Top Tech Jobs & Startup Jobs in Chicago, IL

Develop and close new enterprise technology accounts across a regional territory. Prospect Fortune 1000 and Global 500 organizations, qualify opportunities, conduct consultative sales engagements, build C-level relationships, negotiate technology solutions, collaborate with internal teams and vendors, and drive contractual growth through long sales cycles.

Owns the evolution of Staples’ sales intelligence platform, combining product ownership, analytics, semantic modeling, automation, and AI enablement. Responsibilities include translating business strategy into data and product requirements, analyzing sales performance, developing dashboards and decision-support solutions, managing roadmaps, driving adoption, establishing governance and quality controls, mentoring contributors, and partnering with Sales, Data, Technology, and Strategy teams.

Reviews, drafts, and negotiates commercial contracts, including vendor, manufacturing, licensing, merchandising, and services agreements. Manages contract timelines, approvals, repositories, and data; conducts legal and regulatory research; supports internal training; identifies contract risks and process improvements; and coordinates cross-functional contracting initiatives while balancing legal, financial, operational, and compliance considerations.

Analyzes datasets and investigates cyber fraud and suspicious activity, develops fraud prevention strategies using analytics and predictive modeling, improves detection tools and monitoring, conducts post-incident investigations, communicates risks and recommendations, researches emerging fraud schemes, and supports cross-functional fraud response initiatives.

Leads the administration, support, reliability, security, disaster recovery, and continuous improvement of Staples’ enterprise IBM i and IBM Power Systems infrastructure. Manages hardware and operating system lifecycles, backups, replication, monitoring, capacity planning, incident response, audits, vendors, budgets, modernization initiatives, and operational procedures. Provides technical and people leadership for senior IBM i platform engineers while partnering with cybersecurity, architecture, application, business, and vendor teams.

Lead strategy, roadmap, and scaling of enterprise AI/ML platforms (including GenAI and agent frameworks). Enable cross-functional teams to build, deploy, govern, and operate production-grade AI solutions; define architecture and guardrails; track adoption, reliability, cost, and developer productivity; partner with Security, Privacy, Cloud, and vendor partners; and drive platform delivery through agile execution.

Lead architecture and evolution of enterprise observability platforms (APM, infrastructure monitoring, session replay, log analytics). Define integration patterns, telemetry standards, and governance. Partner with Engineering, SRE, Product, and Infrastructure to embed observability best practices, evaluate new technologies (OpenTelemetry, distributed tracing, AI-driven observability), drive platform standardization, and manage vendor relationships to improve MTTD/MTTR and system reliability.