Top Tech Jobs & Startup Jobs in Chicago, IL

Manage and complete multi-week integration projects, troubleshoot data issues, and provide strategic guidance on implementation and project progress.

Lead full-cycle recruiting across functions and seniority levels, acting as a hands-on individual contributor and trusted talent advisor. Source and manage pipelines, direct contract recruiters, use AI tools, run compensation benchmarking and offer negotiations, manage agencies, own recruiting data/reporting, and improve hiring processes and ATS operations to build diverse teams.

Lead platform security across AWS/EKS: harden supply chain, secrets, IAM, container integrity; build policy-as-code, compliance automation (HITRUST/SOC2), CI/CD security, and operationalize platform security controls while contributing hands-on to infrastructure, observability, and on-call support.

Lead technical sales for mid-market and enterprise healthcare prospects: perform deep technical discovery, independently scope integrations (HL7, FHIR, X12), design solutions, present demos/architectures, manage full sales cycle, collaborate with Product/Engineering, and ensure handoff to Implementation and Customer Success.

Senior SDR responsible for generating and qualifying pipeline for AEs by researching target accounts, executing AI-assisted multi-channel outbound outreach, tracking intent signals, and maintaining accurate CRM records. Partners with Account Executives and Marketing, leverages AI tools for personalization and intelligence, shares field insights, and helps elevate team AI best practices to drive meetings, pipeline, and conversion to opportunity.

Interim Head of Legal to advise CEO and execs on commercial contracts, negotiate complex enterprise SaaS deals, support pricing and packaging, counsel the board on governance, lead a small legal/compliance team, and ensure compliance with HITRUST and SOC 2. Hands-on, strategic, business-minded, and comfortable using AI tools.

Lead enterprise SaaS sales for top Provider accounts: drive new business, manage renewals and expansions (40% growth target), build executive relationships, run full sales cycle, use CRM to track activity, and travel up to 20%.