Executive Assistant to CEO

Executive Assistant to CEO
Full-Time | Remote – Philippines | $1,500 USD/month | 40 hours/week | U.S. business hours

REQUIRED WRITTEN INTERVIEW — COMPLETE TO MOVE FORWARD

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You must complete the written interview to move forward in the hiring process. Submit your resume as instructed below.

THE ONE-SENTENCE TEST

Can you move with urgency, manage a fast-changing executive workload, and use both Kartra and GoHighLevel proficiently without waiting for the CEO to repeatedly tell you what to do?

If the answer is yes, keep reading.

WE AREN’T LOOKING FOR A TRADITIONAL EXECUTIVE ASSISTANT

Speak Your Way To Cash® is looking for a highly responsive, technology-proficient Executive Assistant who operates with speed, urgency, accuracy, judgment, and complete ownership.

Ashley’s schedule and priorities move quickly. Client requests, legal matters, speaking opportunities, sales conversations, sponsorships, travel arrangements, events, and business decisions often require immediate action.

This is not a role for someone who:

• Waits until the end of the day to acknowledge an urgent request
• Takes several days to complete something that could reasonably be handled today
• Needs repeated reminders or constant follow-up
• Waits for detailed instructions instead of determining the next step
• Lists Kartra or GoHighLevel on a résumé but cannot demonstrate hands-on proficiency
• Allows assignments or follow-ups to quietly disappear

The right person quickly determines what needs to happen, gathers missing information, proposes a solution, communicates progress, and drives the assignment to completion.

You must be able to move fast without becoming careless.

ABOUT SPEAK YOUR WAY TO CASH®

Speak Your Way To Cash® is a multiple-time Inc. 5000 company that helps experts, entrepreneurs, speakers, consultants, attorneys, and executives turn their expertise into high-value speaking, training, consulting, and corporate-contract opportunities.

Ashley Kirkwood is an attorney, CEO, international speaker, bestselling author, and entrepreneur managing multiple businesses, client obligations, speaking engagements, events, partnerships, and rapidly changing priorities.

This role exists to protect Ashley’s time, carry the details, anticipate what she will need next, and ensure important work moves forward without her having to repeatedly check on it.

THE MISSION

Your mission is to become the reliable right hand who:

• Responds quickly
• Thinks critically
• Acts independently
• Protects Ashley’s time
• Keeps priorities organized
• Communicates confidently on Ashley’s behalf
• Uses Kartra and GoHighLevel to keep business and client operations moving
• Tracks assignments until every step is complete
• Brings solutions instead of simply reporting problems

WHAT WINNING LOOKS LIKE

You are succeeding in this role when:

• Urgent assignments are acknowledged and acted on immediately during working hours
• Ashley does not have to ask multiple times for an update
• Assignments that can reasonably be completed today are completed today
• Calendar conflicts are caught before they become emergencies
• High-priority opportunities do not sit unanswered
• Client, legal, vendor, and business requests receive timely follow-up
• Kartra and GoHighLevel records, workflows, campaigns, contacts, and tasks remain accurate and current
• Travel plans are complete, accurate, and ready for approval
• Outstanding assignments are tracked until they are fully resolved
• Ashley receives concise updates, recommendations, and clear next steps
• Routine decisions are handled independently within established authority
• Systems continue functioning without constant CEO involvement
• Ashley feels that a significant administrative and operational weight has been removed

YOUR FIRST 14 DAYS

During your first two weeks, you will be expected to:

• Learn Ashley’s communication style, priorities, calendar, and businesses
• Understand what is urgent, what can be delegated, and what must be escalated
• Demonstrate hands-on proficiency in both Kartra and GoHighLevel
• Learn the team’s trackers, communication channels, programs, and workflows
• Begin organizing Ashley’s calendar, inbox, follow-ups, and open assignments
• Establish a reliable system for tracking tasks through completion
• Identify missed deadlines, stalled conversations, and operational gaps
• Demonstrate fast response times and dependable follow-through
• Bring at least one practical recommendation for improving an existing process

CORE RESPONSIBILITIES

EXECUTIVE CALENDAR AND INBOX MANAGEMENT

• Manage a complex calendar involving clients, attorneys, partners, speaking engagements, internal meetings, travel, and personal obligations
• Schedule and reschedule meetings quickly while accounting for priorities, time zones, preparation time, travel, and calendar buffers
• Identify conflicts and propose solutions before involving Ashley
• Monitor and organize Ashley’s inbox
• Prioritize urgent, revenue-generating, client-sensitive, legal, and relationship-sensitive messages
• Draft professional correspondence in Ashley’s voice
• Follow up on unanswered messages until the matter is resolved
• Protect Ashley from unnecessary meetings, interruptions, and overbooking

URGENT EXECUTIVE SUPPORT

• Respond immediately to time-sensitive assignments during scheduled hours
• Begin working without unnecessary delay
• Communicate when an assignment will be completed
• Research missing information independently
• Present recommendations and solutions—not just questions or problems
• Escalate legal, financial, contractual, client, or reputational risks appropriately
• Adjust priorities quickly without losing track of previously assigned work
• Raise concerns before a deadline is missed

KARTRA AND GOHIGHLEVEL ADMINISTRATION

• Work confidently and independently inside both Kartra and GoHighLevel
• Maintain contacts, tags, custom fields, pipelines, calendars, campaigns, automations, and customer records
• Support lead capture, follow-up, scheduling, client communication, and program workflows
• Troubleshoot routine platform issues
• Review records for accuracy and correct errors promptly
• Monitor automations and identify when a workflow is not functioning properly
• Document platform processes so they can be repeated consistently

Candidates must be able to explain exactly what they have personally built, managed, automated, or troubleshot in both platforms. Familiarity without hands-on experience is not sufficient.

TRAVEL AND PERSONAL LOGISTICS

• Research and coordinate domestic and international travel
• Present actual flight and hotel options with prices, schedules, cancellation terms, transportation, and entry requirements
• Prepare complete, easy-to-follow itineraries
• Coordinate speaking engagements, conferences, meals, meetings, and personal or family logistics when assigned
• Build appropriate travel buffers and contingency options
• Contact airlines, hotels, transportation companies, vendors, banks, and service providers on Ashley’s behalf

CLIENT AND EXECUTIVE COMMUNICATION

• Communicate professionally with clients, attorneys, sponsors, prospects, vendors, executives, and partners
• Make and receive telephone calls to and from the United States
• Represent Ashley with warmth, confidence, discretion, and authority
• Resolve routine requests independently
• Protect important relationships through timely and thoughtful communication
• Keep Ashley informed without overwhelming her with unnecessary details

LEGAL AND BUSINESS ADMINISTRATION

• Assist with confidential legal and business records
• Track deadlines, client requests, invoices, documents, and administrative requirements
• Coordinate with attorneys, vendors, banks, and other service providers
• Organize legal, client, and business files
• Maintain complete and accurate records
• Follow through until every required administrative step is completed

SALES, SPONSORSHIP, AND OUTREACH SUPPORT

• Maintain accurate sponsorship, speaking, partnership, and prospect trackers
• Research decision-makers, contact information, events, podcasts, and business opportunities
• Draft personalized outreach and follow-up communications
• Update CRM records promptly
• Follow up consistently when contacts do not respond
• Schedule calls without losing control of Ashley’s calendar
• Ensure valuable opportunities do not quietly disappear

CONTENT AND PROGRAM OPERATIONS

• Organize content calendars, transcripts, applications, assignments, and recurring deliverables
• Track coaching-program homework, client submissions, and outstanding work
• Maintain accurate program and community records
• Prepare concise progress reports
• Document recurring procedures
• Improve systems so work can continue without constant executive intervention

THE STANDARD: SPEED WITH ACCURACY

This is a high-speed environment.

During scheduled hours, you must be reachable, responsive, and prepared to act. When an urgent request arrives, you should acknowledge it immediately, begin determining the next steps, and communicate when the work will be completed.

Fast does not mean careless. It means you know how to:

• Identify what matters most
• Start without unnecessary delay
• Ask focused questions
• Research independently
• Make reasonable decisions
• Produce accurate work
• Communicate progress
• Finish what you start
• Close the loop without being reminded

If something can reasonably be completed today, it should not take several days.

REQUIRED QUALIFICATIONS

• AI proficiency is required. Candidates must be able to use AI tools effectively in their day-to-day work, verify outputs for accuracy, protect confidential company and client information, and explain a practical example of using AI to improve work quality or efficiency.
• At least three years of experience supporting a CEO, founder, attorney, entrepreneur, or senior executive
• Hands-on professional experience with Kartra
• Hands-on professional experience with GoHighLevel
• Demonstrated ownership of executive calendars, inboxes, travel, communication, and follow-up
• Excellent written and spoken English
• Strong critical-thinking and problem-solving skills
• Fast, dependable, and professional communication
• Excellent organization and attention to detail
• Sound judgment and the ability to protect confidential information
• Ability to work independently without constant supervision
• Availability to work 40 hours per week during U.S. business hours
• Occasional availability during evenings or weekends for launches, events, or urgent projects
• Reliable high-speed internet and a dependable backup internet or power option
• Dependable computer, headset, and quiet private workspace
• Ability to make and receive U.S. telephone calls
• Willingness to complete professional reference and background checks

ADDITIONAL TECHNOLOGY EXPERIENCE

Experience with several of the following is strongly preferred:

• Google Workspace
• HubSpot
• Apollo
• Skool
• Substack
• Calendly
• Slack
• Zoom
• ---------- , Asana, ClickUp, or similar project-management platforms
• Loom
• Canva
• QuickBooks
• Zapier, Make, or similar automation platforms

You do not need experience with every preferred platform. However, Kartra and GoHighLevel are required, and you must be prepared to demonstrate your proficiency during the interview or assessment process.

THIS ROLE IS FOR YOU IF YOU

• Naturally operate with speed and urgency
• Thrive in fast-moving environments where priorities change
• Respond quickly and communicate proactively
• Take complete ownership of assignments
• Anticipate what an executive will need next
• Know when to act independently and when to escalate
• Make sound decisions without repeatedly asking the CEO what to do
• Communicate professionally with senior-level contacts
• Pay attention to details while meeting tight deadlines
• Keep following up until the matter is resolved
• Want to become a long-term operational partner rather than remain a task-based assistant

THIS ROLE IS NOT FOR YOU IF YOU

• Need repeated reminders before completing assignments
• Allow urgent messages to sit unanswered during scheduled hours
• Frequently say, “I was waiting for you to tell me what to do”
• Struggle when priorities change
• Require detailed instructions for every step
• Move slowly because you are trying to make every assignment perfect
• Complete only part of an assignment without determining what else is needed
• Are uncomfortable making telephone calls or speaking on an executive’s behalf
• Are balancing another full-time position or multiple competing clients
• Cannot consistently work U.S. business hours
• Need to learn Kartra or GoHighLevel from the beginning
• List software as a skill but cannot explain what you personally managed or built

HOURS AND COMPENSATION

• Full-time independent contractor
• 40 hours per week, Monday–Friday during U.S. business hours
• Occasional evenings and weekends during launches, events, travel, or urgent business periods
• $1,500 USD per month plus performance bonuses
• Selected finalists will complete a one-week paid trial at $250
• International candidates are welcome to apply

HOW TO APPLY — WRITTEN INTERVIEW REQUIRED

Submit your resume and complete the written application:

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Your application must include specific examples showing:

• How quickly you respond to urgent executive requests
• What you have personally managed, built, automated, or troubleshot in Kartra
• What you have personally managed, built, automated, or troubleshot in GoHighLevel
• How you have managed complex executive calendars and travel
• How you independently solved a business or executive-support problem
• How you followed up until an assignment was fully completed
• Your availability to work U.S. business hours
• Your experience communicating with clients, executives, attorneys, or other senior stakeholders

Generic responses will not be enough. Candidates may be asked to complete a practical Kartra and GoHighLevel assessment.

Because responsiveness is central to this position, the speed, completeness, and accuracy of your communication throughout the hiring process will be considered part of the evaluation.

We expect excellence. We value people who move quickly, communicate clearly, exercise sound judgment, and finish what they start.

If you are ready to become the trusted right hand Ashley cannot imagine running the business without, apply now.

Speak Your Way To Cash® provides equal employment opportunities to qualified applicants regardless of location, race, color, religion, sex, national origin, age, disability, or any other protected status.