Top Artificial Intelligence Project Management Jobs in Chicago, IL

Serve as CEO's right hand to define success metrics, lead cross-functional initiatives, build internal systems and processes, analyze product and customer data, run growth experiments, manage vendors, and operationalize high-impact projects to scale the company.

Design and optimize the builder funnel to attract, onboard, engage, and retain developers and founders. Run programs (hackathons, cohorts), create onboarding resources, analyze KPIs to improve conversion and retention, and build partnerships to expand the ecosystem for decentralized AI and blockchain innovation.

Leads a federal Task Order supporting USMEPCOM, serving as the primary government interface and overseeing IT and mission support delivery. Responsibilities include personnel and subcontractor management, scheduling, quality assurance, performance monitoring, risk mitigation, compliance, executive reporting, and process improvement. The role requires active Secret clearance, PMP or PgMP certification, significant federal IT program management experience, and approximately 25% travel to North Chicago, Illinois.

Leads large-scale AI transformation programs for Cresta’s strategic enterprise customers. Serves as executive sponsor and trusted advisor to C-suite stakeholders, manages matrixed implementation and engineering teams, oversees complex deployments, standardizes delivery governance, and drives measurable customer value, adoption, expansion, and advocacy. Partners with Sales, Customer Success, Product, and Engineering while connecting technical outcomes to business ROI.

Work directly with founders to drive zero-to-one strategic projects for a finance super app: market entry, licensing, partnerships, operations, and cross-functional execution. Research markets and regulations, create structured plans, trackers, memos, and operating documents, and own urgent business problems through to resolution.

Own end-to-end commercial drone deployments, including planning, pilots, scaled rollouts, operational handoffs, and post-launch stabilization. Manage cross-functional hardware, software, operational, regulatory, logistical, schedule, dependency, and risk workstreams. Partner with customers to develop procedures, safety controls, training, maintenance, and support plans, while coordinating internal teams and translating field requirements into product and engineering deliverables.

Coordinate multiple technology and business projects by maintaining plans, timelines, task trackers, documentation, and status reports. Schedule meetings, manage stakeholder communication, follow up on deliverables, identify risks and dependencies, and escalate blockers. Support project planning, kickoffs, reviews, and workflow improvements while collaborating with technical and non-technical teams in a remote environment.

Manage large SAP programs or clusters of projects for global customers and partners. Responsibilities include program governance, delivery planning, scheduling, milestone and risk tracking, resource and financial reporting, approval gateways, dashboards, and escalation of issues. The role requires strong client engagement, SAP and ERP knowledge, project management office leadership, and coordination across geographically distributed teams.

Manage end-to-end localization delivery for gaming accounts across multiple titles, languages, and content types. Responsibilities include scoping, scheduling, budgeting, resourcing, transcreation, subtitling, voiceover, video localization, DTP, quality control, customer communication, vendor management, and workflow coordination. The role also maintains translation memories and termbases, manages publishing workflows, tracks risks, and supports other project managers.

Coordinates customer education initiatives across Product, Product Marketing, and Customer Education. Translates roadmap and launch updates into asset requirements, manages content across education channels, maintains templates and workflows, uses AI to automate repetitive tasks, aligns stakeholders, identifies risks, and supports deadlines and prioritization.