Top Tech Jobs & Startup Jobs in Chicago, IL

Lead development and maintenance of cross-platform mobile apps using Flutter/Dart across iOS, Android, and web. Implement scalable architecture, integrate GraphQL/backends, support native build and release pipelines, collaborate with product/design/AI teams, apply AI-assisted coding responsibly, troubleshoot performance and stability issues, and contribute to testing, CI/CD, and documentation.

Provide high-trust executive support to multiple C-suite leaders: manage complex calendars, travel, meeting prep, correspondence, expense reporting, and confidential materials. Coordinate leadership meetings, offsites, onboarding, and vendor relationships; track action items and partner cross-functionally to streamline executive operations and improve efficiency.

Manage and administer ARO/OpenShift clusters, design scalable Kubernetes deployment patterns with Helm, build reusable Helm charts, implement ArgoCD/GitOps CI/CD pipelines, configure service mesh (Istio/Linkerd), write/manage manifests and operators, onboard application teams, and monitor/troubleshoot platform performance.

Provide frontline technical support via phone, email, and chat. Troubleshoot and resolve common platform issues, document cases in Salesforce, escalate complex problems to Tier II, educate customers on features, and contribute to knowledge base improvements.

Field-based role to recruit, train, and develop independent health insurance producers and agencies across a territory. Promote SB product lines, drive adoption of INSXCloud EDE platform, meet recruitment and production quotas, deliver in-person training, and coordinate contracting and compliance. Heavy travel and producer development focus with licensing and FFM certification required.

Own and operate the data plane: develop Envoy/WASM filters for deep packet inspection, deploy and manage EKS workloads with Helm/GitOps and CI/CD, integrate Redis sidecars, provide observability (Prometheus/Grafana/OpenTelemetry), ensure reliable audit log streaming, and author ADRs as the data plane evolves.

Provide strategic legal counsel for global AI products, ensuring compliance with evolving AI safety and privacy laws, enabling sales and product teams, engaging regulators and industry groups, driving AI trust initiatives, applying legal technology to streamline reviews, and mentoring junior lawyers to support product growth while mitigating risk.

Entry-level HR Generalist providing full-cycle HR support for locations in the US, Canada, and Puerto Rico. Duties include talent acquisition, employee relations and investigations, HRIS recordkeeping, performance management, benefits and payroll administration, wage and labor compliance, workers' compensation and safety, reporting, and HR projects. Acts as primary HR contact and advises managers on HR matters.

Manage filing and follow-up of FHA Part B and non‑conveyance claims (CWCOT, SFLS) and loss mitigation claims (PFS, Partial, SFB, Mod, HAMP). Monitor title package submissions, resolve suspended claim exceptions, track payments, maintain reports/queues, and meet investor/HUD timelines to minimize losses.

Lead and grow a Western U.S. enterprise sales organization for managed infrastructure, colocation, and cloud services. Combine hands-on selling in complex deals with coaching, pipeline management, forecasting, hiring, and cross-functional alignment to drive new business and account growth.