Top Tech Jobs & Startup Jobs in Chicago, IL

Leads and develops an SRE team responsible for platform engineering, Kubernetes infrastructure, observability, CI/CD, infrastructure as code, reliability frameworks, disaster recovery, security, and cost optimization. Partners with engineering leaders to establish platform roadmaps and self-service capabilities, manages on-call operations, and drives automation, scalability, developer experience, and operational excellence.

Build and maintain scalable full-stack web application features and distributed microservices. Own complex features from design through deployment, improve application performance and reliability, support on-call operations, troubleshoot incidents, enhance CI/CD and container infrastructure, and collaborate with product, design, infrastructure, and API teams. Mentor engineers and contribute to technical standards while delivering customer-focused shipping and fulfillment experiences.

Own premier customer accounts and escalated support tickets through resolution, coordinating cross-functional teams and managing churn risk. Provide expert support for Shippo’s webapp and API, de-escalate sensitive or executive-level issues, identify recurring product problems, and provide product feedback. Mentor specialists, conduct training, create documentation, and use AI-assisted tools for ticket research, quality assurance, and pattern analysis.

Own Shippo’s API platform roadmap, including label creation, MCP, SDKs, developer documentation, onboarding, and API standards. Define platform architecture and integration testing standards with engineering leadership, represent developer needs across teams, engage customers to identify integration friction, and mentor other product managers. The role requires deep API, developer experience, and SDK expertise, along with experience in MCP, agentic commerce, or LLM-driven integrations.