Boldly: What’s It Really Like to Work from Home as a Virtual Assistant?

So many of you have told me you have an interest in becoming a virtual assistant but you would rather test out the waters working for someone else before going into business for yourself. That’s totally understandable! There’s a sense of security in having someone show you the ropes and best practices as opposed to trying to figure it all out on your own.

Boldly is a company offering remote virtual assistant jobs. Boldly is an award-winning executive assistant company that hires employees who want a long-term career. Boldly employs senior, experienced, and skilled professionals across a variety of disciplines like executive assistants, marketing, project management, customer service, and more. Positions at Boldly offer great flexibility and are considered remote work.

They are well-known in the industry and offer a pretty good wage to those just starting out. Today we are speaking with a virtual assistant who has been with the company for a few years about her experience. We’ll also be talking with a company rep about their application process.

Meet Shari Montgomery, Boldly Virtual Assistant

Why did you choose to work from home? 

After over 15 years of working as an administrative assistant in the corporate world, I had become dissatisfied and unfulfilled, and unsure of my next direction. In 2008, I had a network of friends who had caught the trend of working from home as consultants and entrepreneurs, and I realized that was where my heart was. I wrote about my story for We Are Virtual Assistants, which you can find here.

What made you apply to Boldly? 

I had been freelancing for several years, which was a great experience but it was challenging to retain a solid client base. I started looking for reputable agencies to partner with, and through FlexJobs, applied with Boldly who was advertising for work-from-home Executive Assistants.

How long have you been with the company? 

I started with Worldwide101, which is now Boldly, in February 2015.

How has this position allowed you to meet your personal needs/goals? 

Where do I start? Being able to rely on steady work with plenty of variety is a huge benefit, and I have learned a tremendous amount. Also, it allows me flexibility for other errands or side jobs, such as assisting my husband in his business, helping out an ailing parent get to medical appointments, or working part-time as a massage practitioner. Being able to live anywhere without being dependent on a specific location for a job, is the ultimate freedom that comes with being a Virtual Assistant. And whether it’s my home office, coffee shop, or a Mexican resort, as long as there’s Wifi I’m good.

What challenges do you face in this position? 

As with anyone working remotely, there are no IT support people sitting in the next cubicle for when the inevitable tech glitches occur. Luckily, one of the many advantages of working with Boldy is their amazing support team and the network of other VAs on the team that I can call upon to help. They also have a thorough vault of instructional videos to access anytime. Communication, and clearly understanding the needs and expectations of a variety of clients or coworkers can be at times challenging but easily overcome with the right approach of never assuming and asking plenty of questions. And of course, time zone differences! I once supported a client living in New Zealand which meant she was 16 hours ahead. We made it work though!

What’s your typical week like? 

I work part-time Monday to Friday, and currently, am online no later than 8 AM each morning. I review my email and Slack first thing to see what’s new or in need of immediate action that day, and then start my timer and work my hours for that morning. I’ll get up for a break here and there but put in a concentrated chunk of time. We get paid twice per month in US currency, with direct deposits to our bank account.

Boldly Application Process

The following questions have been answered by a representative of Boldly.

What’s the application process like? 

We have a five-step application process, including an online application, aptitude test, 2 video interviews, and background checks. We want to get to know you as a person, as well as your skills, to make sure the fit is mutually beneficial.

Are there any fees involved? 

No, there are absolutely no fees involved – ever!

How long do you keep resumes on file? 

We keep resumes on file for 3 years.

What timeframe can be expected from acceptance to the first paycheck? 

All of our VAs are paid monthly so on average it will take around 30 days from acceptance to the first paycheck, however, this can, of course, vary depending on how quickly the VA wants to ramp up and how many hours she has available. We don’t provide any “official” training however we “onboard” our team, which includes virtual assistant best practices, and getting used to virtual tools and online processes – and this takes 2 to 3 days.

Is this a good job for someone needing a flexible schedule and/or still working a full-time job outside of the home? 

Yes! All of our positions are part-time and work from home, so they are perfect for someone looking for a flexible schedule that fits their lifestyle. We completely understand the challenges of combining a career with family commitment, a large number of our VAs are parents or caring for elderly relatives. The key for us is that “flexible” must still equal being available during business hours – of course, not all day and we’ll work with you on “when” exactly you can be available for your clients – but this is not an evening or weekend job that you can do while also working in an office all week! Working with Boldly is a career just like any other – with the added advantages of flex, remote, and a supportive family-oriented environment. The other advantage is that a career with Boldly is fully portable, so if you are in a position where you need to move frequently (for example as a military spouse), you can take your career with you, without any downtime at all.

Can you give us an average hourly pay or average pay range? 

We pay our team between $18 and $20/hr depending on skills, seniority, and longevity with the company.

Any tips for applying? 

Give us as much information as possible! We know how hard it is to condense your life into a one-page CV, but if you have some experience outside of the traditional workforce that you think is relevant for the role then we want to hear about it! And take the time to review our website, and our company values – we are keen to onboard team members who share what we we are all about and who believe that the partnership will be mutually beneficial.

Are you ready to apply to Boldly? Click here.