Top Tech Jobs & Startup Jobs in Chicago, IL

Leads AI-first operating model transformation across cross-functional teams. Defines future-state workflows, requirements, and roadmaps; develops evidence-based strategies; manages agile workstreams; advises business, technology, HR, and Finance stakeholders; embeds change management; conducts experiments; and presents recommendations to senior executives. The role focuses on reimagining work, scaling effective AI-enabled operating models, and advancing organizational adoption of AI-first practices.

Lead consultative, value-driven enterprise sales to plan, orchestrate, and deliver AI Workforce solutions (Copilot, Windows 365, Viva, Agents). Build stakeholder strategies, drive pipeline, cross-sell/up-sell, and partner with internal teams to scale AI adoption and measurable business outcomes.

Leads the technical vision, architecture, and execution of AI performance, framework, benchmarking, and developer-productivity initiatives. Drives cross-team architecture, resolves complex systems trade-offs, mentors technical leaders, and contributes hands-on through prototyping, implementation, reviews, debugging, observability, and automation. Delivers measurable improvements in model onboarding speed, runtime performance, reliability, hardware utilization, and Azure capacity efficiency across models, frameworks, compilers, runtimes, systems, services, and hardware.

Leads enterprise sales for Microsoft Azure cloud and AI platforms. Develops customer-specific sales strategies, qualifies and closes complex opportunities, manages pipelines and forecasts, coordinates partners and internal teams, and advises stakeholders on AI-driven cloud transformation. Uses market intelligence, consumption data, and predictive analytics to drive adoption, expansion, renewals, and customer value. Requires strong consultative selling, enterprise relationship management, and knowledge of Azure infrastructure, data, and AI application platforms.

Leads global developer and GitHub sales and technical enablement strategy. Owns role-based skilling, onboarding, readiness planning, product launches, learning journeys, and field community development for Microsoft and GitHub specialists, sellers, partners, and customers. Collaborates across engineering, product marketing, sales, finance, and learning teams to improve capability, content adoption, seller productivity, pipeline, revenue, usage, and customer outcomes.

Leads Azure capacity automation and backend tooling programs across Engineering, Finance, Operations, and capacity planning teams. Translates business needs into requirements, user stories, acceptance criteria, and workflow specifications; manages dependencies, risks, governance, and delivery. Improves processes through automation, data analysis, reporting, and AI-powered solutions such as Microsoft Copilot. Drives stakeholder alignment, change adoption, data quality, documentation, and operational excellence across capacity allocation and prioritization workflows.

Build and govern a repeatable portfolio of AI and enterprise transformation offers. Responsibilities include assessing market demand, competitive positioning, and Microsoft roadmaps; defining reference architectures and solution blueprints; distinguishing reusable components from customer-specific customization; harvesting delivery patterns; supporting sales pursuits; and managing offer prioritization, versioning, adoption, and retirement across delivery, product, engineering, and business architecture teams.

Leads hands-on penetration testing across applications, cloud, networks, hardware, and operational technology. Identifies vulnerabilities, performs adversary emulation, develops attack paths, improves detection, and communicates risks and remediation plans to technical and executive audiences. Provides strategic guidance, directs engagement scope and remediation tracking, mentors team members, researches emerging threats, and applies automation and AI to scale security testing.

Designs and delivers proactive and reactive cloud security and identity support for enterprise customers. Responsibilities include implementing Microsoft identity solutions, troubleshooting incidents, conducting assessments and workshops, improving security governance, collaborating with support and engineering teams, and managing critical customer situations. The role requires expertise in Azure, Entra ID, Active Directory integration, security monitoring, governance, compliance, and customer-facing technical architecture.

Leads resolution of strategic Microsoft Fabric product and platform blockers. Translates customer scenarios into engineering requirements, coordinates engineering, product, support, services, and field teams, develops workarounds, influences roadmap priorities, communicates risks to senior leaders, and measures adoption, revenue, and competitive impact.