Top Tech Jobs & Startup Jobs in Chicago, IL

Design, develop, and deliver scalable .NET back-end and front-end solutions within an Agile, DevOps-oriented team. Lead technical design, code reviews, testing-first practices, CI/CD pipelines, containerized deployments, and ensure non-functional requirements (security, performance, scalability, maintainability). Mentor peers and collaborate across product, design, and architecture to produce high-quality software.

Lead the Health & Benefits PMO to manage intake, prioritization, resourcing, and execution of high-priority initiatives. Oversee program and project managers, enforce governance, report to executives, resolve delivery risks, and drive portfolio health and capacity planning.

Administer and support Inspira's hybrid cloud and on-prem infrastructure including Azure, VMware, networking, security, backups/DR, AD, SQL Server, containers/Istio and Helm. Implement IaC and CI/CD, monitor cost and performance, resolve infrastructure incidents, maintain runbooks, cross-train staff, and support integrations with development and client service teams.

Deliver accurate, timely reporting and ad hoc analyses to support business decisions. Triage and fulfill reporting requests within SLAs, validate and reconcile data, document report logic, automate recurring reports, and collaborate with data engineering, visualization, product, operations, and compliance teams. Handle sensitive PHI/PII per policy and improve reporting processes.

The Cloud Operations Admin is responsible for managing enterprise infrastructure across cloud environments, providing hands-on support, troubleshooting, and ensuring compliance with security policies.

The Sr. Sales Executive will build business in national accounts and develop broker relationships, manage business development efforts, and travel for market engagement. Requires 7+ years of sales experience in benefits or financial services, with strong consultative skills and relationship building.

The Sales Executive drives revenue by selling custodial solutions to businesses, targeting primarily Broker-Dealers, RIA firms, and Fund Managers, while executing strategies to meet sales goals.

Provide phone-based support and education to accountholders on FSAs, HSAs, COBRA and related products. Resolve issues, guide customers through online tools, protect sensitive data, meet quality standards, and may be cross-trained for chat/email/text. Complete mandatory training, pass an 85% product exam, and meet service goals.

The Compliance Analyst will assist in compliance with internal policies, the Bank Secrecy Act, and anti-money laundering regulations, performing investigations, analysis, and training within a collaborative environment.

Support Sales Finance by designing and administering sales incentive plans, building advanced financial models, forecasting, and performing profitability and performance analysis. Partner with Sales, HR, and Finance leadership to evaluate plan effectiveness, ensure accurate commission payouts, create executive presentations, and improve reporting, processes, and key performance metrics.