Top Tech Jobs & Startup Jobs in Chicago, IL

Conduct technical evaluations of cloud and AI platforms by provisioning infrastructure, deploying workloads, benchmarking performance, and assessing architectures. Develop reproducible AI inference benchmarks, analyze competitor products and developer experiences, and translate verified findings into battle cards, technical content, product recommendations, and roadmap insights. Collaborate with product management, architects, engineers, sales engineers, and presales teams while fact-checking competitive claims and presenting data-driven results.

The Site Reliability Engineer II ensures the reliability, availability, performance, and security of critical cloud systems and services. Responsibilities include developing automation for provisioning and configuration management, maintaining monitoring and alerting, optimizing infrastructure performance, supporting high availability, and enabling continuous integration and delivery. The role collaborates with security teams and drives operational improvements across cloud and network infrastructure.

Build and maintain reliable, scalable cloud compute platforms across distributed services. Troubleshoot Linux, networking, and production issues; develop automation and AI-assisted tooling; improve monitoring, alerting, SLIs, and SLOs; conduct incident response and root cause analysis; and partner with engineering teams on system design, deployment safety, and operational readiness.

Lead the multi-year vision, strategy, and roadmap for Akamai Cloud developer tooling. Oversee APIs, CLI tools, SDKs, Terraform providers, API Gateway capabilities, and AI-first developer workflows. Partner with engineering on API standards, schema governance, platform performance, authentication, and traffic management. Modernize enterprise APIs, manage breaking changes, and unify developer experience across cloud platforms.

Lead large enterprise security deployments, provide microsegmentation and Zero Trust design guidance, support platform configuration and integrations, resolve technical issues with Support and Engineering, advise customers on product updates, and deliver training. The role requires extensive customer-facing security experience, cloud platform knowledge, networking and operating system expertise, and familiarity with microsegmentation, EDR, or network security products.

Own strategic customer relationships throughout the lifecycle, serving as the main technical contact and driving adoption, value realization, retention, renewals, and expansion. Lead onboarding, training, workshops, business reviews, usage analysis, and technical escalations. Partner with Sales, Product, and Engineering to support deployments, resolve issues, surface customer feedback, and identify upsell opportunities for a cybersecurity microsegmentation solution.

Drive new-account acquisition and cloud migrations for AI and infrastructure solutions. Generate pipeline through global outbound prospecting, execute multichannel outreach, manage the full enterprise sales cycle, and close large cloud, infrastructure, and data center deals. The role requires deep knowledge of AI computing, cloud infrastructure, power capacity, cooling systems, financial modeling, and B2B enterprise net-new cloud sales. Candidates work from Akamai’s San Francisco office and collaborate across time zones.

Lead business analysis for billing and accounts receivable systems, gather and document requirements, design solutions, coordinate cross-functional teams, support UAT and hypercare, and deliver enhancements across the SDLC using Agile practices.

As a Site Reliability Engineer II, you'll automate tasks, monitor AI workloads, enhance dashboards, support CI/CD processes, and collaborate with engineering teams on complex issues while participating in on-call rotations.

Drive product vision and strategy for IaaS, leading cross-functional teams, enhancing customer satisfaction, and growing revenue through innovative cloud solutions.