Executive Assistant to the CEO

We are seeking a highly organized, proactive, and polished Executive Assistant to support our Chief Executive Officer.

This is a high-trust role for an experienced Executive Assistant who thrives in a fast-paced environment and is comfortable managing competing priorities, confidential information, and a constantly changing schedule. The successful candidate will help keep the CEO organized and focused by managing day-to-day priorities, anticipating needs, coordinating information, and ensuring important details and follow-ups stay on track.

The ideal candidate is both proactive and adaptable—comfortable taking direction while also knowing when to take ownership, follow up, solve problems, and move things forward independently. This is a long-term opportunity for someone who enjoys working closely with senior leadership and becoming a trusted partner to the CEO.

Key Responsibilities

· Manage the CEO’s calendar, meetings, appointments, and travel arrangements, ensuring priorities are well organized and efficiently coordinated.

· Monitor and manage the CEO’s email and communications, prioritizing requests, drafting correspondence, and ensuring timely follow-up.

· Coordinate internal and external meetings with executives, senior leaders, partners, vendors, and other stakeholders.

· Prepare meeting agendas, presentations, briefing materials, reports, and other documents as required.

· Attend leadership meetings, take minutes, track action items, and follow up with stakeholders to ensure commitments are completed.

· Support the CEO with projects and strategic initiatives by coordinating timelines, information, deliverables, and follow-ups.

· Create and manage an organized digital file structure for document control.

· Manage expense reporting and other administrative requirements on behalf of the CEO.

· Coordinate domestic and international travel, including travel to the company’s hotel operations in Barbados as required.

· Serve as a professional and trusted point of contact between the CEO and internal and external stakeholders.

· Anticipate the CEO’s needs and proactively ensure they have the information, materials, and support required to make decisions and stay focused on priorities.

· Handle confidential business, financial, personnel, and strategic information with a high degree of discretion.

· Provide administrative and coordination support to other members of the executive team as required.

· Assist with special projects and other priorities as assigned by the CEO.

Requirements

· 5+ years of experience as an Executive Assistant, preferably supporting a CEO, President, Founder, or other senior executive.

· Exceptional organization and attention to detail, with a high standard for accuracy.

· Highly proactive with strong follow-through and the ability to see tasks through to completion.

· Comfortable managing competing priorities and quickly adapting when plans or priorities change.

· Confident and persistent when following up with others, including senior leaders, to ensure commitments are met.

· Strong judgment and the ability to determine what requires immediate attention and what can wait.

· Excellent written and verbal communication skills.

· Professional, polished, and comfortable interacting with executives and external stakeholders.

· High emotional intelligence and the ability to work effectively with a range of personalities and working styles.

· Strong Microsoft Office skills, particularly Outlook, Word, Excel, PowerPoint, and Teams.

· Comfortable learning and using new technology, systems, and AI-enabled tools.

· Ability to handle highly confidential information with discretion and sound judgment.

· Real estate, legal, finance, construction, property management, or related industry experience is an asset.

· Post-secondary education in Business Administration, Office Administration, or a related field is an asset.

Benefits

• Dental care
• Extended health care
• Vision care
• Extensive EFAP program
• Virtual Urgent Care

Accommodations

Kingsley Management Inc. is committed to providing an accessible and supportive recruitment experience for persons with disabilities. If you require accommodations at any stage of the recruitment process, please notify us in advance at View email address on apply.workable.com

AI Usage

As part of our hiring process, we use AI-powered tools to assist in screening resumes. These technologies help us efficiently identify candidates whose qualifications align with the role, ensuring a fair and consistent evaluation process. By clicking "Apply," you acknowledge and consent to the use of AI in our recruitment workflow

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