Responsibilities

1. Calendar & Meeting Management

• Own and manage the CEO’s full calendar, scheduling, coordinating, and prioritizing all meetings and appointments across time zones
• Prepare detailed briefing documents ahead of every call, including context, goals, relevant background, and talking points
• Coordinate all post-meeting follow-ups, ensuring decisions, actions, and commitments are captured and executed
• Manage all Deal Boardroom-related meeting coordination, including scheduling, materials, and follow-through

2. Inbox Management

• Serve as the primary manager of the CEO’s email inbox
• Triage, prioritize, and flag incoming correspondence for the CEO’s attention
• Draft responses on the CEO’s behalf and maintain a well-organized draft box for review and send

3. CRM & Pipeline Management

• Own contact and pipeline outreach and coordination end to end
• Ensure all contacts are current, pipeline stages are accurately reflected, and nothing falls through without follow-up
• Coordinate handoff to the Chief of Staff at the point of onboarding
• Surface timely reminders and next steps to keep the CEO’s pipeline moving without manual oversight

4. Advisory Board Member Support

• Run regular check-in outreach on behalf of the CEO to maintain an active, open line of communication with all current Advisory Board members
• Support Advisory Board members with questions, resource requests, and coordination needs
• Track engagement across the board and flag any members who may need additional attention or outreach

5. Knowledge Base Management

• Coordinate the capture and ongoing maintenance of all incoming information into the organization’s knowledge base
• Ensure meetings, decisions, research, and key communications are properly documented and categorized
• Maintain a directory and indexing system for recordings, meeting outcomes, and key records

6. AI Implementation & Automation

• Identify repetitive or manual workflows across the CEO’s operations and build automations to eliminate them
• Build, maintain, and iterate on AI agents and skills that support the CEO’s daily functions, including inbox triage, briefing generation, and CRM updates
• Stay current on emerging AI tools and proactively recommend and implement those that improve team efficiency
• Serve as the primary operator of the organization’s AI infrastructure, owning prompt systems, agent configurations, and automation workflows
• Document all automations and agents so they are maintainable, scalable, and transferable

7. Social Media Oversight

• Manage social media approval coordination by routing content drafts through the CEO’s review and approval workflow
• Ensure posts, campaigns, or communications requiring CEO sign-off are handled efficiently and on schedule

8. Travel Planning

• Coordinate all travel logistics for the CEO, including flights, accommodations, ground transportation, and itineraries
• Prepare detailed travel briefing packages including schedules, contacts, and location-specific materials
• Manage travel expense documentation and reimbursements

9. Personal Assistance

• Support the CEO with occasional personal tasks, including appointments, errands, and ad hoc requests
• Handle personal matters with the same discretion, efficiency, and professionalism as business responsibilities

Key Outcomes & Standards

• The CEO’s calendar is expertly managed; meetings are purposeful, briefed, and followed up on without exception
• The CEO’s inbox is clean, organized, and actioned with nothing slipping through
• CRM pipeline stages are always current; prospect relationships move forward without the CEO needing to chase details
• Advisory Board members feel consistently supported and connected to the CEO
• All key information is captured, organized, and retrievable in the knowledge base
• Manual and repetitive workflows are actively identified and replaced with automations or AI agents
• AI systems are documented, maintained, and improved over time
• Travel is seamlessly arranged and the CEO arrives prepared and unburdened by logistics
• All work is conducted with strict confidentiality and professional discretion
• Every interaction and deliverable reflects positively on the CEO and the organization

 

Requirements

Experience

• Minimum 2-3 years as an Executive Assistant, with a strong and verifiable work history
• Demonstrated experience supporting a CEO or C-suite executive in a fast-paced environment
• Experience managing high-volume, complex calendars across multiple time zones
• Hands-on experience building AI automations, agents, or prompt-based workflows
• Experience with CRM platforms, preferably HighLevel

Skills & Competencies

• Expert-level written and verbal communication in English
• Proficiency with Google Workspace, Monday.com, HighLevel, Excel and Notion
• Ability to build and maintain automations using tools such as Make, Zapier, or similar platforms
• Comfort configuring and operating AI agents and prompt systems in a real work environment
• Drafts polished, professional correspondence on behalf of a senior executive
• Strong problem-solving instincts and sound independent decision-making
• Social media scheduling and content management experience

Attributes

• Proactive and solutions-oriented; anticipates needs before they arise
• Works autonomously with minimal direction and is highly resourceful
• Genuinely excited about AI and actively experiments with new tools to improve how they work
• Unafraid of difficult conversations; manages up effectively and pushes back when appropriate
• Exceptional discretion and confidentiality with sensitive business and personal information
• Thrives under pressure and consistently meets tight deadlines
• Adapts readily as the organization grows and responsibilities evolve
• Warm, professional, and builds strong relationships at all levels of the organization

Preferred (Not Required)

• Interest in M&A, entrepreneurship, or high-growth founder ecosystems
• Experience with short-form video creation or content repurposing
• Familiarity with social scheduling tools such as Buffer or Hootsuite

Tools & Tech

• Google Workspace
• Monday.com
• HighLevel
• Notion
• Gmail / Google Calendar
• Slack
• Claude / ChatGPT
• Make / Zapier
• AI Agents & Prompt Systems
• LinkedIn / TikTok / YouTube
• Social Scheduling Tools
• HighLevel CRM

Why This Role

High-visibility access

Work directly with a serial entrepreneur and see brand strategy, acquisitions, and media creation up close

Remote autonomy

Full remote setup with clear expectations and strong team support

Real growth opportunity

Lean, fast-moving team with strong mentorship and a clear path to expanded responsibility

Meaningful impact

You will be the person who keeps everything moving. Your contributions will be visible and valued

Pay: $15,000.00 – $35,000.00 per year

Experience:

• Executive administrative support: 2 years (Preferred)

Work Location: Remote

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