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, and strategy.

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.
• Drive awareness, excitement, and fluency around AI across the organization.
• Run workshops, office hours, and enablement sessions tailored to different audiences (engineers, PMs, operations staff, leadership).
• 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—not just advocacy, but measurable results.
• 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—not just personal experimentation.
• 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.

Skills

• Technical fluency in AI, LLMs, AI copilots, automation tooling.
• Ability to design and prototype AI workflows and tools.
• Experience in a PE-backed, multi-product SaaS environment.
• Strong communication skills to explain complex technical concepts.
• Experience in K–12 education technology or another regulated vertical.
• Familiarity with compliance frameworks relevant to AI deployment.
• Experience in developer experience, internal tools, or platform teams.
• Experience with JavaScript/TypeScript, React, Node.js, AWS.

Benefits

• 401(k) plan with a 4% employer match on total earnings.
• Flexible Open Paid Time Off Plan.
• 16 paid volunteer hours to support the causes that matter most to you.
• Rewards For Referrals: Get a referral bonus when you bring in a new hire!

Pay

Commensurate with experience.

Schedule

TBD.