Top Tech Jobs & Startup Jobs in Chicago, IL

Provide administrative support to ensure smooth office operations: answer and direct calls, schedule meetings, maintain filing, manage correspondence, perform data entry and document preparation, order supplies, coordinate travel and expenses, assist with presentations and company events, and handle confidential information.

Manage complex Employment Practices Liability (EPL) and Fiduciary claims by investigating, evaluating coverage, determining valuation and settlement strategies, attending mediations/trials, drafting coverage correspondence, mentoring junior adjusters, supporting underwriting/actuarial analytics, controlling litigation costs, and maintaining claim records and relationships with brokers, insureds, and counsel.

Manage a large inventory of complex workers' compensation claims, lead investigations to determine liability and compensability, negotiate settlements within authority, maintain detailed claim files, communicate with stakeholders, and potentially coach staff. Remote within Illinois.

Serve as primary contact for prospective and current clients, assess needs, guide onboarding, document interactions, escalate issues, coordinate with internal teams, and improve workflows while managing high-volume communications.

Drive new business and share-of-wallet growth for Challenger by prospecting, managing the full sales funnel, negotiating contracts, and maintaining client relationships. Deliver solution-based sales to premium customers, produce regular activity and CRM reports, and meet/exceed sales targets while collaborating with internal teams.

Monitor and maintain trading systems, diagnose and resolve production issues, manage deployments and automation for Linux/Windows applications, collaborate with trading and risk teams, and build tools to improve reliability and reduce operational effort.

Provide administrative support including calendar management and committee support, coordinate a complex deputy-level calendar, prioritize tasks, anticipate scheduling needs, and support CMAP's program and project operations.

Manage and mentor tax associates; prepare and review corporate, partnership, and individual tax returns (founders/high-net-worth focus); produce tax projections; identify solutions for complex tax issues; handle client inquiries; develop process improvements; perform strategic tax planning and ad hoc tax projects. Partnership track and client book transition opportunities available.

Manage full project lifecycle for facility and emergency operations projects, overseeing scope, budgets, schedules, subcontractors, client relations, risk mitigation, and performance reporting. Provide consulting to clients and leadership, negotiate contracts and change orders, troubleshoot project issues, and implement process improvements.

Lead platform and AI infrastructure including cloud (Azure/OCI), ML/AI production, GPU capacity, model serving, MLOps, data platforms, incident response, and observability. Build scalable AI platform, set SLOs, brief executives, and manage a global team of managers and senior ICs.