EA/Chief of Staff - Greenwich, CT

The British Connection Staffing; Greenwich (CT); Hybrid; USD 160,000 - 180,000; Full time

Benefits offered by this job

Health benefits

Performance bonus

Job summary

The British Connection Staffing is seeking an Executive Assistant / Chief of Staff for a Principal based in Greenwich, CT. This full-time position involves supporting the Principal's professional and personal environments, managing multiple calendars, and overseeing property management.

Ideal candidates will have substantial experience in similar roles, excellent communication skills, and a proactive approach to building effective operational systems. Compensation includes a base salary of $160,000 to $180,000 plus performance bonuses and health benefits.

Qualifications

• Significant experience as an Executive Assistant, Personal Assistant, or Chief of Staff in a private household.
• Proven multi-property estate experience.
• Ability to build and manage household operating systems.

Responsibilities

• Manage multiple calendars for principals.
• Handle email management to drive towards zero inbox.
• Oversee property management and renovation processes.

Skills

Email management

Calendar coordination

Property management

Communication

Operations management

Tech-savvy

Tools

Google Workspace

Microsoft Office

Monday.com

Job description

Executive Assistant / Chief of Staff - Greenwich, CT

Full‑time, | Confidential

4 days in office, 1 WFH, varies when Principal away

This is an interesting household and business support role for a Principal based from a home office in Greenwich, CT, operating at a senior level in finance.

A Family Assistant will sit alongside this role, handling the day‑to‑day family and children’s administration – which means this position operates firmly at a genuinely strategic level. It is operations‑weighted, systems‑minded, and built for someone who sees a household that needs proper infrastructure and feels the pull to build it.

The principals are not micromanagers. They want to build a relationship of trust and confidence with the right person, give them genuine ownership, and get out of the way. If you have wanted a role where you can truly make something your own, this is it.

What you will own

Principal & Business Support

• Multiple personal, professional, and board calendars across both principals — coordinated, consistent, nothing lost
• Email management and distillation — weekly packet model; drives toward zero‑inbox for the principal
• Travel, investor and advisory support, and client correspondence
• School communications, household deadlines, and family events are never missed

Property & Renovation

• A significant ongoing home renovation — full ownership of vendors, contractors, timelines, approvals, and communication
• Greenwich and Hamptons property management — seasonal cadence, maintenance schedules, and vendor relationships
• Natural instinct to check price and budget adherence across all property and vendor activity
• Senior oversight of the Family Assistant; nanny and housekeeper coordination
• Nurture and manage relationships with local Greenwich and CT vendors

Systems & Operations

• Build and own the household operating system from the ground up — Monday.com as the backbone; recurring annual activity fully codified so nothing is rediscovered year over year
• Renewals system across insurance, memberships, registrations, passports, Global Entry, and vendor contracts — caught before they lapse
• Tech forward. Fluent in Google Workspace, Microsoft Office and loves AI tools — abreast of new tech applications that may be applicable. Ultimately, builds systems, not workarounds

A dedicated family office manage the financial infrastructure of the household — bill pay, payroll, investment administration, tax coordination, insurance, and contracts. This is not part of the EA/COS remit. What is required is a proactive and organised point of liaison: supplying documents and information promptly, flagging items that need the family office’s attention, and ensuring nothing falls between the two.

Who you are

• Substantial experience as an EA, PA, or COS in a private‑household or principal‑facing environment — in long‑term positions
• Proven multi‑property estate experience — this is not a nice‑to‑have
• A builder: you create infrastructure, codify recurring activity, and make it better over time
• Calm under pressure, highly discreet, and comfortable with an always‑on pace
• Warm and professional — equally at ease with a Greenwich contractor and a C‑suite contact
• A clear, confident communicator in writing across all contexts
• Valid driver’s licence; must live within easy daily commute of Greenwich, CT

Compensation: $160,000 – $180,000 base + performance bonus. Health benefits provided.