Top Tech Jobs & Startup Jobs in Chicago, IL

Manages national and multi-regional client accounts, developing strategic account plans, strengthening relationships, negotiating contracts and renewals, driving cross-selling and revenue growth, and coordinating internal teams to deliver service excellence. Monitors account metrics, presents performance updates, tracks market trends, and represents the company in client meetings and trade shows. Requires national travel of 30–50% and strong sales, negotiation, presentation, analytical, and relationship-building skills.

Direct multi-state payroll operations for 1,000+ employees, ensuring accurate processing, tax compliance, audit readiness, and regulatory adherence. Manage commissions, bonuses, payroll integrations, HRIS workflows, and M&A-related transitions. Lead process improvements, reporting, internal controls, employee escalations, and collaboration with HR, Finance, Benefits, and People Operations teams.

Lead and operate enterprise IT infrastructure across Azure and Microsoft 365, endpoints, networking, voice, backup, and monitoring. Manage and mentor infrastructure and support teams, drive identity and provisioning processes, support security/compliance, and deliver modernization and automation projects while owning incident escalation and service delivery.

Own national business development for Rose Paving by hunting new accounts, building relationships with key decision-makers, driving revenue growth, preparing estimates and bids, tracking pipeline and KPIs, consulting with customers and subcontractors, and coordinating with field and administrative teams.