Top Tech Jobs & Startup Jobs in Chicago, IL

Own end-to-end acquisition of net-new B2B trade and hospitality accounts, including prospecting, pitching, closing, pipeline management, and relationship development. Build repeatable AI-powered outreach workflows, maintain CRM discipline, improve forecasting and conversion, and coordinate with merchandising, operations, and vendor teams to support trade clients and special orders.

Design and build interfaces for HUD’s AI agent training, evaluation, and marketplace products. Translate complex reinforcement learning workflows, agent runs, evaluation results, reward signals, and quality feedback into clear, actionable experiences. Collaborate with users, researchers, and engineers to ship polished products, conduct user discovery, improve usability, and develop reusable interaction patterns.

The Content & Prompt Operations Specialist manages AI-assisted content workflows, ensuring accuracy and engagement in content produced. Responsibilities include writing prompts, drafting content, proofreading, and improving AI outputs while following structured processes.

Build web-first product experiences, reusable components, RESTful APIs, and scalable data pipelines for Wikimedia’s web and mobile app surfaces. Deliver initiatives from discovery through production, emphasizing accessibility, performance, testing, observability, and maintainability. Collaborate with product managers, designers, analysts, and native app engineers in a fully remote environment while prioritizing user impact, technical quality, and pragmatic delivery.

Build and own Snout’s data foundation, including PostgreSQL and dbt warehouses, ingestion pipelines, dimensional models, data quality, documentation, and reliable rebuilds. Reconcile data from veterinary practice-management systems, support LLM/AI tooling, translate stakeholder needs into technical plans, and establish the foundation for a future data team and analyst.

Manages accounts receivable processing, reconciliations, payment research, collections, refunds, monthly close, journal entries, billing, renewals, audits, and reporting. Resolves member and stakeholder inquiries, supports financial controls, partners with Finance and IT on system issues, and improves AR processes and workflows. Requires strong accounting, analytical, systems, communication, and organizational skills.

Owns the full finance function for a growing e-commerce brand, including financial reporting, cash forecasting, budgeting, profitability improvement, process automation, SOP development, systems implementation, dashboards, and cross-functional financial planning. The role partners with executive leadership to scale financial operations and support sustainable growth.

Make high-volume inbound/outbound calls to engage consumers, identify needs, provide consultative solutions, support Convatec product sampling and campaigns, capture sales, manage customer data, meet sales and efficiency targets, and share consumer insights with the marketing team.

Manage and secure client Windows Server, cloud, virtualization, Active Directory, and Microsoft 365 environments. Administer tenant hardening, migrations, identity integrations, backups, disaster recovery, patching, and compliance controls. Lead P1/P2 incident response, root-cause remediation, change management, documentation, and infrastructure improvement initiatives. Partner with service desk, engineering, and security teams, advise clients on modernization and security enhancements, maintain operational runbooks, and mentor junior technicians.

Leads operational risk assessments, data analysis, management reporting, fraud program reviews, regulatory initiatives, and AI model validation. Evaluates controls, analytical tools, and LLM reliability using benchmark testing, consistency checks, adversarial prompting, and bias assessment. Partners with risk, technology, compliance, audit, and business teams to resolve issues, support responsible AI adoption, and deliver recommendations for regulatory and executive audiences.