Technical Chief of Staff to the CTO

GitLab

28d•Remote

About The Position

As the Technical Chief of Staff to the CTO, you'll scale the impact of GitLab's engineering leadership by closing the gap between technical vision and day-to-day execution. You'll partner closely with the CTO, executive leadership team, and senior engineers to align a multi-year technical vision with product strategy. You'll translate decisions into clear operating mechanisms and make sure they're documented in GitLab's Handbook to support our all-remote, asynchronous culture. You'll lead initiatives such as AI transformation and internal GitLab AI and large language model (LLM) feature testing. You'll define and implement unified metric frameworks to improve R&D quality and efficiency. You'll orchestrate the rhythm of business for the engineering organization, including staff meetings, quarterly business reviews, and offsites. In your first year, you'll be 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.

Requirements

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.

Responsibilities

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.