Jobs and Careers

Administrative Assistant

United Statesfull_timeVerifiedPosted 22 Dec 2025

💰 $70,000/yr

About the role

Title: Administrative Assistant
Department: Operations
Reports to: Leadership Team
Job Type: 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 a