Principal Software Engineer (AI Tooling & Adoption)

TL;DR

Principal Software Engineer (AI Tooling & Adoption): Lead an AI adoption initiative across a large engineering organization by evaluating and integrating AI coding tools into development workflows with an accent on LLM/prompt capabilities, CI/CD integration, security & compliance, and measurable productivity impact. Focus on transforming 500+ engineers into “Bionic Engineers” while implementing “Virtual Engineer” capabilities and building an adoption roadmap with KPIs and enablement at scale.

Location: Oakland, California, United States

Salary: $225,813 — $282,266 USD

Company

Fivetran and dbt Labs are building the data infrastructure layer that helps organizations move, transform, and trust their data for analytics and AI.

What you will do

• Drive engineering-wide cultural transformation from AI-curious to AI-native practices using data-driven change management and enablement.
• Define KPIs and measure adoption progress (from 50% to 100%), running interventions to accelerate uptake.
• Evaluate and select AI development tools (e.g., Copilot, Claude Code, Codex) and recommend them based on evidence.
• Design technical frameworks to integrate AI tools into existing development workflows and CI/CD pipelines.
• Lead proof-of-concepts for “Virtual Engineer” coding agents (e.g., standardized tasks, refactoring, test generation).
• Partner on security and compliance for AI tool usage, and optimize performance and cost-efficiency of AI deployments.

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 (e.g., GitHub Copilot, ChatGPT, Claude).
• Strong understanding of LLMs and prompt engineering, including model capabilities and limitations.
• Experience with CI/CD and DevOps practices in modern software development workflows.
• Proven ability to lead technical initiatives across large engineering organizations (500+ people) and influence senior technical leaders without authority.
• Track record of successful change management and presenting AI initiatives and ROI to C-level executives.

Culture & Benefits

• Hybrid work model with two days in the office each week.
• 100% employer-paid medical insurance.
• Generous paid time-off (PTO), paid sick time, inclusive parental leave, holidays, and volunteer days off.
• RSU stock grants and professional development/training opportunities.
• Monthly cell phone stipend and access to a mental health support platform.

Hiring process

• Interview process includes evaluation of technical leadership, AI tooling adoption approach, and ability to drive measurable change.
• Recruiting may reference both Fivetran and dbt Labs during the integration period.