Top Tech Jobs & Startup Jobs in Chicago, IL

Lead design, implementation, and maintenance of system architectures across applications, infrastructure, and cloud platforms for federal IT modernization. Provide technical leadership, ensure performance, reliability, and integration, produce documentation, and collaborate with DevOps, security, and stakeholders within Agile teams.

Design, build, deploy, monitor, and optimize production machine learning and LLM systems, including RAG pipelines, agentic workflows, fine-tuned models, and embeddings. The role owns technical delivery from architecture through iteration, collaborates with enterprise clients, mentors junior ML engineers, conducts code reviews, and helps establish internal engineering standards and tooling.

Lead the architecture, development, and deployment of scalable APIs and backend systems for Afresh’s AI-powered grocery ordering platform. Partner with product, account management, design, and engineering teams to deliver integrated solutions used across thousands of stores. Drive projects from conception through launch, make high-impact architectural decisions, understand complex business dependencies, and mentor junior engineers.

Supervise staff accountants, review and deliver financial statements, dashboards, KPIs, and forecasts, and maintain strong client relationships. Lead client onboarding, coordinate year-end tax handoffs, provide accounting guidance, train team members, resolve technical issues, and improve firm processes. The role also includes project tracking, client communication, administrative documentation, continuing education, and ensuring timely, accurate deliverables in a fully remote CPA firm.

Leads the enterprise Talent Acquisition function, recruiting strategy, team, hiring standards, executive searches, pipelines, and quality-of-hire initiatives. Partners with the CPO, CEO, executives, and business leaders on workforce planning, market intelligence, compensation benchmarking, and talent decisions. Uses data, AI, and automation to improve recruiting efficiency and decision quality while coaching the recruiting team and supporting scalable growth.

Conducts evaluative and generative UX research for B2B and B2C digital projects. Responsibilities include planning usability tests and interviews, developing screeners, recruiting participants, coordinating studies, synthesizing qualitative findings, creating insight readouts, and delivering actionable recommendations. The researcher manages studies end to end, collaborates with UX stakeholders, handles multiple client projects, and uses generative AI tools responsibly while validating outputs. This is a remote, US-based contractor role averaging 15–20 hours weekly.

Coordinates K-12 standardized testing operations, including calendars, rosters, testing sites, staffing, accommodations, devices, compliance, security, communications, and records. Supports STAAR, SAT, PSAT, and other assessments; trains staff, resolves testing barriers, maintains equipment and office supplies, enters PEIMS data in PowerSchool, and collaborates with families, schools, technology teams, vendors, and state testing authorities. The role requires two weekly San Antonio office days and up to 20% travel.

Lead a team handling complex US and UK insurance complaints, personally investigate escalated motor and property disputes, manage regulatory referrals, conduct root-cause analysis, maintain audit-ready complaint processes, and partner with Claims, Product, Engineering, QA, and Compliance to improve systems and outcomes.

Lead AI strategy and implementation across a digital agency, partnering with senior leadership and department directors. Design AI workflows and systems, run iterative sprints, manage architecture and project planning, and oversee implementation, testing, QA, adoption, and data governance. Translate AI opportunities into scalable operational plans across creative, marketing, ecommerce, lifecycle marketing, and web teams while simplifying complex concepts for cross-functional stakeholders.

Develops and executes regional channel marketing strategies with partners to increase engagement, pipeline, and revenue. Builds co-marketing plans, leads webinars, workshops, tradeshows, and demand-generation campaigns, and coordinates sales, product, and cross-functional participation. Measures campaign performance, reports on marketing metrics and ROI, and ensures partner marketing activities meet business objectives.