Senior Learning & AI Readiness Manager

About the Talent Team

We bring Recruiting, Learning & Development, and Talent Management together to create a seamless, high-impact journey for every teammate — from first interview to leadership growth. As part of the People org, we design experiences that accelerate performance, deepen capability, and strengthen culture so teams can do their best work. We partner closely with executives and managers to align development with business priorities and measurable outcomes across Thumbtack.

About the Role

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.

What You'll Do

• 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

In order to be successful, you must bring

• 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

Expected salary ranges

• For candidates living in San Francisco / Bay Area, San Jose, New York City, or Seattle metros, the expected salary range for the role is currently $159,000.00 - $215,000.00
• For candidates living in Austin, TX or Washington DC metros or in California, Massachusetts, New Jersey, or Washington states, the expected salary range for the role is currently $142,800.00 - $193,200.00
• For candidates living in all other US locations, the expected salary range for this role is currently $135,200.00 - $182,900.00

Actual offered salaries will vary and will be based on various factors, such as calibrated job level, qualifications, skills, competencies, and proficiency for the role.