Executive Email & Operations Assistant (Remote)

Windsor Drake is a boutique investment bank advising founders and shareholders on sell-side M&A transactions. We operate at a high standard, with senior-level counterparties across North America and Europe. This role supports the Managing Director directly and is critical to keeping the firm operating at peak efficiency.

We are looking for an exceptional Executive Assistant who is already trained, confident, and experienced supporting a Western CEO or Managing Director. This is not an entry-level VA role. This is a senior, high-trust position.

Core Responsibilities

Inbox & Communications Management

Manage the Managing Director’s email inbox end-to-end

Read, triage, organize, and prioritize all inbound emails and messages

Draft clear, professional, native-level English replies on behalf of the Managing Director

Flag high-priority items and ensure nothing important is missed

Proactively remind the Managing Director when responses or follow-ups are required

Maintain a clean, zero-clutter inbox at all times

Scheduling & Coordination

Schedule calls and meetings with clients, buyers, and partners

Coordinate across time zones (primarily North America and Europe)

Manage calendar hygiene and protect focus time

Send confirmations, reminders, and follow-ups without being prompted

Executive Support / Chief-of-Staff-Style Tasks

Act as a central point of organization for all administrative tasks

Track open threads, commitments, and action items

Follow up with interns, clients, or external parties as needed

Maintain simple systems to keep operations running smoothly

Anticipate needs rather than waiting for instructions

General Administration

Light document handling and organization

Basic CRM or contact list updates

Occasional research or coordination tasks as required

Requirements (Non-Negotiable)

Exceptional written and spoken English (near-native or native level)

Prior experience supporting a Western CEO, founder, or senior executive

Proven ability to write professional emails independently and confidently

Extremely organized, detail-oriented, and reliable

Comfortable working with minimal oversight and high expectations

Discreet, trustworthy, and professional at all times

Strong judgment and ability to prioritize correctly

Preferred Background

Previous Executive Assistant, Senior VA, or Chief of Staff–type role

Experience in professional services, finance, tech, or consulting

Comfortable acting as a gatekeeper and filter for a busy executive

Compensation & Structure

Competitive pay, above market for the right candidate

Long-term role with stability and growth

Direct access to and trust from the Managing Director

Opportunity to become the central operational support for the firm

How to Apply

Please include:

A brief summary of your experience supporting Western executives

Examples of professional emails you have written (if available)

Confirmation of your availability and time zone

We are looking for someone polished, confident, and already excellent at this role. Training will be minimal. Execution and judgment matter.