Principal, AI Capability & Reskilling

Avalara, Inc.; Northern (KY); Hybrid; USD 153,000 - 306,000; Full time

Job summary

Avalara, Inc. is seeking an Enterprise AI Capability Program Lead to own and evolve the company-wide initiative that embeds AI into workflows and decision-making.

You will guide managers and executives from AI awareness to structured experimentation, shaping how work is redesigned around human-AI collaboration. You will mentor leaders, develop reusable tools, and measure impact in speed, quality, and value realignment, extending the program to broader employee audiences.

Qualifications

• Experience teaching, coaching, or facilitating for adult/professional audiences.
• 8+ years designing and delivering enterprise capability-building or reskilling programs at scale.
• Deep fluency in generative and agentic AI and ability to translate capabilities into roles and workforce implications.

Responsibilities

• Design and own the multi-stage capability program guiding employees from AI awareness to structured experimentation.
• Coach and mentor leaders to drive redesign in their teams and across functions globally.
• Build tools, templates, and frameworks to enable scalable human-AI collaboration and workflow redesign.

Skills

Adult training

Coaching

Workshop facilitation

Data-driven evaluation

AI fluency

Organizational design

Education

Bachelor's degree or equivalent experience

Job description

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.
• 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.”

What You'll Need to be Successful

• 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.

Preferred Qualifications

• 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).

Pay Range Details

• Colorado $153,300-$252,900 (annually)
• Washington $153,300-$279,600 (annually)
• California $153,300-$306,300 (annually)
• NYC $169,400-$306,300(annually)

The pay range above is the general base pay range for a successful candidate in the state listed. The successful candidate’s actual salary/wage may be based on various factors, such as geographic location, candidate experience and qualifications, as well as market and business considerations.

This role is eligible for an annual bonus based on individual and company performance, depending on the terms of the applicable plan and the employee’s role.

Avalara is an AI-first Company

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.

What We’ll Take Care of You

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.

What You Need To Know About Avalara

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.