Building a $4 Million/year Remote Staffing Company

Learn how Sandra built her staffing service to $4m/year

1. Hello! Who are you and what is your business?

I’m Sandra Lewis, and I’m the Founder and CEO of Boldly.

Boldly is a subscription staffing company; a hiring model that allows businesses to get Fortune 500-trained, highly qualified, and hand-selected remote talent for just the hours they need each month.

Boldy is a remote-first, employee-focused company, offering its talented team the freedom to build their own schedules, work remotely, and be an integral part of amazing businesses for the long term while developing their own fulfilling careers. We are ranked as one of the top 50 best small workplaces in the United States, winners of the prestigious When Work Works award, and are Great Places to Work certified.

For me, there is no greater reward than to be able to offer hundreds of professionals seeking a flexible and remote career the opportunity to earn a living doing what they love and what they excel at.

Many of our team are mothers, fathers, military spouses, expats, etc. that have extensive experience in their field of specialty and that really need this lifestyle to thrive in their careers. I’m so proud to have created a win/win environment for our team and our clients.

We’re growing quickly and have more than 100 employees working across two continents, hundreds of high-profile clients, and a great internal infrastructure that is helping us facilitate that fast rate of growth.

This all started back in 2009 when my husband and I moved our family from the US to the UK. After working a very intense and consuming job for 22+ years in NYC, I wanted to find a way to continue to have a rewarding career without the stress of a commute, office politics and an all-around exhausting experience! At the time, freelancing was on the rise so I decided to give it a try.

I started helping entrepreneurs on a virtual basis with HR consultancy and project management and soon my clients started referring their friends for my services. At the same time, I noticed how hard it seemed to be for successful business owners and entrepreneurs to find and train skilled and reliable talent who would work on a flexible basis and without breaking the bank.

I also noticed that there seemed to be quite a lot of people like me – experienced professionals that had stepped back from a high powered job for whatever reason – motherhood, as military spouses, etc and were looking to redefine their career on their own terms.

When it reached the point where I could no longer support demand on my own I started assembling a team of like-minded professionals, a 100% remote company, with our team able to work flexibly but still apply their 10-15 years of corporate experience in a challenging role supporting businesses they were inspired to work with. Almost immediately the business took off with a life of its own.

I’d like to talk about how smart we were validating the concept, creating a business plan, performing viability studies etc. but the truth was that in those early days we were simply responding to demand through word of mouth and growth was completely organic.

It was only later once the business was established that we began to get clearer about strategy, the culture we wanted to create and how we saw the business developing.

2. How do you attract and retain your customers?

We’ve focused all of our energy on building a premium brand and providing outstanding services for our clients on a consistent basis. The result is that the majority of our growth has come from referrals — our clients referring their friends and colleagues.

Because Boldly provides a 100%-remote team to support C-level executives, founders, and business owners, the stakes of providing outstanding support are very high. For this reason, I realized early on that our growth was directly connected to our ability to build a truly outstanding team that can make a real difference — a team that our clients trust with their business!

We’ve learned a lot along the way, especially in our hiring techniques. And I’ll admit that we also failed spectacularly a few times before we mastered recruiting the right professionals.

3. What were your challenges and obstacles of growing your business?

I think there is still some stigma around working remotely, and some people are still somewhat condescending about the notion of “remote work”. My team still gets the famous “do you do anything all day?” question just because they work from their home office!

At Boldly we are on a mission to shatter that concept by providing excellence in the remote workspace and showing the world that working on a remote and flex-basis requires a great level of skill and professional aptitude if done well. In fact, we believe that remote work will only continue to rise as businesses start recognizing the immense benefits to employers, and the increase in productivity that this concept affords.

4. What has been helpful to help you to grow your business?

Premium subscription staffing has really only recently become possible with the convergence of two major movements:

The subscription economy has changed consumer expectations. Innovators like Amazon Prime, Uber, Salesforce and Box have transformed transportation, software, cloud storage, product delivery etc. Now business owners want similar convenience in every area of their business.

In parallel, the remote work revolution has changed employee expectations. Thousands of the world’s “A players”—including many with years of experience at Fortune 500 companies—are leaving the office behind in favor of remotely contributing to teams they’re passionate about. Case in point – we received 32,000 job applications last year.

In the old world, hiring someone is administratively burdensome, expensive and rigid. Recruiting is time-consuming and fraught with risk. Hiring means handling payroll, legal contracts, benefits, tax administration, nexus issues (for remote employment) and more. Work hours are typically either full or part time with little flexibility.

But now, with subscription staffing, business owners can onboard the brilliant remote staff they need to grow their business on a simple monthly subscription without the hiring.

5. What is your advice for those are starting productized services?

I’m a big believer in the idea that keeping a positive outlook is the #1 trait that makes any entrepreneur successful. There will be challenges, difficult times, unanswered questions that are unnerving, and so much more. So keeping positive is key to staying on course and finding the right solutions.

The other thing I would say is “sweat the details”! I am a big believer that it’s all the little things we do day in and day out that amount to a great product. So early on, remember to spend time on creating processes and figuring out how to present your brand. Of course, it’s going to evolve — but don’t underestimate the effect small details can have on your business, and their ability to undermine everything else if you don’t nail them.

And most importantly, be sure to keep your focus on delivering a genuinely outstanding service and experience for your clients — because the rest will just follow.

6. What are your plans for the future?

Our ability to recruit talented and skilled professionals has made the biggest difference for our business. I can’t say it enough – our team is amazing, and our reputation and the premium service that we offer is very dependent on how committed our team is to the success of our clients.

We are currently actively recruiting at a rate of six new professionals a month, and our ability to make these recruits is key to our growth. After learning a lot of hard lessons in hiring, I now interview candidates with 4 Attitudes in mind. I go into that in this episode of the Founder to CEO podcast. *(Note Boldly was still called Worldwide101 when this podcast was recorded.) *

So our big plans are just to continue to grow and excel at what we do! We want to raise awareness of the subscription staffing industry so that more businesses and executives understand the value of hiring a remote professional to support their business growth; no hiring, no interviewing, and no dealing with compliance or HR – just getting access to talented, experienced individuals you can utilize fractionally for the long term. It’s such a win-win.

7. Where can we learn more about you?

Check out – you can learn all about us and the movement we’re pioneering with subscription staffing. 
Find us on Twitter @WorkBoldly, or on LinkedIn and Facebook.

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