Executive Assistant (Operational & Commercial Support)

Employment Type: Full-time, Independent Contractor

Work Model: Remote

Work Hours: US Business Hours alignment (Core overlap to match executive schedules)

Role Overview

We are seeking a proactive, highly organized, and commercially minded Executive Assistant to support two senior directors (serving as the primary operational and sales-pipeline right hand for the Lead Director).

In this seat, your primary mandate is simple: give the directors their time back. You will transform executive operations by taking full ownership of diary scheduling, inbox triage, personal property administration, and operational follow-ups. Crucially, this is not a reactive administrative position—you will act as a commercial partner, managing the directors' sales pipeline, ensuring prospective deal follow-ups never stall, and proactively prompting leadership on high-value sales actions to directly drive business growth.

Key Responsibilities

1. Executive Operations & Inbox Governance

Calendar & Diary Oversight: Proactively manage complex executive calendars, resolve scheduling conflicts, protect director focus time, and coordinate pre-meeting contexts and agendas.
Inbox Triage & Correspondence: Monitor, organize, and prioritize director inboxes; draft executive correspondence, flag urgent communications, and maintain tracking records of open client/partner threads.
Operational Follow-Through: Follow up across internal teams, external clients, real estate agents, and vendors to ensure all executive commitments and action items are completed on schedule.

2. Sales Pipeline Management & Commercial Support

Pipeline Administration: Track deal flow, prospect conversations, and action items inside the CRM; maintain strict visibility over sales pipeline stages and follow-up deadlines.
Executive Accountability: Prompt and remind the Lead Director when specific high-touch sales interactions or technical decisions require his direct input.
Sales Cadence Preservation: Coordinate post-meeting communications and administrative deliverables so prospective revenue opportunities never stall due to administrative bottlenecks.

3. Personal & Property Administration

Property Portfolio Management: Handle property-related invoicing, track lease/contract documentation, coordinate with real estate agents/managers, and resolve administrative property tasks.
Discreet Support: Manage sensitive personal and business executive tasks with strict confidentiality, discretion, and data security.

4. Business Development & Lead Sourcing (Growth Area)

Market Sourcing: Research prospective commercial clients and build target lists to support company business development initiatives.
Outreach Tracking: Support initial outreach campaigns, track prospect responses, and ensure smooth hand-offs to executive leadership.

Required Skills & Qualifications

Professional Experience: 2–10+ years of proven experience as an Executive Assistant, Personal Assistant, or Senior Administrative Specialist supporting C-suite executives, founders, or senior directors.
Commercial & Pipeline Aptitude: Hands-on experience working alongside commercially focused executives, with direct exposure to CRM pipeline management, sales administration, or business development workflows.
Calendar & Inbox Mastery: Advanced proficiency managing multi-executive diaries, complex travel logistics, and high-volume email operations.
Property & Administrative Literacy: Familiarity handling property-related administration, basic financial invoices, and multi-entity documentation.
Communication & Discretion: Exceptional written and spoken English skills; highly articulate, professional, and discreet when handling confidential business and personal matters.
High-Agency Mindset: A self-starter who looks ahead, anticipates operational friction, and executes independently without requiring constant supervision.

Preferred Qualifications

Experience supporting executives across multiple distinct companies or business units simultaneously.
Direct experience building administrative frameworks, SOPs, and tracking systems from the ground up in a growing organization.
Experience with lead generation tools, CRM software, and real estate administration.

Success Metrics (KPIs)

Executive Capacity Creation: Demonstrably reducing time spent by directors on routine administrative, property, and scheduling tasks.
Sales Pipeline Velocity: Zero dropped deal follow-ups; maintaining accurate, real-time pipeline visibility across all active opportunities.
Task Ownership & Autonomy: Proactively anticipating operational needs, managing inbox threads to completion, and establishing trusted execution without daily hand-holding.

Executive Assistant - 21191