Top Tech Jobs & Startup Jobs in Chicago, IL

Lead a world-class engineering organization at Help Scout, define and execute technical and AI strategies, and ensure cross-functional collaboration to drive product innovation and business success.

Lead a product team to drive business outcomes across revenue products. Define strategy, prioritize bets, manage and coach PMs, use customer insight and data (Hex, Mixpanel, data warehouse) to measure impact, and shape AI usage across product and process.

Build end-to-end, customer-facing AI features with a frontend focus: implement LLM-backed flows (RAG, embeddings, agentic tool-calling), craft fast accessible UIs in TypeScript/React, instrument evaluation/guardrails and production monitoring, stay close to customers, and own outcomes from design through production.

Own Mixpanel and partner closely with Product to turn product-level data into decision-grade insights. Define instrumentation and event taxonomy, build dashboards and notebooks, run cohort and retention analyses, design and analyze A/B tests, and collaborate with data engineers to model product event data. Document metrics, maintain a living glossary, and translate findings into actionable product recommendations.