Top Tech Jobs & Startup Jobs in Chicago, IL

Own and evolve GitLab’s authorization systems across its Ruby on Rails monolith and next-generation Rust policy engine. Design fine-grained permissions for users, tokens, roles, and AI agents; secure GraphQL and REST APIs; lead feature-flagged rollouts and migrations; improve performance and reliability; and collaborate across authentication, platform, AI, and modular-service teams in a distributed asynchronous environment.

Provides cross-team technical leadership for complex backend initiatives, modular architecture, monolith modernization, API and platform standards, production operations, and AI-assisted engineering adoption. Designs shared patterns for services, data, eventing, security, testing, observability, deployment, and reliability. Partners with Product and Engineering leadership, mentors engineers, participates in incident response, and drives technical strategy without formal authority.

Delivers federal GitLab implementation work across FedRAMP, DoD, classified, and air-gapped environments. Installs, configures, upgrades, hardens, troubleshoots, and migrates GitLab deployments; supports compliance authorization; leads technical workshops; documents runbooks and automation; manages delivery risks; and collaborates with government stakeholders, architects, Product, and Engineering.

Build, test, ship, and operate production backend features with minimal guidance. Design APIs, background jobs, integrations, data models, migrations, and bounded services while maintaining security, performance, observability, and reliability. Review code, improve automated testing, investigate production issues, address technical debt, participate in operational support, and collaborate asynchronously with product, frontend, infrastructure, and security teams. Use AI coding tools responsibly by validating and correcting generated output.

Owns GitLab’s global security awareness and human-risk program, including training, phishing simulations, behavior-change initiatives, security culture campaigns, multimedia content, platform administration, reporting, vendor management, policy support, audit evidence, and remediation tracking. The role requires measurable risk reduction across a globally distributed enterprise and strategic influence across technical and non-technical teams.

Lead infrastructure security for GitLab’s FedRAMP and federal cloud environments. Set technical direction, architecture, security automation, and compliance patterns; own security posture; lead threat modeling, security reviews, continuous monitoring, and authorization-impacting initiatives. Partner with SRE, engineering, compliance, and leadership to drive remediation and roadmap decisions. Apply AI to constrained security workflows, mentor engineers, and influence security practices across GitLab offerings.

Owns GitLab’s enterprise pricing, packaging, monetization, and commercialization strategy. Develops pricing programs, enterprise agreements, bundling, channel and cloud marketplace structures, discounting frameworks, and competitive deal plays. Partners with Product, Sales, Finance, Marketing, Deal Desk, Revenue Operations, and partners to implement scalable commercial programs. Creates pricing enablement materials, makes data-backed recommendations, influences senior stakeholders, and documents decisions in an asynchronous, globally distributed environment.

Leads more than 10 engineers across Agent Tools, Agent Observability, and Runner Execution. Responsibilities include hiring, coaching, prioritization, technical design, AI tool standards, safe agent execution, sandboxing, observability, and cross-functional partnership across GitLab’s AI organization.

Leads technical direction and develops fullstack purchase experiences using Ruby on Rails and Vue.js. Designs resilient transactional flows, integrates billing and CRM systems, improves reliability and rollout safety, mentors engineers, reviews code, reduces technical debt, and participates in incident response. Partners with Product, Design, Billing, and Support to improve GitLab’s purchase, subscription, discount, and upgrade workflows.

Own operational processes, reporting, and programs for Customer Success Management. Translate ambiguous leadership questions into solutions, improve processes end-to-end, partner with Revenue Technology/Analytics, support planning (capacity, segmentation, territory), and drive cross-functional alignment with Sales and Finance to scale CS operations.