Sr. Principal AI Systems Architect

From Fivetran’s founding until now, our mission has remained the same: to make access to data as simple and reliable as electricity. With Fivetran, customer data arrives in their warehouses, canonical and ready to query, with no engineering or maintenance required. We’re proud that more organizations continue to leverage our technology every day to become truly data-driven. About the Role Fivetran needs an engineer-architect who can make the AI analyst experience real, dependable, and extensible. This role owns the architecture behind the analyst AI system, including metadata contracts, tool interfaces, context assembly, prompt and skill orchestration, evaluation loops, and the operational patterns that make agents useful in real workflows instead of isolated demos. This is a systems role as much as an AI role. The challenge is not just getting an LLM to do something impressive once. The challenge is building a product-quality analyst system that can reason over schema and business context, use tools correctly, recover from ambiguity, and improve through disciplined evaluation and iteration. This is a full-time, hybrid position based at our Oakland, CA office. Our hybrid work model offers a blend of remote flexibility and in-person collaboration, including two days in the office each week to connect and build as a team. What You'll Do Define the architecture for the analyst AI stack across prompts, tools, metadata, memory and context strategies, evaluation, and runtime safety. Build the abstractions and interfaces that allow product teams to add new agent capabilities without creating brittle prompt sprawl. Design retrieval and context strategies that give the model the right information at the right time with strong cost, latency, and quality tradeoffs. Establish evaluation loops, benchmark suites, and review processes so model behavior can be measured, debugged, and improved systematically. Partner with product, engineering, and analyst-domain experts to translate real analytical workflows into robust AI-assisted product capabilities. Drive quality standards around correctness, trust, transparency, and failure handling in analyst-facing AI experiences. What We're Looking For Deep experience building AI-enabled product systems, not just running experiments. Strong software architecture skills, especially around APIs, contracts, orchestration, and system boundaries. Practical understanding of LLM prompting, tool use, retrieval, structured outputs, and evaluation methods. Ability to work fluently across backend engineering, product constraints, and user workflow design. Clear judgment about where agent systems should be flexible and where they should be constrained. Comfort working in ambiguous environments where patterns are still being invented. Why This Role Matters The quality of the AI analyst experience will shape how differentiated Fivetran feels. This role determines whether the system is merely novel or actually reliable enough to become part of an analyst's day-to-day workflow. Strong architecture here reduces product risk and creates leverage for the rest of the team. #LI-HYBRID #LI-DJ1 The compensation range displayed on this job posting reflects the minimum and maximum target for new hire compensation for the target position and level, and may include sales incentives or target bonuses depending on the role. Our compensation ranges are determined by role, level, and location. Our job titles may span more than one career level. Within the range, individual compensation is determined by additional factors, including job-related skills, experience, relevant education or training, business need, market demands. The compensation range is subject to change and may be modified in the future. Your recruiter can share more about the specific compensation range for your location during the hiring process. Oakland Pay Range $251,835 — $314,794 USD Perks and Benefits 100% employer-paid medical insurance * Generous paid time-of