Top Tech Jobs & Startup Jobs in Chicago, IL

Lead customer trust and security governance: oversee contract reviews, security questionnaires, and escalations; partner with Legal, Sales, Product, and Procurement; develop templates, policies, playbooks, metrics, and awareness programs; and apply automation and AI to scale workflows and reporting.

Lead and execute technology audits across cloud, application, and cybersecurity domains to support SOX compliance. Design and test IT general, application, and entity-level controls; perform risk-based planning, testing, and reporting; drive remediation with process owners; and apply data analytics, automation, and generative AI to improve audit quality and efficiency.

Lead renewal analytics and forecasting for direct and channel motions. Build renewal health scoring and predictive models, improve Clari and SFDC processes, surface churn and expansion insights, partner with RevOps/Finance/IT, automate reporting, and present recommendations to senior stakeholders to improve retention and renewal performance.

Lead GitLab's corporate and compliance legal function, advising C-suite and board on governance, securities, SEC reporting, equity compensation, executive compensation, and M&A. Build and manage a remote corporate legal team, implement policies and templates, oversee equity plan administration, manage outside counsel, champion AI-enabled legal workflows, and ensure compliance with public company obligations.

Manage a book of public-sector accounts to drive adoption, retention, and expansion of the GitLab DevSecOps platform. Translate pre-sales plans into measurable objectives, coach customers on Git, CI/CD, and DevSecOps best practices, coordinate cross-functionally for escalations, and use project management to deliver customer enablement and success initiatives.

As Commercial Legal Counsel at GitLab, you will negotiate and draft various complex agreements, advise on risk allocation, support public sector transactions, and enhance the legal team's efficiency and training initiatives.

Own and grow a strategic book of business across Federal Systems Integrators by aligning GitLab's DevSecOps platform to mission priorities. Build account plans, navigate complex procurement, lead pre- and post-sales activities, collaborate with cross-functional teams and resellers, drive adoption, and contribute customer feedback to product development.

Lead the field organizations AI adoption by defining enablement roadmaps, identifying and piloting high-impact field use cases, driving operational scale, building field champions, and owning governance for safe, compliant AI tool adoption. Partner with product, engineering, ops, and analytics to measure impact and embed AI into day-to-day sales workflows.

Design, build, and maintain People systems automations and integrations (Workato, Workday, Greenhouse, Slack) using production-quality code. Improve CI/CD, reliability, observability, and AI-driven automation (Claude, MCP). Serve as technical lead for People Technology, partner with stakeholders, and drive scalable, maintainable automation solutions.

Maintain an inventory of AI tools, index field use cases, track adoption and utilization, manage access requests and provisioning, ensure AI data hygiene, produce simple reporting, and create communications and micro-enablement to drive field AI adoption.