Principal – AI Capability & Reskilling

• 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. 
• Own the long-term, continuous improvement of both the capability program and manager effectiveness in this area; this is a durable mandate you keep improving, not a program you launch once and hand off. 
• Report regularly to senior leadership on program impact, with a clear, evidence-based answer to “how is the organization working smarter because of this program.” 

• Bachelor's degree in business, organization development, human resources, industrial-organizational psychology, or a related field, or equivalent experience. 
• Experience teaching, coaching, or facilitating for adult/professional audiences, comfortable being the person in the room, not just the person who designed the curriculum. 
• 8+ years designing and delivering enterprise capability-building or reskilling programs at scale, with a track record tying program design to measured business outcomes, not completion rates alone. 
• Solid grounding in organizational design (operating models, role clarity, span of control, decision rights, systems thinking), with ability to build credible tools and coach leaders through the redesign process. 
• Deep, current fluency in generative and agentic AI, with the ability to translate capabilities into role, skills, and workforce implications, and hands-on experience applying AI tools to real work (prompt engineering, AI-augmented workflow design, AI-augmented analysis). 
• Strong judgment: able to connect org design, AI capability, and workflow optimization into one coherent, pragmatic program. 
• Comfort working with data and measurement, particularly in demonstrating the value created by capability building programs. 

• Experience building and mobilizing champion networks or communities of practice.  
• Experience running a comparable AI-fluency or reskilling program on an enterprise scale. 
• Process-improvement certification (e.g., Lean, Six Sigma, Kaizen) or Business Process Management certification (e.g., ABPMP CBPA). 

AI is embedded in our workflows, decision-making, and products.  Success here requires embracing AI as an essential capability.

• You’ll bring experience using AI and AI-related technologies, ready to thrive here.

• You’ll apply AI every day to business challenges - improving efficiency, contributing solutions, and driving results for your team, our company, and our customers.

• You’ll grow with AI by staying curious about new trends and best practices, and by sharing what you learn so others can benefit too.

Total Rewards 

In addition to a great compensation package, paid time off, and paid parental leave, many Avalara employees are eligible for bonuses. 

Health & Wellness 
Benefits vary by location but generally include private medical, life, and disability insurance. 

Inclusive culture and diversity 
Avalara strongly supports diversity, equity, and inclusion, and is committed to integrating them into our business practices and our organizational culture. We also have a total of 8 employee-run resource groups, each with senior leadership and exec sponsorship. 

We’re defining the relationship between tax and tech.

We’ve already built an industry-leading cloud compliance platform, processing over 54 billion customer API calls and over 6.6 million tax returns a year. Our growth is real - we're a billion dollar business - and we’re not slowing down until we’ve achieved our mission - to be part of every transaction in the world.

We’re bright, innovative, and disruptive, like the orange we love to wear. It captures our quirky spirit and optimistic mindset. It shows off the culture we’ve designed, that empowers our people to win. We’ve been different from day one. Join us, and your career will be too.

We’re An Equal Opportunity Employer

Supporting diversity and inclusion is a cornerstone of our company — we don’t want people to fit into our culture, but to enrich it. All qualified candidates will receive consideration for employment without regard to race, color, creed, religion, age, gender, national orientation, disability, sexual orientation, US Veteran status, or any other factor protected by law. If you require any reasonable adjustments during the recruitment process, please let us know.