Top Tech Jobs & Startup Jobs in Chicago, IL

Lead a small cloud engineering team to design, maintain, and secure hosting platforms for two global SaaS products. Combine people management (hiring, coaching, performance) with hands-on technical work in Kubernetes, ArgoCD, Azure, IaC, and Linux; troubleshoot stack-wide issues, manage backlog execution, coordinate cross-functionally, produce leadership reports, and serve as escalation point for infrastructure requests and incidents.

Own and administer the Gainsight platform end-to-end: build customer health scoring, configure C360, design playbooks/CTAs, manage account assignments, integrate with Salesforce, create reporting/dashboards, support platform operations, and train CX teams to drive proactive customer engagement.

Lead and scale a global Deal Desk to structure complex SaaS transactions, own deal review and approval workflows, improve quote-to-cash across CRM/CPQ/CLM/billing/ERP, implement AI/ML for efficiency, provide analytics on discounting and deal quality, and build a high-performing global team while advising Sales and executives on strategic deals.

Manage a team of cloud engineers to govern and optimize a multi-cloud environment while implementing security frameworks and managing vendor relationships.