Executive & Personal Assistant to CEO/Entrepreneur

We are seeking an exceptional Executive & Personal Assistant to support a busy entrepreneur and CEO.

This is a unique, high-trust position combining executive support, business coordination, personal assistance, and household/family organization. The ideal candidate is highly organized, polished, resourceful, tech-savvy, and—most importantly—someone who naturally takes ownership and gets things done.

This is not a traditional administrative assistant position. We are looking for someone who can become a true right hand—someone who learns how the CEO operates, anticipates needs, keeps priorities moving, and brings organization to a fast-paced professional and personal schedule.

What You’ll Do

Executive & Business Support

• Manage a business and personal calendar, including meetings, appointments, deadlines, and commitments
• Help manage and prioritize email, correspondence, documents, and follow-ups
• Prepare documents, presentations, meeting materials, and other business correspondence
• Track outstanding projects, deadlines, and action items and proactively follow up to ensure completion
• Coordinate with employees, clients, vendors, professional advisors, and other business contacts
• Assist with research and special projects related to existing businesses, investments, real estate, and new opportunities
• Help organize electronic files, records, subscriptions, accounts, and important information
• Identify opportunities to improve organization, systems, and efficiency
• Handle confidential business, financial, and personal information with complete discretion

Personal & Family Support

• Manage personal appointments, reservations, memberships, renewals, and scheduling
• Research and arrange restaurants, activities, entertainment, services, and special experiences
• Assist with household orders
• Coordinate purchases, returns, deliveries, and other personal tasks
• Help maintain family calendars and ensure important dates and commitments
• Handle occasional errands and other day-to-day personal needs
• Research options and present thoughtful recommendations rather than simply forwarding information
• Coordinate family travel and detailed itineraries

Home & Rental Property Coordination

• Coordinate with household vendors, contractors, designers, maintenance providers, and other service professionals
• Schedule appointments and ensure projects and repairs are followed through to completion
• Receive maintenance requests from Tenants, coordinate with vendors to schedule repairs
• Assist with matters involving multiple residences and properties
• Maintain organized records relating to vendors, warranties, maintenance, projects, and household needs
• Help coordinate deliveries, installations, repairs, and property-related projects
• Coordinate with guests and property management for short term rental.
• Quarterly inspections of residential and commercial properties
• Meet tenants to check them into and out of apartments

Work Location

The majority of the work will be remote, however candidate must complete monthly in person inspections of rental properties in the Boston area, meet outgoing and incoming tenants in person, and occasional errands. Candidate must have their own car and be willing to travel locally.

Who We’re Looking For

The right person is someone who genuinely enjoys making a busy person’s life run more smoothly.

You are:

• Exceptionally organized and detail-oriented
• Proactive—you notice what needs to be done before being asked
• Resourceful and excellent at figuring things out independently
• Comfortable juggling many different priorities at once
• Tech-savvy and quick to learn new software and systems
• An excellent communicator with strong written and verbal skills
• Professional and polished when interacting with clients, executives, vendors, and service providers
• Comfortable handling both high-level business matters and everyday personal tasks
• Discreet and trustworthy with confidential information
• Flexible when priorities change
• Someone who follows through and doesn’t allow things to fall through the cracks
• Good at research and summarizing complicated topics.
• Because this position involves access to confidential business, financial, household, and personal information, discretion and professionalism are essential.

Prior experience supporting a CEO, entrepreneur, executive, business owner, or high-net-worth family is strongly preferred.

What Success Looks Like

Success in this role means the CEO has fewer things to think about because you are already handling them.

You don’t simply wait for a list of tasks. You understand priorities, anticipate what comes next, follow up without being reminded, solve problems independently, and create systems that make both the business and personal sides of life run more efficiently.

Over time, the goal is for you to become a highly trusted partner who can take increasing ownership of responsibilities and projects.

To Apply

Please submit your résumé along with a brief introduction explaining why you believe you would be a great fit for this position.

Expected hours: 40.0 per week

Benefits:

• 401(k)
• Dental insurance
• Health insurance

Work Location: Hybrid remote in Boston, MA 02116