Top Tech Jobs & Startup Jobs in Chicago, IL

Develop new business and grow existing accounts across Western Michigan. Prospect, build relationships, present packaging and labeling solutions, prepare quotes, negotiate contracts, and close sales. Partner with manufacturing facilities to ensure customer fulfillment. Requires extensive daytime travel within the territory, home every night after training, and a six-month training period in Milwaukee or through regular travel there.

Contract 2D Art Generalist creating concept art, character illustrations, and game art. Collaborate with the team to develop a cohesive visual direction, contribute art assets to the project, and iterate based on feedback. Work varies week to week; potential for additional future work.

Full-cycle B2B SaaS Account Executive selling an AI-powered PropTech work OS. Own deals end-to-end, run discovery-based demos, build and manage pipeline, prospect via outbound and industry relationships, sell operational and financial outcomes, maintain forecasts, and surface market feedback to product and leadership.

Own and scale JivPad’s full growth funnel across paid, organic, referral, partnership, and lifecycle channels. Develop data-driven strategies, run marketing experiments, optimize acquisition through retention, manage performance campaigns, analyze cohorts and attribution data, and collaborate with Product, Engineering, Content, Brand, and Community teams to drive adoption and revenue.

Drive private wealth sales across the Chicago, Minnesota, and Wisconsin territory. Manage prospecting, relationship development, sales processes, meetings, and product presentations for financial advisors and their clients. Provide investment, portfolio construction, and market guidance while representing multiple private markets solutions. Leverage existing broker-dealer and wirehouse relationships, build trust, qualify opportunities, and coordinate with senior internal teams to generate sales.

Product Designer responsible for leading mobile and web design projects for Pika’s generative AI creative platform. Duties include developing product strategies, interaction patterns, visual language, design systems, prototypes, and user flows; collaborating with product, engineering, and research teams; engaging creators; and delivering accessible, polished experiences from concept through launch.

Design and operate scalable, secure, highly available AWS infrastructure for a revenue management platform. Build infrastructure automation, CI/CD tooling, monitoring, and developer tools; advise on architecture, improve reliability and security, troubleshoot 24/7 incidents, lead root cause analyses, support AI-enabled DevOps workflows, and mentor engineers. The role participates in a weekly on-call rotation and is remote in the US or Canada.

Conduct open-ended research on markets, companies, products, funding, competitors, technologies, people, and regulations. Transform findings into clear, sourced matrices, briefs, landscape maps, and one-pagers with actionable points of view. Use AI tools and lightweight scripts or scrapers to accelerate research, manage multiple shifting requests, and communicate concise conclusions to leadership.

Own the enterprise architecture vision for scalable, high-performance, cost-efficient multi-tenant SaaS systems. Lead AWS cloud optimization, distributed data and AI infrastructure, architectural governance, and Architecture Review Council activities. Guide engineering teams on microservices, event-driven systems, automation, and cloud-native practices while driving GenAI adoption across the software lifecycle. Build prototypes, establish architectural standards, optimize total cost of ownership, and mentor technical leaders.

Leads worldwide sales transformation through strategic planning, revenue intelligence, fiscal and capacity planning, AI-enabled workflow modernization, and cross-functional execution. The role partners with senior commercial leaders to identify growth opportunities, improve productivity, guide investments, establish governance, and translate data-driven insights into measurable business outcomes.