Top Tech Jobs & Startup Jobs in Chicago, IL

Designs executive presentations, pitch materials, RFPs, case studies, trade show environments, promotional assets, print collateral, infographics, and digital communications. Adapts global branding for North American audiences, maintains brand consistency, manages reusable creative assets, and prepares production-ready files. Collaborates with business development, corporate affairs, product, copywriting, and multimedia teams while managing multiple deadlines and stakeholder feedback.

Design and deploy production AI assistants, copilots, agents, RAG systems, and workflow automation using enterprise data. Build AI backend services, APIs, microservices, and AWS serverless workflows; integrate enterprise platforms; implement observability, responsible AI, human-in-the-loop controls, and traceability. Partner with Data, IT, and business teams to improve operational processes and decision-making while managing production incidents, model rollbacks, performance, accuracy, and cost.

Own end-to-end delivery of core product features, build AI/ML pipelines for construction document and drawing analysis, and shape scalable frontend, backend, and ML architecture. Collaborate with co-founders and construction users, translate workflow needs into product improvements, establish engineering practices, and help grow the team. The role spans computer vision, LLM systems, frontend, backend, and production infrastructure in a fast-moving startup environment.

Leads GumGum’s Central region sales organization across Chicago, Detroit, and Ohio. Owns regional revenue, exceeds sales targets, manages and develops 4–8 sellers, recruits talent, executes account-based strategies, strengthens brand and agency relationships, expands client investment in media solutions, drives new business, and partners with leadership and Product on growth initiatives. Requires deep digital advertising and ad-tech expertise, strong coaching ability, executive presence, and analytical business judgment.

Administer and optimize P21/SQL databases, design logical and physical data models, manage SSRS reports and SSIS packages, ensure security, backups, and recovery, tune performance, collaborate with cross-functional teams and vendors, and document database procedures and policies.

Research target distribution and warehouse accounts, identify decision-makers, conduct high-volume outbound outreach, qualify leads, document account insights in Salesforce, and schedule meetings for enterprise account executives. The role also requires articulating Loadsmart’s SaaS solutions, developing industry and competitive knowledge, refining prospecting messaging, and collaborating with sales teammates to achieve growth goals.

Build and ship production AI agents that help mobile app developers manage subscriptions and paywalls. Own agent orchestration, tool execution, context management, evaluation, observability, permissions, and human-in-the-loop controls. Develop reliable, secure, user-facing backend systems, scope projects independently, monitor adoption, improve features after launch, participate in architecture and incident response, and mentor engineers.

Leads bike computer hardware products from concept through commercialization, including product strategy, requirements, positioning, go-to-market planning, profitability, demand forecasting, customer engagement, technical presentations, sales enablement, training, and lifecycle management. Partners with Engineering, Industrial Design, Sales, Marketing, and external customers to develop products, launch materials, and business strategies. Requires domestic and international travel up to 40% and customer-facing bike demonstrations.

Leads Carina’s cloud infrastructure, internal IT, cybersecurity, risk management, compliance, and business continuity programs. Oversees AWS platform operations, infrastructure as code, deployment reliability, observability, incident response, disaster recovery, employee technology, identity systems, vendors, budgets, and governance. Advises executives on technology strategy, security posture, operational risk, and investments while partnering with Engineering and Data to provide a secure, reliable technology foundation.

Own Energy CX’s revenue operating system, including HubSpot, revenue technology, data quality, forecasting, pipeline intelligence, capacity planning, metrics, quota tracking, and compensation administration. Build reliable reporting and forecasting infrastructure, diagnose pipeline and conversion issues, maintain CRM governance, and partner with engineering on data pipelines connecting HubSpot with billing and analytics tools.