Principal, AI Capability & Reskilling

What You'll Do: At Avalara, we are building a future where AI isn't just something we use—it's seamlessly embedded into how we work, driving faster decisions, fewer manual handoffs, and creating more time for high-impact work requiring human judgment. As the Enterprise AI Capability Program Lead, you will own the system that makes this shift possible. You'll lead our enterprise reskilling and AI capability program, guiding managers, leaders, and eventually all employees from AI awareness to structured experimentation and workflow redesign.

#LI-Remote What Your Responsibilities Will Be: * Design and own the multi-stage capability program that takes employees and managers from AI awareness to structured experimentation, to identifying real use cases in their own work, to changing how that work gets done, and evolving the program's design as the organization matures. * Personally teach, coach, and mentor managers and functional leaders as they build fluency and lead redesign in their own teams, including facilitating workshops and working sessions across functions globally. * Build reusable tools, templates, and frameworks, including ones that help leaders break roles into tasks, assess AI suitability, and redesign around the human-AI boundary so the work scales beyond direct engagement. * Translate complex AI and org-design concepts into approachable, compelling content for a management audience. * Build the infrastructure that turns individual experimentation into organizational learning: mechanisms for surfacing use cases, an AI champions network across functions, and forums where practical wins get shared and repeated. * Own measurement of the program's impact as evidenced by the change in work itself (e.g., speed, quality, capacity redirected to higher value tasks) versus adoption metrics. * Progressively expand the program beyond managers to a full employee-wide reskilling agenda, sequencing where the next capability gap or opportunity matters most