Trusty Oak vs. Wing
Two managed assistant services with different models for talent, pricing, and flexibility. Here's an honest look at how they compare so you can choose the right fit for your business.
A quick overview
Wing and Trusty Oak both provide managed virtual assistant services, but they differ in talent sourcing, pricing structure, and how they scale. Wing offers dedicated assistants — primarily based in the Philippines — at flat monthly rates starting at $499/mo. Trusty Oak provides a flexible team of US-based EAs, Specialists, and Executives through a scalable monthly budget. Below is a side-by-side comparison to help you decide which model fits your needs.
Full-time assistants · Philippines-based · Flat monthly rate 
Flexible team · US-based · Scalable monthly budget Some of our US-based talent
Damaris C. Virginia 
Rachel S. Utah 
Lindsey L. Maryland 
Jill N. Virginia Head-to-head comparison
Trusty Oak vs. Wing
Trusty Oak leads in 4 of 9 categories. Want to see how it works for your business?
Book a Free Discovery CallWhich service fits you better?
Both are legitimate options. The right choice depends on what your business needs.
may be better if… - You want the lowest possible monthly cost for virtual assistant support
- You're comfortable working with internationally-based talent across time zones
- You need task-focused assistants for specific categories like sales, customer service, or social media
- You want a dedicated assistant available part-time or full-time on a fixed schedule
- You prefer a proprietary workspace app for managing tasks and communication
is the better fit if… - You need a flexible mix of administrative, specialist, and strategic support
- You want US-based professionals in your time zone
- You prefer to start with a smaller budget and scale as needed
- You value month-to-month flexibility after an initial commitment
- You need more than an EA, like content creation, CRM management, or operational strategy
- You want built-in oversight with weekly reporting and account management
- You care about working with talent that's fairly compensated and invested in your success
Why businesses choose Trusty Oak
Real people, not ticket queues
You'll work with the same small team of people who know your business, not bots or rotating support reps. When you need something, you talk to a real person who already has context.
Three levels of talent
Access EAs, Specialists, and Executives from one monthly budget. No need to hire separately for admin, creative, or strategic work.
Flexible monthly budget
Start at $1,000/mo and scale up or down as your needs change. No long-term contracts after your initial 3-month commitment.
US-based professionals
Every team member is a vetted, US-based professional. No timezone gaps, no cultural misalignment, no language barriers.
Talent-first pay model
The majority of your budget goes directly to the people doing the work. That means better talent, lower turnover, and professionals who are genuinely invested in your success.
Built-in oversight
Weekly reporting and dedicated account management keep everything running smoothly so you can focus on your business, not managing your assistant.
"Trusty Oak has been a game-changer for our business. The flexibility to access different levels of talent through one budget has saved us time and money compared to hiring in-house."
Sam Baker CEO, Baker Strategy Group Ready to see the difference?
Book a free discovery call to learn how Trusty Oak's flexible model can support your business, without the long-term commitment.