Top Tech Jobs & Startup Jobs in Chicago, IL

As a Client Success Manager, you'll manage client relationships, oversee technical project delivery, and ensure project milestones are met effectively, while using AI tools to enhance workflow and engagement.

As a Founding Engineer, you'll lead product development initiatives, make architectural decisions, and foster engineering best practices in a startup environment. Your expertise will be critical in building a user-friendly AI-driven supply chain platform.

As a Pre/Post Sales Solutions Architect, you will demonstrate Gremlin's reliability solutions to customers, consult on architectures, and engage in technical projects while collaborating with internal teams.

Drive full-cycle net-new enterprise sales (3,000+ employee accounts) for an AI-enabled digital adoption platform. Close $100K–$300K ACV deals, build and manage a growing book for expansion, navigate complex stakeholders (security, legal, procurement), convert PLG usage into commercial agreements, and partner cross-functionally to ensure onboarding and account health.

Lead technical direction with the CTO, architect and build high-scale distributed systems, mentor engineers, ship product roadmap, manage cloud infrastructure and orchestration, enforce CI/CD, testing and fault-tolerance, and collaborate with product and business teams while leveraging AI/ML frameworks.

Manage client invoice processing, monthly retainers, account reconciliations, and collections. Post AR entries, apply payments, update customer records, prepare accruals and statements, and support accounting reporting and ad-hoc projects.

Provide escalated remote and onsite IT support across multiple client environments: troubleshoot OS, server, network, firewall, Microsoft 365/Intune/Azure issues; administer Windows Server and Hyper-V; deploy and maintain Datto and SonicWall solutions; mentor Level I technicians; document work in Autotask and maintain client documentation.

Lead category strategies and end-to-end procure-to-pay for mid-dollar projects. Drive supplier selection, negotiations, contract management, risk mitigation, data analysis, and procurement metrics to optimize cost, service, and partner satisfaction while aligning with business stakeholders.

Drive new customer acquisition via outbound prospecting, cold outreach, discovery calls, pipeline management, and deal closing. Collaborate cross-functionally for smooth onboarding and meet monthly and quarterly sales targets while tracking industry trends and competition.

Lead reporting and analysis across product, call center, and marketing; manage enrollment and revenue reconciliation; produce partner and carrier reports; analyze member engagement and plan performance to surface actionable insights.