# Principal Software Engineer, AI Tooling & Adoption

**Company:** [Fivetran](https://hotfix.jobs/companies/fivetran)
**Location:** Oakland, CA
**Role:** ML Engineering
**Salary:** $226k – $282k/yr
**Experience:** 10+ years
**Skills:** Java, Python, SQL, Kubernetes, Docker, AWS, GCP, github copilot, LLMs, Prompt Engineering, CI/CD, DevOps, Bazel, React
**Posted:** 2026-07-23

> Lead AI adoption and transformation across a 500+ engineer organization to create "Bionic Engineers" and implement Virtual Engineer capabilities, targeting significant productivity gains. Requires 10+ years software engineering experience, deep expertise with AI coding tools like Copilot and Claude, change management, and executive-level influence.

## Job Description

## 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

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