Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and scale an AI-native recruiting venture as Co-Founder & CEO: define strategy, own customer development and pilots, partner on product delivery, raise seed capital, recruit and lead the founding team, and establish company culture and go-to-market motion with FutureSight's venture-building support.

Co-founder and CPTO to build an explainable, audit-ready AI compliance platform: design architecture, ship production LLM features (marketing review, surveillance, trade oversight), own model training, explainability, reliability, security (SOC 2, multi-tenancy), recruit and lead engineering/AI team, convert pilots to customers, and represent technical vision to customers and investors.

Lead Weli AI as Co-Founder & CEO: refine strategy and pricing, run pilot engagements with RIAs, partner on product development, raise seed capital, recruit the founding team, and build go-to-market execution to scale a WealthTech AI embedded in advisor CRMs.

Join as technical co-founder to build and harden an LLM-powered, 24/7 AI Front Desk for small law firms. Own architecture, reliability, RaaS delivery infrastructure, unit economics, roadmap, customer technical representation, and recruit the founding engineering team to scale a managed, privacy-sensitive AI staffing platform.

Lead a new AI-native clinical documentation compliance venture as Co-Founder & CEO: set strategy, run pilots and go-to-market, partner on product development, raise seed capital, recruit and lead the founding team, and drive customer conversions and company direction.

Lead and co-found an AI-native e-commerce SaaS venture: define strategy, run customer development and pilots, partner on product development, raise seed capital, recruit and lead the founding team, and establish company culture.

Lead InfluTracker as Co-Founder & CEO: define product and go-to-market strategy, validate customers and pricing, partner on product development, raise seed capital, recruit and lead the founding team, and build company culture with FutureSight's venture-building support.

Lead and operate a venture-building partnership to build an AI-native accounting agent platform for small-to-mid CPA firms. Define strategy, run customer pilots, partner on product delivery with the studio engineering team, raise seed capital, recruit and lead the founding team, and scale go-to-market and pricing.

Lead Foundry as Co-Founder & CEO: set strategy, run customer development and go-to-market, partner on product and engineering to ship V1, lead fundraising, and recruit and grow the founding team. Build an AI-native recruiting firm that automates sourcing and screening while retaining humans for relationship and final placement work.

Co-founder & CTO to own product and engineering: harden voice/LLM front desk for production reliability, build delivery and observability infrastructure, optimize unit economics, convert pilots to paying customers, recruit the founding engineering team, and represent the company technically to customers and investors.