Principal Software Engineer, Fivetran
AI Tooling & Adoption
$235.7-294.7k
+ RSU stock grants
2 days a week in office (Oakland, CA)
Automated data movement platform
Open for applications
Automated data movement platform
1001+ employees
Open for applications
$235.7-294.7k
+ RSU stock grants
2 days a week in office (Oakland, CA)
1001+ employees
Company mission
To make access to data s simple and reliable as electricity.
Role
Who you are
- 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
Desirable
- 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
What the job involves
- Fivetran is seeking an exceptional Principal Software Engineer to lead our AI adoption initiative across the Engineering organization
- This unique leadership role combines deep technical expertise with strategic business acumen and change management capabilities
- You will be the driving force behind transforming our 500+ engineers into “Bionic Engineers" while implementing Virtual Engineer capabilities to achieve 10% productivity gains in FY26 and 20% in FY27
- As the single point of contact for AI initiatives in Engineering, you will orchestrate an engineering-wide transformation that makes AI-driven productivity a core engineering competency
- This role requires someone who can navigate the rapidly evolving AI landscape, drive adoption across diverse teams, and deliver measurable business impact
- 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
- 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
Our take
Fivetran is a data integration company focused on one simple idea: making data easy to move and use. It provides a fully managed platform that automatically moves data from hundreds of sources into cloud destinations, helping team centralize information without building or maintaining complex pipelines. So, by handling the heavy lifting behind the scenes, Fivetran allows organizations to spend less time managing infrastructure and more time working on their data.
This approach has a real and growing impact, with more than 700 fully managed connectors, Fivetran supports hybrid and multi-cloud environments and keeps data accurate and secure as it flows into analytics and AI systems. Trusted by over 7,600 customers worldwide, the platform helps businesses standardize how data is collected and shared across teams, breaking down silos and making insights more accessible. And the result is a stronger data foundation that supports faster decision-making and innovation.
In 2025, the company's momentum was also recognized with a Microsoft Marketplace Partner of the Year Award and a finalist spot for Microsoft's Americas Emerging Partner of the Year. These milestones reflect its role in helping enterprises modernize data infrastructure on Microsoft Azure and prepare for AI-driven workloads. By continuing to deepen its partnerships and focus on reliable, automated data movement, Fivetran is well positioned to carry this success forward as organizations increasingly rely on data s the backbone of future intelligence.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-2% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Sep 2021
$565m
SERIES D
Jun 2020
$100m
SERIES C
Total funding: $727.7m
Company HQ
Downtown, Oakland, CA
Leadership
George Fraser
(CEO)George graduated with a PhD in Neurobiology from the University of Pittsburgh.
Taylor Brown
(COO)Taylor studied Business Administration (focusing on design strategy) at California College of the Arts to Masters level.
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