Executive Assistants:
From Invisible
to Indispensable
Our Mastery Executive Assistant Program transforms Executive Assistants
into indispensable business partners — and future leaders.
The Problem
The EA career problem
no one is solving
Where you are now
Responsibilities grow, but perceived value declines
Your executive's involvement feels like surveillance, not support
No clear path forward — every promotion feels like a closed door
Workload whiplash: last-minute changes destroying your ability to plan
Wondering if there's more to your career than this
Where you Could Be
Recognized as a strategic business partner, not just support staff
A working rhythm with your executive that eliminates micromanagement
A clear 12-month roadmap to Chief of Staff or operations leadership
Frameworks that absorb chaos instead of amplifying it
The confidence and credentials to advocate for what you're worth
20%
of an executive's daily time can be reclaimed by a skilled EA (McKinsey & Company)
10–15%
increase in leadership team productivity from streamlined EA communication (Globaltize)
80%
of professionals say building soft skills is more important than ever amid AI adoption (Wiley / LinkedIn Learning)
40–60%
reduction in email triage time for EAs proficient in advanced communication frameworks (Oceans Talent)
TRUST IN OUR PROCESS
Built by a practitioner
for the real world
Grounded in Reality
The EA Mastery Program wasn't built from a textbook, HR theory, or abstract research. It was architected by a top-performing, working Executive Assistant and informed by the collective wisdom of high-performing EAs accross industries. This program is forged entirely from the real-world frustrations, breakthroughs, and hard-won lessons of people doing this high-stakes work every day.
Unlike generic administrative training that focuses strictly on tools and software tactics, this program tackles the inner game of the role - the psychological blueprints and tactical frameworks needed to navigate complex executive partnerships and accelerate your career.
The Program Framework
7 Modules Built Around What Actually Blocks You Not a skills catalogue. Each module addresses a specific barrier to recognition, career movement, and performing at the level you're already capable of — the structural gaps no employer training ever covers.
Something Concrete in Every Session Every lesson ends with a deliverable you apply within 48 hours. The measure isn't what you know when you finish. It's how differently you're operating.
Built by People Who've Done This Work Not L&D consultants. Practitioners who have operated at the highest levels of executive support — and know exactly what separates EAs who stay invisible from those who advance.
What You Will Master
Visibility & Impact: How to move from being viewed as a logistical coordinator to being recognized as a strategic partner.
Energy & Boundary Management: How to manage impossible workloads and protect your bandwidth without burning out.
The Executive Partnership: How to navigate, align with, and steady even the most challenging or fast-moving executive relationships.
Self-Advocacy: How to confidently champion your worth, ask for what you need, and advance your career without putting your professional relationships at risk.
"I finally understood why I kept feeling invisible - and more importantly, what to do about it. Within two weeks of Module 1, my executive proactively mentioned my work in a leadership meeting."
Sarah K.
Executive Assistant, Financial Services
"The section on managing up completely changed my relationship with my executive. We now have a weekly rhythm that took the chaos out of my week."
Marcus T.
Senior EA, Tech Startup
"I was doing two jobs with a coordinator title. Eight months after completing Level 1, I was promoted to Chief of Staff and doubled my salary."
Renée M
Former EA, now Chief of Staff
"I used to absorb every emotion in that office. The boundary-setting frameworks in Module 5 genuinely changed my wellbeing - and my career trajectory."
Jordan L.
Executive Business Partner
YOUR PATH FORWARD
Three steps to
transform your career
A clear, structured path from where you are now to where you deserve to be.
Audit.
Before you can fix the right things, you have to find them. We go past the surface-level symptoms to identify exactly where the gaps are — visibility, executive dynamics, workload, career direction — and why they're costing you.
Address.
Most training gives you insight. This gives you infrastructure. Each module ends with a framework, template, or system designed to operationalize the fix — so the solution lives in your workflow, not just your notes.
Apply.
The work doesn't stop when the course does. Every tool is designed to embed into your daily workflow, so you operate at a different level from day one. Recognised. Advancing. Clear on where you're going.
YOUR NEXT MOVE
Wherever you are,
there's a path forward
Stay in Touch
Not quite ready to enroll?
Stay connected and we'll send you resources, insights, and updates as the program grows.
Ready to invest in yourself
Ready to enroll in EA Mastery?
Join the EAs who are done waiting for their organization to invest in them — and are taking their careers into their own hands.
$997
Need employer approval? We can help with that.
WHY PROSPERUS
The career problem no one is solving
EA training exists — but almost all of it focuses on software tools and scheduling tactics. Very little addresses the career, influence, and visibility dimensions that actually determine whether an EA advances or stagnates. ProsperUs exists to fill that gap.
THE RESEARCH
Six EA career barriers. One program built around them.
The EA Mastery Program was built by a senior, working Executive Assistant — not from a textbook, HR theory, or abstract research. The curriculum is grounded in the real-world frustrations, breakthroughs, and hard-won lessons of someone doing this high-stakes work every day, informed by deep community insight into what makes the role hard and what separates the EAs who advance from those who stay stuck.
The course is built around the six EA career barriers that consistently surface as the most common, most emotionally resonant frustrations of working executive assistants. Each module pairs the barrier with a concrete solution framework and a deliverable students can apply within 48 hours of completing the lesson.
WHAT OTHER PROGRAMS OFFER
- Software tool tutorials (calendar, travel, expense)
- Generic productivity frameworks (GTD, time-blocking) not built for the EA reality
- Corporate etiquette and minute-taking
- Skills you mastered in year one of the role
WHAT THIS PROGRAM OFFERS
- How to make your impact visible without self-promotion
- How to manage up and train your executive to work with you
- Prioritization systems built for the always-on EA reality
- Communication that gets results without formal authority
- Frameworks for sustainable performance and setting boundaries
- A clear career roadmap to Chief of Staff and beyond
Feeling invisible and undervalued
The #1 frustration. Good work is invisible by default — and invisible work doesn't get promoted.
No clear career path
EAs are some of the most capable professionals in any organization, with some of the lowest promotion rates.
"Workload whiplash"
Last-minute changes, always-on culture, and the impossibility of planning ahead.
The relationship with the executive
Micromanagement, unclear expectations, and a cycle of eroded trust most EAs don't know how to break.
AI anxiety and role evolution
How to stay relevant and leverage new tools without compromising confidentiality or career security.
Ethical and emotional burden
The weight of confidential information, loyalty conflicts, and moral complexity that almost no course addresses.
THE COST OF WAITING
Every year you wait
costs more than the course
The EA who stays invisible stays underpaid. The EA who can't manage up stays stuck in chaos. The EA without a career roadmap watches others get promoted around them.
$12K+
Average annual salary gap between EAs with strategic skills vs. those without
3 yrs
Average time to first promotion for EAs without a structured career strategy
94%
of employees say they'd stay longer if their organization invested in their development
The EAs who advance aren't smarter.
They're better equipped.
This program gives you the frameworks, language, and confidence that high-performing EAs use — the ones who get promoted, get credited, and get paid what they're worth.
Need to get your employer to pay? Get the approval guide.
Your Guide
Meet the person
behind the program
Sherry Tholenaer
Chief of Staff · Champion Performance Systems Inc.
Sherry Tholenaer is a native Calgarian and a seasoned executive assistant and Chief of Staff with 25 years of experience. She has worked as a fractional EA, recruited top-tier administrative talent, and coached EAs to excel in their roles.
Sherry also consults executives on optimizing their administrative infrastructure, ensuring seamless operations and strategic support. This program is built from her lived experience; not theory, not surveys, but 25 years of doing this work at the highest level.
25 years as a working Executive Assistant, Chief of Staff and COO
Fractional EA, talent recruiter, and EA coach
Consultant to executives on administrative infrastructure and operations
Native Calgarian with deep roots in the EA community
COMMON QUESTIONS
FAQ
Who is this program for?
Practicing EAs with 1–10 years of experience who are frustrated, burned out, underrecognized, or unsure how to grow. It's also ideal for new EAs who want to avoid the pitfalls that derail most people early in this role.
How is this different from other EA training?
Most EA courses teach tools and tactics — PowerPoint, calendar management, travel booking. This program teaches the inner game: how to be seen, how to navigate your executive relationship, how to protect your energy, and how to advocate for your career. It's a strategic accelerator, not a skills refresher.
How long does it take to complete?
The full program is approximately 8 hours of content across 6 modules and 24 lessons. Each lesson is roughly 20 minutes. You can move at your own pace — most students complete one module per week.
What do I actually walk away with?
Six concrete deliverables: a Personal Impact Record, an Executive Profile & Working Agreement, an EA Triage Matrix, a Communication Toolkit with 8 templates, a Personal Sustainability Plan, and a 12-Month Career Roadmap. These are tools you use at work, not just course certificates.
Can I get my employer to pay for this?
Yes — many students do. We have a dedicated page with a step-by-step guide and email templates for making the case to your manager or HR department.
What is Level 2?
Level 1 gives you the tools to excel and protect yourself in your current role. Level 2 is the executive skills track — where you learn to think, communicate, and operate like an executive. Module 6 of Level 1 introduces you to Level 2 and helps you know if you're ready.
Is there a refund policy?
Yes. If you complete the program and apply the frameworks and don't find value, we offer a full refund within 30 days of purchase. We stand behind the work.
Still have questions?
Empowering Executive Assistants to become indispensable business partners and future leaders.
Join ambitious EAs who are transforming their careers through strategic skill-building.