Meet Hollie Swofford, Boldly’s Director of Team Operations! Hollie has been with our team for several years, overseeing Boldly’s entire team. She leads our managers, including Boldly’s Team Leaders, HR, and recruitment.
Hollie’s ultimate driver is to create a better experience for people. She believes that her work across operations, talent, and people management can create a positive and inclusive working environment where everyone has the opportunity to thrive and to focus on what they do best.
How would you describe Boldly’s culture and how does it align with a people-first leadership approach?
First and foremost, Boldly’s culture is rooted in care.
Care is the throughline in everything we do here at Boldly, and it makes sense when you consider our work. We are a team of executive assistants—and executive assistants are generally caretakers.
They get a lot of energy from making other people’s lives easier and more organized. They show a lot of care for their executives behind the scenes so their executives can focus on meaningful work to move the organization forward.
We really work to make sure that we’re taking care of our team so they can take care of their executives, and that plays out in a few different ways. We offer great benefits to our team. We have health insurance available, a retirement plan with a company match, and paid time off so team members can recharge and come back to work as their best selves every day.
Another way we show care for our team is by making sure that flexibility and work-life balance are built into the way we work.
Many executive assistants end up working 24/7. If your executive is awake, your executive is probably working, which means you’re probably working. That’s not sustainable. We make sure that our team members are able to set a schedule that works for them and then we match them with clients who align with that.
Generally, clients need support in the mornings, afternoons, and with reasonable responsiveness throughout the day (within the set number of hours they’ve subscribed to with Boldly).
But within those parameters, our team members get to decide the hours that work best for their schedule—weekdays only—so they can bring their best selves to work, contribute fully, and then go live their lives, be there for their families, and not worry about a midnight text from their executive.
Once our team members have set their schedule and decided what works best for them, Boldly’s Team Leaders help them maintain those boundaries to ensure they’re really living into that work-life balance. After all, that’s probably why they came to Boldly in the first place!
That leads into the biggest way we show care for our team—we’ve got your back!
We work to have transparent, open communication with our team members on all fronts. So if there’s something you need, something you need help with, or something that’s not working, you feel comfortable coming to your Team Leader for a conversation and thought partnership to make improvements.
That way, you have a great work-life experience here at Boldly.
I love that we take care of our people so our people can take care of other people. In your role, you lead the work of multiple managers. Can you share what people-first leadership looks like in practice for you?
For me, it’s rooted in a foundation of trust.
When I’m working with my direct reports (our Boldly Team Leaders, our Recruitment Team, our HR team), I know we’ve hired the right people for those roles. I can trust that they know how to do their jobs, they know their team, they know the challenges they’re facing, and they have great ideas for addressing those challenges.
I really work to build open relationships so they, in turn, can trust me. They can feel safe coming to me with any challenges they’re facing and talking through them.
I am very averse to micromanagement. It’s not something I enjoy, and I know it’s not something people enjoy either! Being micromanaged can really eat away at your confidence, so I try to give all of my managers room to make decisions on how to proceed, using me as more of a thought partner and a coach for any challenges. They can then move forward with what they think is the best course of action.
You lead and work closely with the Recruitment Team — can you share what people-first leadership means for Boldly applicants?
Our goal, beyond hiring amazing people to support our executives, is that applicants leave feeling respected and positive about Boldly—regardless of the outcome of their application.
We treat every application as a human because it came from a human. We’re always interacting with human beings in this work, and that’s so important to keep in mind.
We review every single application, and we respond to every single application. If you apply to Boldly or send us an email, you’re going to hear from us.
We don’t like to let things drag out for a long time because we know you’re anxious in your job search. You’re looking for answers, and we want to give you those answers.
We also value transparency. We’ve put a lot of work into our recruitment materials, everything you see on socials, on our website, and in our job descriptions, to make it very clear what we’re looking for and what you can expect in the application process. This way, you never have questions or doubts about the process, so you can just focus on putting your best foot forward.
What is your advice or encouragement to those looking to apply and join our team of ridiculously talented executive assistants?
I think one way we show care in the application process, and to all applicants, is the respect we have—not just for you as a person but for the executive assistant role.
It’s hard work, and it’s not a job that just anyone can do, right?
You need the right mindset, the right skill set, and significant experience to excel with the clients we support. We respect that role by maintaining a high degree of rigor in our application process. Many job descriptions are a wishlist of qualities, and you might move forward even if you don’t meet all of them, but that’s not the case here. We’ve removed the “nice-to-haves” and included only the essential requirements, so make sure you meet those experience requirements.
Another tip is to take time in your application process to show care and to demonstrate that you align with our value of caring. This shows us how you’ll be with us and with your executives.
Meeting the experience requirements isn’t enough—you also have to show care. One way to do this is by showing strong attention to detail. Make sure your short-answer application questions (there are only three) reflect who you are as a person and truly answer the questions asked. Tell us why you want to work for Boldly specifically, tell us how your experience aligns with Boldly specifically, and pay attention to details like typos. When you work as an executive assistant, you represent an executive externally, so attention to detail is a big deal!
This is something we pay close attention to in the application process, so take your time, show care, and focus on details.
And don’t stop there—continue to demonstrate this in every interaction with our team. Show us who you are and how you’ll interact with our executives, because that’s what we’re ultimately looking for.
And finally, check your spam! This might seem simple, but sometimes emails from us get stuck in spam filters. If you haven’t heard from us and are expecting a response, check your spam folder. We respond to every single applicant, so that’s an important thing to keep in mind.
This transcript has been lightly edited for clarity.
