Clear Investment Group
AI Associate
Chicago, IL - Full Time
| 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 (M-F) | ROLE TYPE Full-Time · This Role based in Chicago |
| 🤖 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
- 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
- Assist in tracking outcomes and impact, building the internal case for what’s working and what needs adjustment
- 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
- 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 · clearinvestmentgroup.com |
