AI Associate

United States·Chicagomid

OtherAssociate

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CLEAR INVESTMENT GROUPAI AssociateChicago,

Technical Tools

OtherAssociate

CLEAR INVESTMENT GROUP
AI Associate

Chicago, IL · In-Office · $65K-$75K Base · Performance Bonus · Full Benefits

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.

→ You will be the connective tissue between CIG’s internal teams and our external AI consulting partner — keeping initiatives on track, ensuring nothing falls through the cracks, and helping the whole organization move in the same direction.

→ This role is ideal for someone early in their career who has gone beyond awareness of AI — you use these tools regularly, have explored what they can and can’t do, and are building a working knowledge of the space — and who is naturally organized and energized by working across teams to get things done.

COMPENSATION
$65K–$75K Base

LOCATION
Chicago, IL —
In-Office

ROLE TYPE
Full-Time

🤖 AI-First Role
Ground floor of a major initiative

▲ Cross-Functional Scope
Work across every department

✦ Real Ownership
Visible impact from day one

ABOUT CLEAR INVESTMENT GROUP

Clear Investment Group is a Chicago-based real estate investment firm with a 20+ year track record of acquiring, rehabilitating, and stabilizing distressed Class C workforce housing across secondary and tertiary markets. We exist at the intersection of financial returns and community impact — delivering institutional-quality asset management while preserving affordable housing for the communities that need it most.
With an active portfolio spanning Chicago, Syracuse, Tuscaloosa, and Washington D.C., and a growing acquisition pipeline, we are scaling rapidly — and building the team to match. AI is central to how we plan to operate smarter and more efficiently at scale.

COMPENSATION & BENEFITS

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

THE ROLE

We are looking for an organized, curious, and people-oriented AI Associate to serve as the internal hub of Clear Investment Group’s AI initiative. This is a newly created role built around a simple but critical need: someone dedicated full-time to keeping our AI programs moving.

Working closely with our external AI consulting partner and every department across the firm, you will coordinate workstreams, remove roadblocks, communicate progress, and ensure that the right people have the right information at the right time. You will be the connective tissue between our vendor and our internal teams — from acquisitions and asset management to finance and operations.

You don’t need to be an AI engineer. You do need to have gone beyond awareness — using AI tools regularly, understanding their practical applications, and staying current on where the technology is headed. Paired with the organizational instincts to manage a complex, multi-stakeholder initiative from the inside, that combination is what will make this role successful.

WHAT YOU’LL OWN

Vendor & consulting partner coordination

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

Cross-functional project management

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

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

WHAT WE’RE LOOKING FOR

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

Preferred

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 · clearinvestmentgroup.com