Principal Software Engineer, AI Tooling & Adoption

Fivetran • Oakland, CA

2h • $225,813 - $282,266 • Hybrid

About The Position

Fivetran is building data pipelines to power the modern data stack for thousands of companies. 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. 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. 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 to connect and build as a team.

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 Haves

• 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

Responsibilities

• Drive Cultural Transformation: Lead the evolution from AI-curious to AI-native engineering practices across all teams
• Champion Change Management: Convert skeptics into advocates through data-driven demonstrations of value and hands-on enablement
• Measure & Accelerate Adoption: Establish KPIs, track progress from the current 50% to 100% adoption, and implement interventions to accelerate uptake
• Build Communities of Practice: Create forums for knowledge sharing, celebrate wins, and foster peer-to-peer learning
• Tool Evaluation & Selection: Continuously assess emerging AI tools (Copilot, Claude Code, Codex, etc.) and make data-driven recommendations
• Architecture & Integration: Design technical frameworks for integrating AI tools into existing development workflows and CI/CD pipelines
• Virtual Engineer Implementation: Lead proof-of-concepts for coding agents in standardized tasks (Lite Connectors via CoIL, code refactoring, test generation)
• Security & Compliance: Partner with Security and Legal teams to ensure AI tool usage protects IP and meets compliance requirements
• Technical Standards: Establish best practices, guidelines, and guardrails for AI-assisted development
• Performance Optimization: Analyze and optimize the technical performance and cost-efficiency of AI tool deployments
• Innovation Pipeline: Maintain awareness of cutting-edge AI developments and identify opportunities for competitive advantage
• Strategic Planning: Develop and execute the three-phase AI adoption roadmap (Explore & Learn → Enable, Train & Adopt → Core Competency)
• Budget Management: Oversee $1M+ annual tool budget, optimize spend across 500+ team members, and demonstrate ROI
• Stakeholder Management: Build relationships with the CEO, Engineering Leadership, Finance, L&D, Legal, and Security teams
• Business Case Development: Quantify productivity gains, cost savings, and strategic value of AI initiatives
• Vendor Relations: Negotiate enterprise contracts, manage vendor relationships, and influence product roadmaps
• Cross-functional Collaboration: Work with Program Managers, Engineering Managers, and other non-IC roles to extend AI benefits
• Competitive Intelligence: Monitor industry trends and ensure Fivetran maintains a leadership position in AI-augmented engineering
• Enable Success at Scale: Design and implement adoption playbooks that work across diverse teams with varying technical backgrounds
• Remove Barriers: Identify and systematically eliminate technical, cultural, and process obstacles to AI adoption
• Communicate Impact: Regularly present adoption metrics, success stories, and ROI to engineering leadership and executives

Benefits

• 100% employer-paid medical insurance
• Generous paid time-off policy (PTO), plus paid sick time, inclusive parental leave policy, holidays, and volunteer days off
• RSU stock grants
• Professional development and training opportunities
• Company virtual happy hours, free food, and fun team-building activities
• Monthly cell phone stipend
• Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching, and self-guided mindfulness exercises for all covered employees and their covered dependents.

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Education Level: No Education Listed