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.
What You’ll Own
Work: ~60–70%
CEO operations + communication
- 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
Execution + organization
- 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., HubSpot): notes, next steps, pipeline hygiene after customer calls
Travel + logistics
- 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
Personal: ~30–40%
- 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
What Success Looks Like (First 30–60 Days)
- Calendar runs smoothly with fewer last-minute scrambles
- Inbox is calmer because drafts and follow-ups are handled quickly and cleanly
- HubSpot 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)
Who You Are
- 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
Requirements
- 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 (HubSpot a plus)
- Reliable computer, phone, and internet
Nice-to-Haves
- 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
Compensation Structure
- $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
How To Apply
Send:
- A short note on why this role fits you
- Your resume / LinkedIn
- A brief example of something you’ve organized or owned end-to-end (school, work, club, life—doesn’t matter)
- Your weekly availability and confirmation you’re Boston-based
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.
