Executive Analyst, Office of the CEO & CFO

United States·Chicagomid

Finance & AccountingFinance Manager

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CLEAR INVESTMENT GROUPExecutive Analyst, Office of the CEO & CFOChicago, IL · In-Office · $85K–$105K Base · Bonus Eligible · Full Benefits Work directly with our CEO and CFO on the analysis, deals,

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Finance & AccountingFinance Manager

CLEAR INVESTMENT GROUP
Executive Analyst, Office of the CEO & CFO
Chicago, IL · In-Office · $85K–$105K Base · Bonus Eligible · Full Benefits

Work directly with our CEO and CFO on the analysis, deals, and decisions that move a growing multifamily investment firm. This is an analyst seat with executive reach, not a traditional assistant role.
→ You’ll own the first pass. Data, contracts, investor documents, and legal material come to you first. You turn them into clear analysis and recommendations so leadership can decide faster.
→ You’ll build with AI. You’ll use tools like Claude, Claude in Excel, and Claude Code to build models, trackers, and workflows that take real work off leadership’s desks.
→ You’ll keep two executives moving. You’ll make sure email, meetings, and commitments never become the bottleneck, so the CEO and CFO can focus on capital and deals.

COMPENSATION
$80K–$100K Base + Bonus

LOCATION
Chicago Loop — In-Office

ROLE TYPE
Full-Time · Exempt

ABOUT CLEAR INVESTMENT GROUP

Clear Investment Group is a Chicago-based real estate investment firm that buys and revitalizes workforce multifamily housing across the Midwest, South, and Northeast. Our homes serve working families, and our operating model rests on hands-on improvements to properties, teams, and systems. With a new equity fund targeting significant portfolio growth and a recently expanded leadership team, this is a moment to build, not just maintain.

COMPENSATION & BENEFITS

Base salary of $80,000–$100,000, based on experience
Eligible for year-end and performance bonuses
Health and dental insurance
401(k)
Paid time off and company holidays
In-office role at our Chicago Loop headquarters, working side by side with the CEO, CFO, and leadership team

THE ROLE

The Executive Analyst sits in the Office of the CEO & CFO and supports both executives across capital raising, underwriting, deal execution, financial reporting, and legal matters. About 70% of the role is analysis and project work, and about 30% is executive support. The right person understands why a request matters, figures out the approach, and delivers finished work with minimal step-by-step direction.

WHAT YOU’LL OWN

Analysis & Decision Support

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.

Capital, Deals & Investor Support

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.

Contracts & Legal Coordination

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.

Executive Support (about 30% of the role)

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.

A TYPICAL WEEK

About 70% of your time goes to analysis and project work, and about 30% goes to keeping the CEO and CFO organized and responsive. On a given day you might summarize the key terms of three vendor contracts, update the data room for an incoming investor, build a Claude-assisted tracker for an investor structuring workstream, and clear the CFO’s inbox of anything waiting on him. You’ll work with nearly every department, from accounting and asset management to acquisitions and investor relations.

WHAT WE’RE LOOKING FOR

Must-have

2 years in an analyst, executive support, paralegal, or operations role where you owned substantive work for senior leaders
Comfortable with Excel
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-have

Real estate, multifamily, or investment firm experience
Project Management 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

GROWTH OPPORTUNITY

This role offers broad exposure to how a real estate investment firm raises capital, underwrites deals, and runs its portfolio. As you demonstrate ownership, there is room to grow into a larger role in finance, investor relations, or operations.

Clear Investment Group is a woman-owned multifamily real estate investment firm based in Chicago, IL. We are an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

CLEAR INVESTMENT GROUP · 105 W Madison Street, Suite 1700, Chicago, IL · clearinvestmentgroup.com