Principal Engineer, Monetization Engineering

About the role

We are looking for a Principal Engineer to help define and drive the next generation of GitLab’s Fulfillment platform.

Fulfillment ensures that customers receive the right product access and can manage seats, usage, and spend across GitLab.com, Self-Managed, Dedicated, and other deployment models. Its core areas include entitlements, licensing and provisioning, seat management, usage visibility, and cost management.

The existing platform has served GitLab for approximately a decade and now faces significant challenges in scale, maintainability, and architectural complexity. This role will help us understand where we are today and define how Fulfillment should work over the next ten years.

This is a senior player-coach role. You will set architectural direction across the Fulfillment portfolio, make critical technical decisions, and work directly with teams to execute the resulting modernization strategy. You will influence across organizational boundaries while remaining hands-on in design, implementation, technical problem-solving, and mentorship.

What you’ll do

• Define and communicate the long-term architecture and technical strategy for Fulfillment, including target state, principles, priorities, and migration sequencing.
• Assess the current platform and address its most important risks across scale, reliability, performance, data correctness, operability, and maintainability.
• Drive architectural decisions across entitlements, provisioning, seat management, usage visibility, and cost management.
• Establish clear service boundaries, data ownership, contracts, and integration patterns across Fulfillment, Monetization, billing, Salesforce, and product services.
• Lead an incremental modernization program that improves the existing platform while continuing to deliver customer and business value.
• Partner with Engineering Managers, Product Management, and cross-functional stakeholders to turn architectural direction into executable roadmaps and shipped outcomes.
• Be hands-on with the hardest problems, including prototypes, critical implementations, migrations, performance improvements, reliability work, and incident learning.
• Champion practical artificial intelligence (AI) adoption across Fulfillment, including agentic coding and AI-assisted engineering workflows, and help teams apply these tools responsibly and effectively.
• Mentor and coach Senior and Staff Engineers and raise the quality of technical decision-making across the organization.

What you’ll bring

• 10+ years of professional software engineering experience, including substantial experience at Staff, Principal, or equivalent technical leadership level.
• Direct experience building, operating, or modernizing Fulfillment systems, including areas such as entitlements, licensing, provisioning, subscription lifecycle, seat management, usage metering, usage billing, or cost controls.
• A track record of setting technical direction across multiple teams and turning architecture into reliable, operated systems.
• Deep experience with distributed systems, scalability, availability, performance, observability, data integrity, and failure-mode analysis.
• Comfort working in one or more of Ruby, Go, and Python, with the ability to navigate both Backend and Frontend in a polyglot system.
• Practical experience using artificial intelligence in software engineering, including agentic coding or AI-assisted development workflows.
• Demonstrated success modernizing mature or degraded platforms without relying on a risky “big bang” rewrite.
• Experience designing systems that span multiple deployment models, such as software as a service, Self-Managed, Dedicated, or disconnected environments.
• Strong product and business judgment, with the ability to connect technical investment to customer experience, revenue, operational efficiency, risk reduction, and time to market.
• Excellent written communication and the ability to influence senior stakeholders across teams without formal authority.