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Principal Software Engineer, AI Tooling & Adoption

Fivetran· Engineering Department
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Hybrid (Oakland, CA)$225.8k - $282.3kfull-timePosted 2mo ago

About the role

Principal software engineer leading Fivetran's AI adoption initiative across the Engineering organization, driving transformation to AI-native practices and implementing Virtual Engineer capabilities to achieve productivity gains. Hybrid role based in Oakland with two days in-office per week.

Responsibilities

  • Adoption Management & Leadership (40%) - Drive Cultural Transformation: Lead the evolution from AI-curious to AI-native engineering practices across all teams
  • Adoption Management & Leadership (40%) - Champion Change Management: Convert skeptics into advocates through data-driven demonstrations of value and hands-on enablement
  • Adoption Management & Leadership (40%) - Measure & Accelerate Adoption: Establish KPIs, track progress from the current 50% to 100% adoption, and implement interventions to accelerate uptake
  • Adoption Management & Leadership (40%) - 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 and make data-driven recommendations
  • Technical Leadership (35%) - Architecture & Integration: Design technical frameworks for integrating AI tools into existing development workflows and CI/CD pipelines
  • Technical Leadership (35%) - Virtual Engineer Implementation: Lead proof-of-concepts for coding agents in standardized tasks
  • Technical Leadership (35%) - Security & Compliance: Partner with Security and Legal teams to ensure AI tool usage protects IP and meets compliance requirements
  • Technical Leadership (35%) - Technical Standards: Establish best practices, guidelines, and guardrails for AI-assisted development
  • Technical Leadership (35%) - Performance Optimization: Analyze and optimize the technical performance and cost-efficiency of AI tool deployments
  • Technical Leadership (35%) - 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
  • Business Leadership (25%) - Budget Management: Oversee $1M+ annual tool budget, optimize spend across 500+ team members, and demonstrate ROI
  • Business Leadership (25%) - Stakeholder Management: Build relationships with CEO, Engineering Leadership, Finance, L&D, Legal, and Security teams
  • Business Leadership (25%) - Business Case Development: Quantify productivity gains, cost savings, and strategic value of AI initiatives
  • Business Leadership (25%) - Vendor Relations: Negotiate enterprise contracts, manage vendor relationships, and influence product roadmaps
  • Business Leadership (25%) - Cross-functional Collaboration: Work with Program Managers, Engineering Managers, and other non-IC roles to extend AI benefits
  • Business Leadership (25%) - Competitive Intelligence: Monitor industry trends and ensure leadership in AI-augmented engineering
  • Business Leadership (25%) - Enable Success at Scale: Design and implement adoption playbooks for diverse teams
  • Business Leadership (25%) - Remove Barriers: Identify and eliminate obstacles to AI adoption
  • Business Leadership (25%) - Communicate Impact: Regularly present adoption metrics and ROI to leadership

Qualifications

  • 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

Skills

Required:Software engineeringAI tooling & copilotsLLMs & prompt engineeringCI/CD & DevOpsChange managementCommunication to leadershipTraining & Enablement

Benefits

  • 100% employer-paid medical insurance
  • Generous paid time away from work, including vacation, sick time, parental leave, holidays, and Global Week of Rest
  • RSU stock grants
  • Professional development and training opportunities
  • Company virtual happy hours, free food, and team-building activities
  • Monthly cell phone stipend
  • Mental health support platform access for employees and dependents
Last updated Sep 23, 2026. Interested? Apply on the company site.
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About Fivetran

Moving data. Powering innovation.

Effortlessly centralize all the data you need so your team can deliver better insights, faster.

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