Elite Executive Assistant to Principal — Travel & Schedule

Bespoke Private Service; Southport (CT); On-site; USD 150,000 - 200,000; Full time

Benefits offered by this job

Medical, dental, vision

401k with company matching

20 days PTO + 8 holidays

Job summary

Bespoke Private Service is seeking an experienced executive assistant to support a senior leader across business and personal matters. You will own the combined calendar, coordinate complex travel, and prepare materials for meetings and events.

The role requires rapid responsiveness, a proactive approach, and a networked, discreet mindset. Expect a mix of in-office coordination and private household tasks, with compensation in the range stated.

Qualifications

• Five+ years supporting a senior executive, founder, or principal in an executive assistant role or equivalent.
• Fast, responsive, and capable of owning calendars and commitments.
• Ability to manage complex travel for business and personal needs.

Responsibilities

• Own the calendar across business and personal life and run weekly planning with the principal.
• Support day-to-day work, including correspondence, documents, budgets, and decks.
• Plan and manage business/personal travel including multi-generational trips.
• Receive deliveries, run errands, source home/office needs, and manage vendor networks.
• Source gifts and plan events reflecting the principal’s style.
• Lead personal administrative projects and process invoices and documents.
• Maintain confidentiality and operate with discretion at all times.

Skills

Executive support

Calendar management

Travel planning

Communication

Discretion

Problem solving

Tools

Microsoft Outlook

Microsoft Teams

Microsoft PowerPoint

Excel

Job description

Bespoke Private Service is seeking an experienced executive assistant to support a senior leader across business and personal matters. You will own the combined calendar, coordinate complex travel, and prepare materials for meetings and events.

The role requires rapid responsiveness, a proactive approach, and a networked, discreet mindset. Expect a mix of in-office coordination and private household tasks, with compensation in the range stated.