Principal Software Engineer - AI Tooling & Adoption

<div class="content-intro"><p>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.</p></div><p><span style="font-size: 10pt;"><strong>About the Role</strong></span></p> <p><span style="font-size: 10pt;">Fivetran is building data pipelines to power the modern data stack for thousands of companies.</span></p> <p><span style="font-size: 10pt;">Fivetran is seeking an exceptional Principal Software Engineer to lead our AI adoption initiative across the Engineering organization. This unique leadership role combines deep technical expertise with strategic business acumen and change management capabilities. You will be the driving force behind transforming our 500+ engineers into “Bionic Engineers" while implementing Virtual Engineer capabilities to achieve 10% productivity gains in FY26 and 20% in FY27.</span></p> <p><span style="font-size: 10pt;">As the single point of contact for AI initiatives in Engineering, you will orchestrate an engineering-wide transformation that makes AI-driven productivity a core engineering competency. This role requires someone who can navigate the rapidly evolving AI landscape, drive adoption across diverse teams, and deliver measurable business impact.</span></p> <p><span style="font-size: 10pt;">This is a full-time, hybrid position based out of 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.</span></p> <p><span style="font-size: 10pt;"><strong>Technologies You’ll Use</strong></span></p> <ul> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Java, Postgres, Oracle, SQL Server, MySQL, Kubernetes, Docker, AWS, GCP, CircleCI</span></li> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Google Gemini, Anthropic Claude, Claude Code, ChatGPT, OpenAI Codex, GitHub Copilot</span></li> </ul> <p><span style="font-size: 10pt;"><strong>What You’ll Do</strong></span></p> <p><em><span style="font-size: 10pt;">Adoption Management &amp; Leadership (40%)</span></em></p> <ul> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Drive Cultural Transformation: Lead the evolution from AI-curious to AI-native engineering practices across all teams</span></li> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Champion Change Management: Convert skeptics into advocates through data-driven demonstrations of value and hands-on enablement</span></li> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Measure &amp; Accelerate Adoption: Establish KPIs, track progress from the current 50% to 100% adoption, and implement interventions to accelerate uptake</span></li> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Build Communities of Practice: Create forums for knowledge sharing, celebrate wins, and foster peer-to-peer learning</span></li> </ul> <p><em><span style="font-size: 10pt;">Technical Leadership (35%)</span></em></p> <ul> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Tool Evaluation &amp; Selection: Continuously assess emerging AI tools (Copilot, Claude Code, Codex, etc.) and make data-driven recommendations</span></li> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Architecture &amp; Integration: Design technical frameworks for integrating AI tools into existing development workflows and CI/CD pipelines</span></li> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Virtual Engineer Implementation: Lead proof-of-concepts for coding agents in standardized tasks (Lite Connectors via CoIL, code refactoring, test generation)</span></li> <li style="font-size: 10pt;"><span style="font-size: 10pt;">Security &amp; Compliance: Partner with Security and Legal teams to ensure AI tool usage protects IP a