Managing Director (AiLO)

ILO Group is seeking an accomplished and strategic Managing Director to lead large-scale initiatives within AiLO, ILO Group’s division dedicated to advancing the use of artificial intelligence in K–12 education systems. This role is ideal for a forward-thinking project leader who thrives on designing and implementing innovative, high-impact strategies that improve how education systems work and evolve. The Managing Director will guide the integration of emerging technologies into client projects and internal operations, connecting creative experimentation with practical, scalable solutions that strengthen impact. This individual will combine strategic vision with hands-on leadership, ensuring that ILO Group remains a trusted national partner in helping school systems harness AI responsibly and effectively. This role requires both strategic vision and executional excellence, someone who can think big, build from scratch, and deliver with precision. The Managing Director is expected to originate ideas, develop first drafts of strategic deliverables, synthesize complex information into compelling recommendations, and drive work from concept through execution, rather than simply oversee the work of others.

Our clients are state education agencies, school districts, and adjacent education organizations, including nonprofits and foundations, who are committed to implementing initiatives that improve student outcomes. In this role, you will work directly with these leaders and their teams to design and manage projects that integrate AI tools into teaching, learning, and operational systems.

We are looking for someone who wants to be close to the work, hold the pen on critical deliverables, test new ideas, and build solutions from the ground up. This role requires someone who can take a strategic direction and translate it into clear, compelling, high-quality work, moving comfortably from ambiguity to execution and from first draft to final product.

You will join a team of high-performing and collaborative individuals who value curiosity, innovation, and disciplined execution. This position offers the opportunity to work on complex, high-impact challenges at the intersection of AI, education, and implementation.

Lead a portfolio of client and internal projects within AiLO, ensuring excellence, clear communication, and measurable outcomes.

Partner with senior leadership to develop and execute a strategic roadmap for the use of AI across ILO Group’s service areas.

Translate early-stage innovation into repeatable systems, processes, and tools that improve efficiency and impact.

Lead the development and personally draft high stakes client-facing deliverables, including strategic decks, frameworks, recommendations, executive memos, and implementation plans. While others may contribute, this role owns the narrative, quality, and final product.

Identify opportunities to apply digital tools and AI-driven systems that streamline collaboration, enhance insight generation, and improve overall performance.

Contribute to business development by cultivating strategic partnerships, identifying new opportunities, and supporting the growth of ILO Group’s client portfolio.

Lead the strategic use of AI tools and emerging technologies across both internal initiatives and client-facing projects to strengthen analysis, content development, and delivery.

Oversee the creation of AI-informed content, frameworks, and resources that help clients understand and apply artificial intelligence within their systems and strategies.

Partner with internal and client teams to explore, pilot, and refine AI tools that enhance the quality, insight, and efficiency of project deliverables.

Develop and share guidance on the effective and responsible use of AI in content creation, communication, and analysis, positioning ILO Group and AiLO as trusted thought partners in this space.

Lead cross-team learning on AI application in education, supporting both experimentation and consistent, ethical implementation.

Champion a culture of curiosity and thoughtful risk-taking, modeling how experimentation can lead to scalable, high-impact innovation.

Serve as a visible leader and subject-matter expert in the evolving field of AI in education, representing ILO Group in external conversations and networks.

Direct the planning and execution of complex client engagements and internal innovation projects, ensuring timelines, budgets, and deliverables meet the highest quality standards.

Own the development of major client deliverables from blank page to final product, synthesizing research, stakeholder input, and analysis into compelling strategic recommendations.

Serve as the primary author of complex reports, presentations, executive briefings, and AI resources.

Guide contributors while remaining accountable for the quality, clarity, and strategic direction of every deliverable.

Move seamlessly between strategic thinking and hands-on execution, rolling up your sleeves to produce exceptional work when needed.

Serve as a trusted advisor to senior education leaders, guiding them through AI implementation and digital transformation strategies.

Cultivate strong, solutions-oriented partnerships with clients and funders.

Provide responsive, hands-on support to ensure client satisfaction and success in every engagement.

Represent ILO Group’s excellence and professionalism at public events and convenings.

Lead and mentor other team members fostering collaboration, growth, and accountability.

Promote a culture of continuous improvement, curiosity, and thoughtful risk-taking in the use of new technologies.

Model low-ego, high-accountability leadership that motivates teams through clarity, collaboration, and shared purpose.

Build structures and systems that enable effective team collaboration across multiple projects and workstreams.

Develop internal professional learning focused on AI literacy, digital tools, and modern project management practices.

Contribute to ILO Group’s thought leadership by developing publications, case studies, and digital content that highlight the firm’s AI and innovation work.

Partner with the research and communications teams to share insights and strengthen ILO Group’s position as a national leader in the AI-in-education space.

Engage in external networks and forums to exchange ideas and elevate ILO Group’s visibility as a trusted voice on the responsible use of technology in education.

The requirements of the position are:

You are an innovative and action-oriented leader who brings together strategic vision, disciplined execution, and a relentless attention to detail.

Education : Bachelor’s degree required; advanced degree in Business Administration, Education, or a related field preferred.

Experience : 10–15+ years of experience in project management, digital transformation, operations, or consulting, including senior leadership roles. Experience integrating or implementing AI tools, automation systems, or digital platforms in an organizational or client-facing context. Demonstrated success leading cross-functional teams through technology-enabled change. Experience in education, nonprofit, or public-sector organizations preferred.

10–15+ years of experience in project management, digital transformation, operations, or consulting, including senior leadership roles.

Experience integrating or implementing AI tools, automation systems, or digital platforms in an organizational or client-facing context.

Demonstrated success leading cross-functional teams through technology-enabled change.

Experience in education, nonprofit, or public-sector organizations preferred.

Skills and Competencies : Expertise in project management and AI-driven innovation, with the ability to connect strategic vision to practical implementation. Skilled in designing and improving systems that enhance collaboration, knowledge sharing, and operational excellence. Exceptional communicator with the ability to synthesize complex ideas into clear, compelling content. Strategic and analytical thinker who thrives in dynamic, fast-paced environments. Comfortable leading both creative exploration and structured execution. Strong relationship-builder and collaborator with a commitment to high standards and measurable outcomes.

Expertise in project management and AI-driven innovation, with the ability to connect strategic vision to practical implementation.

Skilled in designing and improving systems that enhance collaboration, knowledge sharing, and operational excellence.

Exceptional communicator with the ability to synthesize complex ideas into clear, compelling content.

Strategic and analytical thinker who thrives in dynamic, fast-paced environments.

Comfortable leading both creative exploration and structured execution.

Strong relationship-builder and collaborator with a commitment to high standards and measurable outcomes.

ILO Group is an equal-opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status.