Executive Assistant

Clear Investment Group; Chicago (IL); On-site; USD 70,000 - 90,000; Full time

Benefits offered by this job

Health and dental insurance

401(k) with company match

Paid time off & holidays

In-office headquarters Chicago

Job summary

Clear Investment Group in Chicago, IL seeks an accomplished Executive Assistant to support our CEO and CFO in a fast-paced, in-office environment.

You will manage calendars, correspondence, and projects, prepare briefing materials, and coordinate meetings and travel while upholding confidentiality and rigorous organizational standards. This role offers ownership-driven culture and growth opportunities.

Qualifications

• 5+ years of related experience as an EA or similar role.
• Experience supporting C-level executives.
• Excellent organizational and time-management skills.
• Ability to drive projects to completion; discretion essential.

Responsibilities

• Act as primary contact for Leadership Team, manage schedules and correspondence.
• Proactively manage calendars, anticipate conflicts, optimize commitments.
• Coordinate meetings, travel, and agendas; ensure follow-ups.
• Prepare briefing materials and meeting minutes.
• Maintain filing systems and gatekeep requests.

Skills

Executive support

Organizational skills

Communication skills

Time management

Discretion

Tools

Outlook

OneDrive

SharePoint

Word

Excel

Job description

Executive Assistant

CLEAR INVESTMENT GROUP

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