Top Tech Jobs & Startup Jobs in Chicago, IL

The Cloud Engineer II role focuses on managing cloud services, implementing improvements in Azure and Microsoft 365, and collaborating with engineers. Key responsibilities include identity management, troubleshooting issues, and creating automation documentation.

Build and own user-facing features and core platform architecture across frontend, backend, and ML pipelines. Integrate AI workflows (LLMs, embeddings) for curriculum generation and automated evaluation. Manage end-to-end development: requirements, design, implementation, CI/CD, testing, observability, and iteration while collaborating with product, design, ML, and customer teams.

Design, build, and operate scalable backend services and APIs for a SaaS platform using Python/FastAPI. Ensure reliability, performance, and observability across distributed systems. Work with PostgreSQL, SQLAlchemy, Temporal, Redis, AWS, and Terraform. Build frontend features with React and TypeScript, integrate third-party APIs, adopt AI-assisted development tools, mentor engineers, and drive architecture and developer experience improvements.

Lead and close complex enterprise deals with insurance brokers, MGAs, MGUs and wholesalers. Build and manage a qualified pipeline, run RFI/RFP processes, negotiate contracts, present to C-level stakeholders, and expand strategic accounts to drive revenue growth.

Lead retention strategies for DTC clients by managing email and SMS campaigns, analyzing performance, advising clients, and partnering with design and analytics teams to drive measurable growth.

The Customer Success Manager is responsible for onboarding, maintaining customer relationships, and identifying upsell opportunities, ensuring clients achieve desired outcomes.

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.

Lead design and delivery of enhancements to a next-generation AI agent platform. Own large features and infrastructure, mentor engineers, set technical standards, drive cross-team initiatives, improve reliability and SLOs, and influence product and process decisions to scale systems supporting millions of interactions.

Own full-cycle enterprise sales independently — prospecting, discovery, demos, negotiation, and close for complex 6–18 month deals. Build outbound pipeline, run multi-stakeholder sales processes, partner with Product/Engineering, and establish long-term enterprise relationships generating SaaS and transaction commissions.

Design, build, and optimize end-to-end generative AI workflows for image and video production. Integrate ControlNet variants, manage model/versioning and LoRA stacks, create repeatable shot templates, test new tools/models, present findings, and act as a technical resource across creative teams while building external R&D presence.