Principal Technical Program Manager, AI Enablement

About the role

We're looking for an Operational Owner to integrate AI into our operations and help districts thrive. This role involves hands-on enablement, AI initiative ownership, evangelism, change management, strategy, and governance.

Responsibilities

• Embed directly with teams across go-to-market, Engineering, Product, Operations, Finance, and Customer Experience to identify high-value AI use cases and unblock adoption
• Design, prototype, and ship internal AI workflows and tools (prompt libraries, automation scripts, internal apps) that solve real problems
• Evaluate and recommend AI tooling—LLMs, AI copilots, automation platforms—with a bias toward practical deployment over proof-of-concept theater
• Build reusable playbooks, templates, and reference implementations that teams can adopt independently
• Establish measurement frameworks to track adoption, productivity impact, and ROI
• Own select AI-driven initiatives end-to-end, from scoping through delivery
• Drive vendor evaluation, stakeholder alignment, implementation planning, and rollout for assigned initiatives
• Coordinate across Product, Engineering, Customer Experience, and external vendors to hit milestones and manage dependencies
• Define success metrics and own post-launch adoption and iteration
• Evangelize and manage change around AI across the organization
• Run workshops, office hours, and enablement sessions tailored to different audiences
• Co-own and evolve existing programs: The Vanguard (AI champions network), The Forge (internal hackathon series), and LINQ Labs (internal tools environment)
• Translate technical AI capabilities into business-relevant language for non-technical stakeholders
• Surface and amplify success stories to build organizational momentum

Requirements

• 8+ years in technical program management, developer experience, platform engineering, or a similarly cross-functional technical role
• Demonstrated ability to drive adoption of new tools and practices across an engineering organization
• Strong technical fluency: you can review prompts, evaluate AI tools, design workflows, and build prototypes (scripting, light app development, API integrations)
• Experience working with LLMs, AI copilots, or automation tooling in a professional context
• Exceptional written and verbal communication; you can explain complex technical concepts to a CFO and debug a prompt chain with an engineer in the same afternoon
• Comfort operating in ambiguity with minimal direction; you define the path, not just walk it
• Experience in a PE-backed, multi-product SaaS environment (or similar complexity)

Preferred

• Experience in K–12 education technology or another regulated vertical (healthcare, fintech)
• Familiarity with compliance frameworks relevant to AI deployment (FERPA, COPPA, SOC 2)
• Background in developer experience, internal tools, or platform teams
• Experience with JavaScript/TypeScript, React, Node.js, AWS