Executive Assistant

Executive Assistant

Job Type:

Direct-Hire

Location:

chicago - IL

Industry:

Healthcare

Category:

Management

Compensation Range:

$75,000 - $85,000 Per Year

Additional Compensation Info:

Benefits 8 Company Holidays + 1 Floating Holiday 10 Days PTO in Year 1 Subsidized Medical, Dental, and Vision Insurance 401(k) with up to 4% Matching Pre-tax Commuter Benefits Flexible Work Arrangements Casual Dress Environment Referral Bonuses Employee Assistance Fund Paid Parental Leave Paid Jury Duty & Bereavement Leave Length-of-Stay Rewards Annual Company Bonus Pool HSA and FSA Options Company-Subsidized Life Insurance

Job ID

24886

Rich Text Widget

Executive & Personal Assistant to CEO and COO

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.

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