Top Tech Jobs & Startup Jobs in Chicago, IL

Volunteer administrative assistant to support organizational workflows: coordinate across teams, prepare presentations and reports, support internal communications, and assist with ad-hoc support tasks to advance the nonprofit's mission.

Provide Tier I technical support for smart cooler vending operators. Receive and categorize support requests, guide customers through approved troubleshooting, assist with onboarding and app usage, gather connectivity and payment-reader information, document issues, communicate next steps, and follow up. Escalate complex connectivity, backend, hardware, payment integration, and vendor issues to Tier II support while maintaining clear customer communication and accurate records.

You will execute and improve insurance workflows, analyze operational efficiency, collaborate with product teams, and support onboarding and documentation efforts.

Manage customer implementations and ongoing support, train users, troubleshoot issues, gather and synthesize customer feedback, and liaise with product and engineering to improve the product and roadmap while ensuring strong customer relationships.

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.

Own Fi’s data platform and analytics roadmap, building event-driven pipelines, warehouse models, self-serve BI, and experimentation capabilities. Lead and develop a team of four analysts while partnering with Finance, Product, and Hardware on forecasting, unit economics, device analytics, retention, and board reporting. Serve as a strategic data leader in a fast-growing Series B startup.

Leads Re:Build Manufacturing’s U.S. government strategy and sales efforts across defense, energy, and industrial-base ecosystems. Develops federal opportunities, builds relationships with agencies, Congress, defense primes, and industry, shapes Washington policy positioning, and translates government priorities into funded commercial opportunities and internal investment decisions. Requires deep federal networks, defense-market expertise, acquisition and industrial-base policy fluency, and senior-level business development or government experience.

Develops government contracting business by engaging command leadership, identifying prospective customers and partners, reviewing forecasts, assessing requirements, onboarding professionals, supporting administrative activities, and contributing to winning proposals. The role reports to the company president and requires strong communication, email, Microsoft Office, Excel, and AI-tool skills.

Work directly with customers to design, deploy, and integrate end-to-end AI evaluation pipelines. Curate data, define annotation schemes, set up LLM-based judges, run initial experiments, produce actionable results, and translate technical systems into practical workflows for users.

Build and present technical proofs of concept for sales opportunities, create scripts and integrations to demonstrate platform capabilities, and translate customer requirements into viable solutions. Partner with Sales, Product, and R&D teams to validate feasibility, support implementations through production, communicate with technical and executive stakeholders, and turn successful deployments into reusable sales assets.