Top Tech Jobs & Startup Jobs in Chicago, IL

Full-cycle recruiter responsible for sourcing, screening, and closing sales candidates. Partner with leadership to define hiring needs, manage multiple high-priority roles, lead compensation discussions, track recruiting metrics, and improve processes while delivering a strong candidate experience.

Embed with enterprise customers to design, build, and deploy production-grade integrations and data pipelines. Own technical discovery, end-to-end integration lifecycle, AI agent orchestration, customer technical relationships, and feedback to product and engineering. Produce runbooks, templates, and durable handoffs.

Design and implement large-scale product features, build and optimize backend systems and APIs, deploy via cloud and CI/CD, maintain secure reliable code, troubleshoot production issues, conduct code reviews, mentor teammates, and develop client relationships to drive digital outcomes.

Partner with sales to drive enterprise pre-sales engagements: architect and demonstrate solutions, run proof-of-value evaluations, uncover technical/business requirements, and manage technical aspects through the sales cycle.

Contract fractional HR generalist to own HR operations: payroll and HRIS (Rippling), benefits administration, compliance, systems automation and documentation, onboarding/recruiting support, and vendor coordination. Expected ~15 hrs/week for an initial 6-month engagement, with deliverables and system audits in the first 90 days.

Sell Litify's AI-driven legal operating platform to law firms and legal departments. Manage full upsell motions, consult on AI adoption, deliver high-level demos to C-suite, meet sales targets, and articulate ROI of autonomous agents and AI integrations.

Lead and maintain City Cast's visual brand across national and local channels. Create and approve sales, marketing, and campaign assets; build templates and design systems; manage design intake, contractors, and a production designer; and ensure brand consistency while enabling local flexibility and revenue storytelling.

Owner of strategic partnerships with wirehouses, banks, and RIAs to secure product approval and distribution. Lead due diligence, negotiate MSAs and pricing, drive revenue expansion, enable sales through training and co-branded marketing, ensure compliance, and develop multi-level partner relationships to grow adoption and inbound advisor leads.

Design, build, and productionize ML and AI systems (LLMs, embeddings, recommendations, forecasting). Develop end-to-end ML workflows, scalable data pipelines, semantic models, and CI/CD for ML. Collaborate with product and engineering, mentor engineers, and influence platform architecture and standards.

Lead integrated marketing campaign planning and execution, coordinate cross-functional teams, and create scalable campaign toolkits. Drive AI-enabled campaign frameworks, enable regional activation, automate reporting, track performance and readiness, and standardize messaging and demand plans across regions to optimize pipeline and go-to-market goals.