Principal Software Engineer, AI Tooling & Adoption

Fivetran and dbt Labs are bringing together two industry-leading companies with a shared mission: helping organizations unlock the full value of their data. Fivetran automates data movement across systems, clouds, engines, and tools, while dbt Labs pioneered analytics engineering. Together, they support thousands of organizations building a trusted foundation for analytics, AI, and better business decisions.

Fivetran is seeking a Principal Software Engineer to lead AI adoption across the Engineering organization. This role combines deep technical expertise with strategic business acumen and change management. You will drive the transformation of 500+ engineers into “Bionic Engineers” and implement Virtual Engineer capabilities to achieve 10% productivity gains in FY26 and 20% in FY27. As the single point of contact for AI initiatives in Engineering, you will orchestrate an engineering-wide transformation making AI-driven productivity a core competency.

• Lead cultural transformation from AI-curious to AI-native engineering practices.
• Champion change management, converting skeptics into advocates through data-driven demonstrations and hands-on enablement.
• Measure and accelerate adoption, tracking progress from 50% to 100% adoption.
• Build communities of practice for knowledge sharing and peer-to-peer learning.
• Evaluate and select emerging AI tools (Copilot, Claude Code, Codex, etc.) and make data-driven recommendations.
• Design technical frameworks for integrating AI tools into development workflows and CI/CD pipelines.
• Lead proof-of-concepts for coding agents in standardized tasks (Lite Connectors via CoIL, code refactoring, test generation).
• Partner with Security and Legal to ensure AI tool usage protects IP and meets compliance.
• Establish best practices, guidelines, and guardrails for AI-assisted development.
• Analyze and optimize technical performance and cost-efficiency of AI tool deployments.
• Develop and execute a three-phase AI adoption roadmap (Explore & Learn → Enable, Train & Adopt → Core Competency).
• Oversee $1M+ annual tool budget, optimize spend across 500+ team members, and demonstrate ROI.
• Build relationships with CEO, Engineering Leadership, Finance, L&D, Legal, and Security teams.
• Quantify productivity gains, cost savings, and strategic value of AI initiatives.
• Negotiate enterprise contracts, manage vendor relationships, and influence product roadmaps.
• Design and implement adoption playbooks that work across diverse teams.
• Remove technical, cultural, and process obstacles to AI adoption.
• Communicate adoption metrics, success stories, and ROI to engineering leadership and executives.

• 10+ years of software engineering experience with proven expertise across multiple programming languages and paradigms.
• Deep hands-on experience with AI-powered development tools (GitHub Copilot, ChatGPT, Claude, etc.).
• Strong understanding of LLMs, prompt engineering, and AI model capabilities/limitations.
• Experience with CI/CD, DevOps practices, and modern software development workflows.
• Track record of evaluating and implementing new technologies at scale.
• Proven ability to drive technical initiatives across large engineering organizations (500+ people).
• Experience leading without authority and influencing senior technical leaders.
• Track record of successful change management in engineering contexts.
• Demonstrated ability to convert technical innovations into business value.
• Experience presenting to C-level executives and board members.
• Experience driving tool adoption across diverse technical teams.
• Strong communication skills with the ability to create compelling narratives.
• Track record of building training programs and enablement materials.
• Data-driven approach to measuring and improving adoption metrics.
• Patience and empathy when working with skeptics and late adopters.

• Experience with Fivetran's tech stack (Java, Python, C, SQL, Bazel, React).
• Background in developer productivity, platform engineering, or DevEx roles.
• Experience with virtual agents/coding assistants in production environments.
• Knowledge of AI/ML fundamentals and enterprise AI governance.
• Previous experience in high-growth SaaS companies.

Oakland Pay Range: $225,813—$282,266 USD. Benefits include 100% employer-paid medical insurance, generous paid time away including paid vacation or flexible/unlimited vacation depending on role and country, paid sick time, inclusive parental leave, paid holidays including a year-end Global Week of Rest, volunteer days off, RSU stock grants, professional development and training opportunities, company virtual happy hours, free food, team-building activities, monthly cell phone stipend, and access to an innovative mental health support platform.

Apply through the Fivetran careers page for this role.