Staff Software Development Engineer

What You'll Do

Avalara is accelerating its AI-first transformation by building intelligent systems that automate complex compliance workflows. As we work toward our ambition of being part of every transaction in the world, we are investing in a Staff Software Development Engineer to build the next generation of production AI capabilities. You will be joining the Managed Tariff Code Classification team within Content Engineering. Our team handles cross-border transactions for major e-commerce customers (like Amazon, eBay, and Shopify). When products cross international borders, customs requires a Harmonized System (HS) code to identify the package contents. Our customers rely on our API and services to process massive catalogs of products and return the correct HS codes.

To solve this at scale, we use an agentic pipeline and AI-based classification. In this role, you will design multi-tenant, cloud-native services that handle this high classification throughput with low latency. You will bring an AI-first mindset to the team, pushing the boundaries of what is possible by building intelligent, agentic systems that autonomously plan, retrieve, and reason. We are looking for an AI Bar Raiser who applies proven design principles to deliver scalable solutions and makes the team permanently better by sharing AI-assisted development practices.

What Your Responsibilities Will Be

• Lead the end-to-end design of complex, distributed features and agentic AI workflows, from data flow and API contracts through to deployment and observability.

• Build high-quality backend services and APIs in Java (Spring Boot) and Python (FastAPI), and design asynchronous processing pipelines using message queues (e.g., AWS SQS).

• Deploy and operate cloud services on Kubernetes (AWS EKS), building in observability and embedding security best practices across all operations.

• Develop multi-step AI pipelines utilizing retrieval-augmented generation (RAG) and vector databases, implementing human-in-the-loop orchestration for intelligent escalation.

• Build and extend Model Context Protocol (MCP) server capabilities to expose classification APIs that AI agents and partner platforms can invoke autonomously.

• Elevate the engineering team by conducting high-quality code reviews, mentoring junior engineers, and driving measurable AI adoption through hands-on coaching and sharing agentic workflow patterns.

What You’ll Need To Be Successful

• Bachelor's degree in Computer Science.

• Minimum of 10 years of professional software engineering experience with a strong track record of senior-level technical ownership and impact.

• Extensive hands-on experience designing and building distributed backend systems, including RESTful APIs, microservices, and event-driven architectures.

• Proficiency in Java (Spring Boot) or Python (FastAPI / asyncio), with the ability to read and contribute across both stacks.

• Hands-on experience integrating LLMs or ML models into production systems, managing prompt design, output validation, and responsible AI governance.

• Proven experience deploying and operating services on cloud infrastructure (AWS preferred) using containerization and orchestration tools (Docker, Kubernetes).

• Demonstrated, hands-on AI usage that has produced measurable improvements in engineering or product outcomes—casual use is not sufficient; we expect you to accelerate your workflow with AI.

• Exceptional communication skills and a commitment to raising the bar for design, code quality, and engineering debate within a globally distributed team.

AI Bar Raiser Expectations

This role carries explicit Agentic AI expectations. Casual or passive AI use is not sufficient—AI must materially change what you and the team can deliver. We expect you to:

• Accelerate Your Engineering: Actively use AI-assisted tools (e.g., GitHub Copilot, Cursor) daily to reduce cycle time, draft specifications, and improve code quality, while critically evaluating and owning the final result.

• Build Agentic Capabilities: Design classification agents capable of full reasoning loops that autonomously plan, retrieve, and decide, ensuring transparent confidence signals and graceful human escalation.

• Govern Production AI: Secure LLM behavior in production by mitigating prompt injection, monitoring for drift, and applying responsible AI practices.

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.