Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and scale a multi-product, AI-first engineering organization. Define technical strategy with Product and GTM, drive architecture, reliability, and scalable systems across frontend, backend, platform, and infrastructure, champion AI-assisted workflows, remove execution blockers, and foster a high-accountability engineering culture focused on rapid iteration and quality.

Lead end-to-end product development for a multi-product, AI-first SaaS platform. Define strategy and roadmap, conduct market and user research, write PRDs and user stories, partner with Design, Engineering, Data, and Customer Success, and measure results to drive growth and product impact.

Lead full-funnel marketing across B2B and B2C, driving demand generation, product marketing, lifecycle growth, and AI-enabled marketing automation. Build GTM strategy, partner with Sales, run B2C acquisition/retention, and scale AI-first workflows while coaching a small team.

Own Salesforce administration and GTM reporting systems, maintain data quality and integrations (including BigQuery and Chargebee), build dashboards and reports, document processes, and support sales and customer-success analysis for pipeline, forecasting, and account health.

Lead and grow revenue across K-12, higher education, and corporate markets as a player-coach. Carry an individual quota, manage and develop 2-3 AEs, run CRM and forecasting in Salesforce, expand reseller partnerships, refine GTM strategy with marketing/product, and recruit and retain sales talent.