Trusty Oak vs. Upwork
A global freelance marketplace versus a managed staffing service. Here's an honest look at how they compare so you can choose the right fit for your business.
A quick overview
Upwork and Trusty Oak both help you find professional support, but they work in fundamentally different ways. Upwork is a DIY freelance marketplace where you post jobs, review proposals, interview candidates, and manage freelancers yourself. Trusty Oak is a managed service that personally matches you with vetted, 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
Lindsey H. Kentucky 
Cheryl L. Ohio 
Tatum C. Ohio 
Kasi B. Virginia Head-to-head comparison
Trusty Oak vs. Upwork
Trusty Oak leads in 7 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 need a very specific or niche skill set for a one-off project
- You're comfortable screening, interviewing, and managing freelancers yourself
- You want access to a large global talent pool and don't mind variable quality
- You prefer to pay per project or per hour rather than a monthly retainer
- You have the time to manage multiple freelancer relationships
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'd rather be matched with vetted talent than spend hours screening candidates
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 managed service can give you back the hours you'd spend hiring and managing freelancers on your own.