Executive Assistant

Executive Assistant to the CEO

ClearDesk · San Diego (North County) · Full-time, in-office

About ClearDesk

ClearDesk is a remote staffing company that connects US small and mid-sized businesses with exceptional talent in the Philippines. We place and manage ~500 Remote Team Members across home care, real estate, bookkeeping, and home services, on a simple flat-fee model backed by a US leadership team and Philippines-based operations managers. We're six years in, growing quickly, and building the company to run on AI wherever it makes sense.

The role

You'll work directly with our CEO, in person, and own everything that keeps his day, week, and quarter running. This is not a scheduling-only job. The right person becomes the CEO's operating layer: managing his calendar and inbox, running point on travel and logistics, preparing him for meetings, closing loops across the leadership team, and handling a steady stream of personal and business tasks that need a reliable, discreet set of hands.

Our CEO runs ClearDesk and is actively involved in several other ventures. You'll be the person who makes it possible for him to move between them without anything falling through the cracks.

What you'll actually do

• Own the calendar. Protect focus time, resolve conflicts before they surface, and make sure every day is built around what matters most
• Run the inbox. Triage email, draft replies in his voice, flag what needs a decision, and make sure nothing important goes unanswered
• Prepare him for meetings. Pull background, past notes, and key numbers so he walks in ready; capture action items and chase them afterward
• Handle travel and logistics. Flights, hotels, conferences, team events, and the occasional last-minute change
• Close loops. Follow up with the leadership team, vendors, and partners on commitments made; keep a running list of open items and drive them to done
• Manage personal and household administration as needed — appointments, errands, family scheduling, purchases, and vendors
• Use AI as a daily tool. We use Claude, ChatGPT, and similar tools throughout the company. You'll use them to draft, summarize, research, and organize, and you'll be encouraged to find new ways to automate the repetitive parts of the job
• Own the small things that add up: expense reports, office needs, gifts, thank-you notes, and the details that make a CEO's life run smoothly

Who you are

• Sharp and fast. You process information quickly, write cleanly, and don't need to be told twice
• Two steps ahead. You anticipate needs, notice what's about to break, and fix it before it becomes a problem
• Completely trustworthy. You'll see financials, personnel matters, and personal information. Discretion is non-negotiable
• Calm under change. Priorities shift, plans move, and you roll with it without losing track of anything
• Organized to a fault. You have a system for everything and you actually use it
• Comfortable with technology. Google Workspace, Slack, Asana, Zoom, and AI tools are second nature, or you learn new tools in an afternoon
• Warm and professional. You'll represent the CEO to clients, partners, candidates, and his family. People should enjoy hearing from you
• 3+ years supporting a senior executive, founder, or business owner. Experience in a fast-growing small company is a plus

Details

• Location: In-office in North County San Diego, with some flexibility once you're up and running
• Schedule: Full-time. Occasional after-hours responsiveness for travel or urgent items
• Compensation: Competitive salary based on experience, plus benefits
• Reports to: CEO

How to apply

Send us:

1. Your resume or LinkedIn
2. A short note (under 150 words) on the hardest thing you've ever kept organized for someone else, and how you did it
3. One example of how you've used an AI tool to make an executive's life easier — even something small

email to: [email protected]

ClearDesk is an equal opportunity employer.