Top Tech Jobs & Startup Jobs in Chicago, IL

Designs and evolves Cyber Defense Operations’ strategic operating model to address AI-accelerated threats. Responsibilities include identifying operating gaps, advising leadership, establishing governance and cross-functional structures, driving AI adoption frameworks, synchronizing workstreams, and escalating stalled initiatives. The role requires strategic systems thinking, executive communication, incident-response awareness, and experience managing cross-functional programs.

Leads technical sales engagements for Microsoft AI Business Process solutions, using demos, proofs of concept, hackathons, and architecture workshops. Partners with enterprise developers, platform leaders, and engineering teams to design secure, scalable solutions across Dynamics 365, Power Platform, and cloud environments. Resolves technical objections, supports production deployments, develops expertise in business applications, and represents Microsoft through customer forums and developer communities.

Lead complex, enterprise-scale cybersecurity programs and portfolios across Microsoft. Translate CISO strategy into roadmaps, operating models, governance, and reusable capabilities; align senior technical and business stakeholders; manage risks, dependencies, and tradeoffs; use AI, telemetry, and evidence to measure outcomes and course-correct; and advise executives on strategy, investments, and execution.

Leads and develops an engineering team building AI frameworks and serving infrastructure for large-scale model training and inference. Sets technical direction across build systems, runtimes, libraries, release pipelines, benchmarking, optimization, and deployment. Drives automation, reliability, observability, regression detection, and production validation across GPUs and Microsoft hardware. Partners with research, product, infrastructure, and hardware teams while coaching engineers, hiring talent, and advancing developer productivity and Azure hardware efficiency.

Develops secure, isolated attack scenarios across cloud, on-premises, and hybrid environments. Reproduces vulnerabilities, builds multi-step attack chains, creates automated graders and reward signals, and validates outcomes using system state and telemetry. The role also develops attack variants and benign comparisons to evaluate AI security agents, partnering with threat researchers, AI engineers, and environment engineers.

Lead security reviews, code audits, penetration testing, vulnerability research, and mitigation efforts for Microsoft Windows services. Develop reusable security tools and agents, identify attack vectors and architectural risks, demonstrate exploit impact, and collaborate with product engineering teams to design scalable defenses and improve security investments.

Drive technical sales for Microsoft Azure and AI solutions serving state and local government customers. Lead architecture workshops, demonstrations, proofs of concept, migrations, and modernization initiatives across hybrid and cloud environments. Design secure, scalable, resilient, and compliant infrastructure using Azure services, networking, containers, enterprise applications, and partner technologies. Build trusted customer relationships, resolve technical blockers, collaborate with engineering and partners, and guide adoption of cloud, security, resiliency, and AI capabilities.

Drive technical sales and customer adoption of Microsoft’s cloud and AI platforms through demonstrations, proofs of concept, hackathons, and architecture workshops. Design secure, scalable AI and cloud-native application solutions, resolve technical blockers, and guide production deployments. Build relationships with developers and platform leaders while maintaining expertise in AI Foundry, Azure AI, responsible AI, application modernization, and AI management and security.

Leads customer-facing cloud and AI solution architecture engagements, designing, building, troubleshooting, and deploying enterprise-grade Microsoft 365, Copilot Studio, Power Platform, and Azure solutions. Develops agentic AI solutions, roadmaps, proofs of concept, and production implementations while resolving customer blockers. Advises executives, supports pre-sales and partner engagements, manages factory delivery programs, mentors technical teams, influences product direction, and drives adoption, consumption, security, scalability, and measurable customer outcomes.

Leads Windows security assurance across compliance, risk assessment, security controls, vulnerability research, and security tooling. Manages security assurance program managers, partners with engineering and product teams, translates requirements into controls, drives scalable security reviews and scanning, and coordinates high-impact initiatives. The role requires influencing across teams, managing ambiguity, tracking outcomes, and improving security processes throughout the product lifecycle.