AI Associate

CLEAR INVESTMENT GROUP – AI Associate Location: Chicago, IL (In‑Office). Full‑time position. Base salary $65K–$75K plus performance bonus and full benefits. About the Company 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 a team to match. AI is central to how we plan to operate smarter and more efficiently at scale. Position Summary 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 newly created role is built around a simple but critical need: someone dedicated full‑time to keeping our AI programs moving. You will work closely with our external AI consulting partner and every department across the firm, coordinating workstreams, removing roadblocks, communicating progress, and ensuring 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 need to have moved beyond awareness—using AI tools regularly, understanding their practical applications, and staying current on where the technology is headed. Combined with strong organizational instincts to manage a complex, multi‑stakeholder initiative from the inside, that ratio will make you successful. Key Responsibilities Vendor & consulting partner coordination: Serve as the primary point of contact between CIG and the external AI consulting firm; coordinate meetings, manage action items, ensure deliverable follow‑through; communicate recommendations and updates clearly; provide the consulting team with necessary context and access. Cross‑functional project management: Own the internal AI project tracker; maintain visibility into active workstreams, milestones, and open items; work with department heads to gather input and keep them engaged; anticipate blockers and resolve proactively; prepare concise updates for senior leadership. Deployment support & adoption: Support rollout of new AI tools and workflows by coordinating training, documentation, and communication; ensure uptake through follow‑up, feedback collection, and early flagging of adoption challenges; assist in tracking outcomes and building the case for success and adjustments. Day‑to‑day operations: Maintain organized records of project plans, vendor communications, and initiative documentation; schedule and facilitate working sessions; handle coordination and logistics that keep the initiative running smoothly. Qualifications 1–3 years of experience in coordination, operations, project management, or technology implementation. Hands‑on familiarity with AI tools—incorporated them into how you work, understand their applications, and stay current on the technology. Comfortable working with technology platforms, 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. 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 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. 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. Contact CLEAR INVESTMENT GROUP – 105 W Madison Street, Suite 500, Chicago, IL – #J-18808-Ljbffr Clear Investment Group