Executive Assistant (Remote)

About the Role

ClearDesk is seeking an Executive Assistant to the CEO to provide hands-on executive and personal support in its North County San Diego office. Working directly with the CEO in person, you will manage the day-to-day details that keep his schedule, priorities, and responsibilities on track.

This is more than a scheduling position. You will manage the CEO's calendar and inbox, coordinate travel and logistics, prepare meeting materials, follow up on commitments, and handle a range of business and personal administrative tasks. The CEO is also involved in several other ventures, so this role requires someone who can manage changing priorities, maintain strong organization, and ensure important details do not fall through the cracks.

About ClearDesk

ClearDesk is a remote staffing company that connects small and mid-sized businesses in the United States with talent in the Philippines. The company places and manages approximately 500 Remote Team Members across home care, real estate, bookkeeping, and home services.

ClearDesk operates on a flat-fee model supported by a US leadership team and Philippines-based operations managers. The company has been operating for six years and is growing while incorporating AI into its operations wherever it makes sense.

Key Responsibilities

• Manage the CEO's calendar, protect focus time, resolve scheduling conflicts, and organize each day around key priorities.
• Manage the CEO's inbox by reviewing and prioritizing emails, drafting responses in his voice, identifying matters requiring decisions, and ensuring important messages receive attention.
• Prepare the CEO for meetings by gathering background information, previous notes, and relevant figures.
• Record meeting action items and follow up with the appropriate people to ensure commitments are completed.
• Coordinate business travel, including flights, hotels, conferences, team events, and last-minute changes.
• Follow up with the leadership team, vendors, and business partners on outstanding commitments and maintain a list of open items.
• Handle personal and household administration as needed, including appointments, errands, family scheduling, purchases, and vendor coordination.
• Use AI tools such as Claude and ChatGPT to draft communications, summarize information, conduct research, organize tasks, and identify opportunities to automate repetitive work.
• Manage administrative details such as expense reports, office requirements, gifts, thank-you notes, and other tasks that support the CEO's daily responsibilities.

Required Qualifications

• At least 3 years of experience supporting a senior executive, founder, or business owner.
• Strong organizational skills and the ability to manage multiple responsibilities without losing track of details.
• Ability to process information quickly, communicate clearly, and write professionally.
• Strong judgment and the ability to anticipate needs and address potential issues before they become problems.
• High level of discretion and trustworthiness when handling financial, personnel, and personal information.
• Ability to remain calm and organized when priorities and schedules change.
• Comfort with technology and tools such as Google Workspace, Slack, Asana, Zoom, and AI applications, or the ability to learn new tools quickly.
• Warm and professional communication skills when representing the CEO to clients, partners, candidates, and family members.

Preferred Experience

Experience working in a fast-growing small company is a plus.

Location and Work Arrangement

• Location: North County San Diego, California.
• Work arrangement: Full-time, in-office.
• Some flexibility may be available once you are established in the role.

Schedule

Full-time schedule with occasional after-hours responsiveness for travel arrangements or urgent matters.

Compensation and Benefits

Competitive salary based on experience, plus benefits.

Reporting Structure

This position reports directly to the CEO.

How to Apply

Interested candidates should email the following to aman@cleardesk.com:

• Resume or LinkedIn profile.
• A short note of fewer than 150 words describing the hardest thing you have organized for someone else and how you managed it.
• One example of how you have used an AI tool to make an executive's work or daily responsibilities easier, even in a small way.

Equal Opportunity Employer

ClearDesk is an equal opportunity employer.