Executive Assistant/Chief of Staff (CEO Support)

Description

• Handle changes fast (delays, reschedules, cancellations—because travel loves drama)
• Household logistics: research vendors, get quotes, schedule services (example: sofa reupholstery—source options, call shops, compare, book, and coordinate pickup/drop-off)
• Manage life admin: appointments (doctor, dentist, etc.), renewals, recurring tasks
• Book flights/hotels/ground transport; build clean itineraries
• Coordinate meetings end-to-end: scheduling, agenda prompts, notes capture, and follow-ups
• Coordinate event logistics and meeting clusters while traveling
• Maintain task lists and a lightweight “CEO operating system” (weekly priorities, follow-ups, reminders)
• Update and maintain CRM (e.g., HubSpot): notes, next steps, pipeline hygiene after customer calls
• Proactively manage the CEO’s calendar: scheduling, prioritizing, confirming, and protecting focus time
• Draft and polish emails (investors, customers, partners) in the CEO’s voice
• Track action items from meetings and ensure nothing drops
• Set up recurring grocery orders and other “autopilot” routines

Requirements

• Experience with (or ability to quickly learn): Google Calendar/Gmail, spreadsheets, task tools, and CRM basics (HubSpot a plus)
• Extremely organized and allergic to things falling through the cracks
• 10–20 hours/week with responsiveness during agreed windows
• Based in the Boston area with availability for occasional in-person errands/hand-offs
• Prior EA, chief of staff, ops, consulting, or startup experience
• Fast, accurate, and discreet (you’ll handle sensitive info)
• Boston-area local who can do occasional in-person tasks reliably
• Reliable computer, phone, and internet
• Inbox is calmer because drafts and follow-ups are handled quickly and cleanly
• Comfortable building simple systems (templates, checklists, workflows)
• HubSpot stays accurate without the CEO needing to think about it
• Highly ambitious grad student or early-career operator
• Comfortable on the phone coordinating vendors and services
• Strong written communicator with good judgment and tone

Benefits

• Travel is booked efficiently with clear itineraries and backups
• Option for a guaranteed weekly minimum (e.g., 10 hours/week) with additional hours as needed
• Thoughtful reminders and execution: birthdays, gifts, important dates
• $20–$40/hour, depending on capability and pace
• Potential performance bonus after a trial period if it’s a strong fit

Training + Development

Interview process

Visa Sponsorship

Security clearance