Excecutive Level VA/Automation Specialist

Executive Virtual Assistant | AI & Automation Specialist
Location: Remote (Philippines)
Company: Coaching Company/Public Speaker and Figure
About Us
MaryAnne Gillespie is a high-performance coaching and consulting company CEO helping real estate professionals across North America build stronger businesses through better systems, accountability, leadership, and execution.
Founded by Mary-Anne Gillespie—business strategist, keynote speaker, Ironman athlete, and one of Canada's leading real estate coaches—we work with ambitious agents, teams, and brokerages who are serious about growth.
Our company is expanding rapidly through coaching programs, digital education, live events, AI-powered systems, and consulting. We're looking for an exceptional Virtual Assistant who wants to grow with us for the long term.

This Is NOT a Typical VA Position
We're not looking for someone to simply complete tasks.
We're looking for someone who wants to become an indispensable part of our company.
You will work directly with the CEO, helping keep operations organized, systems efficient, projects moving, and clients receiving an exceptional experience.

This is a fast-paced environment where initiative, communication, and problem-solving are valued every single day.
Exclusive Employment

This is a full-time, long-term position.

We are looking for someone who is committed to growing with Red Apple Coaching not someone managing multiple clients or working through an agency. Our compensation will grow as you grow into the position as well.

If selected, this role will become your exclusive full-time position.
We believe that building an exceptional company requires a dedicated team, and we're committed to investing in someone who wants to build a career with us for years to come.

Your Responsibilities

Operations & Administration
Manage client onboarding from signed agreement to first coaching session
Coordinate calendars, appointments, and scheduling
Maintain and improve Standard Operating Procedures (SOPs)
Keep projects organized and moving inside Asana
Ensure nothing falls through the cracks
Support live events, launches, and coaching programs
Help create efficient systems that save time
Automation & Technology
You'll continually look for ways to improve how we operate.
Responsibilities include:
Building and maintaining Zapier automations
Connecting software platforms to eliminate manual work
Managing Go High Level workflows
Maintaining CRM accuracy
Researching and implementing new AI tools
Recommending better systems and more efficient workflows
Platform Management

You should already have experience with most of these platforms:
Go High Level
Kajabi
Zapier
Mailchimp
Skool
WordPress
Stripe
PayPal
Calendly
Canva
Meta Business Suite
Google Workspace
Asana
ChatGPT
Claude

Bonus experience:
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Airtable
Notion
n8n
Cursor
Descript
ElevenLabs

Content Support
Schedule social media content
Upload blogs, guides, and digital resources
Build landing pages
Assist with email marketing campaigns
Organize digital assets
Repurpose existing content into multiple formats

You won't be responsible for creating marketing strategy—you'll help execute it with excellence.

We're Looking For Someone Who...
Thinks before being told.
Takes ownership.
Notices problems and brings solutions.
Loves organization.
Enjoys learning AI and new technology.
Communicates proactively.
Is extremely reliable.
Has outstanding attention to detail.
Can prioritize without constant direction.
Wants to build a long-term career.

This Position Is NOT Right For You If...
You currently work with multiple clients and want to continue doing so.
You need constant supervision.
You wait to be told every step.
You miss deadlines.
You disappear when things become busy.
You are still learning the software listed above.
You are looking for short-term freelance work.

Position Details
Employment Type: Full-Time
Schedule: Monday to Friday *Sunday to Thursday also possible EST
Required Overlap: Minimum availability between 9:00 a.m. and 2:00 p.m. Eastern Time
Location: Remote (Philippines)
Start Date: Immediate
Compensation: Competitive and based on experience, technical ability, and demonstrated performance.

How to Apply
Please email ---------- with the following:
A Loom video (maximum 3 minutes) walking us through the best automation you've built and what problem it solved.
Your résumé or LinkedIn profile.
A list of the software above and rate your experience with each from 1–10.
Tell us about one process you improved that saved significant time or money.
In one sentence, tell us why you're the right person for this role.
Applications without a Loom video will not be reviewed