Top Tech Jobs & Startup Jobs in Chicago, IL

Research regulatory, consumer protection, product, and compliance questions and provide actionable legal recommendations. Manage escalations, regulatory inquiries, entity compliance, audits, intellectual property enforcement, and policy reviews. Partner with Product, Engineering, Operations, and business leaders while improving legal processes through AI, low-code tools, and automated workflows.

Own hands-on HR operations, including multi-state compliance, policy drafting, payroll, benefits, leave escalations, audits, handbook updates, and process improvement. Review HR administration work, resolve complex employee questions, and introduce AI-native approaches to reduce repetitive work. The role is expected to grow into broader day-to-day HR operations ownership.

Own multi-state HR compliance, policy updates, annual audits, handbook refreshes, and escalated payroll, benefits, and leave issues. Review HR administration work, improve operational processes with an AI-native approach, and gradually assume broader day-to-day HR operations management. The role requires hands-on, in-house generalist experience in a fast-paced, multi-state environment.

Own end-to-end analytical support for a business unit in growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; surface insights; and drive recommendations and decisions with cross-functional stakeholders. The role requires independent data work, strong analytical thinking, persuasive communication, and ownership of ambiguous problems using SQL and Python.

Own the end-to-end creation of performance-driven advertising across paid social, CTV, YouTube, and emerging channels. Develop concepts, scripts, hooks, creative frameworks, briefs, and edited video assets while maintaining high visual and brand standards. Partner with media, growth, analytics, agencies, and production teams to translate performance data into creative direction. Use AI tools to accelerate ideation and production, manage external partners, and increase creative volume and effectiveness.

Own end-to-end data science for growth, product, AI and automation, or strategic partnerships. Define business problems, establish metrics, build reports, analyze data, design experiments, communicate insights, and drive decisions with cross-functional stakeholders. The role requires strong analytical judgment, independent execution, first-principles thinking, and persuasive communication.

Leads insurance compliance and regulatory operations, including complex customer escalations, state Department of Insurance complaints, carrier audits, regulatory correspondence, complaint logging, and audit-ready documentation. Partners with Legal, Product, and Engineering to resolve systemic issues, improve controls, and implement product or process fixes. Provides coaching and subject-matter guidance to customer service, compliance, and claims support teams while maintaining regulatory deadlines and carrier relationships.

Own the operating model, annual budget, long-range plan, forecasts, variance analysis, executive reporting, and business reviews. Build financial cases for new products, markets, channels, and partnerships; evaluate unit economics, capital allocation, and vendor spend. Support corporate development, diligence, transaction analysis, and planning-system implementation while partnering with executives and functional leaders.

Own the analytical function for a business area such as growth, product, AI and automation, or strategic partnerships. Define business questions and metrics, build reports, analyze data, design experiments, and deliver insights that influence decisions and key performance indicators. Partner with product, growth, finance, and operations leaders to communicate recommendations and drive initiatives through execution.

Work directly with the CEO on high-leverage business problems across product, growth, operations, finance, engineering, and data. The program provides broad exposure to Jerry’s rapidly expanding business lines, with the expectation that successful participants eventually own P&L for a business line. The role requires strong ownership, urgency, resilience, learning ability, and in-person collaboration in Palo Alto during the initial 6–12 months.