AI Savvy Executive Assistant to the CEO

ROLE

Are you a master at providing executive support and thriving in the orbit of a CEO's work? Are you excited about using AI and automation to create leverage, efficiency, and clarity? Do you take pride in being the right hand to a visionary leader building in an AI-driven environment?

We're seeking an exceptional AI-savvy Executive Assistant to support the flow of a CEO's genius in a fast-moving, growth-oriented AI company. This role is for someone who thrives in ownership, anticipation, and execution — not task waiting.

You will act as a force multiplier by protecting focus, driving follow-through, and using AI tools to streamline workflows across both business and personal logistics. This is a full-time position ideal for a highly organized, proactive, resourceful professional who thinks in systems and leverage.

RESPONSIBILITIES

The Executive Assistant is expected to support Stephen in the following areas:

Creating Time Freedom (Through Systems & AI)

• Free up Stephen's time by taking tasks off his plate so he can focus on CEO-level vision, strategy, and growth.
• Use AI tools and automations to reduce manual work, improve speed, and increase clarity across workflows.
• Keep days themed and aligned with work buckets (Admin, Strategic, Creative, Deep Work, Meetings, Personal).
• Document, prioritize, and manage all Stephen's tasks based on urgency and strategic importance.
• Delegate tasks that do not require CEO-level involvement.
• Develop a clear update cadence so Stephen never has to ask for task or status updates.
• Serve as gatekeeper for meetings and requests to protect focus.

Collaboration, Communication & Execution

• Collaborate with Stephen's leadership team and direct reports on his behalf.
• Ensure quarterly Rocks and strategic priorities are consistently moving forward.
• Review recordings of meetings and calls; extract, prioritize, and track action items.
• Execute follow-up from L10s and 1:1s so Stephen can remain in his zone of genius.
• Send clear post-meeting follow-ups (email, Slack, or text).
• Exercise relentless follow-up and follow-through on commitments.

Administrative, AI Systems & Logistics

• Fully manage Stephen's email and calendar using filters, rules, templates, and AI where appropriate.
• Respond to communications on behalf of Stephen with clarity, confidence, and discretion.
• Build and maintain AI-powered systems to:
  • Summarize meetings and calls
  • Track tasks and commitments
  • Improve internal organization and knowledge management
• Implement and maintain a second-brain system in Notion.
• Create SOPs and playbooks for recurring tasks and workflows.
• Track compensation-related reporting and invoicing as needed.

Travel

• Plan and manage complex travel itineraries for Stephen (and family, when applicable).
• Prioritize speed, convenience, comfort, and luxury.
• Create clear, easy-to-follow travel itineraries.
• Remain on-call during travel to resolve issues.
• Begin major travel planning at least six (6) months in advance.
• Ensure all travel is booked and reflected on the calendar no later than three (3) months in advance.

Research & Development

• Independently research, prioritize, and execute special projects.
• Prepare briefing notes for external meetings and calls.
• Vet vendors, partners, and tools (including AI tools) and present concise recommendations.

Personal Tasks

• Approx. 70% business / 30% personal support.
• Review personal and family calendars before scheduling Stephen.
• Coordinate occasionally with Stephen's spouse regarding priorities.
• Purchase gifts and draft notes.
• Serve as point of contact for CPA, family office, banks, and legal team.
• Manage family travel when required.
• Handle life administration (appointments, renewals, bills, budgets, expense categorization, tax prep support, etc.).

RESULTS

• Calendar Optimization: Protect 10–15 hours per week of uninterrupted deep work.
• Inbox Management: Maintain Inbox Zero daily using filters, templates, and AI assistance.
• AI Leverage: Manual work is consistently reduced through smart use of AI tools and automations.
• Strategic Execution: Meetings, ideas, and commitments move to completion.
• Travel Excellence: Travel reconfirmed one month and two weeks prior.
• Personal Life Optimization: Friction is removed so Stephen can focus on leadership, vision, and family.
• All tasks are tracked and updated daily in

REQUIREMENTS

• Highly action-oriented with zero procrastination.
• Strong ability to anticipate needs before they surface.
• Exceptional written and verbal communication skills.
• Ability to confidently represent the CEO in written and verbal communication.
• Proactive, reliable, and self-directed.
• Minimum 2 years supporting a CEO or senior executive.
• Minimum 2 years arranging travel for high-level executives.
• Comfortable working U.S. hours (8am–5pm PST) with flexibility.
• High discretion and confidentiality.

AI & Tech Requirements

• Strong proficiency using AI to free up time and create leverage.
• Experience with AI automation tools such as:
  • ChatGPT / AI assistants
  • Zapier, n8n, or similar automation tools
  • AI agents or workflow-based AI systems
• Tech-savvy with tools such as:
  • Google Workspace
  • Slack
  • Monday
  • Zoom

Key Attributes

1. Predictive Attunement & Solutionary

Anticipate needs and risks, presenting thoughtful solutions before problems arise.

2. Follow-Through in the Big & Small

Ensure execution matches intention through completion.

3. Force Multiplier & AI Leverage

Think in systems, automation, and efficiency. Constantly ask: How can AI do this faster, cleaner, or better?

AGREEMENT TERMS

• Base Pay: $1,600 per month
• Hours: 40–50 hours/week (tracked via Clockify)
• Paid Time Off: 35 paid days per year
  • 25 US & Philippine holidays
  • 5 paid vacation days
  • 5 paid sick days
• Location: Remote (work from anywhere)