Top Tech Jobs & Startup Jobs in Chicago, IL

Own product and engineering as technical co-founder, writing production code and defining architecture for a reliable AI legal front desk. Build voice and workflow infrastructure, observability, audit trails, secure multi-tenant delivery systems, and cost-effective AI operations. Convert pilots into paying customers, guide the roadmap toward additional AI staff roles and self-hosted models, represent the technical vision to customers and investors, and recruit the founding engineering team.

Co-found and lead the technical direction of a new B2B AI venture. Own problem framing, architecture, system design, AI product development, customer discovery, product validation, fundraising support, and eventual technical team building. The role requires shipping reliable AI products to real users, designing maintainable LLM and agentic systems, translating ambiguous requirements into executable specifications, and committing full-time and exclusively as a founder.

Lead Orbitwell as Co-Founder and CEO, defining strategy, target customers, pricing, positioning, customer development, product iteration, fundraising, and team building. The role partners with FutureSight’s product, engineering, growth, and fundraising teams to validate retention and willingness to pay, launch the go-to-market motion, ship the initial product, raise seed capital, and establish the company’s culture.

Lead Closeline, an AI-native mortgage origination venture, by defining strategy, validating customers, developing pricing and positioning, guiding V1 product development, raising seed capital, recruiting the founding team, and establishing company culture. The role requires prior venture-backed founding experience, B2B SaaS go-to-market expertise, fundraising ability, talent leadership, and direct mortgage origination or lending operations exposure. This is an equity-based co-founder partnership rather than a salaried executive role.

Lead LucentAI from venture creation through launch as Co-Founder and CEO. Define strategy, target customers, pricing, positioning, and go-to-market; lead customer pilots and convert firms to paid engagements; partner with product and engineering teams to ship an AI litigation-operations product; raise seed capital; recruit and lead the founding team; and build company culture. Deep insurance-defense or claims-operations expertise and prior venture-backed founding experience are required.

Lead Concordance as co-founder and CEO, setting strategy, refining ICP and pricing, developing customer pilots, driving go-to-market, partnering on AI product development, raising seed capital, recruiting the founding team, and establishing company culture. The role requires deep healthcare revenue cycle and denial-management expertise alongside venture-backed founding, B2B SaaS or AI go-to-market, fundraising, and talent leadership experience.

Lead Omnex from inception as Co-Founder and CEO, setting strategy, refining product positioning, developing ecommerce seller customers, launching pilots, driving sales, partnering on V1 development, raising seed capital, recruiting the founding team, and establishing company culture. The role requires prior venture-backed founding experience, B2B SaaS go-to-market success, fundraising ability, talent leadership, direct multi-channel ecommerce experience, and a strong seller-community network.

Lead Crossfoot as Co-Founder and CEO, setting strategy, validating the ICP, driving CPA-firm customer development, shaping product delivery, raising seed capital, recruiting the founding team, and establishing company culture. The role requires deep CPA-firm accounting expertise, B2B AI or SaaS go-to-market experience, prior venture-backed founding experience, fundraising ability, and strong talent leadership. This is an equity-based partnership with committed pre-seed support, not a salaried executive position.

Lead Weli as Co-Founder and CEO, defining strategy, ICP, pricing, product positioning, customer development, pilots, sales, fundraising, and team building. Partner with FutureSight’s product and engineering teams to launch and iterate the V1 AI operations platform for wealth management firms. Build relationships with RIAs, convert pilots into paid customers, lead the seed raise, recruit the founding team, and establish company culture.

Lead the creation and execution of an AI-native recruiting venture as Co-Founder and CEO. Own strategy, ideal customer profile, pricing, positioning, customer development, pilot placements, go-to-market, product iteration, seed fundraising, and founding-team recruitment. Partner with FutureSight’s design, engineering, growth, and fundraising teams to launch the MVP, secure customers and capital, and establish the company’s culture.