Executive Assistant

About the role

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. ClearDesk is an equal opportunity employer.

What you'll do

• 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

What you'll bring

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