Executive Assistant

Core Spaces•Chicago, IL

13d•$100,000 - $120,000•Hybrid

About The Position

Core Spaces is seeking an exceptional Associate, Executive Assistant who will provide high-level executive support and operational leverage to executive leadership, with primary support for the Chief Operating Officer (COO). This role combines advanced executive assistance, thoughtful prioritization support, cross-functional coordination, and polished communication. This role is well suited for an Executive Assistant who enjoys understanding business priorities, anticipating needs, and applying judgment to support executive decision-making in a dynamic environment. You bring clarity, organization, and follow-through to a fast-moving environment where precision and discretion are paramount.

Requirements

Minimum five (5) years of experience in C-Suite executive support or advanced administrative roles.
Mastery of Microsoft Office (Word, Excel, PowerPoint, Outlook).
Exceptional written communication, editing, and organization skills.
High emotional intelligence, professionalism, and executive presence.
Ability to understand business context and manage competing priorities.
Absolute discretion and integrity.

Nice To Haves

Supporting senior executives in fast-paced, high-growth, or operationally complex environments (real estate, investment, or similar).
Providing high-trust, executive-level support that applies sound judgment, discretion, and business context.
Proactively anticipating needs, solving problems, and taking action with minimal direction.
Navigating ambiguity while bringing structure, clarity, and follow-through.

Responsibilities

Act as a trusted executive support partner to the COO by helping manage priorities, preparing materials, and ensuring time is organized around key commitments.
Prepare the COO for meetings with clear objectives, context, briefing materials, and follow-up items.
Apply business context and judgment to anticipate needs, identify gaps in preparation, and proactively surface considerations for upcoming meetings and priorities.
Support coordination across teams by facilitating communication, gathering inputs, and tracking action items as directed.
Track commitments and support follow-through on priorities, timelines, and deliverables.
Draft, edit, and refine executive communications, presentations, and written materials to an executive-ready standard.
Compile and organize complex information into concise briefing summaries and reference materials.
Protect and manage highly sensitive information using sound judgment and discretion.
Develop base materials and coordinate content contributions to presentations and materials for leadership meetings, company‑wide communications, investor, board, or partner engagements, and strategic planning and business reviews
Collaborate with internal teams to gather inputs, validate data, and ensure accuracy and completeness.
Support and maintain the COO’s established operating cadence (weekly, monthly, quarterly) by ensuring preparation, materials, and follow-ups are organized and timely.
Partner with the Manager, Events & Travel Planning to coordinate internal and external meetings, leadership offsites, and key events.
Coordinate agendas, materials, attendee logistics, and follow-up actions to support productive meetings.
Oversee calendar, travel, and expense workflows to maximize executive efficiency and minimize administrative friction.
Manage special projects that require proactive problem‑solving, coordination, or research.
Support operational needs including document handling, technology coordination, and workflow optimization.
Handle general administrative functions as required to support seamless executive operations and decision-making.
Occasional travel may be necessary as needed
Perform all other duties and tasks as assigned by management
Must be able to complete all physical requirements of this role with or without a reasonable accommodation

Benefits

A culture that provides you with a sense of belonging
Hybrid or remote work options may vary by role to support work-life balance
Competitive pay that values your contributions
Incentives designed to reward your achievements
Paid flexible PTO to disconnect or celebrate life milestones
Paid 14+ holidays, including your birthday, to disconnect and celebrate
Paid Parental Leave that begins after 90 days
Paid volunteer time off to give back to your community
Monthly workshop weeks; fewer meetings & more collaboration
Robust health plan options that begin within at least 30 days of your employment
Monthly phone reimbursement
Wellness allowance and perks, including a yearly subscription to a meditation app
An environment that provides you a voice to share your perspectives
Employee Assistance Program (EAP) for access to confidential support services
Company retirement options including 401(k) + matching & Roth account option