Senior Program Manager, Learning & Development

Summary

Join Thumbtack's Talent Team as a L&D Senior Program Manager to lead AI enablement. Shape the AI learning strategy, design impactful learning experiences, partner with business leaders, create scalable resources, and experiment with AI in L&D. Support broader L&D priorities, including onboarding, leadership development, and career growth. Collaborate with a high-trust team. This role offers the opportunity to make a real impact by helping people unlock the power of AI in practical ways. The team is small but mighty, and you will be instrumental in its growth.

Requirements

• 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

Responsibilities

• 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

Benefits

#LI-Remote