Top Tech Jobs & Startup Jobs in Chicago, IL

Own Windsor Path’s M&A deal origination function by managing the Affinity pipeline, sourcing and qualifying acquisition opportunities, leading early owner conversations, coordinating preliminary diligence, and supporting LOI advancement. Manage external BDR firms and a junior Business Development Associate, establish scalable outreach processes, maintain pipeline KPIs, and develop relationships with brokers and industry contacts. Track competitive acquisition activity and represent the firm professionally in the accounting and advisory market.

Founding Technical Account Executive responsible for creating and executing a technical infrastructure sales motion from scratch. The role targets organizations distributing real-time data, replaces cloud WebSocket and CDN delivery, develops data monetization opportunities, and manages deals from discovery through pilot. The executive will travel extensively, build relationships with technical and commercial stakeholders, relay customer insights to product and engineering, and eventually help hire and lead the sales team.

Designs electrical control systems for conveyor and material-handling equipment, including power calculations, 480V and 120V schematics, I/O drawings, PLC and panel layouts, field-device layouts, and material specifications. Collaborates with customers, sales engineers, and project managers to define requirements. Inspects, tests, commissions, and troubleshoots motor control panels for compliance with design standards, codes, and project specifications.

Design, build and maintain Microsoft Cloud applications using Power Apps/Pages and Azure services. Implement Entra ID authentication, Azure Functions/App Services, Logic Apps and Blob storage. Create Azure Data Factory pipelines and APIs (REST/GraphQL), integrate external services and LLM data pipelines, and ensure performance, security, and scalability while collaborating with customers to turn requirements into streamlined apps.

General sales talent-pool application for potential future opportunities in business development, account management, inside sales, outside sales, and other customer-focused positions. Applicants are encouraged to monitor the employment page and apply directly to specific openings. Qualified profiles may be reviewed for current or future sales needs, with selected candidates contacted for further discussion.

Coach Leland customers pursuing private equity careers through interview preparation, resume reviews, recruiting guidance, and career navigation. Mentors host virtual sessions, set their own hours and rates, and provide practical insight into recruiting at leading private equity firms. The role requires substantial private equity experience and interviewing expertise while partnering with Leland to deliver a high-quality coaching experience.

Design, build, and deploy production-grade agentic AI systems, including autonomous and multi-agent architectures, tool-use orchestration, memory, retrieval, and function-calling workflows. Integrate agents with enterprise tools and databases, implement evaluations, guardrails, observability, fallback paths, and human-in-the-loop controls. Lead technical strategy, client collaboration, prototyping, and product direction for enterprise AI initiatives.

Design polished web and mobile experiences across banking and travel products, owning work from concepts through production-ready UI. Extend the design system, translate the premium brand into product experiences, and collaborate with engineering and product to ship high-quality designs. Provide occasional brand and marketing support while working autonomously in a fast-moving, lean startup.

Conduct title examinations, chain-of-title research, curative work, and oil and gas contract drafting and negotiation across West Virginia. Manage client relationships, prepare title and acquisition materials, coordinate multiple projects, mentor junior landmen, and ensure accurate, timely work product. Requires deep knowledge of West Virginia recording systems, oil and gas law, county procedures, and industry documents, along with regular travel throughout the state.

Own the architecture, roadmap, and production operation of search and recommendation systems across discovery surfaces. Lead retrieval, ranking, personalization, relevance measurement, experimentation, OpenSearch infrastructure, signal pipelines, and candidate generation. Partner with Product, Data, ML, and Trust & Safety to balance relevance, freshness, safety, latency, and cold-start behavior. Establish engineering standards, instrumentation, rollout processes, and runbooks while mentoring backend engineers.