AI Innovation & Portfolio Lead

Year Up • Tampa, FL

1d • $135,000 - $160,000 • Hybrid

About The Position

The AI Innovation & Portfolio Lead sits within Year Up United’s Product & Design team, the transformation function inside Transformation & Technology (TnT). The role owns the organization’s operating picture of AI initiatives and develops the innovation pipeline that turns business problems into tested pilots before committing build capacity. It determines which opportunities merit investment, validates them through evidence-based experimentation, and hands successful pilots to technical AI build and agile delivery teams for production and scale.

This is a senior, influential role rather than a project-management or technical-build position. The lead maintains a trusted view of AI initiatives, owns intake and governance through the Strategic AI Leadership group (SAIL), and helps leaders make prioritization and investment decisions. The role also builds AI fluency and safe experimentation across the organization through skill shares and the AI Champions program, while tracking external AI developments and translating their relevance for Year Up United.

The position requires regular in-person engagement and is hybrid. Employees are expected to work onsite at least two days per week starting January 5, 2026. Applicants must live and work in a state, or approved proximate state, where Year Up United operates, within reasonable commuting distance of a location. Occasional travel to Year Up United sites is expected. The lead also mentors a small group of students and participates in weekly group sessions, staff meetings, and training as part of the broader Learning Community.

Requirements

• 5–7 years of experience in product management, portfolio management, innovation, or digital transformation; strong portfolio and operations backgrounds paired with a drive to innovate are welcome.
• Experience building and maintaining portfolio views, operating dashboards, or initiative roll-ups that leaders rely on for decisions.
• Demonstrated track record of standing up pilots or prototypes and making evidence-based go/kill decisions.
• Deep, current fluency in AI and the ability to distinguish real capabilities from hype without needing to be an engineer.
• Genuine passion for AI, active experimentation with new tools, and enthusiasm for finding ways to transform service to students and staff.
• Comfort with ambiguity and lean experimentation, with a bias toward running several low-cost tests rather than writing one perfect plan.
• Strong facilitation and stakeholder skills, including the ability to engage senior leaders and run a vendor pilot.
• Ability to partner with technical builders and agile delivery teams to move validated work into production.
• Senior-operator capability to lead 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 that understanding quickly.
• Passion for Year Up United’s mission and belief in the potential of young adults navigating the Opportunity Divide.
• Commitment to diversity, equity, inclusion, and belonging.
• Must live and work in a state where Year Up United operates or an approved proximate state, within reasonable commuting distance of a location.

Nice To Haves

• Proficiency with Salesforce or a similar ecosystem.
• Experience in nonprofit, education, or workforce development environments.
• Prior experience presenting to senior leaders or an executive/governance committee.

Responsibilities

• Maintain a current, trusted view of every AI initiative, including status, cost, adoption, outcomes, and readiness to graduate.
• Own the state of each AI bet and the lessons it produces; surface portfolio insights to inform prioritization and investment decisions.
• Move AI use cases from intake through discovery to clear go/kill decisions, using evidence against defined milestones.
• Run discovery with people closest to the work to identify worthwhile business problems and opportunities.
• Design and orchestrate fast, low-cost pilots using flexible resourcing such as contractors, vendor pilots, or borrowed capacity.
• Retire unsuccessful pilots quickly and cheaply, and prepare validated pilots to graduate into scaled builds.
• Co-chair the Strategic AI Leadership group (SAIL), Year Up United’s AI governance committee.
• Own the SAIL intake process by collecting and triaging AI use cases from across the organization.
• Bring SAIL the innovation pipeline and evidence needed to decide which initiatives should proceed to a real build.
• Apply a workforce development lens to AI decisions, considering opportunity talent, employer expectations, and the students served.
• Lead biweekly AI skill shares (Lunch & Learns) and use them to identify work teams are undertaking and surface opportunities to the innovation funnel.
• Co-lead and manage the AI Champions program, including strategy for recruiting, developing, and activating the national network.
• Create shared resources, playbooks, and peer learning for Champions; track program health through participation, use-case volume, and the quality of items entering SAIL intake.
• Represent the Champions program to senior leadership as an indicator of organizational AI fluency and culture.
• Partner across program, partnerships, marketing, Development, and operations to identify opportunities and reflect the full scope of the organization’s work.
• Connect TnT with the broader organization and serve as a go-to resource on current AI capabilities.
• Track AI tools, models, capabilities, policy developments, philanthropic investments, sector initiatives, and major releases; assess relevance and brief internal leaders.
• Identify opportunities to position Year Up United’s AI work in national conversations and funding moments.
• Hand validated pilots to technical AI build capability and agile delivery teams for hardening and scale, ensuring a clean transition from proof to durable implementation.
• Coach or mentor a small group of current students and participate in weekly group sessions, staff meetings, and training as part of the Learning Community.
• Perform other duties as assigned.

Benefits

• Comprehensive healthcare options.
• Dental coverage.
• 401(k) match for eligible participants.
• Three weeks of paid vacation in the first year and four weeks after the initial year.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed