Finding Your Trusted Assistant: Virtual Assistant Team or Freelance Virtual Assistant?

Kelsey Opel
SquaredAway
Published in
6 min readJan 7, 2020

We’re in an age where remote work is the way of the future, and it’s how many companies are getting things done today. There’s a rise in the amount of outsourcing that is occurring, especially in the realm of administrative duties and day to day operations management. When considering the opportunity to take on a remote assistant/teammate, the choice between a virtual assistant team (company) and an individual virtual assistant has to be made.

Why Would I Work With An Assistant Team?

There are many cost-savings benefits. For starters, you’re not hiring another full or part-time person to your team; you don’t have to pay a full (or part) time salary, and you don’t have to pay for a benefits package. It’s a flat-rate that you’re aware of upfront. You also know what to expect from each monthly cycle, and can scale up or down as your company needs see fit.

If you’re nearing full time with your current assistant or another member of your team/company is needing help, you can seamlessly add another assistant to your team without needing to add a second full or part-time salaried individual. The best part of this is the original assistant can assist in training the incoming assistant. You can build your team on your timeline, and when you add a new teammate, you bring a whole new set of skills.

Vacation/Time Off

When you work with a trusted assistant from a company, you have guaranteed coverage for your assistant’s offline periods. The assistant you work with trains the covering teammate, ensuring they are entirely up to speed on all processes before the assistant goes offline for a vacation period. It generally feels like your assistant never took time off; you are supported, and your assistant takes time to reset and refresh, so when they come back, they’re ready to support you again fully.

When you choose to work with an assistant team, you have the company’s guarantee that you will have a designated assistant. Many virtual assistant agencies also have processes and systems in place that ensure a seamless transition to a temporary assistant if your assistant takes time off or needs to take parental leave. There will always be someone there for you; through vacation time, illness, and if the assistant resigns, there is another assistant ready to handle a seamless turnover and take on your tasks. The goal is that you, as the client, feel supported by your assistant and the team that is backing them up.

Vetted, Trained and Qualified

It’s daunting to find your trusted assistant, never-mind sorting through resumes, applications, and outreach attempts. Assistants that work with a team are vetted, qualified, and fully-trained by the company.

At Squared Away, there is a multi-step application process that each of our assistants must complete before moving onto the training phase. Not all applicants make it through the application process, and there are a small number of applicants who choose to remove themselves from the rigorous training process. We sort through every resume that is sent to us, we screen the candidates and get to know them on a personal level then we train them thoroughly to ensure the best possible outcome with your client-assistant partnership.

What Are The Downfalls Of An Assistant Team?

When you make a choice to work with an assistant team, you will likely be asked to sign a contract. This contract would be between the client and the assistant company.

As a client, why should I work within a contract? The contract protects you, as the client, legally. When you work with an assistant, to have a legal working relationship, there must be a contract in place. Contracts establish a plan and common ground between two entities. If your working relationship with an assistant were to go poorly and there were grounds for termination, you would legally be able to cut all ties with the person you are working with. They are essential for a business to safeguard its resources, and for a contractor to have legal grounds for payment.

Potential downsides of working with an assistant team also include set working hours and company-wide days off. Some freelancers do not set working hours, so they are available to the client 24/7/365. This can be a significant aspect of working with an assistant (having unlimited access to them), but it can also result in burnout for the freelancer. It can, in turn, result in delayed, botched, or incomplete tasks.

Why Would I Want To Work With A Freelancer?

As the client, looking to take on an assistant, you may want to look into hiring a freelancer if you’re going to be in total control of the screening, interviewing, and selection process. Working with a freelancer means you can work with and hire anyone you would like. You have total control of what your working relationship will look like (depending on what the freelancing assistant agrees to).

Additional positives of working with a freelancer are the possibility for the rate or payment to flex as needed (while we don’t recommend this, there is generally less of a regular payment structure involved).

Why Wouldn’t I Want To Work With A Freelancer?

If you choose to work with a freelancer, there are a few topics you should keep in mind. Working with a freelancer generally means you are working one-on-one with a single individual.

What happens if the freelancer becomes sick, needs to take a vacation, or choose to resign suddenly? These are great questions to ask when doing an initial screening of potential candidates for your virtual assistant needs.

Additional issues that may arise when working with a freelancer are the lack of formal training. Assistant companies generally have full training processes in place for each of their people, in addition to further training opportunities in specialized areas. There are set policies and procedures in place with companies, and you generally know exactly what the standard is for all work that is being completed.

If you opt for a freelancer, there is the possibility of an external third party completing the work without your knowledge; any NDA’s and contracts you have with the freelancer may be loosely held, and they may be delegated to subcontractors that you are entirely unaware of. With a company, if another teammate were to help with a simple task, you know there are systems, policies, and processes in place to ensure the work is being done in an accurate, efficient, and confidential manner, posing minimal, if any, risk to you. The same is not guaranteed with a freelancer.

How Many Clients?

A final consideration is the number of clients a freelancer has vs. a company. Many companies are upfront about the number of clients they set their assistants up with, such as 1 or 2 clients, resulting in a focus on maximizing your delegation abilities. Freelancers can take on as many clients as they feel comfortable with, which can be upwards of 5 or 6. If you choose to work with an assistant company, the focus is on building the client relationship instead of being seen as a paycheck or a number on a list.

Which Direction Should I Go?

Both virtual assistant firms and freelancers have their strengths. Companies will generally have more regulation, training, and processes in place. In contrast, freelancers will have more flexible schedules and be available to handle work at any time of day/on weekends/through holidays depending on their work schedules. Virtual assistant companies have a guarantee that you will always have an assistant, and they focus on helping you build your relationship with your trusted assistant through delegation processes.

Squared Away is comprised of military spouses who are your trusted assistants. We help CEOs, VCs, executives, and startup teams get their time back. US-based. #SquaredAwayLife #ChiefExecutiveAssistant

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Kelsey Opel
SquaredAway

Startup Operator // Snowboarder // Taco connoisseur. Follow along for my journey in operations and lessons learned in this territory.