Top Tech Jobs & Startup Jobs in Chicago, IL

Own and redesign Jerry’s post-purchase customer experience across document verification, payments, policy changes, renewals, re-shopping, and issue resolution. The role focuses on improving retention and accelerating growth from 5 million to 50 million customers. Responsibilities require strong consumer product instincts, data-driven analysis, ownership, and collaboration with founders and cross-functional teams in a high-growth startup environment.

Own end-to-end data science for a business area such as growth, product, AI, or strategic partnerships. Define business questions, metrics, reports, analyses, and experiments; generate actionable insights; and influence product, growth, finance, and operations decisions. The role requires independently structuring ambiguous problems, using SQL or Python, communicating findings clearly, and driving measurable business outcomes.

Own end-to-end business operations and analytics for a core business area such as growth, product, AI, automation, or strategic partnerships. Define business questions, establish metrics, build reports, conduct analyses and experiments, communicate insights, influence leadership decisions, and drive initiatives through execution. The role requires strong analytical thinking, independent data work, persuasive communication, and ownership of ambiguous problems.

Own the analytical function for a business unit such as growth, product, AI and automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; communicate insights and recommendations; and drive decisions and outcomes with cross-functional stakeholders. The role requires independent data work, first-principles problem solving, persuasive communication, and ownership of ambiguous initiatives.

Owns the P&L, strategy, product development, customer growth, partnerships, and operations for a new business within Jerry.ai. The General Manager will scale an emerging product line, work closely with the CEO and executive team, and initially lead a small team. Candidates need 6+ years in venture capital, private equity, or hands-on startup operating roles, a bachelor’s degree, and the ability to work in person in Palo Alto.

Own end-to-end data science for growth, product, automation, or strategic partnerships. Define business problems, metrics, reports, analyses, and experiments; generate actionable insights; and influence product, growth, finance, and operations decisions. The role requires strong SQL or Python skills, independent analytical problem-solving, clear communication, and ownership of ambiguous initiatives.

Build and scale new product verticals under direct mentorship from the CEO. Identify customer problems, execute product and growth initiatives, navigate operational complexity, and collaborate across product, operations, finance, engineering, and data. The role offers broad exposure to startup strategy and execution, with potential progression into product or commercial leadership.

Work directly with the CEO on high-leverage business problems during Jerry's rapid growth. Rotate across product, growth, operations, finance, engineering, and data; develop broad business expertise; and help scale new business lines. The program is designed to prepare successful candidates to own P&L for a business line.

Own and scale a new product bet from concept or early launch through product-market fit. Responsibilities include ramping up on new domains, analyzing quantitative and qualitative customer insights, prioritizing high-impact opportunities, building and shipping consumer products, gathering feedback, iterating, and contributing to the product roadmap. The role requires strong ownership, analytical thinking, consumer product instincts, and comfort operating in complex, ambiguous environments.