Executive & Personal Assistant to CEO

Responsibilities

Are you a highly organized, intuitive, and dependable professional who thrives in a fast-paced environment where no two days are the same? Do you take pride in being the steady hand behind a successful executive, balancing both professional priorities and personal responsibilities with discretion, initiative, and grace?

We are looking for an experienced Executive & Personal Assistant to support a busy CEO who manages a demanding schedule involving travel, philanthropic leadership, and family commitments. In this pivotal role, you’ll manage everything from calendar coordination and financial reporting to domestic and international travel arrangements and personal task management. You will also support the CEO and his wife in their ongoing service to Catholic charities and nonprofit boards.

If you are detail-driven, solutions-focused, and comfortable operating with a high degree of confidentiality, we invite you to apply.

Key Job Duties

• Prepare and deliver daily reports summarizing completed activities and upcoming tasks
• Actively manage the CEO’s calendar and proactively resolve scheduling conflicts or present options to facilitate decision-making
• Provide support for the CEO’s personal finances including donations, bill payments, check deposits at the local bank, errands, and phone communications
• Perform all administrative duties necessary to maintain the CEO and Executive Assistant office environment
• Work annually with accountants and investment entities to gather tax preparation materials and assist with information required for audits
• Arrange complex domestic and international travel for both personal and business purposes, including 3 to 5 international and 20 domestic trips annually
• Maintain familiarity with travel policies and vendor relationships, including use of AMEX Centurion services for premium travel coordination

Job Duties

• Screen calls and respond to letters and emails on the CEO’s behalf
• Coordinate conference calls, Teams meetings, and Executive Leadership Team meetings
• Prepare monthly personal expenses and revenue reports, travel reports, and related financial summaries
• Maintain files for correspondence, records, and personal matters, ensuring all confidential documents are handled with discretion
• Assist with reconciliation of corporate and personal credit card statements and monitor charges for accuracy and alignment with budgets

Qualifications / Education

• Must be highly motivated, detail-oriented, and comfortable stepping outside defined job responsibilities as needed
• Team player with a collaborative spirit and willingness to assist across various levels of the organization
• Professional appearance and demeanor required
• Must have reliable personal transportation and a valid driver's license
• Availability to support the CEO and his wife with occasional evening or weekend communications or responsibilities
• Bachelor’s degree preferred, or equivalent combination of education and relevant experience

Skills

• Discreet and trustworthy with sound judgment in handling sensitive and confidential matters
• Proficient in Microsoft Word, Excel, Outlook, and PowerPoint
• Exceptional written and verbal communication skills, including notetaking and follow-up
• Strong problem-solving and prioritization abilities in dynamic environments
• Calm and composed under pressure with a high degree of emotional intelligence
• Able to work independently while managing multiple priorities efficiently
• Strong organizational and time management skills
• Able to evaluate processes and recommend improvements or alternative solutions
• Strong interpersonal skills and ability to maintain cooperative working relationships across internal teams and with external business associates

Insight Investments, Corp. is an Equal Employment Opportunity and Affirmative Action employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, national origin, gender, age, sexual orientation, gender identity, disability, veteran status, or any other protected classification.

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