Executive Assistant

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

EXPECTATIONS

• Five or more years supporting a senior executive, founder, or principal in an executive assistant capacity, or a shorter record that demonstrates equivalent range.
• Responsiveness as a defining standard, meaning quick acknowledgment, closed loops, and reliable follow-through on anything time-sensitive.
• Full calendar ownership across business and personal life, including family travel, run through a collaborative weekly planning cadence with the principal.
• Complex travel planning end to end, business and personal, including multi-generational family trips.
• Advanced Microsoft fluency across Outlook mail and calendar, Teams, Word including tracked changes, Excel to working-model level, and confident PowerPoint production, plus OneNote, OneDrive, and Dropbox, comfort with AI tools, and effortless smartphone fluency.
• Producing finished work product, including decks, spreadsheets, guest lists and mail merges, meeting agendas, document summaries, and comparative analyses of service providers with a recommendation attached.
• Errands and deliveries, both hands-on and delegated, from personally handling ad hoc errands, pickups, and inbound deliveries (including occasional weekend coverage of high-value shipments) to building a vetted network of local runners and vendors that extends capacity when delegation is the smarter path.
• Sourcing and procurement across both home and office.
• Technology translation, meaning setting up a tool, simplifying it, and making it usable for others so the work moves.
• Genuine multitasking, with many concurrent threads held to completion and sequenced by logic rather than by whoever asked last.
• Legal authorization to work in the United States.

WHO YOU ARE

• Urgent by temperament. You move quickly by default and treat responsiveness as part of the craft of the job.
• A fast synthesizer. You absorb new information quickly, connect it to what you already know, and get to the next step without being walked there.
• Resourceful by instinct. When something is hard, you find the angle, the resource, or the vendor, and you bring options rather than obstacles.
• An owner. Once a task is yours, it stays yours through to completion, tracked with clear commitments along the way.
• Collaborative and unafraid to ask. You raise questions early, take direct feedback in stride, and are straightforward about what you do not know.
• An adopter of existing systems. The household already runs on established processes, and your first instinct is to learn them and keep them running rather than rebuild them your own way.
• Humble and confident at once. No task on either side of the desk is beneath you, and you represent the family well in any setting.
• Professionally polished. Your presentation, on video and in person, matches the standard of the family you represent.
• Discreet without exception. Nothing about the family, the household, or its rhythms is shared or posted, ever.
• Personable, with self-aware humor. You connect easily, read the register of the moment, and default to formal and professional when in doubt.

PREFERRED

• Experience blending corporate executive support with personal or family support for an owner, founder, or principal.
• Familiarity with household management platforms and building simple systems for preferences, properties, and projects.
• Working knowledge of the coastal Connecticut and New York vendor and service market.

RESPONSIBILITIES

Calendar and Scheduling:

Own the calendar across business and personal life as one picture. Triage competing priorities on an overbooked schedule, chase down availability, confirm and reconfirm details across multiple parties, and earn growing latitude in judgment calls about how the principal’s time is spent. Run a forward-looking weekly planning meeting with the principal, structure the week ahead, and coordinate with peer executives and their assistants by email for business scheduling.

Executive Support and Production:

Support the principal’s working day, including correspondence, document preparation and summarization, agendas, spreadsheets such as event budgets and guest lists with mail merge, and PowerPoint deck creation and modification.

Travel:

Plan and manage all travel, business and personal, including family vacations and trips that include extended family, from itinerary through on-the-ground contingencies. Resolve disruptions in real time so travel appears seamless and never becomes the principal’s problem.

Household and Personal Coordination:

Receive and manage deliveries, including occasional weekend coverage for high-value shipments when the family travels; run ad hoc errands such as package pickups and drop-offs, personally when that is fastest and through a vetted local runner and vendor network you build for the rest; handle sourcing for home and office, noticing what is about to run out and ordering it before anyone has to ask; support the principal’s spouse and family day to day as directed by the principal; and interface with property managers and vendors on the principal’s behalf. The primary residence is the center of gravity, with additional properties entering the rotation over time.

Gifting and Events:

Source and purchase gifts for family, friends, and special occasions that reflect the principal’s style and feel personally selected, and plan events across both personal and professional life.

Projects and Analysis:

Carry personal administrative projects to completion, including international documentation, estate-plan support materials, property documentation, comparative vendor analyses, and the recurring weekly processing of invoices, scans, and documents requiring signature.

Scope Boundary:

The measure of this seat is that outcomes are met, and some of that is hands-on. Errands, pickups, and receiving deliveries are a real and recurring part of the work, and not everything can or should be outsourced. The judgment lies in knowing which is which, handling it personally when that is fastest and delegating through the vendor and runner network when that is smarter. The role does not include housekeeping, childcare, or property maintenance, and when a process this seat has set up fails, closing the gap falls to this seat rather than to the family.

Confidentiality and Discretion:

Uphold absolute confidentiality across the family, the household, the properties, and the business. A non-disclosure agreement is required at screening, and confidentiality and non-solicitation agreements are signed at offer.

COMPENSATION

Compensation:

$150,000 to $200,000, depending on experience. Salaried, exempt

Benefits:

Medical, dental, and vision; 401k with company matching

Paid Time Off:

20 days, plus 8 paid company holidays including 1 floating day