Top Tech Jobs & Startup Jobs in Chicago, IL

Build and deploy AI-powered solutions across Sales, Marketing, and Customer Support. Diagnose workflows, identify constraints, evaluate whether AI is appropriate, and own initiatives from discovery through deployment. Develop LLM applications using prompt engineering, RAG, agentic architectures, orchestration, guardrails, and enterprise integrations. Measure business value through flow metrics, adoption, ROI, and feedback loops while partnering with technical and non-technical stakeholders.

Lead GitLab’s US Government Support Engineering team, overseeing complex enterprise troubleshooting, case resolution, hiring, onboarding, coaching, escalation management, and process improvement. Partner with product and engineering teams to address government-specific needs, participate in manager on-call coverage, support critical incidents, and improve service delivery for regulated customers.

Own Secret Detection and Vulnerability Research as a product: define strategy across prevention, detection, validation, revocation, and reporting; ship detection content and intelligence with measurable quality; drive adoption, retention, and revenue; partner with engineering, research, and Field; use AI to accelerate research and productization.

Drive enterprise growth in the Seattle territory by leading complex B2B SaaS sales cycles for GitLab's AI-powered DevSecOps platform. Build C-level relationships, develop strategic account plans, coordinate cross-functional teams, manage full sales lifecycle from discovery to implementation, and drive net ARR and account expansion while contributing to forecasting and go-to-market improvements.

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.

Provide post-sales technical expertise to help customers adopt GitLab via webinars, labs, workshops, and consultative engagements. Collaborate with CSMs, AEs, and renewals to support implementations, architecture, CI/CD, SCM, DevSecOps, and Agile Planning. Create reusable enablement content and maintain specialty competency.

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.

Design, implement, and evolve complex backend features and architecture. Improve reliability, performance, and security at scale. Mentor engineers, participate in incident response, set backend standards, and integrate agentic AI into production workflows.

Build and scale partner-sourced pipeline by designing and executing repeatable partner-led campaigns, account mapping, and whitespace analysis. Enable and activate distributors, longtail resellers, and hyperscalers (AWS, Google Cloud), integrate partners into territory planning, run event-driven and 1:many motions via partner portals, and provide forecasting and reporting on partner impact to accelerate new customer acquisition and marketplace transactions.