Principal Software Engineer, AI Tooling & Adoption

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. This is a full-time position based out of our Oakland office. Our hybrid work model offers a blend of remote flexibility and in-person collaboration, including two days in the office each week.

Responsibilities

Drive cultural transformation from AI-curious to AI-native engineering practices across all teams; Champion change management by converting skeptics into advocates; Measure and accelerate adoption, tracking progress from the current 50% to 100% adoption; Build communities of practice for knowledge sharing and peer-to-peer learning; Continuously assess emerging AI tools 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; Partner with Security and Legal teams to ensure AI tool usage protects IP and meets compliance requirements; Establish best practices, guidelines, and guardrails for AI-assisted development; Analyze and optimize the technical performance and cost-efficiency of AI tool deployments; Develop and execute the three-phase AI adoption roadmap; Oversee $1M+ annual tool budget and demonstrate ROI; Build relationships with the CEO, Engineering Leadership, Finance, L&D, Legal, and Security teams; Quantify productivity gains, cost savings, and strategic value of AI initiatives; Negotiate enterprise contracts and manage vendor relationships; Design and implement adoption playbooks for diverse teams; Identify and eliminate technical, cultural, and process obstacles to AI adoption; Regularly present adoption metrics, success stories, and ROI to engineering leadership and executives

Requirements

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 for different audiences; 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

Nice to have

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

Benefits

100% employer-paid medical insurance; Generous paid time away from work, 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, and volunteer days off; RSU stock grants; Professional development and training opportunities; Company virtual happy hours, free food, and team-building activities; Monthly cell phone stipend; Access to a mental health support platform offering therapy, coaching, and self-guided mindfulness exercises for covered employees and dependents