Startup Story: Boldly


Hey there,

Steve Jackson again,

Today, I am excited to share Boldly Story.

Boldly is a subscription staffing company which allow business to hire top rated employees on hourly basis whenever they need.

Without any further ado, let’s see whatSandra Lewis, Co-Founder at Boldly have to share with us.

Here we go:

Q1) Tell us about your startup – Boldly

(When and how did you start? How did the idea come up?)

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.

Q2) What are the real world problems that Boldly is solving?

(Why do you think that now is the perfect time for your startup to exist?)

Finding reliable, trustworthy, and competent help has always been one of the foremost challenges of running a successful business or project—and it’s even more relevant when using remote resources. Boldly’s team (W2 employees) of experienced, reliable, and vetted professionals provide businesses with the specialist support they need to grow – all on a flexible monthly subscription.

For us, this was the perfect time to pioneer a new era of subscription staffing. 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.

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.
Businesses get fast matching to talented, guaranteed staff without recruitment.

They pay a single monthly payment without the burden of payroll, contracts, and other legal issues. Most importantly, they get the flexibility and scalability to work with someone or multiple people on a fractional basis for the exact amount of time they need each month.

In this new world, shifting to subscription staffing isn’t just good for businesses. Unlike the rigidity of traditional employment, subscription staffing offers talented workers greater flexibility, the opportunity to work remotely, and the opportunity to work with a variety of interesting companies, leading to greater satisfaction, stimulation and ongoing learning.

Unlike the Gig Economy, which offers quick access to remote workers but exposes them to significant risk and leaves workers without any of the benefits and protections of employment, we take care of employment requirements, leaving a simple win-win for businesses and staff alike.

Q3) Brief about the Founding members

Boldly was born in early 2012, when founders Sandra Lewis, Matt Criticos and a group of experienced remote professionals began collaborating to offer business clients a well-rounded range of services.

With our commitment to quality and reliability, word of mouth spread and our client pool quickly began to grow beyond the scope of what we could support as individuals. Boldly took shape as we continued to add more and more professionals to the team who share the same values—friendly, skilled, responsible, “can do” support, grounded in quality.

As our clients were able to hand over more ongoing responsibilities and focus on the growth of their business, Boldly saw a shift in demand from short-term projects to long-term, ongoing monthly tasks, with team members working as an integral part of our clients’ businesses.

What became apparent in working closely with our first clients was that, while most tasks fell under “general admin support,” each business was unique, with very particular needs. To successfully provide our clients with the best solution, we needed to understand their business and provide a tailored approach to their specific requirements.

In listening to our clients’ pain points and concerns, we also noted that assigning a team member who would get the job done was very often only 40% of what mattered to them. The remaining 60% was in HOW the tasks would get done, and BY WHOM.

We all have our preferences in work style and the type of person we like to work with, and these preferences matter A LOT in building trust, and a long-term partnership.

In our first year of business, it also became apparent that small business owners very often need more than just admin support—that they often don’t have time to find someone to do their social media, create an email marketing campaign, or project manage the launch of their books.

Clients started asking us for more help, and we began to assemble an array of team members with the versatility required to support business owners with more complex and specialized skills.

Why should a client struggle to find a designer for a new brochure or a Web developer to create a new sales page? With a diverse skillset and constantly growing team, we’ve been able to assign team members for ongoing tasks as well as to support clients on an ad hoc basis when they have a particular need, or in cases where they suddenly need to scale up to respond to demand.

Boldly’s ability to provide highly personalized and tailored solutions and to match our clients with remote staff who have the skills, interest, and personality to support their business for the long term has been our greatest accomplishment. It has contributed to our rapid growth and our astonishingly high client and team retention rates.

Our vision hasn’t changed since day one; our unequivocal passion for excellence, quality, and care still drives our decision-making and is the foundation for how we’ve structured our business. If you share our values and need help, then we would love for you to experience what we are all about!

Q4) Is Boldly funded?

(If Yes, then how you succeeded in getting the funding. If No, how do you run the show?)

We bootstrapped our business from day one, and I’m so happy we did! A key aspect of what made that possible is choosing a recurring revenue model so that cash flow was always positive. We focus on providing a long term solution so that our churn is always at a minimum, and our clients pay us a monthly subscription fee for our services.

During our first year in business, we would invoice clients at the end of each month for the services they had consumed. As you can imagine, we had the problem that so many businesses have: some clients would pay late, leaving us unsure, month after month, if we’d be able to make payroll.

In year two, I began to understand that most of our customers not only loved us, but wanted us to thrive. That gave me the confidence to start asking new clients to pay us in advance of services rendered, with a satisfaction guarantee. I braced myself for the angry backlash, but it never came: not one client challenged the request. This is how subscription staffing came to be.

We also built a proprietary Dashboard, so that all of our payments and reporting can be handled seamlessly. It has revolutionized the way we interact with our clients, saving us time so we can concentrate on bigger things. It has also yielded incredibly valuable data about how we can better serve customers.

Q5) What is the biggest challenge that you face? And, how do you plan to overcome it?

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.

Q6) Top 3 marketing strategies that are working for you?

  • Referrals (first and foremost)
  • Content Marketing
  • Partnerships

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 we are a 100% remote company, and we provide a team to support c-level executives, founders and business owners, the stakes of providing outstanding support are very high. For this reason, early on, I realized that our growth was directly connected with 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. I write quite a bit about that in this Medium article.

Q7) What is your biggest achievement to date that you are proud of?

Pioneering a whole new industry – premium subscription staffing – took a lot of guts. Before we launched our new brand in 2018, we had labeled ourselves as a virtual assistant company, but that term never quite captured the depth of experience on our team or the premium service we offered our clients.

When I informed our team of 100+ staff members of our market evolution, I was initially discouraged by the most common reply: “Um, isn’t premium subscription staffing what we’ve been doing all along?” Eventually, though, I came to see that as a positive: we weren’t shifting to a new market as much as broadening our old one, so their reaction signaled that our new category description covered the work they have always done, as well as work they want to continue doing.

As we move forward, I hope that being able to source ridiculously talented remote staff on a monthly subscription — without having to hire them directly — will appeal to mainstream businesses who want more than a virtual assistant, or who were turned off by that phrase.

Q8) Where do you see your startup – Boldly heading in next one year?

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.

Q9) What is that one advice you’ll like to give to all the budding entrepreneurs out there?

As much as possible, I try to keep things simple. There are many complex issues that every entrepreneur is faced with, so I try to be mindful not to complicate things even more! To quote Richard Branson, “Complexity is your enemy. Any fool can make something complicated. It is very hard to make something simple.”

I’m a big believer in keeping a positive outlook as 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 affect 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.

Q10) Your favorite Quote

As one of our clients, who led his own company through a similar repositioning, told me: “These things usually go one of two ways. Either you let the fears and risks drive you mad or you let yourself get excited about the possibilities. On balance, I find the excitement buoys you past the fears.”

Boldly- Website

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Steve is a business analyst and researcher having experience of over 7 years in scaling up the businesses from Startups to Entreprises. He works for The Startup INC as a Senior Editor. Steve lives in Bristol, UK, with his wife & he likes traveling on weekends.

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