Top Tech Jobs & Startup Jobs in Chicago, IL

Lead pricing strategy and packaging across GitLab’s SaaS portfolio, including AI and usage-based products. Analyze market, competitor, customer, and usage data; build financial models; evaluate monetization opportunities; support product launches and SKU mapping; monitor post-launch results; and influence senior leaders across Product, Marketing, Finance, Sales, Deal Desk, and fulfillment.

Build and improve GitLab authentication services across Ruby on Rails and Go codebases. Design token issuance, validation, identity, access management, passwordless authentication, workload identity federation, and secure automation features. Migrate authentication paths to GATE while supporting multiple deployment models, address reported vulnerabilities, optimize performance, review code, establish engineering standards, and collaborate on complex projects in a remote, asynchronous environment.

Drive enterprise sales growth across California by managing strategic accounts, generating pipeline, and expanding GitLab’s AI-powered DevSecOps platform. Lead consultative sales cycles from discovery through negotiation and implementation; build C-level relationships, develop account plans, coordinate cross-functional and channel partners, forecast pipeline, analyze wins and losses, and communicate customer value through presentations and proposals.

Lead complex, end-to-end technical programs across product, engineering, data, and security teams. Translate strategic priorities into roadmaps, manage risks and dependencies, coordinate distributed teams, and align executive stakeholders. Drive AI platform, data, infrastructure, security, reliability, and enterprise adoption initiatives from inception through launch and continuous improvement while ensuring predictable execution and transparent communication.

The Staff Forward Deployed Engineer at GitLab works with strategic accounts to adopt GitLab and GitLab Duo Agent Platform, guiding technical discovery and building reusable solutions for complex enterprise environments.

Partners with engineering and finance leaders on cloud and AI infrastructure investments. Manages expenses, forecasts, accruals, allocations, reconciliations, variance analysis, and month-end close. Builds financial models, analyzes cloud billing and operational data, supports annual planning, and translates findings into recommendations. Collaborates cross-functionally with procurement, accounting, product, and engineering teams while using AI tools to automate finance workflows in a remote, asynchronous environment.

Serves as strategic partner and force multiplier to the Chief Revenue Officer, driving revenue leadership operations, strategic planning, goal tracking, executive and board communications, customer and partner engagement, and cross-functional resolution of business priorities. The role manages CRO office initiatives, optimizes executive time, builds scalable operating processes, and coordinates with senior leaders across Sales, Finance, Operations, People, and other teams.

Lead corporate endpoint security architecture with a focus on macOS, designing secure-by-default controls, automation, patching, software distribution, and security baselines across macOS, iOS, Windows, and Linux. Manage configurations through Terraform, GitOps, version control, CI pipelines, and automated rollouts. Partner with IT and security teams to improve telemetry, detection, response, auditability, and operational efficiency. Mentor engineers and serve as a senior escalation point for complex endpoint security issues in a fully remote environment.

Advise enterprise customers on GitLab adoption, DevSecOps practices, Git workflows, CI/CD, and platform maturity. Own a customer portfolio, develop success plans, lead technical workshops and Accelerator programs, coordinate escalations across internal teams, analyze usage signals, and drive adoption, retention, expansion, and customer satisfaction.

Design, produce, and deliver internal events (virtual, hybrid, occasional in-person) to strengthen connection and align employees with company priorities. Own event lifecycle from concept, budgeting, vendor management, and production to measurement; partner with executives and cross-functional teams; use event tech and AI tools to scale inclusive, accessible experiences for a global remote workforce.