Top Tech Jobs & Startup Jobs in Chicago, IL

Senior Strategy & Ops generalist focused initially on Billing: optimize collections and cash conversion, build predictive analytics and underwriting, vet AI vendor solutions, redesign payment conversion processes, and potentially manage Billing Account Managers to improve profitability while preserving customer experience.

Calculate and process sales commission payouts, maintain commission plans and models, reconcile revenue data using SQL, investigate discrepancies, support compensation plan rollouts, answer rep questions, and build transparent commission dashboards and self-service tools.

Build and operate systems supporting the sales organization, including Salesforce workflows, data pipelines, automations, reporting, Slack bots, and internal tools. Investigate ambiguous business problems, direct and quality-check AI agents, analyze revenue data with SQL, and maintain data accuracy through deduplication, account mapping, enrichment, and system reliability improvements.

As a Content Creator, you'll lead the Million Dollar Nurse YouTube channel, managing production, content strategy, and audience engagement, while appearing on camera as the host.

The Tooling Program Manager will define and execute the roadmap for AI and automation tooling, ensuring delivery across multiple initiatives and enhancing operational efficiency.

Owner/operator role responsible for structuring ambiguous problems, owning a revenue stream, building durable systems and automation, driving cross-functional execution, and validating initiatives convert to business outcomes. Requires strong analytical and system-building skills, comfort with ambiguity, influence without authority, and an outcome-driven mentality.

The Operations Associate role involves solving various operational challenges, managing teams, and improving processes within a fast-paced, remote-first environment.

Advise on legislative goals and regulatory changes, engage stakeholders, provide legal advice, manage compliance and contracts, support business operations.

The Manager, Strategic Partnerships will develop and manage partnerships to grow Clipboard's healthcare staffing marketplace, ensuring mutual value and strong market presence.

The Tech Ops Generalist will own the technical delivery of AI-powered operational tooling and the Zendesk ecosystem, helping to build a scalable operational tech platform for the organization.