Fivetran · 2 days ago
Principal Software Engineer - AI Tooling & Adoption
Oakland, California, United States, AMER
Full-time
Hybrid
Lead/Staff
$236K/yr - $295K/yr
10+ years expFivetran is a company dedicated to simplifying data access and empowering organizations to be data-driven. They are seeking a Principal Software Engineer to lead AI adoption initiatives across the engineering organization, driving cultural transformation and technical leadership to enhance productivity through AI tools.
AnalyticsCloud Data ServicesData Integration
Responsibilities
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
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
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
Qualification
Required
10+ years of software engineering experience with proven expertise across multiple programming languages and paradigms
Experience with Fivetran's tech stack (Java, Python, C, SQL, Bazel, React)
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
Preferred
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
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
Company virtual happy hours, free food, and fun team-building activities
Monthly cell phone stipend
Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching, and self-guided mindfulness exercises for all covered employees and their covered dependents.
Company
Fivetran
Fivetran is a technology company that automates replicating data into a cloud data platforms.
1001-5000 employees
H1B Sponsorship
Fivetran has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (11)
2024 (11)
2023 (8)
2022 (30)
2021 (13)
2020 (12)
Funding
Current Stage
Late StageTotal Funding
$853.11MKey Investors
Vista Credit PartnersAndreessen HorowitzMatrix
2023-05-18Debt Financing· $125M
2021-09-20Series D· $565M
2020-06-30Series C· $100M
Leadership Team
George Fraser
Chief Executive Officer
Taylor Brown
COO & Cofounder
Recent News
General Catalyst
2025-12-30
The Philadelphia Inquirer
2025-12-19
Morningstar.com
2025-12-11
Company data provided by crunchbase