Top Tech Jobs & Startup Jobs in Chicago, IL

Provide first-line support to enterprise customers by triaging and resolving tickets, troubleshooting the Scout platform, and escalating issues when needed. Build support workflows, knowledge-base documentation, routing rules, SLAs, and escalation paths. Analyze recurring issues and share product insights with engineering and product teams. Support customer engagement projects and grow into a customer success role focused on enterprise relationships, adoption, and retention.

Generate qualified outbound pipeline targeting manufacturers, dealers, and fleet operators through phone, email, and LinkedIn. Research accounts, personalize messaging, conduct discovery conversations, qualify prospects, and book meetings for sales leadership. Use AI-native sales and CRM tools, maintain accurate pipeline data, meet activity targets, refine outreach with leadership, and share market feedback with product teams. The role offers consultative sales training and a path toward an Account Executive position.

Lead the engineering function and remain hands-on while building an AI-powered freight billing platform. Own architecture, data infrastructure, AI/ML validation, enterprise integrations, security, CI/CD, observability, testing, and scalability. Partner with Product and Data Science to automate invoice validation, discrepancy detection, exception handling, and auditability. Build and mentor distributed engineering teams, establish technical direction, and deliver rapid MVP iterations for enterprise adoption.

Lead end-to-end deployments of AI for hotel revenue teams: integrate PMS/CRS/RMS, ship ML/optimization models and agentic workflows, validate recommendations with revenue managers, define metrics, drive adoption, and hire/mentor the forward deployed engineering team.

The Founding Engineer will develop full-stack applications, shape product direction, and work in ambiguous environments from concept to validation.