Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and manage regulatory licensing and export-control programs for spacecraft and Earth-observation operations. Develop export classifications, licensing strategies, Technology Control Plans, and governance frameworks. Advise on international collaborations, supplier engagements, and mission compliance. Partner with engineering, operations, legal, security, and executive teams to integrate regulatory requirements across product lifecycle, launches, and global expansion. Build training, policies, and monitor emerging regulatory changes.

Lead and grow the commerce capability into a profitable business line: source and close enterprise deals, create GTM strategy, manage P&L and global delivery, build strategic vendor relationships, and drive modern composable/headless commerce transformations across B2B and B2C.

Manage and grow relationships with independent insurance agents on First Connect's platform. Train agencies on carriers/products, drive production and upsell opportunities, use data to identify growth trends, collect feedback, and collaborate internally to remove obstacles and transition high performers to additional contacts.

Design, author, and iteratively optimize LLM evaluation prompts for Five9 AQM; define evaluation scope and pass/fail criteria with customers; select and analyze call samples; measure precision/recall; maintain a versioned prompt library; collaborate with QA and implementation teams; debug prompt failures; develop standards, templates, and support pre-sales demonstrations.

Lead full-cycle recruiting for corporate, G&A, product, and engineering roles. Partner with hiring leaders on strategy, build pipelines, manage multiple searches, improve recruiting operations, create reporting and dashboards, and deliver an excellent candidate experience in a fast-growing startup.

Lead product marketing for an AI-native B2B SaaS real estate platform. Define positioning, messaging, launches, enablement, and PMM systems; translate complex AI, data, and automation capabilities into clear buyer and field-facing stories; partner with Product, Sales, CS, GTM AI, and executives to drive adoption, retention, and scalable go-to-market operations.

Lead Mersenne’s federal go-to-market: build BD pipelines with DoD/DOE/NASA, drive proposals (OTAs, SBIR, BAAs), manage partners and policy engagement, shape product-market fit for STARFALL, and represent the company at conferences and hearings. Navigate procurement, regulatory pathways, and coordinate internal/external stakeholders to secure prototype and production opportunities.

Full-cycle Account Executive selling Pear Suite to community-based organizations, health systems, FQHCs, and government programs. Responsibilities include prospecting and pipeline building, structured discovery, tailored demos, negotiating and closing deals, CRM hygiene (HubSpot), handoff to implementation, and shaping territory strategy and playbooks. Role involves travel for priority meetings and representing the company at events.

Supervise repossession and remarketing operations, manage vendor relationships, hire/train remote staff, maximize vehicle recovery value, ensure compliance and documentation, audit expenses, and monitor KPIs to improve efficiencies.

Lead design, development, testing, and documentation of cloud-hosted web applications. Deliver production-quality C#/.NET code, mentor juniors, lead reviews, build test automation, and use AI-assisted tools responsibly.