Top Tech Jobs & Startup Jobs in Chicago, IL

Own centralized workforce forecasting, capacity planning, headcount strategy, and cost optimization across multiple lines of business. Model trade-offs involving FTEs, BPO, overtime, productivity, and shrinkage; analyze demand changes; identify capacity risks; and translate findings into executive recommendations. Partner with Finance, Product, and Operations to govern assumptions, investigate plan variances, standardize planning frameworks, and support strategic staffing decisions.

Leads Clipboard’s Applied Science function and team, setting the science roadmap across marketplace pricing, auctions, causal models, metrics, and experimentation. The manager balances production modeling with analytical work, partners with engineering, product, finance, and operations, and mentors and hires scientists. Responsibilities include developing and deploying quantitative models, designing experiments, defining marketplace metrics, prioritizing initiatives, and communicating findings to business and technical stakeholders.

Prospect, pitch, and close new long-term care facility partners across rural U.S. markets. Build relationships with facility decision-makers, create demand, manage territory pipelines, plan regional travel, attend industry events, and support customer adoption. The role combines remote inside sales with approximately one week of monthly travel for facility visits, meetings, and market development.

Own and improve Clipboard’s internal operations tooling ecosystem, including workflows, integrations, automations, support platforms, and AI-driven systems. Translate operational needs into technical solutions, partner with engineering, troubleshoot production issues, improve system reliability, and execute tooling initiatives that increase operational efficiency and scalability.

Own end-to-end product design for Clipboard’s worker and workplace applications, from research and problem definition through launch and iteration. Partner with product and engineering, conduct customer research, create high-fidelity prototypes, contribute to the design system, and ensure polished visual and interaction quality. The role also involves using AI tools throughout the design process and influencing product direction across complex, interconnected experiences.

Generalist operations strategy role focused on analyzing operational data, identifying bottlenecks, building dashboards and models, implementing AI and automation tools, designing scalable workflows, and leading cross-functional initiatives. Projects may include improving payment collection, onboarding AI vendors, developing predictive payer-risk models, or managing operations teams to improve performance, quality, and customer experience.

Own complex enterprise customer and operational problems from diagnosis through resolution. Work with customer stakeholders and cross-functional Product, Engineering, and Operations teams to lead implementations, troubleshoot payroll, time clock, and integration issues, define workstreams, remove blockers, and drive outcomes without direct authority. Use customer insights, operational context, and data to improve processes and products. Occasional travel to customer sites is required.

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.