Top Tech Jobs & Startup Jobs in Chicago, IL

Administer FMLA, ADA, disability, personal, military, and state-specific leaves from initial request through return to work. Serve as the primary contact for employees, clients, managers, and benefits vendors; maintain documentation, timelines, records, and compliance. Provide leave-policy guidance, resolve routine claims and HRIS issues, coordinate benefit and payroll impacts, manage leave technology data, and report on leave metrics and trends.

Build scalable infrastructure for LLM-based agentic AI supporting autonomous security operations. Responsibilities include designing agent orchestration frameworks, LLM inference and resource-management systems, MCP servers, supporting APIs, and distributed backend services. The role collaborates with machine learning, security research, engineering, and product teams. Required experience includes backend infrastructure, distributed systems, APIs, microservices, cloud deployment, containerization, orchestration, and Python, Java, or Go.

Hunts and closes new SMB customers for cloud, backup, disaster recovery, and managed infrastructure services. Builds primarily self-sourced outbound pipeline, conducts discovery, develops business cases, partners with solution engineers, negotiates contracts, and maintains accurate forecasts. Supports customers through onboarding and go-live before handing accounts to Account Management. The role focuses exclusively on new-logo acquisition rather than renewals or expansion sales.

Drives sales revenue for payroll and ASO services, identifies opportunities in assigned accounts, develops proposals and pricing, manages client communications, tracks proposal components, coordinates cross-functional project plans, maintains client relationships, and supports marketing, product, and service enhancements.

Sell real estate acquisition contracts to homeowners through inbound and follow-up leads. Build trust, uncover seller motivations, handle objections, negotiate within pricing guidelines, make offers, and secure profitable agreements. Respond to leads within 90 seconds, maintain disciplined long-term follow-up, document CRM activity, and ensure signed contracts convert to closed transactions. Participate in training, roleplay, call reviews, pipeline meetings, and KPI reporting. The role offers a base or recoverable draw plus performance-based commissions.

Supports corporate narrative development, Japanese-language web and marketing collateral, media outreach, white-paper research, stadium advertising, vendor coordination, communications delivery, AI-enabled content creation, and international market research. The intern works remotely with senior leadership across U.S., UK, South Korean, and Japanese markets, managing meaningful projects and timelines while producing audience-specific content and building repeatable AI workflows.

Design and improve user experiences across 15 life sciences websites, email newsletters, and a B2B SaaS RFP platform. Create wireframes, high-fidelity Figma designs, responsive layouts, design-system components, developer specifications, accessibility guidance, and analytics requirements. Collaborate with product, engineering, editorial, and commercial teams, review implementations, and apply AI tools to accelerate design workflows.

Lead and scale Liquibase’s Customer Success organization, overseeing account executives responsible for renewals and expansion. Own retention, net revenue retention, customer health, adoption, and post-sale experience. Build repeatable processes, playbooks, dashboards, and forecasting models; manage account risk; develop customer relationships with technical executives; accelerate implementation and adoption; and provide customer insights to Sales, Product, Engineering, and Support.

Conduct local sports and entertainment sponsorship research, identify brands and sponsorship assets, document signage and activations, and submit accurate observations to SponsorUnited’s database. Scouts complete training, communicate progress, manage assignments independently, and may attend approved local events. The six-month internship is remote and assignment-based, with potential in-person venue scouting. Compensation is unpaid, though approved event and venue-access costs may be covered.

Lead the architecture and development of enterprise analytics models, dbt transformation pipelines, semantic layers, and BI datasets. Apply dimensional modeling, data governance, quality testing, observability, and performance optimization to deliver trusted business data. Partner with executives and cross-functional teams, standardize metrics, improve legacy workflows, support AI/ML integrations, and mentor engineers. Own key domain models and contribute to the analytics platform roadmap as a technical leader.