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.

Key Responsibilities:

Key Metrics

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

Innovation Pipeline

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

AI Portfolio Management

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

Strategic AI Leadership (SAIL) Governance & Intake

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

AI Community of Practice

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

Use these sessions to sense what teams are building on their own and feed that into the funnel

Build cross-org AI fluency and a culture of safe experimentation

Co-lead and manage the AI Champions program, a national network of staff building with AI across every function and market

Set the strategy for how future Champions are recruited, developed, and activated, ensuring the network grows in reach and depth over time

Use Champions as eyes and ears across the organization, surfacing what teams are building independently and feeding promising use cases into the innovation funnel

Create shared infrastructure for Champions, including resources, playbooks, and peer learning, so staff can experiment safely and effectively

Track program health through participation, use case volume, and the quality of what surfaces into SAIL intake

Represent the Champions program to senior leadership as a leading indicator of organizational AI fluency and culture

Cross-Functional Partnership

Partner across program, partnerships, marketing, Development, and operations to surface AI opportunities and ensure initiatives reflect the full scope of Year Up United’s work

Serve as a connective layer between TnT and the rest of the organization, not a siloed technical function

Staying at the Frontier

Track the latest and greatest in AI — tools, models, and capabilities

Evaluate what is real and applicable, and bring it back to sharpen the bets we make

Serve as a go-to resource on current AI capabilities for teams across the organization

Monitor the external AI landscape, including major model releases, philanthropic investments, policy developments, and sector initiatives, and brief internal leaders on what matters for Year Up United

Identify opportunities to position Year Up United’s AI work within larger national conversations and funding moments

Handoff to Scale

When a pilot earns it, hand it cleanly to the technical AI build capability and agile delivery teams to be hardened and scaled

Ensure a clean transition from “proven it works” to “built to last”

Learning Community

Serve as a coach/mentor to a small group of current students

Participate in weekly group sessions, staff meetings, and training as part of the broader Learning Community

* Other duties as assigned

Qualifications:

Minimum 5–7 years of experience in product management, portfolio management, innovation, or digital transformation — we welcome strong portfolio and operations backgrounds paired with genuine drive to innovate

Experience building and maintaining portfolio views, operating dashboards, or initiative roll-ups that leaders rely on to make decisions

Demonstrated track record standing up pilots or prototypes and making evidence-based go/kill decisions

Deep, current fluency in AI — you follow the field closely and can distinguish real capability from hype without needing to be an engineer

Genuine passion for AI — you actively experiment with new tools and are energized by finding where they can transform how we serve students and staff

Comfort operating with ambiguity and lean experimentation; a bias toward running several low-cost tests over writing one perfect plan

Strong facilitation and stakeholder skills — able to hold a room with senior leaders and run a scrappy vendor pilot in the same week

Ability to partner with technical builders and agile delivery teams to move validated work into production

A senior operator comfortable leading through influence, without a dedicated team

Experience building or scaling a community of practice, ambassador program, or distributed change network across a complex organization

Ability to track and synthesize external AI developments and translate them into strategic implications for a mission-driven organization

Understanding of workforce development, skills-based hiring, or economic mobility, or genuine drive to develop it quickly

A passion for the mission of Year Up United and belief in the potential of young adults navigating the Opportunity Divide

Preferred

Proficiency with Sal