Boldly Founder & CEO Sandra Lewis started Boldly more than a decade ago with the goal of creating a work environment that was supportive and caring and 100% remote. Today, Boldly has grown to more than 100 employees with a waitlist of clients.
How is Boldly different from other executive assistant or virtual assistant companies out there?
First, I want to talk about the culture — we have an amazing culture at Boldly and it comes back to having values that we honor and onboarding people that share those same values. Our culture is really special to me and it’s something that I’ve spent a lot of time thinking about when I very first started the company.
Our culture is all about care — we care about our team, we care about each other, we care about our clients. And that’s something that I’m really, really proud of.
And then on a practical level, our team is employed as W2 employees by us. Most other companies hire as 1099 and contractors. Being W2 means that we are able to offer our team PTO, whether they’re part-time or full-time. We have a 401k for retirement. We have a full-on benefits and many other things that obviously as 1099 contractors you might not get the benefit of having.
A lot of people don’t realize this, but Boldly is actually bootstrapped. Can you talk a little bit about how Boldly’s independence from investor funding influences our culture and our approach to growth?
The whole point of Boldly was to have work-life balance, so It would have defeated the purpose if we’d had people pressuring us to grow.
As soon as there’s funding, those people who fund a company want a return on their investment. And the quicker, the better. And I thought, you know, better to be slow but profitable — and focus on quality and on building great systems and on building a great culture.
I’ve spoken to so many founders who have received investments and that puts them under a lot of stress — it puts the whole team under a lot of stress to show results month after month and be pressured to grow at all costs.
Over the years, Boldly has grown a lot and we are continuing to grow. What do you see Boldly looking like in the future?
We’ve been so, so fortunate to have grown so much in the last decade. Back when we very first started, we were kind of like a unicorn — remote, flexible, what is that?
And a lot of people really didn’t put a lot of trust in who we were. And as the years have passed, we’ve built such a great team and our reputation has grown so much that we’ve been able to really sustain that growth. The future is about continuing that same steady growth.
I’ve never been about rushing because I find that it’s exhausting and you make a lot of mistakes. So for me, it’s always been, you know, steady like the tortoise and the hare.
I believe that remote work will continue to be the best thing that anyone has ever invented!
We get a lot of interest in our open positions. And many of the candidates possess the skills and experience we’re looking for but they don’t make it through the application process. Can you shed light on some of the things that Boldly is looking for that go beyond experience?
We say it’s 70 percent attitude and 30 percent skills — skills can be learned and the requirement is seven years of experience minimum. Most of our team have many, many more.
Experience is a given — you’ve applied, you’ve got the experience, now you have to show us that you’ve got the right attitude and that you share our values.
And that comes across throughout the process, from how people answer emails to the applications team, to how they come across in the interview, to whether they show up on time, to whether they are professional in answering the questions. All these little things really add up to the big picture.
You can see when you watch our team’s videos and our testimonials from clients how care is one of our core values and that our team really demonstrates. We always say, you know, when you apply, showcase that you care, and you can do that by making sure there’s no grammatical error, by making sure that, you know, you answer the asked, you know, those that care know how to showcase that they care.
It’s an innate thing, right? You can’t teach someone how to care. People who care know how to do that.
What advancements in technology, particularly AI, how do you see those impacting the executive assistant in the future?
It’s a great question because we’re not going to be able to avoid AI and the technology advancing.
There’s always going to be the need for humans. So it’s about humans using technology. I think we’re going to get more and more efficient with technology, which is going to be amazing as our team learns new tools, which we’re already doing. We’re are to be more efficient and we’re able to serve our clients better.
It’s not about replacing us. It’s about making sure that our team knows how to use technology in the most efficient way. And therefore, you know, perhaps someone who has two clients now can have four clients. The goal is just to continue to enhance what we as humans know how to do best — caring and the personalized aspect of things.
It’s using the tools to help us do our job better, like in any industry. People who are executive assistants do need to stay up to date with technology because otherwise, technology will definitely kind of take over those people who don’t know how to use it.
But if you learn how to take advantage of it, it’s going to be amazing.
So we’re talking about technology here. A lot of companies are using technology to monitor their team and make sure that they’re staying online or maybe they’re recording them while they work. But at Boldly, we don’t do that. We very much have a company based on trust and autonomy — how do we cultivate that culture?
Well, we hire the right people to start with. Our hiring process is very, very thorough. We get thousands of applications and we hire very, very few people each month.
We hire people who have that innate sense of service, who want to do a good job, who want to retain their job. And we have a lot of experience in in how to do that.
Then we trust those people to do a great job. It sounds really simple, but it’s very, very difficult. Anyone who has hired and who’s been in recruitment or, in fact, any executive who comes to us, knows how hard it is because usually people have tried.
So it sounds simple — hire the right people. And obviously we have a proven formula. We’ve been doing this now for 12 years and know how to hire the right people that we can trust to do a good job.
A lot of applicants want to know what kind of client are they going to work with. Can you talk more on the insights of our clients and that dynamics there and how a new team member will be supporting them on their day to day, what that’ll look like?
We choose the clients that we onboard just like we choose the team that we on board because to retain an amazing team, you have to have amazing clients — and our team is what makes Boldly, right?
So we spend a lot of time recruiting the right talent and then we retain them at all costs. So to retain great people, you have to have great clients.
We screen our clients very diligently and similar the way that we hire our team, looking at our values of care, of kindness. We want clients that are going to treat our team well, that are respectful, that are going to train our team to succeed, that are caring.
So we’re very diligent on making sure that our clients will be really great over the long term. We never take on clients just for projects or because someone just wants something done here or there.
This is a long term partnership and for that reason, we’re diligent in who we who onboard as a client and we turn away many clients who don’t fit that. And that’s okay.
It’s more important to us to have longevity and great quality of life for both our team and clients.
So not only do we then onboard good clients, but then once we have a great client, we look to see who on our team might be interested. And then if they’re interested, and if they have the availability, they meet with the client. And then clients and team decide whether they match and whether they want to work together.
When you work with someone and in an industry you’re interested in, then it’s really rewarding.
What is it about Boldly that you are most proud of?
Our team.
I started the company because I was looking for something for myself. And I’m so proud and so grateful that so many people joined us in this venture. You know I never at the beginning thought that Boldly would become such a big company, such a reputable company.
And it is because of the people that we’ve onboarded.They make what Boldly is today. And I’m really pretty proud of that. We talked earlier about investments and bootstrapping and of course we’re a business, so we have to be really, really careful and diligent about how we manage the business. But it all falls into place when you do good.
When you have the right people, when you have the values of kindness and care that we have — it doesn’t have to be super complicated. You just have to do the right thing. And so I’m most proud of our team at Boldly and most proud of what everybody has created.
For all of those people who are out there looking and maybe considering applying to work at Boldly, what is your number one tip?
Make sure that you read the job description really carefully and then fill out the application really carefully.
Don’t apply if you don’t meet the requirements. We are really, really, really stringent. My one tip is don’t waste your time if you are not absolutely certain that you’re going to have a chance — it’s going to be a waste of your time. And if you do apply, be really, really careful in answering the question asked and showcasing that you care by reviewing your application for grammar and being diligent.
This transcript has been lightly edited for clarity.
