AI Associate

CLEAR INVESTMENT GROUP AI Associate

Location:

Chicago, IL – In-Office (M-F). Salary: $65K–$75K base. Full-Time. Performance Bonus.

This role is at the center of a firm-wide transformation, connecting people, systems, and ideas at a fast-moving real estate investment firm. The AI Associate will act as the connective tissue between internal teams and an external AI consulting partner.

• Base salary of $65,000–$75,000, commensurate with experience
• Performance bonus tied to AI initiative milestones and organizational impact
• 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

Serve as the internal hub of Clear Investment Group’s AI initiative, coordinating work streams, removing roadblocks, communicating progress, and ensuring that the right people have the right information at the right time. You will collaborate with an external AI consulting partner and all departments across the firm.

• Vendor & consulting partner coordination
  • Serve as the primary day‑to‑day point of contact between CIG and the 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.
• Cross‑functional project management
  • Own the internal AI project tracker – maintaining visibility into active work streams, 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.
• Deployment support & adoption
  • 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.
  • Assist in tracking 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.

• This role is based in Chicago. Position is Full Time in office 5 days a week.
• 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.

• Experience in real estate, financial services, or a similarly operationally complex environment.
• Prior exposure to AI implementation, software rollouts, or technology change management.
• Bachelor’s degree in business, information systems, communications, or a related field — or equivalent experience.

CLEAR INVESTMENT GROUP
· 105 W Madison Street, Suite 500, Chicago, IL ·