Executive Analyst, Office of the CEO & CFO

Clear Investment Group•Chicago, IL

3d•$80,000 - $100,000•Onsite

About The Position

This role is for an Executive Analyst in the Office of the CEO & CFO at Clear Investment Group, a growing multifamily investment firm. The position involves working directly with the CEO and CFO on analysis, deals, and decisions. The analyst will be responsible for the first pass of data, contracts, investor documents, and legal materials, turning them into clear analysis and recommendations. The role also involves using AI tools like Claude to build models, trackers, and workflows, and ensuring that email, meetings, and commitments do not become bottlenecks for leadership. The Executive Analyst supports capital raising, underwriting, deal execution, financial reporting, and legal matters, with approximately 70% of the role focused on analysis and project work, and 30% on executive support. The ideal candidate can understand the importance of a request, determine the best approach, and deliver finished work with minimal direction.

Requirements

3–6 years in an analyst, executive support, paralegal, or operations role where you owned substantive work for senior leaders
Advanced Excel (lookups, pivot tables, building models and trackers) and comfort reading financial statements
Hands-on AI use beyond drafting: you’ve built a workflow, tool, or analysis with Claude, ChatGPT, Copilot, or similar, and you check the output
Clear writing, sound judgment, and discretion with confidential financial and legal information
Able to work 100% in office in the Chicago Loop

Nice To Haves

Real estate, multifamily, or investment firm experience
Paralegal, contract review, or litigation support experience
Investor relations, fund administration, or data room experience
Claude Code, Python, or other automation experience
Bachelor’s in Finance, Accounting, Business, or Legal Studies

Responsibilities

Review financial, operating, and deal data, and deliver a first-pass analysis with a clear recommendation.
Research open questions for leadership and turn findings into short, decision-ready briefs.
Pull information from accounting, asset management, and operations to answer leadership’s questions without creating extra work for them.
Build and maintain deal rooms and investor data rooms for acquisitions and capital raises.
Support investor structuring work by coordinating with tax advisors and outside counsel, assembling documents, and tracking open items to closing.
Prepare materials and respond to investor requests accurately and on time.
Complete a first-pass review of contracts and summarize key terms, dates, obligations, and risks for the CFO.
Organize and screen litigation-related material before it goes to outside counsel, so attorney time is spent on what matters.
Track contract renewals, legal deadlines, and follow-ups so nothing lapses.
Triage the CEO’s and CFO’s inboxes, draft responses, and make sure time-sensitive requests are answered promptly.
Manage calendars, meetings, and travel, anticipating conflicts and protecting priority time.
Prepare agendas, briefing materials, and follow-up notes, and hold leaders and teams accountable to action items.
Handle sensitive financial, investor, and legal information with discretion.