Executive Assistant​/Chief of Staff; CEO

The Role

This is a high-trust, high-impact role supporting a venture-backed startup CEO. You’ll help keep both the company and the CEO running at full speed by eliminating friction, staying ahead of problems, and turning chaos into a clean plan.

The split is roughly 60–70% work support / 30–40% personal support
, depending on week-to-week needs. If you love building systems, making plans, and being the person who “just gets it done,” you’ll do well here.

• 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

• Coordinate meetings end-to-end: scheduling, agenda prompts, notes capture, and follow-ups

• Maintain task lists and a lightweight “CEO operating system” (weekly priorities, follow-ups, reminders)

• Track action items from meetings and ensure nothing drops

• Update and maintain CRM (e.g., Hub Spot): notes, next steps, pipeline hygiene after customer calls

• Book flights/hotels/ground transport; build clean itineraries

• Handle changes fast (delays, reschedules, cancellations—because travel loves drama)

• Coordinate event logistics and meeting clusters while traveling

• Manage life admin: appointments (doctor, dentist, etc.), renewals, recurring tasks

• Thoughtful reminders and execution: birthdays, gifts, important dates

• Household logistics: research vendors, get quotes, schedule services (example:
  sofa reupholstery—source options, call shops, compare, book, and coordinate pickup/drop-off
  )

• Set up recurring grocery orders and other “autopilot” routines

• Calendar runs smoothly with fewer last-minute scrambles

• Inbox is calmer because drafts and follow-ups are handled quickly and cleanly

• Hub Spot stays accurate without the CEO needing to think about it

• Travel is booked efficiently with clear itineraries and backups

• Personal errands/admin happen without prompting (the dream)

• Highly ambitious grad student or early-career operator

• Extremely organized and allergic to things falling through the cracks

• Proactive
  : you don’t wait to be asked; you notice, flag, and fix

• Fast, accurate, and discreet (you’ll handle sensitive info)

• Strong written communicator with good judgment and tone

• Comfortable on the phone coordinating vendors and services

• Boston-area local who can do occasional in-person tasks reliably

• Based in the Boston area with availability for occasional in-person errands/hand-offs

• 10–20 hours/week with responsiveness during agreed windows

• Experience with (or ability to quickly learn):
  Google Calendar/Gmail, spreadsheets, task tools, and CRM basics (Hub Spot a plus)

• Reliable computer, phone, and internet

• Prior EA, chief of staff, ops, consulting, or startup experience

• Comfortable building simple systems (templates, checklists, workflows)

• Interest in startups/venture and learning how CEOs actually operate

• $20–$40/hour
  , depending on capability and pace

• Option for a guaranteed weekly minimum (e.g., 10 hours/week) with additional hours as needed

• Potential performance bonus after a trial period if it’s a strong fit

Send:

Optional (but helpful): Include a 5–8 sentence draft email you’d send to schedule a meeting with an investor, and a simple sample weekly “CEO priorities” checklist.