Technical Chief of Staff to the CTO

Technical Chief of Staff to the CTO at GitLab

GitLab is the intelligent orchestration platform for DevSecOps. We enable organizations to increase developer productivity, improve operational efficiency, reduce security and compliance risk, and accelerate digital transformation. More than 50 million registered users and over 50% of the Fortune 100 trust GitLab to ship better, more secure software faster.

Our product principles are reflected in our team's work: we embrace AI as a core productivity multiplier, expecting all team members to integrate AI into daily workflows for efficiency, innovation, and impact. GitLab is where careers accelerate, innovation flourishes, and every voice is valued. Our high-performance culture, driven by values and continuous knowledge exchange, empowers team members to reach full potential while collaborating with industry leaders to solve complex problems. Co-create the future with us as we build technology that transforms how the world develops software.

An Overview of This Role

As the Technical Chief of Staff to the CTO, you will amplify the impact of GitLab's engineering leadership by bridging the gap between technical vision and daily execution. You will collaborate closely with the CTO, executive leadership team, and senior engineers to align a multi-year technical vision with product strategy. Your role involves translating decisions into clear operating mechanisms, documented in GitLab's Handbook to support our all-remote, asynchronous culture. You will spearhead initiatives such as AI transformation and internal GitLab AI and large language model (LLM) feature testing. Additionally, you will define and implement unified metric frameworks to enhance R&D quality and efficiency. You will orchestrate the rhythm of business for the engineering organization, including staff meetings, quarterly business reviews, and offsites. In your first year, you are expected to establish trusted proxy relationships on behalf of the CTO, drive measurable improvements in engineering velocity and organizational health, and act as a key liaison for high-stakes moments, including board materials, M&A technical diligence, and major security or infrastructure incidents.

What You'll Do

• Lead the execution of the CTO's 3-year technical vision by aligning engineering and product strategy with clear priorities and accountable owners.
• Drive the technical narrative and content for board materials, investor decks, and keynotes, while owning competitive and market intelligence, including technical due diligence for potential acquisitions, to inform executive decisions and external storytelling.
• Guard and evolve the CTO's operating model by documenting decisions and processes in the GitLab Handbook and orchestrating the rhythm of business (staff meetings, quarterly business reviews, and offsites) to drive clear decisions, follow-through, and fewer unnecessary meetings.
• Lead GitLab's internal AI transformation as "Customer Zero," ensuring engineering teams adopt and rigorously test GitLab's AI and LLM capabilities and provide actionable feedback to Product.
• Implement and maintain standardized R&D metric frameworks such as DORA and SPACE to track and improve engineering quality, velocity, and efficiency.
• Partner with Finance, the executive leadership team, and the FinOps Technical Program Manager to steward the engineering budget and optimize infrastructure and cloud spend.
• Define and monitor organizational health metrics, collaborating with the People team on engagement, retention, and talent strategies while leading communication and change management for organizational pivots aligned with GitLab's values and mission across global teams.
• Serve as a trusted advisor and proxy to the CTO by synthesizing complex technical proposals into clear decision options, resolving executive-level escalations, unblocking cross-functional dependencies, and acting as a primary liaison during major security incidents or critical infrastructure issues, coordinating technical and executive communication to internal and external stakeholders.

What You'll Bring

• Executive Operations: 12+ years of experience, including 3+ years as a direct partner to an executive, managing an R&D organization of 500–1,000+ members.
• Strategic Influence: Proven track record of drafting Board of Directors materials or lead-managing annual strategic planning and long-range technical roadmaps.
• Massive Scale Execution: Experience leading company-wide technical programs (e.g., migrations, security mandates) that impacted 1,000+ engineers and required cross-functional alignment across 5+ departments.
• Architectural Depth: Previous experience as a Director of Engineering or Principal TPM overseeing global scale high-availability systems (99.99%+), with the ability to bridge deep technical trade-offs and business ROI.
• Data-Driven Rigor: Expert-level implementation of DORA or SPACE frameworks, with a history of using these metrics to drive measurable improvements in developer productivity or system reliability.
• Organizational Design: Experience leading org-wide change management, including headcount allocation and talent strategy for departments with budgets exceeding $50M+.
• Communication Mastery: Exceptional ability to synthesize complex technical "noise" into 1-page executive briefs and drive alignment in a high-scale, asynchronous/distributed work environment.

About The Team

You'll be part of a small, high-impact group that connects engineering, product, finance, and people partners. We share context across senior leaders, pressure-test ideas, and help each other tackle complex technical and organizational problems. Team members come from varied backgrounds in engineering, product management, and operations, and we rely on clear writing, direct feedback, and a bias for iteration. You'll have peers who offer perspective, collaboration, and support as you take on ambiguous, high-impact work.

Key skills/competency

• Executive Operations
• Strategic Planning
• AI Transformation
• R&D Metrics (DORA/SPACE)
• Organizational Design
• Financial Stewardship
• Cross-functional Alignment
• Technical Due Diligence
• Executive Communication
• Incident Management