AI Innovation & Portfolio Lead

Overview:
Year Up United is a $160M national workforce development nonprofit operating in 20+ locations, closing the Opportunity Divide for tens of thousands of young adults every year. The AI Innovation & Portfolio Lead sits within the Product & Design team — the transformation function inside Transformation & Technology (TnT) — and owns two things at once: the operating picture of AI across the organization, and the engine that turns a business problem into a tested pilot before we commit real build capacity.

This is not a project management role. The AI Innovation & Portfolio Lead does not run delivery standups, manage tickets, or chase status team to team — the portfolio is a living operating picture leaders pull from, not a report that gets chased. It is also not a technical build role: turning validated pilots into production systems belongs to our technical AI build capability and agile delivery teams.

This role’s job is to decide what is worth building, prove whether it works, and hand winners off to be scaled. Year Up United is already investing in AI and using it to solve real business problems, and this role connects that work — giving the organization one place where AI initiatives are seen, tested, and moved forward. To succeed, you will breathe AI: you track the frontier, know the latest tools and capabilities, and can tell a real advance from hype.

This is a hybrid role requiring regular in-person engagement. Applicants must live within a reasonable commutable distance to a Year Up United location. In keeping with Year Up United’s values, this leader also engages directly with students as a mentor and advocate.

• Maintain a trusted, current view of every AI initiative in flight that leaders use to make decisions
• Move AI use cases from intake through discovery to a clear go/kill decision each cycle
• Achieve a healthy graduation rate of validated pilots into scaled builds — and end the rest quickly and cheaply (a fast, evidence-based “no” is a successful outcome, not a failure)
• Grow cross-org participation in AI through the community of practice
• Evaluate pilots on validated learning against defined milestones — not on features shipped or first-quarter ROI

• Take a business problem and stand up a fast, low-cost pilot to test whether it is worth solving — “here is the problem, and we are going to pilot X, Y, Z”
• Run discovery with the people closest to the work to surface the problems most worth solving
• Design and orchestrate experiments using flexible resourcing (contractors, vendor pilots, borrowed capacity) rather than a standing team
• Make evidence-based go/kill decisions and retire most pilots quickly and cheaply
• Prepare validated pilots to graduate into scaled builds

• Maintain the single trusted view of every AI initiative — status, cost, adoption, outcomes, and readiness to graduate
• Own the state of every bet and what it teaches us
• Surface portfolio insights that inform prioritization and investment decisions

• Co-chair the Strategic AI Leadership group (SAIL), Year Up United’s AI governance committee
• Own the SAIL intake process — collecting and triaging AI use cases from across the organization
• Treat intake as the top of the innovation funnel: where the problems worth piloting surface
• Bring SAIL the pipeline and the evidence it needs to decide what graduates to a real build
• Bring a workforce development lens to every AI decision, understanding how Year Up United’s work intersects with opportunity talent, employer expectations, and the students we serve

• Lead the biweekly AI skill shares (Lunch & Learns) that bring staff together from across the…