Principal Software Engineer, AI Tooling & Adoption

What You’ll Do

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

Skills We’re Looking For

Technical Expertise

• 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

Leadership Experience

• 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

Adoption & Enablement Skills

• 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

Bonus Skills

• 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

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