What You'll Do

About the role 

Avalara is looking for a Principal-level Head of Generative AI & Business Operations to help scale Avalara’s Micro and Emerging Business portfolio, with a focus on DAVO, MyLodge, and future product-led growth opportunities for small and emerging businesses. 

This is a senior individual-contributor role for an operator, systems thinker, and AI-first builder who can turn fragmented data, manual processes, and disconnected workflows into a measurable growth and efficiency engine. The role will own the business operations architecture for the portfolio, including operating rhythms, performance instrumentation, data models, workflow automation, AI-enabled internal tools, and cross-functional execution systems. 

The right candidate will not simply report on the business. They will design how the business runs. They will build the mechanisms that help Product, Growth, Operations, Support, Engineering, Finance, and Go-to-Market teams make faster decisions, reduce manual work, improve customer outcomes, and scale without adding unnecessary organizational complexity. 

Why this role exists now 

Avalara is expanding its product-led, partner-led, and direct-to-market motions for micro and emerging businesses. These customers need simple buying paths, fast onboarding, low-friction support, clear product journeys, and efficient fulfillment. That model only works if the business has a purpose-built operating layer: clean data, clear ownership, reliable instrumentation, automated workflows, and a single view of performance. 

This role exists to establish that operating layer. The Head of Generative AI & Business Operations will build the systems, metrics, and AI-enabled workflows that allow the business to move with startup velocity while still leveraging Avalara’s trusted platform, compliance, finance, security, and customer-success capabilities. 

What Your Responsibilities Will Be

Build the operating system for the business 

• Define and run the business operating cadence across weekly performance reviews, roadmap reviews, experiment reviews, launch readiness, partner readiness, support health, and executive updates. 

• Establish a single operating model for goals, ownership, decision rights, intake, prioritization, escalation, and follow-through across Product, Growth, Operations, Engineering, Support, Finance, Legal, and Go-to-Market. 

• Create dashboards and decision surfaces that make the business visible: acquisition, conversion, activation, onboarding throughput, support demand, automation rate, churn, expansion, partner performance, revenue, margin, and customer effort. 

• Identify operational bottlenecks and translate them into automation, process, data, tooling, or organizational recommendations. 

Lead generative AI strategy and applied AI execution 

• Define the generative AI roadmap for the business, focused on measurable business impact rather than generic AI experimentation. 

• Build and operationalize AI-enabled workflows that reduce manual work in onboarding, support, data intake, account setup, compliance handoffs, partner operations, reporting, and internal decision support. 

• Partner with Product, Engineering, Data Science, Security, Legal, Support, Tax Content, and Compliance to ensure AI-enabled workflows are accurate, governed, explainable, auditable, and scalable. 

• Develop reusable AI patterns, prompts, agents, evaluation methods, and operating controls that can be adopted across the portfolio. 

• Measure AI impact through time saved, cost avoided, quality improved, cycle time reduced, support deflection, faster onboarding, improved conversion, or increased operating leverage. 

Own business performance instrumentation 

• Define the metric architecture for the portfolio, including north-star metrics, scorecards, funnel analytics, operational health metrics, automation KPIs, partner-channel metrics, and financial performance views. 

• Partner with Finance, Data, Revenue Operations, Marketing Operations, Support Operations, and Product Analytics to ensure metrics are trusted, repeatable, and decision-ready. 

• Build business review materials for the VP, GM and senior stakeholders, translating data into decisions, tradeoffs, risks, and recommended actions. 

• Establish leading indicators that identify churn risk, onboarding friction, support spikes, partner underperformance, and low-value operational work before they become escalations. 

Automate manual operational work 

• Map high-volume manual workflows and prioritize automation opportunities based on business value, customer impact, risk, and implementation effort. 

• Convert repeatable manual processes into structured workflows, AI-assisted tools, self-serve dashboards, templates, playbooks, and operational controls. 

• Partner with shared services and platform teams to consume existing Avalara systems where appropriate rather than creating duplicate tooling. 

• Create clear operating handoffs between business teams and central teams for billing, provisioning, filing, support, tax content, customer communications, and partner operations. 

Enable partner and direct-to-market execution 

• Build operational visibility across partner-led, embedded, marketplace, and direct-to-market motions. 

• Instrument the full customer journey from acquisition and purchase through onboarding, activation, support, retention, and expansion. 

• Partner with Product, Growth, Business Development, Sales, Support, and Operations to identify friction in the funnel and translate it into measurable execution plans. 

• Create repeatable operating patterns that help the business scale across both partner ecosystems and direct digital channels. 

Drive cross-functional execution without formal authority 

• Influence senior leaders and functional owners across Avalara to align on priorities, data definitions, tooling decisions, operational standards, and customer-impacting tradeoffs. 

• Create formal networks with key decision makers across Product, Engineering, Go-to-Market, Finance, Support, Data, Security, and Compliance. 

• Lead complex, cross-functional initiatives from ambiguous problem statement to shipped operating capability. 

• Serve as the VP, GM’s principal business-operations partner, helping convert strategy into execution discipline and measurable outcomes

What You’ll Need To Be Successful

Required qualifications 

• 12+ years of experience in business operations, product operations, strategy and operations, revenue operations, analytics, AI transformation, product management, or operational leadership in SaaS, fintech, marketplace, compliance, tax, payments, or e-commerce environments. 

• Demonstrated experience operating at principal or senior-strategic individual-contributor level, with influence across multiple functions and senior stakeholders. 

• Proven ability to design operating systems for high-growth businesses, including planning cadences, scorecards, decision rights, KPI architecture, executive reporting, and cross-functional governance. 

• Strong applied AI fluency, including hands-on experience using LLMs, agents, automation platforms, prompt systems, workflow tools, evaluation methods, or AI-enabled analytics to improve measurable business outcomes. 

• Deep analytical capability: ability to structure ambiguous business problems, define metrics, interrogate data quality, build dashboards or requirements, and translate insights into action. 

• Strong systems thinking: ability to connect customer journey, product experience, data flow, operational process, financial impact, and organizational design. 

• Ability to work through influence rather than hierarchy, especially in matrixed environments with shared platform teams and distributed ownership. 

• Excellent written communication skills, including executive narratives, operating memos, decision briefs, business cases, scorecards, and launch/readiness materials. 

• Strong judgment around responsible AI, customer data, compliance-sensitive workflows, operational risk, and quality controls. 

• Bachelor’s degree in business, analytics, computer science, engineering, economics, or equivalent practical experience. 

Preferred qualifications 

• Experience building business operations or product operations functions for a product-led growth, self-serve, embedded, marketplace, partner-led, or SMB-focused SaaS business. 

• Experience with tax, compliance, accounting, payments, POS, hospitality/lodging, e-commerce, or regulated workflow automation. 

• Experience implementing AI-enabled internal tools, operations copilots, support deflection, onboarding automation, data-ingestion automation, or executive decision-support systems. 

• Experience with BI and operating data ecosystems such as Salesforce, Gainsight, Power BI, Snowflake, Looker, Tableau, Jira, Zendesk, or equivalent platforms. 

• Experience partnering with product and engineering teams to translate operational needs into scalable internal products or platform capabilities. 

12-month success signals 

• The business has a clear operating cadence with trusted weekly, monthly, and quarterly business reviews. 

• The VP, GM and leadership team have a single source of truth for product, growth, customer, partner, support, automation, and financial performance. 

• Manual operational workflows are mapped, prioritized, and materially reduced through AI, automation, tooling, or process redesign. 

• AI use cases are deployed against measurable business outcomes, with clear governance, evaluation, and operating controls. 

• Product, Growth, Operations, Support, Engineering, Finance, and Go-to-Market teams have clear handoffs, decision rights, and escalation paths. 

• Key portfolio metrics are instrumented and actively used to make roadmap, investment, staffing, partner, and operational decisions. 

• The role has created reusable operating patterns that can scale across the business without creating additional overhead. 

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.