Head of Product, Avalara Micro and Emerging Business

Avalara is looking for a Senior Director of Product Management to lead the product strategy, customer experience, and execution model for a high-growth Product-Led Growth portfolio serving emerging businesses, e-commerce sellers, lodging operators, and embedded partner channels.

This leader will own a multi-product portfolio spanning self-serve compliance solutions, online purchase and onboarding experiences, partner-embedded workflows, and next-generation calculation and returns capabilities. The role requires a product executive who can set a clear multi-year strategy, translate that strategy into measurable business outcomes, and lead through a team of product leaders, senior PMs, and cross-functional partners.  

The ideal candidate has scaled digital-first SaaS or fintech products, optimized self-serve buying and onboarding funnels, built durable embedded distribution through partner ecosystems, and used AI and automation to remove customer friction. This role is accountable for making Avalara’s PLG experiences simpler, faster, more intelligent, and easier to buy, activate, and expand.  

Lead portfolio strategy and business outcomes  

• Define the multi-year product vision, portfolio strategy, roadmap, and operating priorities for Avalara’s PLG product portfolio.  

• Establish measurable OKRs across acquisition, conversion, activation, retention, expansion, partner adoption, and customer effort reduction.  

• Make clear investment recommendations, including where to accelerate, simplify, partner, integrate, or stop lower-value work.  

• Build the product business case for PLG investments and communicate progress, tradeoffs, and risks in executive forums.  

Own the self-serve buying and activation experience  

• Lead product strategy for digital buying experiences, including pricing and packaging presentation, cart and checkout flows, trials, payment methods, and conversion paths.  

• Improve the end-to-end customer journey from discovery through purchase, account setup, activation, first value, and recurring use.  

• Use funnel analytics, experimentation, qualitative research, and customer journey telemetry to identify friction and prioritize the highest-impact work.  

• Partner with growth marketing, sales, finance, legal, customer support, and engineering to deliver scalable online-buy motions that complement Avalara’s broader go-to-market model.  

Build AI-first, low-friction product experiences  

• Identify practical ways to use AI, automation, and modern interfaces to simplify compliance workflows for small and emerging businesses.  

• Drive product experiences that automate data intake, guide setup, recommend next-best actions, and resolve common customer questions in-product.  

• Partner with engineering, data science, tax content, support, and compliance experts to ensure AI-enabled workflows are accurate, explainable, measurable, and customer-trusted.  

• Translate emerging AI capabilities into product strategy, roadmap priorities, and differentiated customer value.  

Scale embedded and ecosystem distribution  

• Lead product strategy for embedded experiences across e-commerce platforms, POS ecosystems, app marketplaces, lodging/property management platforms, and developer surfaces.  

• Partner with business development and go-to-market teams to define partner product requirements, marketplace experiences, commercial packaging, implementation patterns, and success metrics.  

• Ensure embedded partner experiences are simple to discover, install, configure, use, support, and expand.  

• Build repeatable product patterns that allow Avalara to scale through partner ecosystems without one-off operational complexity.  

Lead a high-performing product organization  

• Recruit, coach, and develop product managers and product leaders who demonstrate ownership, curiosity, urgency, simplicity, adaptability, and customer focus.  

• Create a strong product operating rhythm across discovery, prioritization, roadmap planning, experimentation, launch readiness, KPI review, and post-launch learning.  

• Hold the team accountable for clear problem statements, customer personas, journey maps, business value, requirements, release planning, and measurable outcomes.  

• Build a culture of rapid learning and high-quality execution while maintaining alignment with Avalara’s platform, compliance, security, and enterprise standards.  

Partner across Avalara’s platform and compliance ecosystem  

• Work closely with platform engineering, tax content, compliance operations, design, data, security, and support to deliver PLG experiences on durable Avalara capabilities.  

• Ensure PLG products consume core calculation, filing, registration, account, billing, identity, and support capabilities through scalable platform patterns.  

• Navigate complex cross-functional tradeoffs and align stakeholders around decisions that improve customer value and long-term business impact.  

• 10+ years of product management experience, including leadership of digital-first SaaS, e-commerce, fintech, payments, marketplace, tax, accounting, or compliance products.  

• 6+ years of people leadership experience, with demonstrated ability to lead through managers, senior PMs, or cross-functional product leaders.  

• Proven success setting product strategy for a multi-product portfolio and translating strategy into business outcomes, roadmap priorities, and measurable execution plans.  

• Deep experience with self-serve buying motions, checkout/cart optimization, pricing and packaging tests, digital onboarding, activation funnels, and lifecycle experimentation.  

• Demonstrated experience launching or scaling embedded products through third-party platforms, app marketplaces, POS systems, e-commerce ecosystems, API-first partnerships, or developer channels.  

• Strong fluency with funnel analytics, cohort analysis, retention metrics, activation telemetry, experimentation design, and unit economics.  

• Practical AI fluency, including the ability to identify where AI, automation, assistants, recommendations, or agentic workflows can reduce customer effort and improve product outcomes.  

• Ability to operate in a matrixed environment, influencing executives and cross-functional leaders while maintaining clear ownership and decision quality.  

• Strong written and verbal communication skills, including executive-ready strategy narratives, investment cases, roadmap tradeoffs, and performance updates.  

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

Preferred qualifications  

• Experience serving SMB customers or emerging businesses through PLG, self-serve, marketplace, or embedded distribution models.  

• Experience in tax, compliance, accounting, payments, hospitality/lodging, POS, e-commerce, or financial operations software.  

• Experience building AI-powered onboarding, product recommendations, support deflection, workflow automation, or intelligent data-ingestion experiences.  

• Experience managing portfolios that include both standalone web applications and embedded partner products.  

• Experience partnering with platform engineering teams to consume shared services, APIs, data capabilities, and compliance infrastructure at scale.  

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.