Senior Executive Assistant (Global, Travel-Intensive Role, AI-Fluent)

SpencerPruitt, Inc.

Senior Executive Assistant

AI-Fluent | Global Travel | Multi-Entity Operating Environment

West Palm Beach, Florida

Travel-intensive; extended domestic and international travel required

$100,000–$115,000 base + 0–20% discretionary bonus + full benefits

Target start within 30–90 days

Head of Executive & Administrative Operations (daily partnership with senior principal)

Confidential — multi-entity holding company spanning consulting, energy, technology, media, aviation, and financial services

The Opportunity

We are hiring an Executive Assistant who operates like a force multiplier — not a gatekeeper.

This role supports a senior principal who leads a founder-built operating platform spanning 11+ active business entities across consulting, energy and commodities, AI and technology, media strategy, marketing, entertainment, private aviation, and financial services. The environment functions more like a family office than a traditional corporation — fast-paced, high-trust, and high-stakes.

The right person for this role doesn't just manage a calendar. They use AI tools to prepare meeting briefs in minutes, draft and refine executive correspondence, summarize complex documents, coordinate across multiple business contexts simultaneously, and anticipate what the principal needs before being asked. This is a technology-forward role in which AI fluency is not a bonus — it is a core competency.

This is a long-term position (4–5 year horizon) with meaningful growth potential as the organization scales. You will have a front-row seat to how a complex, multi-entity business is built and run — and a direct hand in making it work.

What Makes This Role Different

Most EA roles support one executive at one company. This role requires you to navigate across an entire ecosystem of businesses, each with its own rhythm, stakeholders, and priorities. On any given day, you may be coordinating a consulting engagement, managing logistics for an international trip, preparing materials for a capital transaction, and ensuring nothing falls through the cracks across the platform.

We expect you to leverage AI tools — Claude, ChatGPT, Microsoft Copilot, and others — to work at a speed and quality level that would be impossible manually. An EA who can use Claude to draft a polished brief in 10 minutes is worth more to us than one who spends two hours doing it by hand, regardless of how many years of experience they have.

Travel & Availability

This is a travel-intensive, availability-driven role. Readiness to travel is a core condition of employment. Candidates must be prepared for:

• Extended domestic and international travel, including assignments ranging from 1 week to 60 consecutive days
• Periods of heightened availability during travel and active transaction cycles
• Variable work rhythms depending on geography and business cadence

Travel is not constant, but readiness is. During extended international assignments, work follows local business rhythms with natural breaks. After prolonged travel periods, recovery time is provided. When not traveling, the role is office-based in West Palm Beach with an 8:00 a.m. start time.

Role Composition

~90% Executive Assistant responsibilities. Calendar management, communications, travel coordination, meeting preparation, follow-up tracking, and multi-entity operational support.

~10% limited personal execution (exception-based). Backup coverage when the Personal Assistant is unavailable; travel-related personal tasks such as organizing hotel suites, managing reservations, or packing logistics. Personal tasks are infrequent, situational, and strictly tied to executive mobility.

This is not a Personal Assistant or lifestyle-management role.

Key Responsibilities

Executive Support & AI-Powered Productivity

• Manage complex calendars across time zones with strong judgment and prioritization
• Control executive access and scheduling with discretion and confidence
• Draft, coordinate, and manage executive communications — leveraging AI tools to produce polished output quickly
• Prepare meeting briefs, background research, and document summaries using AI (Claude, ChatGPT, Copilot)
• Track follow-ups, commitments, and priorities across 11+ business entities with precision
• Represent the principal in scheduling and logistics conversations
• Proactively identify opportunities to streamline workflows using technology and AI

Travel & Logistics

• Coordinate domestic and international travel itineraries across multiple time zones
• Prepare and manage travel documentation, visas, and logistics
• Support continuity of work during extended travel periods
• Ensure seamless transitions between offices, hotels, and temporary workspaces

Multi-Entity Coordination

• Navigate across multiple business entities, each with distinct operations and stakeholders
• Route and prioritize information flow to the principal across the platform
• Maintain awareness of active priorities across consulting, energy, technology, media, and other verticals
• Coordinate with other executive assistants and administrative staff across the organization

Authority & Boundaries

• Authorized to speak on behalf of the principal regarding scheduling, logistics, and availability
• Not authorized to represent the principal on financial, commercial, or monetary matters without explicit direction
• Expected to exercise judgment, discretion, and restraint at all times

Qualifications

Required

• 3–7 years of experience as an Executive Assistant, Chief of Staff, or comparable high-trust operational role
• Demonstrated proficiency with AI productivity tools (Claude, ChatGPT, Microsoft Copilot, or equivalent) — must be comfortable using AI daily to draft communications, prepare research, summarize documents, and streamline workflows
• Experience navigating complex, multi-stakeholder environments — family offices, holding companies, founder-led platforms, or multi-entity organizations strongly preferred
• High mobility and flexibility: valid passport, ability to obtain international visas, and genuine comfort with extended travel
• Exceptional written and verbal communication skills
• Strong proficiency with Microsoft Outlook, Teams, and standard productivity software
• Impeccable discretion, judgment, and professionalism

Preferred

• Experience supporting UHNW individuals, principals, or C-suite executives
• Familiarity with legal or financial services environments
• Experience with iManage, Clio, or similar document/practice management platforms
• Background coordinating across multiple business units or portfolio companies
• Comfort building and maintaining systems (trackers, dashboards, SOPs) to manage information flow

Culture & Environment

This role is best suited for someone who:

• Thrives in ambiguity and can operate effectively without a rigid playbook
• Works well with strong, opinionated leadership personalities and earns trust through competence
• Values polish, professionalism, and executive presence
• Understands that trust and discretion outweigh process
• Sees AI as a tool that makes them better, not a threat to their role
• Wants to grow with an organization, not just fill a seat

Candidates seeking highly rigid structures, narrow role definitions, or purely transactional work may find this environment challenging.

Compensation & Benefits

• Base salary: $100,000–$115,000
• Discretionary bonus: 0–20% annually
• All business travel fully covered
• Company-provided phone or soft phone (phone bill covered)
• Home internet/cable reimbursement up to $150/month
• Comprehensive healthcare benefits, including concierge medical services
• Long-term growth trajectory as the organization scales

NDA required. Exceptional discretion and reputational sensitivity expected.

How to Apply

Submit your resume and a brief note (3–5 sentences) explaining how you currently use AI tools in your work. We are not looking for a cover letter — we want to see how you think and communicate concisely.

Candidates who demonstrate AI fluency in their application will be prioritized.

SpencerPruitt, Inc. • West Palm Beach, Florida

An Equal Opportunity Employer