Senior Executive Assistant

About the Role

Are you a seasoned executive support professional who brings a systems-level perspective, acts as a trust builder, and exercises sound judgment and quiet leadership?

We are seeking a Senior Executive Assistant to serve as a trusted partner to our Chief Operating Officer (COO). In this role, you will be the operational backbone of the Executive Office—protecting executive bandwidth and focus, streamlining complex workflows, and fostering clear, empathetic communication across teams.

You won’t just manage a calendar; you will organize information flow, prepare leadership for key decisions, strengthen cross-team follow-through, and manage executive administration with care and foresight.

What You’ll Do

• Executive Workflow & Bandwidth Protection: Proactively manage the COO’s calendar, inbox, daily workflow, travel, site visits, conferences, and reimbursements. Strategic guidance of workflow helps amplify leadership capacity, creating intentional space for high-level strategy, decision-making, and organizational health.
• Executive Preparation & Decision Support: Assemble key background context, discussion points, outstanding questions, and decision parameters before daily meeting series. Develop concise briefing materials, summaries, agendas, presentations, reports, and talking points. Help establish clear expectations for staff updates and ensure solution-oriented proposals are encouraged before topics reach the COO.
• Meeting Facilitation & Sustainable Rhythms: Lead preparation and follow-through for executive, departmental, Board committee, and project meetings. Capture decisions, commitments, project owners, and deadlines in a transparent tracking system. Support sustainable communication by introducing asynchronous updates, clean dashboards, and clear written summaries over unnecessary meeting time.
• Internal Coordination & Bridge-Building: Build trusted relationships across Full Circle Communities, serving as an approachable, responsive bridge between executive leadership and other teams. Adapt communication styles recognizing that site-level property staff and corporate leadership operate in very different day-to-day contexts. Navigate sensitive dynamics with emotional intelligence, empathy, and discretion.
• Administrative Systems & Playbooks: Establish intuitive systems, templates, trackers, and records. Maintain a flexible working playbook for supporting the COO that captures key relationships, preferred operating routines, recurring rhythms, and decision-making frameworks. Identify processes that can be simplified, standardized, automated, or delegated.

What You Bring

• Core Experience: At least 4 years of direct experience serving as an Executive Assistant to an executive team, president, executive director, or senior leader responsible for multiple departments or complex operational initiatives.
• Administrative Craft & Judgment: Exceptional administrative craft with a track record of creating calm, dependable systems. Strong judgment regarding what requires executive attention versus what can be resolved independently.
• Communication & EQ: Superior written communication skills to synthesize complex information into clear briefing materials. High emotional intelligence, strong listening skills, and demonstrated discretion regarding personnel, financial, legal, and executive matters.
• Software & Systems: Proficiency in Google Workspace or Microsoft Office (calendar, email, documents, spreadsheets, presentations, and shared files), with familiarity in task-tracking tools (e.g., Asana, Monday.com, Smartsheet).
• Mobility & Physical Requirements: Based in Chicago, IL, with a valid driver’s license, insurance, reliable vehicle, and ability to handle occasional light setup (handling materials up to 20 lbs).
• Inclusive Hiring: No formal degree required. Relevant professional, educational, and lived experience will be fully considered.

Preferred Qualifications:

• 7+ years of progressive executive support experience, ideally supporting a COO or executive with broad operational oversight.
• Background in nonprofit, affordable housing, real estate, community development, or multi-site organizations.
• Experience developing administrative operating playbooks, structured meeting routines, or guiding organizations toward clearer written reporting and asynchronous decision-making.
• Certified Administrative Professional (CAP) cr…