Top Tech Jobs & Startup Jobs in Chicago, IL

Own product and engineering as technical co-founder, writing production code and hardening AI voice workflows for reliability, observability, auditability, and scalability. Build the managed RaaS delivery infrastructure, balance AI quality with cost-per-call economics, guide the roadmap, represent the venture to customers and investors, recruit the founding engineering team, and establish technical culture. The role requires production experience with LLM-powered voice systems, secure SaaS, human-in-the-loop workflows, and trust-sensitive applications.

Co-found and lead the technical direction of a new B2B AI venture. Own problem framing, architecture, system design, product judgment, AI product development, customer discovery, verification, fundraising support, and eventual technical team building. Build maintainable AI and agentic systems that solve real customer workflows, prioritizing traction before scale. The role requires a full-time, exclusive founder commitment with meaningful equity and authority.

Lead Closeline, an AI-native mortgage origination venture, by setting strategy, refining its market and pricing, leading customer discovery and pilots, shaping the MVP with product and engineering teams, 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, and direct mortgage origination exposure.

Lead the creation and execution of LucentAI, an AI-native litigation operations venture for insurance-defense firms. Own strategy, customer development, pilots, pricing, product direction, fundraising, hiring, and company culture. Partner with FutureSight’s design and engineering teams to launch the MVP, convert design partners into paying customers, establish go-to-market, and lead the seed raise.

Lead the strategy and execution of Foundry, an AI-native recruiting venture. Responsibilities include defining the ideal customer profile, pricing, and positioning; securing pilot customers and building go-to-market; partnering on the V1 product; leading the seed fundraising process; and recruiting the founding team. The role requires deep recruiting or talent acquisition expertise, B2B AI or SaaS go-to-market success, prior venture-backed founding experience, fundraising capability, and strong talent leadership.

Lead Concordance as Co-Founder and CEO, setting strategy, refining the ICP and pricing, developing customers, converting pilots into paid engagements, guiding V1 product development, raising seed capital, recruiting the founding team, and establishing company culture. The role requires deep healthcare revenue cycle and medical billing expertise alongside prior venture-backed founding and B2B SaaS or AI go-to-market experience.

Lead Orbitwell as co-founder and CEO, defining strategy, positioning, pricing, customer development, product direction, fundraising, and team building. The role involves validating demand with creators, teams, and agencies; partnering with product and engineering teams to launch and improve the AI content platform; developing creator-led go-to-market; raising seed capital; and recruiting the founding team. This is an equity-based founder partnership rather than a salaried executive position.

Lead Weli, an AI-native B2B WealthTech venture, by refining strategy, validating the ideal customer profile, developing pricing and positioning, leading RIA customer pilots and sales, partnering on V1 product development, raising seed capital, and recruiting the founding team. The role requires building customer and investor relationships, establishing company culture, and navigating wealth management operations and financial services compliance.

Lead Crossfoot as Co-Founder and CEO, setting strategy, refining ICP and pricing, developing CPA-firm customers, guiding V1 product delivery, raising seed capital, and recruiting the founding team. The role requires prior venture-backed founding experience, B2B AI or SaaS go-to-market expertise, fundraising ability, talent leadership, and deep hands-on accounting experience within CPA firms.

Co-Found and lead Omnex, an AI-native operating system for multi-channel ecommerce sellers. Own venture strategy, customer development, product direction, fundraising, hiring, and company culture. The role requires prior startup founding experience, B2B SaaS go-to-market success, fundraising ability, talent leadership, direct ecommerce expertise, and a strong seller-community network. This is an equity-based co-founder partnership with pre-seed funding and venture-building support, not a salaried executive position.