Administrative Assistant

Title: Administrative Assistant
Department: Operations
Reports to: Leadership Team
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 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 Core Values are:

• Get it Done: Drive progress. Be solution-oriented, determined, diligent
• Ride the Wave: Embrace the new. Be adaptive, flexible, agile
• Add Value: Deliver excellence — in communication, transparency, results
• Exhibit Passion: Strive to be the Ideal Team Player. Be humble, hungry, smart

Compensation and Benefits

• Base Salary: $70,000 plus commensurate with experience
• Eligible for year-end and performance bonuses
• Access to 401(k) with company matching
• Health & dental insurance, including company contribution
• PTO policy

Overview
We are seeking a highly motivated Administrative Assistant to support our Leadership Team and help keep the organization operating efficiently and accountably. This role is critical to ensuring priorities stay on track, schedules run smoothly, and leadership commitments are executed with discipline and follow-through.
The ideal candidate is proactive, organized, and energized by ownership. This is not a passive support role — we are looking for someone who takes initiative, anticipates needs, flags conflicts early, and continuously looks for ways to improve how the Leadership Team operates. Over time, this role has the opportunity to expand in responsibility and scope for the right person.

Key Responsibilities
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

Qualifications

• Associate’s degree required; Bachelor’s degree preferred
• 3 - 5+ years of relevant experience
• Strong organizational and communication skills
• High professionalism and discretion
• Proficiency in Microsoft Office

Preferred Qualifications

• Experience supporting leadership teams
• Comfort driving accountability
• Interest in expanding responsibilities