What You'll Do

This role leads the Tax Research and Technology team responsible for maintaining and building the tax compliance content that powers AvaTax, Avalara Tax Research, and Avalara Exemption Certificate Management. Reporting to the Director, Indirect Tax, you will lead a team of 15 tax researchers spanning sales and use tax and other indirect taxes across the U.S. and Canada, with direct ownership of customer-facing tax compliance content escalations for these products.

As AI reshapes how tax content is researched, validated, and delivered, this role also sets the direction for how AI is adopted, governed, and scaled across the function, turning subject-matter expertise into AI-ready content and repeatable, defensible workflows that keep pace with a rapidly changing indirect tax landscape.

Why This Role Matters

Team Impact:

• Leads and develops a team of tax researchers, setting priorities, workload balance, and quality standards across three core products.
• Raises the technical and AI fluency of the team, establishing repeatable methods for AI-assisted research, validation, and tax content production.

Business Impact:

• Owns tax compliance content quality and freshness for the products that represent the core products in Avalara’s tax automation product suite, directly supporting growth and gross revenue retention (GRR).
• Builds and maintains a defensible, authoritative indirect tax compliance content base covering sales and use tax and other U.S. and Canadian transaction taxes.

Customer Impact:

• Ensures customer tax compliance content escalations across AvaTax, Tax Research, and ECM are resolved accurately and quickly, protecting trust in Avalara's compliance content.
• Improves the speed and accuracy with which customers get answers to complex indirect tax questions, reducing time customers spend researching and reconciling tax content themselves.

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What Your Responsibilities Will Be

• Lead Indirect Tax Content Research: Direct the team responsible for researching, building, and maintaining sales and use tax and other indirect tax content for the U.S. and Canada across AvaTax, Tax Research, and ECM.
• Own Customer Escalations: Serve as the accountable owner for customer-facing content escalations across all three products, triaging, prioritizing, and driving issues to resolution.
• Deliver Against the AI Roadmap: Ensure the team executes on the function's AI roadmap comprehensively and on schedule, providing input and subject-matter perspective into roadmap priorities.
• Uphold Governance and Guardrails: Ensure the team consistently follows established AI governance documents, quality standards, and operating guardrails when producing and validating tax content, including controls that trace every answer back to a primary authority. Provide input on governance requirements based on hands-on team experience.
• Interpret and Communicate Legislative Change: Review and translate complex, evolving indirect tax rules and legislation into clear, actionable tax compliance content and guidance for stakeholders across the organization.
• Collaborate Cross-Functionally: Partner with Product, Engineering, and Support to align content priorities, scale AI-enabled workflows, and ensure content changes are reflected accurately in Avalara's compliance products.
• Scale Repeatable Operating Rhythms: Build reusable frameworks, prompt libraries, and review standards that let the team respond consistently and at scale to regulatory change.
• Communicate Consistently: Maintain regular, consistent communication with the team through standing 1:1s, team meetings and timely updates to ensure alignment on priorities, roadmap changes, and governance requirements.
• Manage Team Performance: Coach, mentor, and develop team members; manage workload and resourcing; and lead year-end performance reviews. Evaluate performance objective against clear, data-driven standard, making sound, well-supported distinctions between high, core, and low performers.
• Stay Current: Track changes in U.S. and Canadian indirect tax law, regulations, and industry trends, and identify high-impact opportunities to apply AI to improve research speed, scale, and quality.

What You'll Need to be Successful

Required

• Bachelor's degree in Accounting, Finance, Tax, Law, or a related field.
• 8+ years of experience in U.S. and Canadian sales and use tax or broader indirect tax research, advisory, or compliance, including experience with multi-jurisdictional legislative change.
• 2+ years of leadership experience with a track record of managing tax teams and driving measurable results.
• Hands-on experience applying AI tools to research or content workflows. For example, prompt design, validation frameworks, or structured AI-assisted research with measurable outcomes.
• Strong analytical and legal research skills, with the ability to turn ambiguous or evolving tax authority into clear, well-organized, and defensible content.
• Effective verbal and written communication skills, with the ability to explain complex tax and AI-governance topics clearly to both technical and non-technical stakeholders.
• Experience managing customer-facing escalations in a compliance, tax, or SaaS environment.

Preferred

• Advanced degree or certification (J.D., LL.M. in Taxation, CPA, or M.S. in Taxation).
• Familiarity with large language model (LLM) behavior, retrieval-augmented generation (RAG), or AI agent architectures.
• Experience with structured data formats (e.g., JSON, XM, MD), or legal research platforms.
• Understanding of ERP systems and their database structures (SAP, Oracle, or similar).
• Experience with Agile or other project management methodologies.
• Familiarity with JIRA or similar tools.

How You'll Raise the AI Bar

At Avalara, applied AI capability is evaluated against a company-wide AI persona framework used in performance reviews. This role is evaluated on relentless execution: ensuring every process and procedure on the team leverages AI, and that every researcher on the team is fully capable of training Avalara's AI models.

As an Execution-tier AI leader for the team, you will:

• Establish a strong bias toward AI-first execution, actively moving legacy and manual workflows to AI-enabled alternatives across the team.
• Ensure every researcher on the team can write and edit research skills used to train Avalara's AI models, with a clear plan to close capability gaps.
• Ensure the team consistently follows established AI governance documents and policy.
• Provide informed opinions and hands-on team perspective into AI roadmap and governance decisions.
• Translate function-level AI priorities and guardrails into clear team-level operating rhythms and day-to-day execution.
• Identify and close gaps where the team has not yet adopted AI into a workflow, and escalate roadmap or governance gaps to the appropriate owner.

In practice, that means:

• A demonstrated bias toward AI-first execution, including a commitment to reviewing and migrating legacy workflows that could be AI-enabled.
• 100% of researchers on the team are proficient in authoring and editing research skills that train AI models, with a clear plan to close any gaps immediately.
• Experience operating within governance frameworks for AI initiatives, including following documented controls and escalation paths.
• Applying established decision rights, accountability standards, and quality measures for AI use within the team.
• Running scalable day-to-day operating rhythms that hold up under regulatory change and growth.

How We Define Success

Success in this role is defined by measurable gains in tax compliance content velocity, escalation resolution speed, and responsible AI adoption.

12-month success signals include:

• Zero validated inaccuracies in customer-facing content across AvaTax, Tax Research, and ECM post-release.
• A documented, adopted AI roadmap for the content function with clear governance and decision rights in place.
• Reduced average resolution time for customer content escalations across all three products.
• Standardized, repeatable AI-assisted research and validation workflows adopted team-wide.
• Demonstrated measurable impact; cycle time, quality, or cost; from AI initiatives led by the team.
• A content team with elevated AI fluency, supported by documented best practices and knowledge transfer.

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.

How 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.