Senior Learning AI Readiness Manager

Thumbtack

1d • Remote

About The Position

This role sits at the intersection of AI adoption, organizational change, and leadership development. You will help shape how Thumbtack builds readiness for the future — supporting leaders, managers, and teams in not just understanding AI but actually changing how they work because of it. Learning and leadership development are core levers you'll use to drive that change, but the job is bigger than any single program: it's about accelerating the development of the skills and capabilities our workforce will need for the future. You are an equal parts change partner, AI builder, learning designer, and forward thinker.

Requirements

• Demonstrated AI fluency and curiosity: You've built AI solutions and designed AI-first experiences, deeply experimented with AI tools well beyond chat interfaces, and have a clear, evolving point of view on how AI will shape the skills needed for the future
• Experience in Change Management, Organizational Design, L&D, Consulting or Program Management — with meaningful experience owning end-to-end initiatives
• Leadership and capability development expertise, including designing and scaling programs for managers and senior leaders
• High agency: You see what's needed, proactively tackle it, and leverage strong organizational change instincts to make it happen
• High-velocity operator: You work fast, iterate, and are able to navigate constant change
• Strong facilitation skills with the ability to engage senior audiences
• Proven stakeholder management and influence without authority

Responsibilities

• Help shape Thumbtack's organizational readiness for the changes ahead — with a particular focus on how AI is transforming how we work, what skills matter, and what leaders should do to prepare
• Own the leadership development portfolio as a core lever for future readiness, including programs for leadership onboarding and manager development
• Build AI-first solutions designed for real behavior change and skill transfer
• Shape the leadership development strategy and annual roadmap with an explicit lens on where leadership capability needs to go, not just where it is
• Serve as an internal change partner to senior leaders navigating AI and future transformation
• Partner with Talent Management, HRBPs, and business leaders to assess capability gaps, co-create solutions, and integrate development into talent cycles
• Establish measurement frameworks that track behavior change and business impact; use data and feedback to iterate continuously

What This Job Offers

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