Principal Software Engineer - AI Tooling & Adoption

Fivetran Inc.

Job Overview

Location

Oakland, California, United States, AMER

Job Type

Full-time

Full Job Description

📋 Description

• As the Principal Software Engineer for AI Tooling & Adoption at Fivetran, you will be the driving force behind transforming 500+ engineers into "Bionic Engineers" by implementing AI-driven productivity initiatives that target 10% gains in FY26 and 20% in FY27, directly impacting the company’s mission to make data access as simple and reliable as electricity.
• You will serve as the single point of contact for all AI initiatives in Engineering, orchestrating a company-wide cultural and technical transformation that embeds AI as a core engineering competency through strategic leadership, technical innovation, and business acumen.
• Day to day, you will drive cultural transformation by leading the shift from AI-curious to AI-native practices, championing change management to convert skeptics into advocates, measuring and accelerating adoption from 50% to 100%, and building communities of practice for knowledge sharing and peer-to-peer learning across engineering teams.
• You will provide technical leadership by evaluating and selecting emerging AI tools (GitHub Copilot, Claude Code, Gemini, etc.), designing architectures for integrating AI into CI/CD pipelines, leading proof-of-concepts for Virtual Engineers (coding agents) in tasks like Lite Connector development and test generation, ensuring security and compliance with IP protection, establishing technical standards and guardrails, optimizing performance and cost-efficiency, and maintaining an innovation pipeline for cutting-edge AI developments.
• In business leadership, you will develop and execute a three-phase AI adoption roadmap, manage a $1M+ annual tool budget with ROI demonstration, build stakeholder relationships with CEO, Engineering Leadership, Finance, L&D, Legal, and Security, develop business cases quantifying productivity gains, negotiate enterprise vendor contracts, collaborate cross-functionally with Program and Engineering Managers, monitor competitive intelligence, design scalable adoption playbooks, remove technical and cultural barriers, and communicate impact metrics to executives.
• You will work in a hybrid model from Fivetran’s Oakland, CA office, contributing to a company valued at over $5.6 billion that champions core values of Get Stuck In, Do the Right Thing, and One Team, One Dream, while promoting diversity, equity, inclusion, and belonging as a strategic advantage in serving global customers.
• This role offers the opportunity to learn and achieve mastery in enterprise-scale AI adoption, influence the future of AI-augmented software engineering at a high-growth SaaS leader, and leave a lasting legacy by embedding AI as a foundational competency that elevates the entire engineering organization’s productivity, innovation, and strategic impact.

🎯 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.) and strong understanding of LLMs, prompt engineering, and AI model capabilities/limitations
• Proven ability to drive technical initiatives across large engineering organizations (500+ people) and lead without authority while influencing senior technical leaders
• Experience driving tool adoption across diverse technical teams with a data-driven approach to measuring and improving adoption metrics
• Track record of evaluating and implementing new technologies at scale, including CI/CD, DevOps practices, and modern software development workflows
• Experience presenting to C-level executives and board members, with demonstrated ability to convert technical innovations into business value

🏖️ 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
• Monthly cell phone stipend
• Access to an innovative mental health support platform offering personalized care in therapy, coaching, and self-guided mindfulness exercises for employees and dependents

Skills & Technologies

Python

Java

React

PostgreSQL

MySQL

Senior

Remote

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Fivetran Inc.

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About Fivetran Inc.

Fivetran Inc. provides automated data integration software that replicates application, database, and event data into cloud data warehouses. It manages schema drift, incremental updates, and normalization, enabling analysts to query live data without engineering overhead. The company serves enterprises needing reliable, governed data pipelines across systems like Salesforce, MySQL, and Snowflake. Founded in 2012, it is headquartered in Oakland, California, with global offices, and operates on a subscription revenue model.

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