Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and conduct complex, confidential workplace investigations; advise and coach leaders on employee relations and performance issues; develop proactive programs, policies, and scalable solutions; analyze case trends and partner with Legal and People teams to reduce risk and improve team member experience across jurisdictions.

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.

Manage large-scale software and consulting projects end-to-end for enterprise customers. Coordinate cross-functional teams, executive stakeholder communications, escalations, delivery schedules, scope, risks, and revenue recognition while improving Professional Services PM processes, tools, metrics, and templates.

Lead technical engagements to install, migrate, configure, and onboard customers to GitLab. Create SOWs, migration plans, training, documentation, and automation; communicate risks/status; collaborate with Product and Engineering; support quoting and process improvements. Travel approximately 20%.

Lead long-range bookings and ARR financial modeling, support pricing and packaging, build business cases for new products and partnerships, assess unit economics and market opportunity, and provide strategic finance recommendations to executives and the Board.

Design, maintain, and extend abuse detection and prevention systems for GitLab's SaaS platform. Serve as a core maintainer of a Ruby on Rails monolith, build anomaly detection and agentic AI mitigations, automate abuse response, collaborate with peer engineering and security teams, and produce runbooks and operational documentation.

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.

Design and deliver scalable, role-based enablement programs and content for GitLab's AI capabilities and Duo Agent Platform. Lead cross-functional launch and release-readiness initiatives, create playbooks, demos, labs, certifications, and blended learning experiences, publish and organize materials, and measure program effectiveness to continuously improve field readiness and adoption.

Lead Workday strategy and people technology architecture to scale a global remote workforce. Translate business needs into durable system design, build scalable integrations, drive complex Workday configuration, ensure SOX ITGC compliance, coordinate cross-functional programs, create reporting and dashboards, facilitate executive design discussions, and promote AI/automation to reduce manual work and improve team effectiveness.

Drive subscription renewals and retention for German customers through negotiation, usage evaluation, true-ups, and cross-team collaboration. Close renewals timely, manage strategic/complex accounts, mitigate churn risk, and help design renewals best practices to improve predictability and gross retention.