OP Recruiting is hiring: Executive Assistant in Chicago

We are seeking a highly organized, professional, and proactive Executive & Personal Assistant to provide comprehensive administrative and personal support to both the Chief Executive Officer (CEO) and the Chief Operating Officer (COO). The ideal candidate thrives in a fast‑paced environment, maintains strict confidentiality, and excels in organization, communication, and problem‑solving. A background as a paralegal or legal secretary is a strong plus.

Responsibilities

Executive and Administrative Support (70%)

• Calendar & Scheduling: Manage complex and dynamic calendars for the CEO and COO, scheduling internal and external meetings, appointments, and events while resolving scheduling conflicts.
• Travel Coordination: Plan and book detailed travel arrangements, including flights, accommodations, ground transportation, and itineraries.
• Communication Management: Handle executive correspondence (email, phone, and mail), prioritize communications, and draft professional messages, reports, and presentations on behalf of leadership.
• Meeting Coordination: Prepare meeting materials and agendas, attend select meetings to take notes, and track follow‑up actions and deadlines.
• Expense Management: Process and reconcile expense reports, invoices, and credit card statements accurately and in compliance with company policy.
• Document Management: Maintain well‑organized and confidential electronic and physical filing systems for executive and board‑related documents.

Personal Support (15%)

• Provide personal assistance for the executives, including managing personal appointments, coordinating household logistics, making reservations, and handling personal correspondence.
• Run occasional errands and assist with event planning or personal administrative needs, maintaining full discretion at all times.

Legal & Compliance Support (15%)

• Act as a liaison between executives and internal or external legal counsel.
• Assist with the preparation, organization, and distribution of confidential legal and corporate documents.
• Oversee compliance‑related deadlines and filings, ensuring all required legal documents are submitted accurately and on time.
• Draft, proofread, and format standard agreements (e.g., NDAs) and basic corporate resolutions.

Qualifications

• 5+ years of experience supporting C‑level executives in a fast‑paced, corporate environment (preferably within software, technology, or professional services).
• Advanced proficiency in Google Workspace (Gmail, Calendar, Docs, Sheets) and Microsoft Office Suite (Outlook, Word, Excel, PowerPoint).
• Proven ability to manage sensitive and confidential information with the highest level of discretion.
• Excellent written and verbal communication skills with strong attention to detail and proofreading ability.
• Outstanding organizational and prioritization skills with a proactive, solution‑oriented mindset.
• Preferred: Prior experience as a paralegal, legal assistant, or legal secretary, with familiarity in legal terminology, document management, and corporate compliance.