Top Tech Jobs & Startup Jobs in Chicago, IL

Leads sales strategy enablement for Microsoft’s retail and consumer goods segment. Develops AI transformation narratives, identifies repeatable customer and commercial patterns, and converts successful engagements into scalable sales motions, playbooks, discovery methods, value frameworks, and partner pathways. Supports strategic opportunities, pipeline acceleration, executive engagements, and deal closure while coordinating across sales, engineering, marketing, customer success, advisory, and partner teams.

Lead commercial strategy and execution for complex Defense Industrial Base accounts. Own large, multi-year negotiations; assess financial, contractual, and compliance risks; shape deal structures; influence Sales, Finance, Legal, Deal Desk, and Policy teams; maintain forecast accuracy and audit-ready agreements; and serve as a senior commercial expert and mentor without formal people-management responsibilities.

Lead technical vision and architecture for AI frameworks, performance, benchmarking, and tooling. Drive cross-team alignment, mentor engineers, ship high-performance distributed software, and improve model onboarding, runtime performance, reliability, and Azure hardware efficiency.

Perform advanced threat hunting and deep analysis of attacker activity across on-premises and cloud environments, notify customers of imminent threats, build proof-of-concept hunting tools and automations, synthesize findings into mitigation recommendations, and drive product/tool improvements by transferring threat intelligence and investigation best practices to engineering and customer teams.

Develop production-ready AI applications, agents, integrations, and workflows using Microsoft Cloud and AI platforms. Guide partners on architecture, software engineering, security, governance, privacy, Responsible AI, testing, CI/CD, observability, and operational readiness. Co-engineer solutions with external teams, build reusable accelerators, and help scale agentic and LLM-powered applications from concept through production while delivering measurable business outcomes.

Leads internal and external communications for Frontier Company executives, developing messaging, narratives, social media strategies, executive thought leadership, and communications plans. Advises senior stakeholders, manages speaking and media requests, translates complex technology topics for varied audiences, and drives communications programs aligned with business priorities in an ambiguous, fast-paced environment.

Designs and develops secure, performant Copilot products and platform services across Windows, Mac, and mobile. Builds distributed AI and agent-driven systems capable of reasoning, planning, and executing tasks. Collaborates with infrastructure, platform, application engineering, and research teams to ship high-quality software. Champions AI-assisted development, coding-agent adoption, prompt design, tooling best practices, and human-in-the-loop systems.

Secure Windows products and devices through offensive security research, code and design reviews, penetration testing, vulnerability discovery, fuzzing, and mitigation development. Build reusable security review tools, identify vulnerabilities in operating system features and native applications, collaborate with Windows engineering teams on durable defenses, engage security researchers, and communicate the business value of security investments.

Leads customer-facing demonstrations and solution discussions for radiology and healthcare AI products. Partners with Account Executives on enterprise sales strategy, discovery, product positioning, RFP responses, and customer follow-up. Serves as a subject matter expert on radiology workflows, diagnostic imaging, and healthcare technology, translating technical capabilities into business value for clinical, operational, technical, and executive stakeholders. Maintains customer and partner relationships, communicates field feedback, and travels approximately 25% of the time.

Manages strategic Microsoft customer accounts by developing multi-year plans, expanding executive relationships, closing complex cloud agreements, and driving digital transformation. Builds sales opportunities, coordinates internal and partner teams, presents value propositions, and influences customer strategy. Requires extensive executive engagement, complex deal experience, active U.S. Top Secret clearance, U.S. citizenship, and successful Microsoft Cloud background screening.