Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and coach a new-business SaaS sales team serving community banks. Build a disciplined prospecting and pipeline culture, coach representatives through complex sales cycles, develop executive and consultant relationships, manage referral channels, and support strategic opportunities. The role requires an established community-banking network, strong consultative selling skills, CRM proficiency, and approximately 20–25% travel. It is remote-first but requires residence in the Midwest or Southeast United States.

Lead product vision, strategy, and roadmap for LoanVision; build and run the product organization; prioritize portfolio investments; drive buy/build/partner decisions and strategic partnerships; represent the customer and market to executives; partner with engineering, sales, and customer success to deliver product and growth.

Serve as a technical implementation lead for Hancock Cloud: onboard clients, configure and validate software, support and diagnose issues, create documentation and training, run data imports and scripting, coordinate tasks, and translate business needs into technical specifications.

Lead design and delivery of a global, AI-native People Operations function: select and implement HRIS, build comp programs, benefits infrastructure, TA systems, automation and people analytics, and hire and lead a global team while ensuring global compliance and cross-functional integration.

Lead AI product strategy and personally design, build, and ship LLM-based features for an EHR platform. Engage clients, translate clinical workflows into AI solutions, implement RAG/vector search pipelines, ensure HIPAA-compliant production deployments, and coach engineers while establishing AI governance and review processes across the company.

Design, build, and operate a centralized AWS data lake and AI experimentation platform. Define target-state architecture, guardrails, data contracts, and standards. Stay hands-on writing code, ship infrastructure, run reliability and cost controls, and hire and lead a small platform team while onboarding functional verticals and delivering production AI use cases.

The Territory Sales Manager will drive growth for O.R. TRAX in healthcare by managing a defined territory, engaging stakeholders, and closing sales while ensuring client satisfaction.

Lead Bitcentral's product vision, strategy, and roadmap to modernize broadcast and media software. Drive transition to hybrid cloud, champion AI-first product initiatives, manage pricing and business-model evolution toward recurring revenue, partner with sales, finance, and engineering, and build a customer-led product organization while preserving platform reliability for mission-critical broadcast workflows.

Lead and personally build NCTs initial AI capabilities (RAG, LLM orchestration, multi-agent workflows), refactor legacy Microsoft-stack components into cloud-native services, deploy compliant AI features (HIPAA, CJIS), then scale and mentor an AI-native engineering team while partnering with Banyan centralized AI initiatives.

Lead Medicats commercial organization as Chief Revenue Officer: own sales, marketing, and revenue operations; build scalable sales processes; drive demand generation and brand; align cross-functionally with product and customer success; own forecasting, pipeline, contracting, and board-level commercial reporting.