Top Tech Jobs & Startup Jobs in Chicago, IL

The Senior Software Engineer will build and ship full-stack features, design scalable systems, integrate AI tools, and maintain high coding standards in a fast-paced startup environment.

Design, deliver, and maintain end-to-end training programs for Claims operations including onboarding, refresher/upskilling courses, e-learning and simulations, LMS/KM administration, SME coordination, and evaluation of training effectiveness to ensure floor readiness.

Lead B2B marketing initiatives at Sidecar Health, focusing on demand generation, paid media, content strategy, and team development to drive growth and revenue.

Lead AI product strategy and execution at Sidecar Health, focusing on AI-member experiences for healthcare. Drive development of AI features, evaluate AI product quality, and manage cross-functional teams to enhance healthcare shopping and transparency.

As a Senior SDET, you will design and maintain test automation frameworks, embed with product teams to ensure quality, and implement AI-powered testing solutions.

Act as primary liaison for existing employer groups, drive satisfaction and retention, attend virtual and in-person meetings across Texas, lead renewals and negotiate pricing, provide enrollment education and support, resolve escalations, and collaborate with internal teams to ensure successful implementation and group outcomes.

Design, build, and operate high-throughput distributed data pipelines and platform infrastructure. Own end-to-end systems from architecture to production, write production-grade Python, optimize SQL at scale, architect service contracts, mentor engineers, and instrument systems for observability.

Contract Senior Technical Recruiter owning full-cycle recruiting for Engineering and Product. Partner with hiring managers to define roles, build sourcing strategies, proactively source active/passive candidates, manage pipelines and interview processes, report on metrics, and collaborate cross-functionally. Operate independently in a fast-moving, remote environment (California-based).

The Head of Enterprise Sales will lead the sales strategy, drive growth, secure national client accounts, and collaborate with internal teams at Sidecar Health.

Lead product strategy and roadmap for claims automation, defining where AI and deterministic logic apply. Design human-in-the-loop workflows, audit trails, evaluation frameworks, and metrics. Lead cross-functional teams to deliver integrations, migrations, and AI-powered features while navigating regulatory constraints and measuring performance with data-driven experiments.