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Avalara is betting that its tax software's future growth will come from conversational, agent-driven workflows, so it is putting a product-led growth leader in charge of growing the AI assistant itself, treating the agent as the main acquisition and expansion channel rather than a feature.
Aviator is Avalara’s AI-native command center, shifting customers from navigating complex software menus to achieving complete tax and compliance outcomes through conversational, guided, and autonomous agent workflows.
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As the Principal Product Manager - Head of Growth, Agentic Experiences</strong>, you will be the growth architect, experimentation engine, and customer experience driver across Avalara’s AI platform. You sit at the intersection of AI Customer Experience (AI CX)</strong>, conversational interface design, and high-velocity product experimentation.</p> Own the overarching Product-Led Growth (PLG) vision and experimentation roadmap for Aviator, driving user activation, time-to-first-value (TTV), retention, and self-serve expansion. Turn Aviator into the primary growth flywheel for Avalara by designing intelligent, in-agent growth loops where conversational interactions naturally guide customers toward deeper automation and multi-product capabilities. Lead a high-cadence experimentation program, testing conversational UX patterns, agent prompts, proactive contextual triggers, dynamic UI elements, and onboarding flows. Partner with Data Science, AI Labs, UX Research, Product Analytics, Product Marketing, and Core PM teams to scale high-impact growth flywheels across all customer touchpoints.</p></li></ul> Establish and run a continuous, sprint-based experimentation cadence, deploying high-velocity multivariate and A/B tests across the entire user journey (Acquisition, Activation, Retention, Referral, Revenue).</span> Apply behavioral psychology, conversion rate optimization (CRO), and user friction reduction to test in-app messaging, interactive onboarding tours, contextual tooltips, and dynamic defaults.</span> Continuously test and refine conversational touchpoints, including agent prompt variations, response structures, tone, dynamic cards, and proactive notification triggers.</span> Design self-reinforcing in-agent growth loops that guide users seamlessly from their initial conversational query to full delegation of complex, multi-product autonomous workflows.</span> Optimize the AI customer journey to build trust and eliminate cognitive friction, calibrating human-in-the-loop verification checkpoints to balance user control with automated efficiency.</span> Leverage real-time contextual triggers (e.g., filing deadlines, transaction volume spikes, nexus threshold updates) to proactively surface intelligent next-best-action recommendations.</span> Architect frictionless self-serve upgrade pathways and contextual cross-sell mechanisms for core Avalara products (AvaTax, Managed Returns, Exemption Certificate Management, Tax Registrations) within agent workflows.</span> Build repeatable frameworks that convert low-tier or exploratory conversational engagement into qualified trials, automated tier upgrades, and multi-product expansion.</span> Partner with Product Marketing and domain teams to ensure newly released domain agents and tools are instantly discoverable and monetizable.</span> Instrument and monitor core PLG and AI CX metrics, including Experiment Velocity &; Win Rate, Conversational Task Completion Rate, Time-to-First-Value, Agent Trust/CSAT, Cohort Retention, and Expansion ARR.</span> Partner with Data Science and Product Analytics to evaluate model output quality, conversation drop-off funnels, and prompt effectiveness.</span> Ground roadmap prioritization in validated statistical data, leading weekly experimentation readouts and sharing reusable testing frameworks across Avalara product teams.</span></p></li></ul> 10+ years of Product Management experience, with 4+ years dedicated to Product-Led Growth (PLG), rapid growth experimentation, self-serve SaaS funnels, or conversion optimization.</span> Proven track record of architecting, launching, and scaling high-velocity A/B and multivariate testing programs that delivered measurable ARR growth, user activation, or retention gains.</span> Direct experience designing or optimizing AI Customer Experiences (AI CX)</strong>, conversational UX, LLM-powered copilots, or autonomous agentic workflows.</span> Strong fluency with quantitative analysis and growth tooling (e.g., Amplitude, Mixpanel, Pendo, Heap, Optimizely, LaunchDarkly, Statsig, SQL).</span> Deep understanding of user motivation, behavioral psychology, and trust-building in automated / AI-assisted decision-making systems.</span> Exceptional cross-functional leadership and executive communication skills, with demonstrated ability to align product, engineering, data science, and commercial teams.</span> Experience with complex B2B SaaS platforms, FinTech, tax, compliance, or enterprise ERP integrations.</span> Technical familiarity with LLM agent frameworks, prompt evaluation benchmarks (Evals), and retrieval-augmented generation (RAG) paradigms.</span> Experience scaling PLG strategies within a hybrid product-led and enterprise sales-led SaaS organization.</span></p></li></ul> AI is embedded in our workflows, decision-making, and products.  Success here requires embracing AI as an essential capability.</span></p> You’ll bring experience using AI and AI-related technologies, ready to thrive here.</span></p></li> You’ll apply AI every day to business challenges - improving efficiency, contributing solutions, and driving results for your team, our company, and our customers.</span></p></li> 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.</span></p></li></ul> Total Rewards </u></span></p> In addition to a great compensation package, paid time off, and paid parental leave, many Avalara employees are eligible for bonuses. </span></p> Health &; Wellness</u> </span> Inclusive culture and diversit</u>y </span> We’re defining the relationship between tax and tech.</span></p> 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.</span></p> 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.</span></p> We’re An Equal Opportunity Employer</span></strong></p> 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.</span></p>
In this role, you will:</p>
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</p></li>What Your Responsibilities Will Be</h3>
1. High-Velocity Growth Experimentation</span></h3>
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</p></li></ul>2. Agentic Growth Loops &; AI Customer Experience (AI CX)</span></h3>
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</p></li></ul>3. Self-Serve Expansion &; Monetization</span></h3>
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</p></li></ul>4. Telemetry, Analytics &; Experimentation Rigor</span></h3>
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</p></li>What You’ll Need To Be Successful</h3>
Required Qualifications:</span></h3>
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</p></li></ul>Preferred Qualifications:</span></h3>
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</p></li>Avalara is an AI-first Company</h3>
How We’ll Take Care Of You</h3>
Benefits vary by location but generally include private medical, life, and disability insurance. </span></p>
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. </span></p>What You Need To Know About Avalara</h3>
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