Executive Assistant

Job Title: Executive Assistant
Department: Executive Leadership
Reports to: CEO and CFO
Job Type: Full Time; 100% in office (located in the Chicago Loop)

Company Overview

Clear Investment Group is a boutique real estate investment firm in Chicago specializing in rehabilitating and stabilizing distressed multi-family assets. We are based in Chicago, with portfolios across the Midwest, South, and Northeast. With a focus on acquiring distressed properties, we aim to improve communities by investing in local real estate. Our companies Core Values are:

• Get it Done 2. Ride the Wave 3. Add Value 4. Exhibit Passion

Compensation and Benefits

• Base Salary: $70,000-$90,000 based on experience
• Eligible for year-end and performance bonuses
• 401K
• Health & dental insurance
• PTO and Paid Holidays

Overview:
We are seeking a highly organized and detail-oriented Executive Assistant to provide comprehensive support to our CEO and CFO. The ideal candidate will be proactive, resourceful, and capable of managing multiple tasks along with managing the daily appointments of the CEO and CFO. This role offers the opportunity to work closely with senior leadership and contribute to the success of our dynamic and fast-paced organization.

The ideal candidate is initiative-taking and drives projects through to completion. The ability to work in a fast-paced, high-stress environment is key, but so is a sense of camaraderie: our team values working collaboratively. We are looking for candidates who possess the qualities of an Ideal Team Player. We want someone who is Humble, Hungry, and Smart.

Humble – someone with experience who can learn and grow
Hungry – someone who wants drive results, create new standards and who constantly wants to improve
Smart – someone who is people and business smart and able to collaborate well with a diverse team of people

About you:

• 5+ Years related experience

• Proven experience as an executive assistant or similar role supporting C-level executives.
• Excellent organizational and time-management skills, with the ability to prioritize tasks effectively.
• Strong communication skills, both written and verbal, with a keen attention to detail.
• Has the ability to “drive” a project to the finish line
• Highly proficient in Outlook, OneDrive, SharePoint, and Word; basic proficiency in Excel
• Ability to maintain confidentiality and exercise sound judgment in all interactions.
• Flexibility and adaptability to work in a fast-paced environment and manage multiple priorities.
• Previous experience in the real estate industry is a plus but not required

Core Responsibilities:
Included but not limited to:

Leadership & Administrative Support

• Act as the primary point of contact for the Leadership Team, managing schedules, appointments, and correspondence
• Proactively manage calendars by anticipating conflicts, prioritizing commitments, and recommending adjustments to maximize effectiveness
• Hold leadership accountable to meetings, deadlines, and action items by tracking follow-ups and ensuring commitments are closed out
• Coordinate and prioritize meetings, conferences, and travel arrangements, ensuring all logistics are well-planned and executed seamlessly
• Prepare agendas, briefing materials, and follow-up notes to ensure meetings are productive and outcomes are clearly documented

Communication & Organization

• Support communication across the Leadership Team, including voicemail and inbox triage, organization, and drafting responses as appropriate
• Prepare, edit, and format correspondence, reports, presentations, and internal documents
• Serve as a gatekeeper for incoming requests, helping filter, prioritize, and route information effectively
• Maintain organized digital and physical filing systems to ensure information is easily accessible

Project & Process Support

• Oversee ad-hoc projects as assigned and drive them to completion, coordinating across departments as needed
• Conduct research and compile data to support leadership decision-making
• Assist in the preparation of board and leadership meetings, including agenda creation, document distribution, and meeting minutes
• Identify opportunities to improve administrative processes, workflows, and internal coordination

Confidentiality & Collaboration

• Handle sensitive and confidential information with discretion and professionalism at all …