Job Description
CLEAR INVESTMENT GROUP
Executive Assistant
Chicago, IL · In-Office · $70K-$90K Base · Full Benefits
ABOUT CLEAR INVESTMENT GROUP
Clear Investment Group (“CIG”) is a Chicago-based, real estate investment firm specializing in opportunistic, value-add multifamily investments. CIG focuses on revitalizing communities while delivering strong risk-adjusted returns to investors through disciplined execution and operational expertise. CIG’s leadership team has a combined 100+ years of real estate and investment experience, with a historical net IRR exceeding 37% across all realized investments since 2011.
COMPENSATION & BENEFITS
Base salary of $70K - $90K, commensurate with experience
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
THE ROLE
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
WHAT YOU’LL OWN
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 times
Collaborate closely with members of the Leadership Team and provide support on special projects as required
Assist with personal or time-sensitive duties for leadership, as needed
WHAT WE’RE LOOKING FOR
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
Job Tags
Work at office