Principal Software Engineer, Fivetran

• 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

Desirable

• 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
• Technologies You’ll Use:
• Java, Postgres, Oracle, SQL Server, MySQL, Kubernetes, Docker, AWS, GCP, CircleCI
• Google Gemini, Anthropic Claude, Claude Code, ChatGPT, OpenAI Codex, GitHub Copilot
• Adoption Management & Leadership (40%):
• 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
• Technical Leadership (35%):
• 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
• Business Leadership (25%):
• 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