Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the supply side of an early-stage two-sided marketplace: recruit and retain partner businesses and contributors across verticals and geographies, own geo rate cards, capacity forecasting, contributor experience (onboarding, payments, support), and partner with platform on self-serve tooling. Close partners directly and optimize pricing, economics, and systems for scale.

Lead product strategy, planning, and delivery for RPA, AI, and technology initiatives. Define requirements, roadmaps, success metrics, and ROI. Coordinate cross-functional teams, manage multiple projects, mitigate risk, support change management, and ensure projects deliver on scope, schedule, and budget.

Own the full enterprise sales cycle for large, complex accounts: prospecting, managing multi-stakeholder deals, running technical proofs-of-concept with engineering, refining enterprise sales plays, and feeding customer insights to product and leadership to drive repeatable revenue.

Lead Enterprise product marketing: develop positioning and messaging, partner with Product/Sales/Marketing, run AI-enabled GTM experiments, conduct market research and competitive analysis, create enterprise collateral, support strategic deals and enablement, and iterate on campaigns to drive pipeline.

Lead design and implementation of scalable APIs and agent communication layers for an AI-agent driven advertising marketplace. Build high-throughput backend systems, integrate agent frameworks and adtech partners, drive architecture for authentication and protocols, mentor engineers, and prototype agent communication patterns while collaborating with product and design.

Administer and optimize DRB SiteWatch, Patheon, and ICS POS systems across multiple locations. Configure items, pricing, promotions, and site settings; test changes; provide Level 3 troubleshooting for terminals, kiosks, payment and connectivity; liaise with vendors; maintain data integrity, SOPs, and training materials; monitor performance and reporting; and partner with teams to improve processes and customer experience.

Manage a regional portfolio of higher education institutions to drive revenue growth, adoption, and retention. Build multi-level relationships with faculty and administrators, lead virtual and in-person engagements, execute territory go-to-market strategy, negotiate agreements, and collaborate with cross-functional teams. Use Salesforce and analytics to monitor usage, identify opportunities, and design targeted campaigns. Travel frequently across the US West region to strengthen partnerships and promote HBI learning solutions.

Solve unprecedented, high‑ambiguity problems end‑to‑end: create solutions, then build repeatable systems to run them without you. Own outcomes, act autonomously, generate options relentlessly, operate under scarce resources and tight deadlines, and continuously scale impact across the company.

Lead the transformation of marketing strategy for an AI-native positioning, focusing on website overhaul, developing marketing strategies, and managing campaigns.

Plan and lead human factors research and analyses (requirements discovery, task/workflow analyses, usability studies, compliance audits, workload experiments), analyze data, make design recommendations, document results (HEDADs, CTAs), oversee junior staff, ensure standards compliance, and contribute to proposals.