Executive & Personal Assistant to CEO

About the role

This is a true personal assistant role that blends executive support, light bookkeeping, personal affairs, and operational coordination across business and personal life. The right person is discreet, resourceful, and self-directed. They anticipate needs, take ownership without being told twice, and thrive in a fast-paced environment where the line between business and personal is intentionally blurred.

Responsibilities

• Manage and maintain the CEO's calendar — scheduling, prioritization, and conflict resolution
• Fully manage the CEO's personal email inbox — triage, respond on his behalf, escalate what matters
• Book all travel — flights, hotels, ground transportation, and full itineraries
• Coordinate business and personal events, dinners, and restaurant reservations
• Serve as a professional liaison between the CEO and external parties, including investment firms, vendors, and service providers
• Coordinate with project managers, HR, and other leadership to delegate and track tasks on behalf of the CEO
• Manage personal errands, deliveries, and time-sensitive tasks across multiple locations
• Coordinate seasonal preparation and ongoing upkeep of the CEO's homes and properties — gardeners, contractors, household vendors
• Oversee household and property vendors — ensure quality, accountability, and follow-through
• Conduct online research to source the best deals, vendors, and options
• Manage day-to-day personal and business bill pay
• Categorize, track, and reconcile personal and business expenses
• Communicate with investment firms, accountants, and financial advisors on the CEO's behalf
• Maintain organized financial records — physical and digital
• Prepare monthly budget and spending summaries for CEO review
• Bookkeeping in QuickBooks Office & Vendor Management
• Oversee the appearance and function of the office (you coordinate vendors and janitorial — you are the point of contact, not the laborer)
• Receive and manage incoming deliveries, mail, and shipments
• Keep office food, groceries, and supplies stocked at all times
• Interview, vet, and onboard new vendors as needed

Requirements

• 3+ years directly supporting a CEO, founder, or business owner — you understand the pace, the discretion required, and the fluid boundary between personal and professional
• Hands-on QuickBooks experience
• A background in bookkeeping, accounting, or personal finance administration
• Hands-on experience with project management tools like Asana, ClickUp, or Monday
• Highly proficient at booking travel, coordinating events, and managing complex calendars
• An excellent online researcher — you find the best deal, the best vendor, the best option
• Discreet and trustworthy with highly sensitive personal and financial information
• Comfortable being responsive to texts and time-sensitive matters outside of standard business hours, including evenings and weekends as needed
• A reliable personal vehicle and clean driving record (required)
• Comfortable using AI tools (ChatGPT, Claude, etc.) to draft communications and work more efficiently

Benefits

• Health, Dental & Vision
• 401k Plan
• Amazing, Pet-Friendly Office Environment
• Doordash Friday Lunches