Top Tech Jobs & Startup Jobs in Chicago, IL

Own the technical strategy for GitLab’s strategic technology partnerships, translating partner roadmaps into integrations, architecture, and product opportunities. Evaluate AI models and agents, build prototypes, facilitate technical workshops, develop business cases, and influence product roadmaps. Coordinate Engineering, Product, Finance, FinOps, Sales, Marketing, R&D, and partner teams through delivery while tracking cloud, AI, and DevSecOps developments. The role is remote and requires quarterly travel with EMEA-overlapping hours.

Lead the vision, strategy, roadmap, and adoption of GitLab’s test and code coverage capabilities. Identify customer problems involving pipeline failures, flaky tests, test automation, coverage, and recovery. Partner with Engineering and Design to create agent-driven workflows for diagnosis, test optimization, coverage analysis, and safe recovery. Measure outcomes, validate solutions with customers, influence cross-functional stakeholders, and mentor product managers.

Leads an eight-person analytics engineering team and sets strategy for trusted semantic models, governed data, enterprise BI, AI-powered data access, and production data applications. Oversees data modeling, evaluation datasets, telemetry, LLM routing, governance, security, and self-service capabilities. Partners cross-functionally to establish engineering standards, roadmaps, and measurable business impact while hiring, coaching, and developing team members.

Leads FP&A for GitLab’s R&D organization and serves as strategic finance partner to the CTO. Owns annual planning, rolling forecasts, headcount and cost planning, investment decisions, efficiency metrics, financial modeling, and process redesign. Evaluates AI, cloud, tooling, and build-versus-buy investments; partners with Accounting, Procurement, and People teams; drives AI-enabled finance transformation; and leads and develops the R&D finance team.

Build GitLab code security capabilities spanning dependency analysis, SBOM and lockfile parsing, vulnerability detection, AI-assisted analyzers, and automated dependency remediation. Design evaluation harnesses, package analyzers for CI and AI workflows, improve security report accuracy, and extend ecosystem coverage. Own initiatives from design through delivery, mentor engineers, collaborate across product and engineering teams, document systems, and participate in on-call support.

Leads the architecture and delivery of GitLab’s static analysis engine and evaluation tooling. Owns program modeling, vulnerability detection quality, SAST rules, AI-assisted development guardrails, and benchmark validation. Sets technical direction, mentors engineers, coordinates complex initiatives, contributes to research and open source, and participates in on-call rotations. The role requires deep program analysis, application security, systems programming, performance optimization, containerized CI/CD, and experience building trustworthy LLM tooling.

Supports Workday and other People Technology systems by managing recurring processes, security roles, audits, configurations, testing, upgrades, reports, dashboards, documentation, and data loads. Partners with People Operations, HR business partners, and Talent Acquisition to resolve issues, improve processes, support SOX controls, train users, and deliver system enhancements in a remote environment.

Lead securities, public company reporting, corporate governance, entity management, and M&A legal work for GitLab. Manage SEC filings, proxy statements, board matters, equity plans, subsidiary governance, transactions, and outside counsel. Advise senior stakeholders on legal risks, maintain compliance processes, and create scalable legal playbooks, templates, and workflows. Collaborate with globally distributed cross-functional teams and train junior legal professionals.

Owns and improves the operational toolkit supporting Solutions Architects, including systems, workflows, reporting, documentation, support requests, engagement tracking, capacity planning, and data quality. Partners with revenue technology, analytics, and system owners to translate field needs into requirements, automate processes, improve handoffs, and sustain adoption. Supports SA leadership through reporting, business reviews, operating rhythms, testing, rollouts, and continuous operational improvements.

Manage the AMER Support Engineering team, including hiring, mentorship, performance development, and technical growth. Lead customer support quality, process improvement, automation, AI adoption, and cross-functional collaboration. Build scalable workflows, promote team ownership and psychological safety, and ensure Support Engineers resolve complex technical issues throughout the support lifecycle. Partner with product and development teams to improve customer outcomes and support efficiency.