Top Tech Jobs & Startup Jobs in Chicago, IL

Lead GitLab’s global Deal Desk to scale quote-to-cash for complex subscription and consumption deals. Own deal structure, approvals, bookings fidelity, reconciliations, and commercial guardrails while partnering with Sales, Finance, Product, Pricing, Legal, and Ops to operationalize pricing, automate workflows, and enable the field. Serve as executive escalation for non-standard transactions and improve systems, controls, and processes to support a consumption-first GTM.

Lead and grow a team of Solutions Architects serving public sector customers; drive technical pre-sales strategy, guide evaluations, collaborate with sales and cross-functional teams, improve team practices and execution, track KPIs, and act as a hands-on architect for strategic opportunities.

Serve as a trusted technical pre-sales advisor to financial services customers, leading technical discovery, demos, POCs/POVs, solution design, and workshops. Map GitLab and cloud-based DevSecOps capabilities to regulatory, security, and business requirements, collaborate with sales and product teams, and drive platform adoption and long-term customer advocacy.

As Manager of Solutions Architects, lead a team delivering technical solutions, mentor staff, and drive customer adoption of GitLab while collaborating across departments to ensure customer success and team performance.

As Lead Commercial Legal Counsel, you will negotiate complex commercial contracts, provide legal guidance, and manage risks for strategic transactions in a fast-paced environment.

The Solutions Architect will guide GitLab customers in North America through digital transformation by leveraging the DevSecOps platform, facilitate technical evaluations, and collaborate with sales teams to drive customer adoption and trust in GitLab's solutions.

As a Senior Contracts Manager, you will draft and negotiate complex agreements, advise on contract risks, and improve contracting processes in collaboration with Sales and Legal teams.

The Director, Enterprise Architecture & Intelligent Automation will define and govern GitLab's internal systems architecture, integration, and automation strategies to support business scaling and ensure compliance with enterprise standards.

Provide high-trust executive support to the CFO, managing complex calendars, communications, meetings, travel, expenses, and leadership cadences. Improve Office of the CFO operations, prepare briefings, track action items, coordinate with HR/IT/recruiting, and use AI and collaboration tools to increase efficiency and accountability.

Own and architect the TA technology stack: ATS configuration, integrations, and vendor management. Build, deploy, and monitor AI agents and automation workflows. Lead AI governance, bias auditing, compliance reviews, and enablement for recruiters. Drive roadmap, RFPs, and incident response for TA systems while providing performance reporting and documentation.