MASTERMIND PROGRAM ASSISTANT

We aren’t looking for a basic virtual assistant. We’re looking for a Client Accountability Operator who protects retention, enforces standards, and ensures no client slips through the cracks.

At Speak Your Way To Cash®, we’ve grown from zero to an Inc. 5000 company — and we’re just getting started. Our mission is to empower experts and entrepreneurs to turn their voices into revenue.

This role is not about “helping.”
It is about protecting revenue, enforcing follow-through, and keeping our 400+ clients moving.

You will be the operational heartbeat behind our Mastermind and Academy programs. If someone misses a payment, you call. If someone misses a call, you follow up. If engagement drops, you flag it. If a client wins, you capture it.

This is a performance role. Not a passive one.


WHAT YOU’LL DO

You will support the Director of Client Success, Mastermind Coach, and Academy Coach.

Daily Responsibilities
• Monitor missed payments and immediately call clients who fall behind.
• Send payment follow-up emails and document all communication in CRM.
• Track revenue submission forms and flag missing reports.
• Monitor engagement dashboards (Green/Yellow/Red).
• Flag 30+ day inactivity.
• Follow clients on social media and track major life or business updates.
• Alert leadership to major milestones, crises, or contract wins.
• Track missed Q&A or hot seat calls and reach out when clients miss both.
• Update CRM notes and automations.
• Track birthdays and personal milestones.

Weekly Responsibilities
• Update retention dashboards.
• Prepare Red/Yellow/Green client reports for Director review.
• Monitor WhatsApp inactivity and missed submissions.
• Follow up on testimonial opportunities (3–5 month mark).
• Support testimonial collection and coordination.
• Audit onboarding completion (forms, activation milestones).
• Track challenge participation and engagement levels.

Monthly Responsibilities
• Assist in renewal pipeline tracking.
• Compile client wins for internal Wins Report.
• Monitor onboarding completion rates.
• Prepare milestone tracking summaries.
• Support white-glove gift coordination (birthdays, bereavement, celebrations).


CRITICAL FUNCTION: PAYMENT & ACCOUNTABILITY CALLS

If a client misses payment:
• You call within 24 hours.
• You speak clearly, confidently, and professionally.
• You follow a structured script while remaining human.
• You document the outcome immediately.

You must have a strong, confident, polished phone voice. This is mandatory.


WHO THIS ROLE IS FOR

? You are confident on the phone and not afraid of difficult conversations.
? You speak clear, professional English with strong verbal communication skills.
? You have experience in client success, collections, or account management.
? You are organized and love dashboards, trackers, and systems.
? You follow up until something is resolved.
? You understand urgency and move fast.
? You are comfortable enforcing standards politely but firmly.
? You can work US time zone hours consistently.


WHO THIS ROLE ISN’T FOR

? You avoid confrontation.
? You dislike making phone calls.
? You need constant supervision.
? You struggle with follow-through.
? You get uncomfortable asking clients about payments.
? You are looking for a low-pressure job.

This role protects revenue. It requires backbone.


WHAT YOU BRING

• Proven experience in virtual assistance, client support, collections, or CRM management.
• Demonstrated track record of managing multiple clients or accounts simultaneously.
• Experience using CRMs and tracking systems.
• Strong written and spoken English.
• Bachelor’s degree preferred.
• Strategic + tactical thinking with clean execution.
• Strong phone presence with professional tone and confidence.


COMPENSATION & BENEFITS

• $800/month (Full-time negotiable).
• Performance-based bonuses possible based on retention and payment recovery.
• Direct impact at a high-growth Inc. 5000 company.
• Visibility, ownership, and growth opportunities into higher client success roles.


HOW TO APPLY

Email: ashley@ashleynicolekirkwood.com
Subject line: Program Assistant – Your Name

Include the following:
1. A written sample email to a client who is 14 days behind on payment.
2. A Loom video (3–5 minutes) explaining:
• Why you want this role
• Why you are confident making payment collection calls
• Why you are a strong fit for a high-performance environment

Applications without both requirements will not be reviewed.


This is not a content company.
This is a results company.

We show up on our clients’ worst day and their biggest contract day.

Apply now. Show us how you’ve done this before, what you’ve built, and how you’ll take this role to the next level.