Staff Software Development Engineer

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 Youll 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.