Chief of Staff

FlowerHire; New York (NY); On-site; USD 60,000 - 90,000; Full time

Job summary

FlowerHire is seeking a Chief of Staff / Personal Assistant to serve as the right hand to an entrepreneur overseeing multiple businesses and a busy family life in the Hudson Valley.

This role requires someone who can operate at both strategic and tactical levels, create structure around a fast-moving founder, manage calendars, prioritize tasks, coordinate travel, and support nonprofit and board responsibilities.

Qualifications

• 3+ years directly supporting a founder, entrepreneur, owner, principal, or senior executive
• Experience spanning executive support, personal assistance, project management, operations, or Chief of Staff-type responsibilities
• Excellent calendar, task-management, and organizational skills
• Strong judgment, discretion, and comfort handling confidential business and personal matters
• Valid driver’s license and reliable transportation
• Available to work onsite in the Hudson Valley, NY, five days per week

Responsibilities

• Serve as trusted right-hand to the founder and coordinate priorities across multiple businesses
• Create a reliable system for capturing, prioritizing, tracking, and resurfacing tasks and ideas
• Manage and strategically prioritize a complex business and personal calendar
• Anticipate upcoming commitments, deadlines, seasonal priorities, and potential conflicts
• Help determine what needs the founder’s attention, what can be delegated, and what can be handled independently
• Coordinate across multiple businesses and act as a point person to keep projects and priorities moving
• Manage travel, appointments, family scheduling, and personal logistics
• Handle hands-on errands, pickups, and local coordination as needed
• Support nonprofit and board responsibilities, including organizing materials and tracking important deadlines
• Provide light business administration and project-management support
• Build processes and systems that reduce the amount of information the founder needs to personally hold onto
• Follow through relentlessly so that nothing important gets lost in a text, voice note, conversation, or busy week

Skills

Executive support

Personal assistance

Project management

Calendar management

Discretion

Problem solving

Job description

We’re hiring a Chief of Staff / Personal Assistant to serve as the right hand to an entrepreneur overseeing multiple businesses and a busy family life in the Hudson Valley.

This is a unique role for someone who can operate at both the 30,000-foot and highly tactical levels. One moment you may be helping prioritize business initiatives or preparing for a board obligation; the next, you’re coordinating an appointment, handling a local errand, or making sure something mentioned in passing three weeks ago gets resurfaced at exactly the right time.

At its core, this person will create the structure around a fast-moving founder so he can stay focused on the areas where he has the greatest impact.

What You’ll Own:

• Serve as a trusted thought partner and organizational right-hand to the founder
• Create a reliable system for capturing, prioritizing, tracking, and resurfacing tasks and ideas
• Manage and strategically prioritize a complex business and personal calendar
• Anticipate upcoming commitments, deadlines, seasonal priorities, and potential conflicts
• Help determine what needs the founder’s attention, what can be delegated, and what can be handled independently
• Coordinate across multiple businesses and act as a point person to keep projects and priorities moving
• Manage travel, appointments, family scheduling, and personal logistics
• Handle hands-on errands, pickups, and local coordination as needed
• Support nonprofit and board responsibilities, including organizing materials and tracking important deadlines
• Provide light business administration and project-management support
• Build processes and systems that reduce the amount of information the founder needs to personally hold onto
• Follow through relentlessly so that nothing important gets lost in a text, voice note, conversation, or busy week

Who Will Thrive Here:

You’re highly organized, but this role requires more than maintaining a great calendar. You know how to bring structure to someone else’s constantly changing priorities without slowing them down.

You anticipate rather than wait to be asked. You’re comfortable receiving an incomplete thought and figuring out the next step. You have the judgment to know when something needs immediate attention and when it can wait. Most importantly, you enjoy being the person behind the scenes who makes a busy person’s professional and personal life function better.

This is not a traditional corporate Chief of Staff role, nor is it a traditional Personal Assistant position. It sits somewhere in between and requires someone equally comfortable with executive-level organization and rolling up their sleeves to handle the details.

The environment is entrepreneurial, hands-on, and connected to agricultural businesses, including a licensed cannabis operation. The founder’s office isn’t always a desk, so this position is best suited for someone who enjoys being active and comfortable working in a farm environment.

What We’re Looking For:

• 3+ years directly supporting a founder, entrepreneur, owner, principal, or senior executive
• Experience spanning executive support, personal assistance, project management, operations, or Chief of Staff-type responsibilities
• Exceptional follow-through and ability to manage a high volume of moving pieces
• Strong judgment, discretion, and comfort handling confidential business and personal matters
• Excellent calendar, task-management, and organizational skills
• Comfortable communicating through texts, voice notes, and quick conversations
• Ability to operate independently and proactively solve problems
• Comfortable supporting a licensed cannabis business
• Valid driver’s license and reliable transportation
• Available to work onsite in the Hudson Valley, NY, five days per week

Experience supporting a family office, entrepreneurial founder, estate, farm, ranch, or other nontraditional working environment is a plus.