addressing efficacy, accessibility, bias and equity risks, implementation needs, total cost of ownership, privacy, and security.

• Serve as the final decision-maker on AI vendors, use cases, and methodologies for Foundation and regional initiatives.

• Make recommendations for scaling, continuing, or discontinuing initiatives based on pilot data, and present findings to senior leadership.

• Identify, negotiate, and manage partnerships with research and development collaborators, vendors, and academic researchers.

• Conduct structured assessments with the Data and Technology team regarding potential platforms.

• Assist Foundation teams in effectively integrating AI into their operations.

• Coordinate AI initiatives across KIPP regions and keep an inventory of tools, costs, funding sources, outcomes, lessons learned, and privacy considerations.

• Advise regions on AI tools and the requirements for evidence.

• Facilitate multi-region pilots addressing shared challenges and evaluation methodologies.

• Cultivate relationships with funders and coordinate philanthropic outreach with the Development team.

• Represent KIPP at AI education conferences, gatherings, and forums.

• Provide a weekly overview of the AI ecosystem to the CEO.

• Manage the strategic narrative and evidence base utilized externally by the Development team.

• Prepare updates for the AI Working Group for the KIPP Foundation Board.

• Incorporate findings from pilots into national guidance and the annual One KIPP planning process.

• Report to the Chief of Staff to the CEO and participate in the CEO-chartered AI Working Group.

• Collaborate with Foundation teams and regional leaders, as well as funders, researchers, and vendors.

⛳️ Requirements

• Strong passion for and commitment to KIPP’s mission, with the ability to uphold KIPP’s core values.

• Proven track record of setting ambitious goals and consistently achieving them.

• Skilled in establishing a clear vision for complex projects and executing agile project plans.

• Ability to create and sustain knowledge management systems and cross-team processes.

• Proficient in defining relevant metrics and making data-informed decisions.

• Capability to articulate the rationale for change and customize communications for diverse audiences.

• Exceptional interpersonal, diplomatic, relationship-building, and communication abilities.

• Deep, current knowledge of AI tools and a solid understanding of their capabilities and limitations.

• Skill in evaluating AI products for instructional effectiveness, accessibility, bias/equity risks, and student data privacy.

• Experience in designing measurement systems to determine the effectiveness of AI tools for various student demographics.

• 7–10+ years of professional experience.

• At least 5 years of experience in K-12 education.

• Progressive leadership experience in complex, mission-driven organizations.

• Bachelor's degree or equivalent experience; an advanced degree is preferred.

• Extensive expertise in AI and its applications in education.

• Experience in teaching or leadership within schools serving populations similar to those KIPP serves.

• Background in leading strategy or significant initiatives across a school system, charter management organization, or a multi-region network.

• Experience aligning senior leaders and teams without direct authority.

• Proven experience in designing measurement or evaluation systems for programs or pilot initiatives.

• Experience collaborating with research partners on comparative designs, subgroup analysis, and data strategies.

• Ability to translate evaluation results into clear recommendations.

• Experience in negotiating and managing partnerships with vendors, research organizations, or academic institutions.

• Familiarity with student data privacy regulations, FERPA, and various state regulatory environments.

• Preferred experience in building relationships with funders or securing philanthropic support.

• Experience with budget management and vendor contract oversight is a plus.

🏝️ Benefits

• 25 holidays.

• 18 additional flexible PTO days, increasing to 23 days for years 3 and 4, and 28 days for years 5 and beyond.

• 100% paid parental leave.

• Full coverage of premiums for employee medical, dental, and vision plans.

• 75% coverage of premiums for employee + family medical, dental, and vision plans.

• Fitness reimbursement programs.

• Discounts on tickets to theme parks and attractions.

• Backup care support for children and adults/elders.

• Employee assistance program.

• 401(k) retirement plan with a 4% match.

• Employer-sponsored legal plans.

• Life and disability insurance.

• Flexible spending accounts.

• Option to work fully remotely.

• Up to 10% travel (up to 20 days per year).