Top Tech Jobs & Startup Jobs in Chicago, IL

Provide subject-matter input on criminal law to train AI: review and analyze court filings and case materials, draft and annotate scenarios, evaluate AI outputs for legal accuracy and ethics, flag nuanced issues, and collaborate remotely to deliver actionable feedback while staying current on statutes and case law.

Analyze computer systems and business processes, gather and validate stakeholder requirements, create BPMN/UML process models, use SQL for data analysis and troubleshooting, and collaborate remotely on customer projects. The role also contributes domain expertise to AI training data and scenario validation.

Manage the full customer lifecycle for public sector accounts, from onboarding through renewal. Build relationships across government organizations, drive adoption and retention, identify expansion opportunities, handle escalations, and advocate for customer needs. Use AI, BI tools, and data analysis to monitor account health and inform account strategies. The role requires executive communication, change management, cross-functional collaboration, and up to 80% travel for on-site customer engagement.

Support execution of large-scale B2B outbound and demand-generation campaigns: build outreach sequences, manage outreach tools, enrich and QA data, maintain outbound infrastructure, coordinate webinar and content syndication operations, research target accounts/ICPs, assist reporting, and apply AI tools to automate workflows.

Lead Recruiter sources, screens, and hires healthcare professionals using job boards, social media, and ATS. Partners with hiring managers, schedules interviews, negotiates offers, manages onboarding, maintains candidate records, and represents the company at recruitment events to expand the talent pipeline.

Provides legal guidance on mergers and acquisitions, contract negotiations, corporate governance, and related matters. Responsibilities include drafting and negotiating agreements, conducting M&A due diligence, advising on legal and regulatory issues, collaborating with business partners, overseeing outside counsel, and monitoring legal developments. The role requires a law degree, bar licensure, and at least four years of legal experience, with M&A expertise required and financial services or securities law experience preferred.

Design and deliver intuitive web experiences and native mobile apps for permitting, inspections, and code enforcement products. The role owns end-to-end UX/UI design, MVP scoping, product judgment, information architecture, visual design, cross-platform consistency, and design-system maintenance. It also enables engineers to ship quality UI independently through shared principles, critique practices, and scalable components. The designer will work autonomously in an ambiguous startup environment and report to the Founder & CEO.

Own and operate the data plane: develop Envoy/WASM filters for deep packet inspection, deploy and manage EKS workloads with Helm/GitOps and CI/CD, integrate Redis sidecars, provide observability (Prometheus/Grafana/OpenTelemetry), ensure reliable audit log streaming, and author ADRs as the data plane evolves.

Refresh and publish blog articles, make minor website edits, coordinate content and vendor deliverables, maintain Jira boards and change logs, and identify repetitive marketing tasks suitable for automation. The role requires hands-on experience with Claude or similar AI tools, careful copy and link review, strong English, and comfort using GitHub, WordPress, Jira, Figma, and Notion.

Design and build scalable native iOS and Android features using Swift and Kotlin. Integrate with backend services, optimize performance, write unit tests, maintain code quality, and lead end-to-end delivery of mobile product modules.

Design, develop, and maintain scalable, high-performance backend and middleware services on the JVM using Java and Spring/Spring Cloud. Build and enhance microservices, work with AWS and Docker, implement SQL/noSQL solutions (MySQL, Elasticsearch), use Git-based source control and JIRA, collaborate across engineering, design, and QA, and mentor teammates while following best practices and Agile methodologies.

Design, develop, and execute manual and automated tests for front-end, back-end, APIs, and large-scale services. Build and maintain automated test suites and frameworks (Java, JUnit, Selenium, TestNG), analyze logs, report results, and collaborate with stakeholders; ensure test coverage across devices and drive test strategy and sign-off.

Lead editorial strategy that drives commercial outcomes: build multi-channel, data- and AI-driven editorial programs and narratives, translate technical research into market-facing stories, measure pipeline attribution and engagement, and mentor contributors while collaborating with GTM, engineering, and executive teams.

Design, build, and maintain production-grade AI-powered go-to-market automations (prospecting, lead scoring, campaign orchestration, attribution). Integrate ML/LLM tools into marketing and sales workflows, track business-critical metrics, ensure reliability and scalability, and collaborate with GTM strategists and non-technical stakeholders to drive measurable pipeline and revenue outcomes.

Founding CEO to lead product, technology, and go-to-market for a programmatic influencer marketing platform: define strategy, build AI-driven creator matching and orchestration, establish global payments/compliance, hire and lead engineering and commercial teams, and secure market adoption with venture-studio support.