Top Tech Jobs & Startup Jobs in Chicago, IL

Manage property and casualty claims recovery and subrogation portfolios from investigation through settlement and collection. Evaluate liability, damages, coverage, collectability, and recovery potential; prepare demand packages; negotiate settlements; track legal deadlines; coordinate arbitration, litigation, counsel, experts, and vendors; maintain accurate claims documentation, forecasts, payments, and reconciliations.

Sell RELEX supply chain and retail planning SaaS to enterprise customers across retail, wholesale, manufacturing, and CPG. Manage full sales cycle: prospecting, pipeline management in Salesforce, value-based selling, contract negotiation, and closing with C-level stakeholders while collaborating with internal teams to drive customer satisfaction and growth.

Own and architect core AI pharmacy products, including prior authorization pipelines, Epic integrations, patient communications, and production agentic systems. Build hands-on software using LLMs, RAG, function calling, and evaluation workflows in a regulated healthcare environment. Set engineering standards, make architectural decisions, manage delivery across product milestones, and collaborate across teams to ship reliable solutions that improve pharmacy operations.

Own the product roadmap for AI-enabled data products, lead customer discovery with CPG and foodservice stakeholders, translate insights into requirements and priorities, and guide cross-functional delivery from concept through launch. Develop go-to-market and adoption plans, monitor product performance, manage risks, and communicate business impact. The role requires practical AI and machine learning fluency, strong customer research, commercial product management experience, and 20–30% travel.

Research and analyze cybercriminal activity across dark web and underground platforms, track threat actors and campaigns, produce intelligence reports, maintain covert sources and personas, investigate cryptocurrency and money laundering, and deliver actionable findings to customers. The role also uses OSINT, AI-assisted workflows, and intelligence platforms while contributing to automation and proactive threat research.

Leads consultative mid-market sales for women's health and family-building benefits. Owns pipeline development, relationship building, solution design, presentations, negotiations, forecasting, and full-cycle closing with employers and benefits consultants. Partners cross-functionally to advance opportunities, gathers feedback for product development, and consistently achieves sales targets. Requires Texas residence, U.S. work authorization without sponsorship, and travel up to 40%.

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.