AI Associate

About the role

This is an opportunity to sit at the center of a firm-wide transformation — connecting people, systems, and ideas at a fast-moving real estate investment firm building for its next phase of growth.

Responsibilities

• Serve as the primary day-to-day point of contact between CIG and our external AI consulting firm
• Coordinate meetings, manage action items, and ensure follow-through on deliverables across both internal and external stakeholders
• Communicate consultant recommendations and project updates clearly to internal teams at every level
• Provide the consulting team with the organizational context and access they need to do their work effectively
• Own the internal AI project tracker — maintaining visibility into active workstreams, upcoming milestones, and open items across departments
• Work with department heads across acquisitions, asset management, finance, and operations to understand their workflows, gather input, and keep them engaged throughout the process
• Anticipate where initiatives might stall and proactively work to resolve blockers before they become delays
• Prepare clear, concise updates for senior leadership on initiative status, progress, and next steps
• Support the rollout of new AI tools and workflows by coordinating training, documentation, and internal communication
• Help ensure that new capabilities are actually used — following up with teams, gathering feedback, and flagging adoption challenges early
• Track outcomes and impact, building the internal case for what’s working and what needs adjustment
• Day-to-day operations
• Maintain organized records of project plans, vendor communications, and initiative documentation
• Schedule and facilitate working sessions, keeping meetings focused and moving toward decisions
• Handle the coordination and logistics that keep a complex, multi-team initiative running smoothly

Requirements

• 1–3 years of experience in a coordination, operations, project management, or technology implementation role
• Hands-on familiarity with AI tools — you’ve incorporated them into how you work, you understand their practical applications, and you stay current on where the technology is headed
• Comfortable working with technology platforms and learning new software quickly; some exposure to AI or automation tools is a plus
• Exceptionally organized with strong attention to detail and the ability to manage multiple moving pieces without losing track
• Natural communicator who can connect with people across all levels and functions — from a property accountant to a senior principal
• Self-starter who takes ownership, follows through, and doesn’t wait to be told what to do next
• Comfortable operating in a fast-moving, entrepreneurial environment where things change and priorities shift

Qualifications

• Bachelor’s degree in business, information systems, communications, or a related field — or equivalent experience

Skills

• Strong organizational skills
• Excellent communication and interpersonal skills
• Ability to manage multiple tasks and prioritize effectively
• Understanding of AI tools and their practical applications

Benefits

• Comprehensive health and dental insurance
• 401(k) with company match
• Paid time off and company holidays
• In-office environment at our Chicago headquarters — a collaborative, ownership-driven culture with direct access to senior leadership

Pay

$65K–$75K Base

Schedule

Full-Time · This Role based in Chicago