Executive Analyst, Office of the CEO & CFO

Clear Investment Group; Chicago (IL); On-site; USD 85,000 - 105,000; Full time

Benefits offered by this job

Health and dental insurance

401(k)

Paid time off and company holidays

In-office role at Chicago Loop HQ

Bonus eligible

Job summary

Clear Investment Group in Chicago, IL seeks an Executive Analyst to work directly with the CEO and CFO in the Chicago Loop. This in-office role blends high-impact analysis with executive support on capital, underwriting, deals, and legal matters.

Approximately 70% of your time is analysis and project work, with 30% on executive coordination, travel, and calendars, using Claude AI tools to build models and trackers.

Qualifications

• 2 years in an analyst, executive support, paralegal, or operations role supporting senior leaders.
• Strong Excel skills and ability to build workflows with AI tools.
• Clear writing and discretion with confidential information.
• Must be 100% in office in the Chicago Loop.

Responsibilities

• Review financial, operating, and deal data and deliver first-pass analysis with a recommendation.
• Build and maintain deal rooms and investor data rooms for acquisitions and capital raises.
• Complete first-pass review of contracts and summarize key terms for executives.
• Triage inboxes, manage calendars and travel, and prepare briefing materials.

Skills

Analytical mindset

Executive-facing work

Discretion

Education

Bachelor’s in Finance or related field

Tools

Excel

Claude in Excel

Claude Code

Job description

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