Top Tech Jobs & Startup Jobs in Chicago, IL

Build and maintain production-grade iOS apps using Swift and SwiftUI; integrate RESTful APIs for insurance and payments; implement AI-assisted features; optimize performance and reliability; add analytics and crash reporting; collaborate with backend, design, and AI/ML teams to ship scalable App Store-ready releases.

Act as an embedded HR advisor to business leaders across regions, guiding performance management, employee relations, workforce planning, talent initiatives, and people-data analysis to translate business goals into practical people actions.

Designs and runs company-wide engagement and learning programs, manages calendars and training logistics, coordinates internal and external trainers, runs onboarding culture sessions, tracks participation and effectiveness, and partners with People Ops and leaders to embed culture and continuous improvement.

Hands-on Head of People to build and run global HR across multiple countries. Own talent acquisition, performance management, payroll, compensation, benefits, compliance, and HR operations. Partner with founders and senior leaders on org design, workforce planning, and leadership development while building a small, execution-focused HR team.

Design, build, and operate backend systems that orchestrate LLMs and AI workflows for insurance products. Implement inference pipelines, optimize latency/throughput/cost, ensure observability and reliability, debug distributed production issues, and collaborate cross-functionally to deliver scalable, production-ready AI capabilities.

Execute core HR operations across the employee lifecycle: prepare and maintain HR documentation, manage HRIS records, support onboarding/offboarding, track attendance and timesheets, assist benefits administration, and perform HR audits to ensure data accuracy and compliance.

Own execution and improvement of compensation and benefits programs. Design and maintain salary structures, conduct benchmarking, prepare salary review proposals, administer benefits, ensure statutory compliance, liaise with providers, maintain records and reporting, and support rewards-related HR projects.

Lead and run global business operations: set up offices and entities, implement payroll and local ops, manage vendors, support recruiting, run events, track initiatives, and improve processes to scale the company.

Lead design, development, and delivery of production AI systems and orchestration connecting LLMs, backend services, and workflows. Own inference pipelines, routing, caching, observability, and incident response. Drive decisions on latency, reliability, cost, and scalability; mentor engineers; collaborate cross-functionally to ship production-grade, reliable AI automation for insurance workflows.

Design, build, and productionize LLM-powered features integrated into insurance workflows. Develop prompts, reasoning flows, structured outputs, guardrails, and validation. Evaluate model performance with real data and experiments, integrate AI into APIs and automation, collaborate with product and engineering, and continuously improve user-facing AI interactions and reliability.