AI-Enabled Executive Assistant

HireKayana; Philippines; Remote; PHP 2,318,000 - 4,637,000; Full time

Benefits offered by this job

Weekly pay

1-Year Travel Bonus

Year-End Bonus

HMO Coverage

Paid Time Off (PTO)

Paid US Federal Holidays

Job summary

HireKayana is seeking an AI-enabled Executive Assistant to support the CEO of a US-based cybersecurity consulting firm from the Philippines. You will manage calendars, draft SOWs, and coordinate executive communications with high accuracy and process discipline.

The role emphasizes precise, rule-driven work, using approved AI tools, and maintaining strict review before sending any output. You will support senior leadership and ensure timely, error-free delivery across time zones.

Qualifications

• 3+ years as an executive or virtual assistant to a US-based leader
• Hands-on experience with AI tools such as Claude to improve quality and speed
• Strong written and spoken English, with professional emails
• Exceptional attention to detail: catch wrong dates, names, numbers, and time zones
• Experience managing a busy calendar across time zones in Google Workspace
• Experience editing contracts, proposals, or SOWs in Google Docs or Word
• Follows written rules exactly and asks when a rule doesn't cover the case
• Able to work US Eastern business hours every weekday, with reliable internet and quiet workspace

Responsibilities

• Own the CEO's calendar, resolving conflicts and ensuring scheduling rules are followed
• Send daily/next-day calendar review with video links, agenda, and attendees
• Reschedule meetings per priority rules and confirm in writing
• Send complete calendar invites with correct time zones, video links, dial-ins, and attachments
• Protect the CEO's focus time by declining unnecessary meetings
• Attend routine calls with the CEO and capture notes and actions
• Draft and edit SOWs using templates and pricing instructions
• Track SOWs from draft to signature and verify all details

Skills

Executive Assistant

AI tools Claude

English proficiency

Attention to detail

Calendar management

Contract editing

Google Workspace

Tools

Claude

Google Docs

Word

Google Calendar

Calendly

e-signature tools

Job description

HireKayana is a talent agency that connects Filipino Remote Professionals with global companies that operate within real systems and value disciplined execution. These are long-term professional roles—not gig work. Our partners build structured teams where accountability, clear communication, and operational discipline matter.

About the Role

We're looking for an AI-Enabled Executive Assistant to support the CEO of a US-based cybersecurity consulting firm, with additional time spent supporting senior leadership in business operations. You'll own the CEO's calendar, stand in for him on routine calls, support his email and reminders, and prepare Statements of Work (SOWs) using the firm's written rules and templates.

This is precise, rule-driven, high-trust work: one wrong date, name, or price in an SOW affects a client. You'll use approved AI tools as part of your daily workflow to work faster and more accurately, without cutting corners on review. The role suits someone organized, consistent, and proud of getting every detail right, who follows an explained process the same way every time and does what they say they will do.

What You'll Do

Calendar Management

• Review the CEO's calendar every Friday for the coming week, resolving conflicts, double bookings, missing travel time, and meetings that break his scheduling rules
• Send the CEO a review of the next day's calendar before the end of each US workday, confirming every meeting has a video link (if virtual), an agenda, and the right attendees
• Reschedule meetings following the CEO's priority rules: contact the other party, propose new times, and confirm in writing
• Send complete calendar invites on the CEO's behalf with the correct time zone, video link, dial-in, agenda, and attachments, checking every invite before it goes out
• Protect the CEO's focus time by declining or redirecting meetings that don't need him

Calls and Follow-Through

• Attend routine, non-confidential calls with the CEO (vendor demos, intake calls, check-ins), recorded with Gemini, and capture notes and action items
• Send the CEO a summary within 2 hours of every call covering decisions, action items, owners, and due dates
• Remind the CEO ahead of his next meeting about anything still outstanding, and follow up on action items until they close

Statements of Work

• Draft and edit SOWs using the firm's templates, rules, and pricing instructions
• Check every SOW for client name, dates, scope, pricing, payment terms, and signatory details, and remove any leftover text from other clients or templates
• Flag anything that doesn't match the rules instead of guessing, and track each SOW from draft to signature

General Support and AI-Enabled Workflow

• Provide email and reminder support for the CEO
• Keep a running list of open items current with project-management-style follow-up, and report on it weekly
• Use approved AI tools such as Claude to draft, summarize, check, and organize work, while verifying every output before it goes out

What We're Looking For

Non-Negotiables

• 3+ years as an executive or virtual assistant to a senior leader, supporting a US-based client
• Hands-on experience using AI tools such as Claude to improve the quality and speed of your work
• Strong written and spoken English, with clear, professional emails
• Exceptional attention to detail: you catch wrong dates, names, numbers, and time zones before anyone else does
• Experience managing a busy calendar across time zones in Google Workspace (Gmail, Calendar, Meet, Docs)
• Experience editing contracts, proposals, or SOWs in Google Docs or Word, including track changes
• Follows written rules exactly and asks when a rule doesn't cover the case
• Able to work US Eastern business hours every weekday, with reliable internet, backup power, and a quiet workspace (laptop provided)

Preferred Qualifications

• Experience in professional services, consulting, or cybersecurity
• Familiarity with Calendly or an e-signature tool

You’ll Thrive Here If You

• Always do what you say, so nothing falls through the cracks
• Check your work before it goes out
• Take clear instruction, confirm understanding, and follow it consistently, preferring clear structure to open-ended flexibility
• Work independently once direction is given, look things up first, and take direct feedback as useful information
• Communicate clearly, promptly, and consistently
• Weekly Pay: get paid every week, not every two weeks or every month
• 1-Year Travel Bonus: a milestone bonus we put toward a trip after your first full year with Kayana
• Year-End Bonus: annual recognition for the year you put in
• HMO Coverage: real health coverage for you
• Paid Time Off (PTO): real rest, not unpaid leave
• Paid US Federal Holidays: recognized days off aligned to your client's calendar