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Remote Raven

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Executive Assistant

Our client is a US-based IT and cybersecurity services firm with a team of roughly 45–50 people and a CEO who operates across multiple business entities inside the same group. We are hiring a full-time executive assistant who can be the CEO's right hand in a genuinely fast-moving environment—one where calendars shift twice before the day begins and decisions are made in short bursts.

The role sits at the intersection of scheduling, meeting execution, follow-through, systems hygiene, and executive communication. The CEO moves quickly and communicates briefly, so success is less about receiving detailed instructions and more about reading the situation, moving first, and creating visibility as you go.

The best fit is a Catalyst/Persuader-profile professional—sociable; structured-but-flexible; precise without over-thinking; matched in intensity to a fast-paced CEO; and emotionally steady when pressure spikes. Predictability-seekers will find this role overwhelming; motion-first operators will find it energizing.

Key Responsibilities

Calendar & Scheduling Systems

  • Manage complex calendars across multiple business entities and stakeholder groups—leadership, clients, vendors, and occasional personal commitments.
  • Resolve conflicts before they surface: protect focus blocks, sequence meetings sensibly, and verify time zones for every external booking.
  • Implement and optimize scheduling systems and light automation to reduce touches per meeting.

Meeting Support & Decision Capture

  • Attend leadership and cross-entity meetings; capture decisions, owners, and deadlines in real time.
  • Distribute clean recaps within the day and load follow-ups into the appropriate trackers.
  • Prep and clean up recurring cadences—weekly leadership meetings, quarterly reviews, and board-style discussions.

Follow-through & Priority Management

  • Track priorities, deadlines, and commitments across entities; resurface items before they slip.
  • Chase on the CEO's behalf in a tone that keeps peers responsive rather than defensive.
  • Flag risks and slippage early and in writing.

Systems, Documentation & Knowledge

  • Maintain organized SOPs, contact lists, and knowledge bases across MS Teams and OneDrive.
  • Own file hygiene: naming conventions, sensible folders, current version at the top.
  • Manage sensitive credentials through a password vault — grant, revoke, and audit access cleanly.

Executive Communication

  • Draft and send email on the CEO's behalf in the CEO's voice—brief, direct, and warm when it matters.
  • Prepare short pre-meeting briefings so the CEO is oriented in under two minutes.
  • Handle inbound requests from staff, clients, and vendors with a decisive next step every time.

AI-Assisted Productivity

  • Use ChatGPT, Gemini, and Microsoft Copilot to accelerate drafting, summarization, and research.
  • Apply judgment about what still needs a human pass before it leaves the CEO's desk.

Trusted Operator Behaviors

  • Move before being asked when direction is clear; pause and clarify when it is not.
  • Turn ambiguity into a written next step within the hour.
  • Hold confidentiality across sensitive commercial, personnel, and client-related information—a firm operating in cybersecurity is right to expect this by default.

Requirements

  • Proven experience as an executive assistant to a C-level or senior leader (direct, not shared team EA).
  • Strong complex-calendar management across time zones with demonstrable follow-through.
  • Comfort operating in a fast-paced, low-instruction environment with minimal supervision.
  • Excellent written and verbal English suited to a US professional audience.
  • Tech-fluent with the ability to learn new systems quickly.
  • Available Monday to Friday during US business hours anchored to US Mountain Time (MST).
  • Stable internet with a backup connection and a quiet, professional home-office setup.

Preferred Qualifications

  • Experience supporting multiple businesses, entities, or brands under one executive.
  • Familiarity with EOS, Bloom Growth, Ninety.io, or Traction Tools.
  • Working experience with HubSpot or a comparable CRM.
  • Established use of AI tools (ChatGPT, Gemini, Copilot) inside a real workflow.
  • Prior support of an IT services, professional services, or consulting firm.

Tools & Software

  • Microsoft Office (Outlook, Word, Excel, PowerPoint)
  • Microsoft Teams and OneDrive
  • OneNote
  • HubSpot or comparable CRM
  • Password vault (1Password, Bitwarden, Keeper, or similar)
  • Adobe Acrobat
  • AI productivity tools (ChatGPT, Gemini, Microsoft Copilot)
  • EOS platform (Bloom Growth, Ninety.io, Traction Tools) — nice-to-have

What Makes You a Great Fit

  • You anticipate small collisions get fixed weeks out, not the morning of.
  • You write briefly and cleanly. One good line beats three careful ones.
  • You build trust fast with people you have never met.
  • You hold discretion by default and never need to be reminded.
  • You are calm on the ninth priority shift of the day.
  • You take ownership of outcomes without needing recognition for the work.

Benefits

What We Offer

  • Up to $8/hour
  • 100% remote work
  • Full-time role

⭐ We hire for the long haul, so a steady track record of staying and growing always moves you up our list.

To apply:

Ensure your LinkedIn profile and resume are up-to-date and comprehensive (submit a comprehensive resume in English), and complete the assessment in this link:

By applying, you consent to being contacted via the contact information provided in your application for recruitment purposes only.

Interview Scheduling Notice

Initial screening calls are conducted in the US Mountain Standard Time (MST) zone, with available windows between 3:00 AM and 1:00 PM MST. In local time that is approximately 6:00 PM to 4:00 AM Philippine Time (PHT), 1:00 PM to 11:00 PM East Africa Time (EAT), and 12:00 PM to 10:00 PM South Africa Standard Time (SAST). We sincerely appreciate the flexibility of our candidates across different time zones and will make every effort to schedule at a time that works for you. Your willingness to accommodate the time difference is genuinely valued.

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What this application asks

workable

First name, Last name, Email, Headline, Phone, Address, Photo, Education, Experience, Summary, Resume, Tell me about yourself, Cover letter, How many years of experience?, How long have you been in the position for which you are applying? In how many years?, Are you amenable to working the graveyard shift?, Are you amenable to using a time tracker (hubstaff) during work hours?, Asking salary per hour in USD, How many companies did you work in the past 5 years?, Are you looking for a Full-time job?, Can you start immediately?, How soon can you start? Select tentative date., Upload File: Please share a screenshot of your Personal Computer specs and your back-up device, Upload File: Screenshot of your Internet Speed, Upload File: Please share a screenshot of your Personal Computer specs and your back-up device. Remote Raven Minimum Standard PC specs -RAM: 8GB -Processor: i3 8th Generation or equivalent -OS: Windows 7 or higher Back-up device should also have equivalent specs, Please select all of the Tools that you are currently using, Any tools you have experience working with?, Character Reference: Provide three active references in the following format: Name / Relationship / Contact Number

  • Do you have at least 2 years of experience supporting a CEO, Founder, or senior executive? yes / no
  • Are you able to work full-time during U.S. Mountain Standard Time (MST) hours? yes / no
  • What is your expected hourly rate?
  • Do you have a stable internet connection with a backup option? yes / no
  • Are you comfortable working in a fully remote setup long-term? yes / no
  • Which of the following tools have you used? (Select all that apply) choose one
  • How have you used AI tools (like ChatGPT) to improve your productivity or output? yes / no
  • Are you comfortable supporting both business and occasional personal executive tasks? yes / no
  • Are you comfortable working in a fast-paced environment with constantly shifting priorities? yes / no
  • Can you perform effectively with minimal instructions or guidance? yes / no
  • Are you confident making decisions even when you don’t have complete information? yes / no
  • Do you take initiative without waiting to be told what to do? yes / no
  • Are you comfortable handling multiple urgent tasks at the same time? yes / no
  • Are you comfortable being held highly accountable for results? yes / no
  • Are you comfortable pushing back or asking clarifying questions when needed? yes / no
  • Do you have experience managing complex calendars with multiple stakeholders? yes / no
  • Have you created or improved workflows or systems in a previous role? yes / no
  • Do you have a reliable system for tracking tasks, deadlines, and follow-ups? yes / no
  • Are you comfortable working in an environment with little structure or predictability? yes / no
  • Do you thrive in high-pressure, high-speed work environments? yes / no

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