Top Tech Jobs & Startup Jobs in Chicago, IL

Own end-to-end UI/UX for Headstarter's consumer and B2B products, create user flows, wireframes, high-fidelity designs and a cohesive design system, collaborate with founders and engineers, iterate on feedback and data to drive product and hiring outcomes.

Manages client questions and feedback, analyzes inquiry trends, develops operational efficiencies, refines business rules and automations, and coordinates with internal teams to improve processes, products, and client experience.

Own a company performance domain, diagnose ambiguous business problems, set cross-functional priorities, and deliver measurable portfolio value. Lead executive decision-making, analytical standards, operating rhythms, and translation of operational needs into Product, Data Engineering, and AI roadmaps. Manage and develop a team of three to four, hire talent, evaluate AI investments, and drive durable operating change while remaining hands-on in analysis and implementation.

Own the development and launch of a new service line from ideation through revenue generation. Define the business case, delivery model, technology and staffing needs, procedures, and success metrics; run pilots, evaluate client outcomes and unit economics, and integrate successful offerings into sales, fulfillment, account management, and reporting processes.

Own and scale customer education for a healthcare SaaS platform through role-based onboarding, self-service learning, assessments, certifications, and train-the-trainer programs. The role includes selecting and implementing an LMS, developing accessible training content, partnering with Product and Engineering on in-platform learning, managing compliance-sensitive training data, measuring learning outcomes, and eventually hiring and leading a customer education team.

Own an engineering team’s architecture, delivery, roadmap, product outcomes, and operational health for commerce application platforms. Lead hands-on development, AI-assisted engineering adoption, technical scoping, cross-team dependencies, testing, releases, DORA performance, on-call operations, incident reduction, hiring, and engineer growth. Partner closely with Product to deliver reliable software predictably while maintaining high engineering standards.

Develop new staffing and recruiting clients among small and midsized businesses. Responsibilities include prospecting through networking, LinkedIn, email, phone, referrals, and industry groups; building relationships with decision-makers; identifying hiring needs; generating qualified opportunities; managing a sales pipeline; nurturing prospects; and identifying new markets and partnerships. This is a remote, flexible, commission-only role with uncapped earning potential.

Build and scale Bubble’s backend infrastructure and platform services, improving performance, reliability, observability, capacity management, and data scalability. Contribute to workflow engines, data-tier systems, cloud infrastructure tools, and high-volume services. Participate in triage and on-call processes, diagnose incidents, and implement preventative improvements while collaborating effectively with engineering teammates.

Manage data collection and market research for telecom and datacenter suppliers, support RFP/RFQ creation, build vendor partnerships, coordinate cross-functional evaluation and contracting, track supplier performance and market trends, and provide data-driven recommendations to inform network expansion and procurement strategy.

Supports commercial insurance claims across GL, Cyber, D&O, Property, and Marine/Cargo lines. Responsibilities include submitting notices, gathering documentation, tracking deadlines and responses, assisting with coverage analysis and litigation recovery, drafting correspondence, maintaining audit-ready claim files, preparing reporting, and improving claims workflows through automation and technology.