Executive Assistant to Chief Executive Officer

We are seeking an Executive Assistant to the CEO of a multi-brand company that spans two clothing brands (Ellsworth & Ivey, Mon Coco), a thriving retail store (The Skinny Dip), and multiple hospitality properties including a wedding venue (Witsend Farms) - Scroll below for more information on the businesses.

This is a remote position that offers the flexibility to work from home, but occasional travel may be required to support the CEO and company operations. Candidates located in or around New York City will be prioritized.

This is a unique opportunity to gain hands-on experience across three exciting industries while working directly with the CEO.

• Conduct market research and competitive analysis in fashion, retail, and real estate sectors.
• Support retail store and clothing brands with special projects, including events, store openings, etc
• Organize domestic and international travel logistics for the CEO and key team members.

• Handle confidential and time-sensitive information with discretion.
• Manage organizational files, contracts, and records.
• Manage expense reports, invoices, and other financial documentation.
• Maintain a pulse on industry trends to anticipate needs and contribute fresh ideas.

• Assist in the CEO’s travel arrangements, and meeting preparation.
• Assist with email correspondence, task prioritization, and follow-ups.
• Prepare meeting agendas, take detailed notes, and track follow-ups.
• Assist in drafting correspondence, presentations, and reports.

Guest Support:

• Manage inquiries, reservations, and communications 
• Oversee booking platforms, calendars, and guest experiences to ensure smooth operations

Local Renovation & Permitting Support:

• Work with contractors, designers, and local officials to support renovations and permitting processes.
• Coordinate project timelines, budgets, and deliverables for scaling the wedding venue and bed & breakfast operations.
• Research zoning and compliance requirements, ensuring all projects meet local regulations.

Operational Oversight:

• Coordinate vendor relationships, maintenance schedules, and property upkeep with local property managers to ensure a seamless guest experience.
• Implement processes and systems to optimize efficiency and improve operational performance.
  

• A Jack/Jill of All Trades: You’re eager to learn and adapt to diverse challenges across multiple industries.
• Organized and Detail-Oriented: You excel in managing schedules, juggling tasks, and keeping things running smoothly.
• Proactive Problem Solver: You anticipate needs, identify issues, and solve problems before they arise.
• Self-Starter: You thrive in an independent environment, taking initiative without waiting for direction.
• Excellent Communicator: Your written and verbal communication skills are top-notch.
• Resourceful and Curious: You’re a natural researcher with a passion for uncovering solutions.

• 2 years of experience as an Executive Assistant, Office Manager, or in a similar role.
• Familiarity with property management, fashion, retail, or real estate/hospitality industries is a plus.
• Strong proficiency with Google Workspace, and task management tools, and Excel.
• Ability to work independently, prioritize effectively, and meet deadlines.
• Flexibility to adapt to a dynamic and fast-paced work environment.

You will be working directly for Taylor Ivey, the CEO, behind Ellsworth & Ivey, Mon Coco and The Skinny Dip, three dynamic brands that reflect her passion for fashion, entrepreneurship, and community. Taylor founded Ellsworth & Ivey in 2012 and has built the brand to become a multi-million dollar custom knitwear business designing  for companies such as Soul Cycle, Anthropologie and Carbon38. 

Founded The Skinny Dip in 2016, Taylor has cultivated a one-of-a-kind retail experience with two store locations that brings together emerging designers, established brands, and a coastal lifestyle aesthetic.



Additionally, Taylor is also the owner of a boutique real estate portfolio that highlights her keen eye for design and love of hospitality. Her portfolio features Witsend Farms, a newly acquired wedding and events compound in Connecticut, where she is cultivating a charming countryside destination for unforgettable celebrations. Additionally, she manages three thoughtfully designed Airbnb properties.