Senior Program Manager, Learning & Development (AI & Innovation)

The Talent Team, a department under our broader People org, brings together Recruiting, Learning & Development, and Talent Management under one unified vision to create seamless and impactful experiences for every individual who joins Thumbtack. From the first interaction with a prospective candidate to their journey as high performing team members, our integrated approach ensures that every step is thoughtful, aligned, and geared toward long term success. This alignment allows us to attract top tier talent, foster a culture of continuous learning, and nurture high potential individuals, all while delivering exceptional results. By thinking bigger and collaborating as one team, we're not just shaping careers, we're building the future of Thumbtack.

If the idea of helping people unlock the power of AI actually excites you (not in a buzzword kind of way, but in a real, practical, “let’s make this useful” kind of way) this role might be your sweet spot. We’re looking for a L&D Senior Program Manager to lead AI enablement at Thumbtack. You’ll shape the strategy, build the programs, and create the tools that help our team learn how to use AI in meaningful, effective ways. You’ll also flex your L&D skills more broadly, jumping in on programs like onboarding, leadership development, and career growth as priorities evolve. No two days will look exactly the same, but the thread that ties it all together is curating learning experiences people actually want to engage with.

You’ll be joining a small but mighty team. Right now, L&D is a team of one. This role will double that. And while your L&D leader will be on parental leave when you join, you won’t be totally on your own. In the interim, you’ll report into our VP of Talent, and you’ll be supported by a broader Talent team that collaborates closely and cares deeply. We’re big on trust, light on red tape, and excited about what the future of learning can look like when it’s done right.

• Shape Our AI Learning Strategy: Build trust across the organization and quickly assess learner needs to develop a thoughtful, multi-pronged strategy for AI learning enablement, ensuring employees at all levels feel confident and empowered to leverage AI in their work.
• Design Impactful, Org-Wide Learning Experiences: Create and launch learning programs that meet employees where they are by tailoring content for different levels of AI familiarity, from cautious beginners to confident power users. 
• Partner with Business Leaders: Collaborate with teams across the company to uncover high-impact opportunities for AI integration within their functions.
• Create Scalable Resources: Design practical resources—such as playbooks, job aids, and functional guides—that enable teams to confidently embed AI into their daily workflows.
• Experiment with AI in L&D: Apply your curiosity and creativity to test out new ways AI can be used within L&D by integrating smart tools into programs, systems, and operations to increase impact and efficiency. 
• Adapt and Support Across L&D Priorities: Roll up your sleeves to support the broader L&D roadmap as priorities shift, jumping in on initiatives like onboarding, leadership development, career growth, and more.
• Collaborate Across a High-Trust Team: Partner closely with a small, nimble team of experienced Talent pros who move fast, support each other, and care deeply about building a culture of continuous learning.

• Learning & Development Expertise: 8+ years of hands-on experience designing and scaling learning programs that actually move the needle, grounded in adult learning principles and tailored to different audiences. You’ve built initiatives that connect to real business goals and know how to measure their impact.
• AI Fluency: You’re not just interested in AI, you’ve actually used it. Whether applying AI to learning content, using tools to boost your own efficiency, or staying current on trends, you’re energized by the potential it holds for the future of work.
• Strategic Program Leadership: You’re a master of managing moving pieces. You’ve led multi-phase L&D programs from idea to launch, kept cross-functional partners aligned, and know how to navigate shifting priorities without losing momentum.
• Operational Hustle: You take pride in staying five steps ahead. You think strategically, sweat the details, and thrive in the weeds. This is a high-performing team and we rely on each other to deliver.
• Engaging Facilitation & Comms: You’ve facilitated live learning sessions that people don’t dread, and you know how to write internal communications that actually get read and spark action.
• Growth Orientation: You welcome feedback, adjust with ease, and keep a steady head when working in the messy middle. You approach work with curiosity, accountability, and just the right mix of confidence and humility.
• Bias for Action in Ambiguity: You know how to move forward without all the answers, and you’re skilled at creating clarity for others too. You’ve worked in fast-paced, high-change environments (like tech) and know how to bring order to chaos, make confident decisions, and keep your eye on the long-term vision.

• 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 $151,700 - $196,400.
• 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 $136,600 -  $176,800.
• For candidates living in all other US locations, the expected salary range for this role is currently $128,900 - $166,900.

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.

#LI-Remote