Hello! Who are you and what business did you start?
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 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.
Our leadership team at a company retreat last Spring
What's your backstory and how did you come up with the idea?
Back in 2009, 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.
Describe the process of starting and launching the business.
After our initial founding almost by accident, and with steady growth coming out of referrals we realised -- OK this is real -- we’d better figure out where we are going and what we want it to look like.
Even in those early days around mid-2012, we knew that the pressure for “extreme growth” would be counter to the type of company we wanted to build. We avoided taking any funding even though we were approached by multiple investors – and have bootstrapped since day one.
One of the most pivotal decisions we made at the end of 2012 made bootstrapping possible and laid the foundation for the business we are today. One of our early clients was John Warrillow, author of Built to Sell and *The Automatic Customer. *He generously agreed to be an advisor, and suggested that we bill customers in advance on a recurring basis.
Before that, during our first year, we would invoice clients at the end of each month for 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. That’s how the subscription aspect of our business started and has become the underpinning of our business model.
The shift to billing customers in advance on a subscription model, not only made us cash flow positive but set the scene for long term relationships with our clients rather than short one off projects. These long term relationships were a win-win both for clients who wanted consistent staff and our team who wanted ongoing work. It gave the company the consistency we needed to build a strong foundation and develop a strong culture.
Instead of focusing on creating hype around our offering with no solid legs to stand on, we poured ourselves into building that strong foundation, knowing that if we continued to offer a service that was better than the rest, focused on premium quality and unique personal relationships (as any people business should be) the growth would happen based on continuing reputation and referral. And it has!
Since launch, what has worked to attract and retain customers?
We’ve focused all of our energy on building a premium brand and providing outstanding services for our clients on a consistent basis. Like I mentioned above, the result is that the majority of our growth has come from referrals–our clients referring their friends and colleagues, and from existing clients growing their business successfully with our help, and then needed more team members.
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 determined that we would only hire team members that have considerable experience in their area of specialty, at least 7+ years and usually 10-15, even though it made it much harder to find team members.
But even then we made the mistake of hiring only for skills, which led us to make some hires that failed spectacularly before we realised the importance of culture fit and mastered the right mix in our recruiting.
We’ve also built and installed 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.
How are you doing today and what does the future look like?
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 episodeof 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.
(Boldly HQ and our designated “Chief of Happiness” Simha.)
Through starting the business, have you learned anything particularly helpful or advantageous?
As a startup CEO, at the beginning, my tendency was to push through obstacles to achieve goals no matter what. And, to be honest, I can attribute a great deal of our success to building a culture that values not giving up.
That said, sometimes goals get in the way, and the best course of action may be to change or abandon them. Goals can become toxic. The challenge, of course, is identifying when to abandon (or change) a goal, and when to press on. As a serial presser-on, I’ve learned to identify toxic goals by pressing the brakes a bit, identifying priorities when goals conflict, and staying mindful about why the goal was important in the first place. I write about that internal conflict pretty extensively in this article. (Note: Boldly was called Worldwide101 when this article was written.)
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!
When we started we didn’t have a clear vision for “who” our ideal customer was. As the years have gone by, we’ve become very clear about the kind of client we want to work with -- leaders who know how to collaborate, who are looking for the kind of quality of service that we offer, and recognize its value.
What platform/tools do you use for your business?
We’re 100% remote so we couldn’t function without tools like Slack, Zoom, Google Docs (we use the entire Google Suite across our whole team).
Today’s online platforms have made it so easy to interact seamlessly online, we don’t feel like being a 100% remote team has inhibited our productivity in the least, in fact, quite the opposite.
What have been the most influential books, podcasts, or other resources?
I read and reread Raising the Bar: Integrity and Passion in Life and Business: The Story of Clif Bar Inc. by Gary Erickson.
It’s an account of how to do company culture really well, how to inspire a team towards a common goal, and most of all — how to live a life worth living!
I love how Gary’s positive attitude influenced his decision making and how inclusive and genuine his communications were. I also loved how he wasn’t afraid to roll up his sleeves and get to work to keep driving the company’s efforts.
I would recommend this book to any entrepreneur and business owner who wants to make a difference in the world in a genuine and caring way. Ultimately it’s not all about profits. People matter too — a whole lot.
Advice for other entrepreneurs who want to get started or are just starting out?
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.
Are you looking to hire for certain positions right now?
Yes! We’re constantly hiring to support our growth. Right now, we’re seeking professionals with 7+ years of experience in:
- Executive Assistance
- Marketing and Social Media
- Project Management
- Paralegal assistance
All of our US positions are W-2 employed positions and start at part-time. If you really want to know what it’s like to Boldly, check out our Glassdoor reviews (where we’ve managed to maintain a 5 star rating we’re very proud of) and learn more about the values we strive to hold.
Where can we go to learn more?
If you have any questions or comments, drop a comment below!
Discover the best strategies of successful business owners
Join our newsletter and receive our handcrafted recap with the best insights shared by founders in Starter Story each week.
Useful, convenient, and free:
Are you ready to boost your revenue?
Using Klaviyo will open up a massive, untapped sales channel and bring you closer to your customers!
Level up your email marketing with Klaviyo!