Feeling overwhelmed with admin work? Struggling to keep up with daily tasks? A virtual assistant (VA) can help you save time and focus on what matters most. But where should you hire one? We’ll be spotlighting Upwork and Wing Assistant today.
Upwork.com is one of the most popular freelance sites, connecting businesses with independent professionals worldwide. Whether you need help with admin, marketing, or customer service, Upwork gives you access to skilled workers who can get the job done. However, hiring through Upwork freelancing takes time, as you need to screen, interview, and manage your VA yourself.
This is where Wing Assistant shines. Unlike Upwork, Wing provides fully managed VA services, taking care of recruitment, training, and support. In this guide, we’ll compare Upwork and Wing Assistant to help you choose the right platform for your needs.
What is Upwork?
Upwork is a leading freelance website where businesses can hire freelancers for different tasks. It was created in 2015 after freelance platforms Elance-Odesk merged. Today, it's one of the largest platforms for remote jobs.
How Upwork Works
- Job Posting: Businesses create detailed listings describing their projects, including the scope of work, required skills, deadlines, and budget expectations. This helps attract the most suitable freelancers.
- Freelancer Bidding: Freelancers on Upwork browse available jobs and submit customized proposals. These proposals typically highlight their relevant experience, rates, and how they plan to approach the project.
- Hiring & Payment: Businesses review freelancer profiles, assess proposals, and conduct interviews to choose the best fit. Once hired, payments are processed securely through Upwork’s escrow system, ensuring freelancers get paid only when milestones are met or work is approved.
Key Features of Upwork
- Large Talent Pool: Upwork offers access to a vast range of freelancers skilled in various fields such as graphic design, writing, software development, web developers, and marketing.
- Flexible Hiring: Businesses can hire freelancers for short-term gigs, ongoing hourly work, or fixed-price projects, giving flexibility based on interests and project needs.
- Secure Payments: Upwork’s escrow system ensures freelancers are paid money only when the client is satisfied with the work, providing peace of mind for both parties.
- Self-Managed: While Upwork offers support tools, businesses are responsible for screening, interviewing, training, and managing their freelancers.
Upwork is great for short-term projects but requires hands-on management.
What is Wing Assistant?
Wing Assistant is a managed VA service that helps businesses delegate tasks easily. Unlike Upwork, it provides pre-vetted professionals and handles hiring, training, and management for you.
How Wing Assistant Works
- Custom Matching: Wing analyzes your business needs and assigns a VA who fits your specific requirements. This ensures your assistant has the right skills and experience to support your operations effectively.
- Ongoing Support: Each Wing client is assigned a dedicated account manager who monitors performance, handles concerns, and ensures seamless communication between you and your VA.
- Managed Service: Wing eliminates the need for you to post jobs, interview candidates, or train new hires — everything is handled for you.
Key Features of Wing Assistant
- Fully Managed VAs: Wing VAs are pre-trained and equipped with the necessary skills to handle common business tasks like scheduling, customer support, research, and more.
- Dedicated Support: Each Wing client gets a dedicated manager to provide ongoing support, address concerns, and ensure their VA is meeting expectations.
- Fixed Pricing: Wing operates on a simple, flat monthly rate with no hidden fees, giving businesses cost certainty and predictable expenses.
- Scalable: As your business grows, Wing allows you to easily increase or decrease the level of support based on your changing needs.
Wing is perfect for businesses needing long-term, reliable support without the hiring hassle.
Upwork vs. Wing: A Side-by-Side Comparison
Choosing the right platform for hiring a virtual assistant depends on your needs, budget, and desired level of involvement. Upwork offers direct freelancer hiring, giving you full control, but requires more effort.
Wing Assistant, on the other hand, provides a fully managed service, handling recruitment, training, and support for you. Below is a detailed comparison to help you decide which platform suits your business best.
Pros and Cons of Each Platform
Choosing between Upwork and Wing Assistant depends on your business needs, budget, and preferred management style. Upwork offers flexibility and access to freelancers worldwide, while Wing Assistant provides a fully managed VA service for a hands-off experience. Below is a detailed breakdown of each platform's pros and cons to help you decide.
Upwork
✅ Pros:
- Flexible Hiring Options: Upwork allows you to hire freelancers for short-term tasks, ongoing projects, or one-off assignments. This flexibility is ideal for businesses with fluctuating workloads or occasional project needs.
- Large Talent Pool: With thousands of freelancers worldwide, Upwork offers professionals with expertise in various fields, from graphic design to data entry, giving you plenty of choices.
- Budget Control: Businesses can set budgets, compare rates, and negotiate with freelancers to find the best match for their project.
❗ Cons:
- Time-Consuming Process: Finding the right freelancer can be challenging. You’ll need to post job listings, review applications, conduct interviews, and assess skills before making a hire.
- Lack of Quality Control: While Upwork offers reviews and ratings, there’s no guarantee of consistent quality. You’ll need to actively monitor work and provide feedback.
- Freelancer Availability Issues: Many freelancers on Upwork manage multiple clients, which may lead to delays or limited availability during peak periods.
Wing Assistant
✅ Pros:
- Fully Managed Service: Wing handles the entire process — from recruitment and onboarding to training and supervision — ensuring you get a ready-to-go assistant without the hassle.
- Consistent Support: Wing assigns dedicated supervisors to oversee your assistant’s performance, ensuring tasks are completed efficiently and to your standards.
- Transparent Pricing: With fixed rates and no surprise fees, businesses can budget more effectively without worrying about fluctuating costs.
❗ Cons:
- Higher Initial Investment: While Wing’s managed service saves time, it often comes at a higher starting cost compared to hiring individual freelancers on Upwork.
- Limited Hiring Control: Since Wing handles recruitment and training, you won’t have direct control over choosing your assistant, which may be a concern for businesses with specific hiring preferences.
Why Wing is a Better Choice for Long-Term VA Needs
For businesses needing ongoing virtual assistance, Wing Assistant offers a seamless, fully managed solution that eliminates the stress of hiring and supervising freelancers. In contrast to Upwork, where companies must find, interview, and train VAs repeatedly.
Here is why Wing is a better choice for long-term VA needs
- Managed Hiring and Training:
- With Wing Assistant, you don’t need to search for, interview, or train virtual assistants yourself. Wing handles these steps for you, saving you time and effort.
- Consistent and Reliable Support:
- Wing assigns you a dedicated assistant who learns your processes and becomes familiar with your business. This reduces the risk of frequent turnover and the disruptions it causes.
- Skilled Professionals Ready to Work:
- Each Wing assistant is pre-screened and trained before being assigned to your business. This means they can start working right away without needing extensive guidance.
- Flexible Support as Your Business Grows:
- If you need more help during busy seasons or want to reduce support during slower periods, Wing allows you to adjust your service without having to find new assistants.
- Reduced Management Workload:
- Since Wing oversees your assistant’s performance and ensures they stay on track, you won’t need to spend extra time supervising their work.
Who Should Use Upwork?
Upwork is best for businesses and professionals who need short-term help or specialized skills for a project.
Ideal for:
- ✅ Businesses needing short-term or project-based help
- ✅Companies seeking specialized skills in areas like graphic design, web development, or content writing
- ✅ Teams that prefer direct control over hiring and task management
Key Benefits:
- Freelancers work independently, so you’ll need to monitor progress, provide feedback, and ensure quality.
- Many freelancers juggle multiple clients, which may lead to delays or limited commitment.
Best For:
- Businesses with the time and resources to manage recruitment, training, and supervision.
- Companies that require temporary or one-off assistance with full control over the hiring process.
Who Should Use Wing Assistant?
Wing Assistant is ideal for businesses looking for long-term, dedicated support without the time-consuming effort of recruiting and managing remote workers.
Ideal for:
- ✅ Businesses seeking long-term, dedicated support
- ✅Companies needing ongoing help with admin, marketing, customer service, or operations
- ✅ Teams that prefer a turnkey solution with minimal hiring effort
Key Benefits:
- We can easily scale from one VA to an entire team, adapting to your business’s changing needs.
- Professionally trained assistants from Wing are ready to start without delay.
- Your dedicated account manager will oversee performance, manage training, and ensure tasks are handled efficiently.
Best For:
- Businesses wanting consistent, reliable support without the hassle of constant hiring and supervision.
- Companies that value structure, quality control, and reduced turnover.
Conclusion: Which Platform is Right for You?
Both Upwork and Wing Assistant offer great solutions for hiring virtual assistants, but the right choice depends on your business needs. If you require short-term assistance or have a one-time project, Upwork allows you to hire freelancers with specialized skills. However, hiring through Upwork requires time, effort, and ongoing management to receive quality results.
For businesses looking for consistent, long-term virtual assistance, Wing Assistant provides a fully managed solution that eliminates the stress of recruitment, training, and oversight. Wing’s dedicated support, scalability, and hassle-free service make it the ideal choice for companies that need ongoing administrative, customer service, or operational support.
If your priority is flexibility and direct freelancer management, Upwork freelancing may be a suitable option. But if you want a turnkey, hands-off approach with a dedicated VA who grows with your business, Wing Assistant is the better choice.
Ready to streamline your business with a dedicated virtual assistant?
Explore Wing’s services or schedule a free consultation today!
Nick Saraev is a writer & entrepreneur who pivoted from a path in medicine to forge a series of successful digital media businesses. He’s been featured in Popular Mechanics, Apple News, & Bloomberg, and is an Amazon Kindle best-seller.
