Top Tech Jobs & Startup Jobs in Chicago, IL

Early-stage full-stack engineer to build a 0-1 procurement platform: develop front-end and back-end, ship prototypes with great UI/UX, implement API and ERP integrations, design cloud infrastructure, lead technical strategy, and work directly with initial customers.

Own end-to-end product design for a two-sided affordable housing marketplace, from research and strategy through prototyping, launch, and iteration. Simplify complex workflows, conduct user research, collaborate cross-functionally, design polished Figma interfaces, run experiments, and create AI-powered experiences. Connect design decisions to customer needs, business metrics, and marketplace outcomes.

Own and build the clinical recruiting function for a fast-growing virtual behavioral health company. Lead workforce planning, sourcing, market intelligence, candidate screening, stakeholder partnership, recruiting operations, analytics, and process improvement. Recruit licensed behavioral health clinicians, including psychologists and therapists, while optimizing hiring speed, quality, candidate experience, and retention. Partner with executives and clinical leaders to scale hiring across multiple states and telehealth markets.

Manage school and district accounts using an AI master-scheduling platform. Lead onboarding, training, schedule implementation, troubleshooting, data integration, stakeholder relationships, success metrics, and renewals. Act as a strategic partner to school leaders, coordinate cross-functionally with sales, marketing, product, engineering, and support sales demos during the off-season.

Secure, harden, and scale AWS and Kubernetes production infrastructure. Build Terraform-based infrastructure as code, maintain Linux and Windows systems, improve IAM and CI/CD security, remediate vulnerabilities, support compliance audits, and administer security controls. The role also involves incident response, troubleshooting, documentation, operational runbooks, and collaboration with platform, engineering, and security teams supporting regulated and government environments.

Lead client-facing AI transformation and enablement engagements for mid-market companies. Design and deliver practical sessions that drive executive confidence, behavior change, and measurable AI adoption. Own client relationships between sessions, provide follow-up support and strategic guidance, stay current on AI tools, and identify adoption patterns that improve the company’s methodology. The role is full-time and remote, with travel to client sites required for some engagements.

Leads advertising and media strategy for a portfolio of marketplace brands across Amazon, Walmart, and Target. Owns media planning, forecasting, budgets, performance analysis, audience development, experimentation, and incremental growth. Manages Amazon Sponsored Ads, DSP, and AMC programs while coaching analysts and presenting recommendations to senior client leadership. Partners with retail and creative teams to improve advertising outcomes.

Lead the design, delivery, and production adoption of integrations-platform features, including SDKs, agents, job pipelines, developer tooling, and related services. Drive AI-enabled integration authoring, reliability, scalability, observability, and cross-platform support. Partner across product, platform, and customer teams to translate needs into technical solutions while providing architectural leadership, mentorship, and hands-on guidance across distributed systems and workflow orchestration.

Design, build, test, refactor, and maintain production Rails software using Rails, Bootstrap, Stimulus, and Postgres. Own a defined codebase area, design data models, review code, maintain disciplined testing, collaborate with product managers, and mentor 1–3 junior engineers. Contribute in a fast-moving startup environment, evaluate third-party tools and APIs, and use AI development tools such as Claude Code or Codex.

Lead architecture, scalability, and reliability for the Integrations Platform across SDKs, agents, job pipelines, and developer tooling. Drive platform roadmap, observability, workflow orchestration, AI-enabled integration authoring, and cross-functional initiatives while mentoring engineers and collaborating with product and customer teams.