Top Tech Jobs & Startup Jobs in Chicago, IL

Manage high-volume customer invoicing for managed services, recurring contracts, tickets, sales orders, and projects using ConnectWise and NetSuite. Reconcile billing data, process credits, support month-end close, resolve billing discrepancies, and improve invoicing processes while collaborating with operations, finance, and customer success.

Lead development and ownership of core MDR platform components (high-performance log analytics, post-processing, multi-tenant syslog cluster, cross-platform agents). Make architectural decisions, mentor engineers, drive CI/CD/cloud deployments, ensure security, observability, and zero-downtime production operations.

Serve as primary client contact to retain, onboard, and grow MSP cybersecurity and IT accounts. Lead onboarding, drive renewals, run executive business reviews, manage at-risk clients with improvement plans, identify expansion opportunities, and collect feedback/NPS to improve service and advocate client outcomes.

The Account Executive will drive new logo acquisition in IT services, manage the full sales cycle, and collaborate with teams to build solutions, aiming for revenue growth.

Lead network architecture and delivery for MSP engagements across LAN/WAN, SD-WAN, wireless, and network security. Provide pre-sales design, hands-on implementation of Extreme and Fortinet platforms, develop standards and templates, perform network assessments, mentor junior engineers, and represent the practice in client-facing strategy discussions.

Own end-to-end delivery of professional services engagements (infrastructure, cloud, Modern Work). Lead initiation, scoping, scheduling, resource coordination, risk and budget management. Act as primary client contact, protect scope and margin, manage change orders, maintain project data in ConnectWise Manage, produce documentation, coordinate cross-functional teams, and contribute to PMO process and tooling improvements.

Support sales by leading technical discovery, designing solutions across managed IT, cybersecurity, cloud, AI, and professional services, producing SOWs/BOMs, delivering presentations/demos, responding to RFPs, and ensuring clean handoffs to delivery teams.

Lead billing operations for recurring, project, and hardware-as-a-service revenue in a $100M+ MSP. Ensure invoice accuracy, ASC 606 alignment, month-end cutoffs, and cross-team validation. Drive automation, system integrations (PSA/CRM/ERP), process documentation, audit support, and manage a small team of billing specialists to improve scalability and collections.