Chief of Staff

Following a highly successful business career, our client - a private principal - is establishing a single family office in Connecticut. He is seeking a Chief of Staff to become his true right hand: a trusted operator who will build the office from the ground up and run it for the long term.

This is not a conventional family office role. The mandate is to make this one of the first family offices of its kind: the Chief of Staff will lead the design and rollout of an AI agent infrastructure across the office's operations - whether it’s deploying off-the-shelf capability using tools like Claude, or it’s a more advanced custom build. You will have a genuine budget and buying power to make this happen, alongside a small team of direct reports managing the family's physical assets (art collections, vehicles, and properties).

The principal has a decades-long track record of hiring exceptional people and keeping them. This role is designed the same way: a long-term partnership with someone who becomes a trusted confidant to the principal and his wider family - not a stepping stone.

The Role

AI & Technology Leadership

• Lead the build and rollout of AI agents across family office operations

• Establish the office as an early adopter and reference point for AI-enabled family office operations

Executive & Personal Support

• Act as the principal's right hand: day-to-day priorities, communications, and scheduling

• Coordinate travel, appointments, and personal logistics

• Handle confidential matters with absolute discretion and judgment

Financial Administration

• Oversee payroll, bill pay, vendor relationships, and expense reconciliation across personal and business accounts

• Maintain organized financial records; support reporting and budgeting

Operations & Office Management

• Establish efficient systems for documents, workflows, and internal processes

• Coordinate external providers (accountants, attorneys, vendors)

• Manage a small team responsible for the family's physical assets

Business & Negotiation Support

• Lead or support negotiations for leases, contracts, and service agreements

• Conduct research and due diligence for business decisions and investments

• Represent the principal with vendors, partners, and stakeholders

Philanthropy

• Support the principal's substantial philanthropic activity - a major and growing component of the office's work. The family runs or attends circa 200 events per year, support here will be hands-on.

About You

• Technologically strong: hands-on with AI tools (experience with Claude is highly beneficial), comfortable evaluating and implementing new systems, and confident managing everyday technology

• High emotional intelligence, with the judgment to operate seamlessly across business and personal spheres

• Genuinely willing to work "high and low" - from strategic builds to day-to-day detail

• Strong financial acumen: payroll, expense management, budgeting

• Proven negotiation and vendor management experience

• Exceptional organization, discretion, integrity, and professionalism

• Bachelor's degree required; family office, executive support, or operations experience strongly preferred

• Seeking a long-term home, not a short-term role

The Environment

The principal is relaxed, humble, and easy to work with - someone who doesn't take himself too seriously and offers a genuinely great working environment. The office transition will unfold over roughly 16 months, with onboarding targeted for January, though the priority is finding the right person rather than moving fast.

This role will be based in the office five days a week - and it's an office worth showing up for. Newly built and architect-designed, it's an award-winning, Bauhaus-inspired building powered entirely by on-site renewable energy, elevated above its landscape with views of greenery from every window. Inside, living green walls, natural daylight, and the sound of falling water make it feel more like a treehouse retreat than a workplace - complete with an on-site art gallery and maker facility. It's a genuinely contemplative place to work, designed to encourage creativity, collaboration, and well-being.

Relocation support is available from within the US - comprehensive and well-practiced, drawn from the principal's decades of experience relocating people throughout his career as a leading CEO.