Executive Personal Assistant

We’re hiring an Executive & Personal Assistant to support a founder and entrepreneur overseeing multiple businesses, including a cannabis company.

This is not your typical corporate EA role. We’re looking for someone who thrives in a dynamic, entrepreneurial environment and genuinely enjoys being the person who keeps everything moving behind the scenes. You’ll serve as a trusted right-hand, capturing priorities as they arise, keeping schedules and projects organized, anticipating what’s coming next, and making sure important details don’t fall through the cracks.

The role blends executive support with personal and business logistics, including:

• Managing a fast-moving calendar and competing priorities
• Capturing, organizing, and following through on tasks and requests
• Anticipating deadlines and resurfacing priorities at the right time
• Coordinating travel, appointments, meetings, and personal logistics
• Supporting light administrative needs across multiple businesses
• Managing occasional errands, pickups, and local logistics
• Helping coordinate family scheduling and activities
• Supporting special projects and nonprofit/board-related responsibilities
• Building simple, effective systems that keep an entrepreneurial principal organized

The right person is highly organized but flexible, proactive without needing constant direction, and comfortable working with a founder whose priorities can change quickly. You should have excellent judgment, strong communication skills, and the ability to distinguish between what needs attention now, what can be handled independently, and what can wait.

This is a hands-on position for someone who enjoys variety and doesn’t want to spend every day behind a desk. The businesses include agricultural operations, so comfort working around a farm environment and a licensed cannabis business is required.

Qualifications:

• 3+ years supporting a founder, owner, principal, or senior executive
• Strong calendar, task-management, and organizational skills
• Ability to handle confidential personal and business information with discretion
• Comfortable with changing priorities and informal communication, including texts and voice notes
• Experience with project-management and productivity tools
• Valid driver’s license and reliable transportation
• Comfortable supporting a licensed cannabis business
• Available to work onsite in the Hudson Valley, NY, five days per week

Experience supporting a family office, estate, farm, ranch, seasonal business, or entrepreneurial founder is a plus.