Principal Software Engineer, AI Tooling & Adoption

Triwill Group; Oakland (CA); Hybrid; USD 225,813 - 282,266; Full time

Benefits offered by this job

100% employer-paid medical insurance

RSU stock grants

Professional development

Job summary

Fivetran is seeking a Principal Software Engineer to lead our AI adoption initiative across the Engineering organization. You will drive the transformation of 500+ engineers into AI-native practices and oversee the implementation of Virtual Engineer capabilities to boost productivity.

This full-time role is based in our Oakland office with a hybrid schedule, two days in the office weekly, and collaboration across AI, security, and product teams.

Qualifications

• 10+ years of software engineering experience across multiple languages.
• Proven leadership of large engineering teams (500+ people).
• Experience driving AI tool adoption and change management.

Responsibilities

• Lead adoption management and drive AI-native engineering practices across teams.
• Evaluate and select AI tools; design integration into CI/CD pipelines.
• Oversee a multi-year AI adoption roadmap and measure KPI progress.

Skills

AI Adoption

Technical Leadership

Change Management

CI/CD

Tools

GitHub Copilot

Claude

ChatGPT

Job description

About Us

From Fivetran’s founding until now, our mission has remained the same: to make access to data as simple and reliable as electricity. With Fivetran, customer data arrives in their warehouses, canonical and ready to query, with no engineering or maintenance required. We’re proud that more organizations continue to leverage our technology every day to become truly data-driven.

Fivetran and dbt Labs are bringing together two industry-leading companies with a shared mission: helping organizations unlock the full value of their data. Together, we’re delivering the data infrastructure layer that helps organizations move, transform, and trust their data — from the moment data moves, through every transformation, to the context teams and AI systems rely on. Fivetran helps organizations automate data movement across the systems, clouds, engines, and tools they rely on. dbt Labs pioneered analytics engineering, helping teams transform data into reliable, governed insights. Together, we support thousands of organizations as they build a trusted foundation for analytics, AI, and better business decisions. As we bring our teams and technology together, we’re building on the strengths of both companies while continuing to deliver the products and experiences our customers know and trust. It’s an exciting time to join us: we’re creating a company with the scale, talent, and technology to help more organizations put their data to work with greater speed, confidence, and impact. During this transition period, you may see references to both Fivetran and dbt Labs throughout our recruiting process as we integrate our teams, systems, and career sites.

About the Role

Fivetran is building data pipelines to power the modern data stack for thousands of companies.

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.

This is a full‑time position based out of our Oakland office. Our hybrid work model offers a blend of remote flexibility and in‑person collaboration, including two days in the office each week to connect and build as a team.

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

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: Negotiating 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

#LI-HYBRID #LI-EM1

The compensation range displayed on this job posting reflects the minimum and maximum target for new hire compensation for the target position and level, and may include sales incentives or target bonuses depending on the role. Our compensation ranges are determined by role, level, and location. Our job titles may span more than one career level. Within the range, individual compensation is determined by additional factors, including job‑related skills, experience, relevant education or training, business need, market demands. The compensation range is subject to change and may be modified in the future. Your recruiter can share more about the specific compensation range for your location during the hiring process.

Oakland Pay Range

$225,813 — $282,266 USD

Perks and 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.

*May vary by country and worker type - please reach out to your recruiter for more information

Fivetran brings together high‑quality talent across the globe to make data access as easy and reliable as electricity for our customers. We value and recognize that our customers benefit from having innovative teams made of people from many backgrounds, experiences, and identities. Fivetran promotes diversity, equity, inclusion & belonging through attracting, recruiting, developing, and retaining a diverse workforce, not only because it is the right thing to do, but because it helps us build a world‑class company to better serve our customers, our people and our communities.

We are committed to ensuring that all candidates have an equal opportunity to participate in our interview process. If you require accommodations at any stage of the process due to a disability, medical condition, or any other circumstance, please don't hesitate to submit your request by filling out this form. We will work with you to provide reasonable accommodations to facilitate your participation and ensure a fair and accessible interview experience. Your request and any information provided will be kept confidential and will not impact your candidacy. We look forward to hearing from you and accommodating your needs to the best of our ability.