Introducing The Boldly Podcast, where Director of Team Operations Hollie Swofford and Recruitment Manager Devin Drake take you behind the scenes of working at Boldly and answer your most frequently asked questions.
If you’ve been considering a career with Boldly, we encourage you to listen to these episodes and read through our FAQs.
Listen to all the Boldly Podcast episodes on YouTube.
Episode 1 – Open Positions & Experience Requirements
In this episode, Hollie and Devin answer the top questions about what it takes to work at Boldly. They break down key details about the role, including work hours, location requirements, and what counts as executive assistant experience.
Episode 1 covers:
- How our part-time and full-time positions work
- What the ramp-up process looks like before you’re fully booked
- Where you need to live to be eligible
- What counts as relevant experience if you haven’t held the EA title
Listen to Episode 1 on YouTube or read the transcript.
Episode 2 – The Hiring Process & Application Review
Hollie and Devin guide you through Boldly’s hiring process, explaining each step from application to interview. Learn what we look for in applicants and how you can increase your chances of standing out.
Episode 2 covers:
- Who reviews your application (spoiler: it’s not AI)
- What makes a strong application and short answer response
- How the skills assessment and video interview work
- How long the hiring process typically takes
- Why we’re always hiring—and what that really means
Listen to Episode 2 on YouTube or read the transcript.
Episode 3 -What To Know About Working At Boldly
This episode gives a peek into daily life at Boldly. Hollie and Devin discuss the flexibility of your schedule, performance reviews, and what tools you’ll need to work with clients.
Episode 3 covers:
- How to set your own schedule (with structure and flexibility)
- How performance reviews work and why transparency matters
- What equipment you’ll need to work remotely with clients
Listen to Episode 3 on YouTube or read the transcript.
Episode 4 – Pay & Benefits
Hollie and Devin break down what you can expect in terms of pay and benefits at Boldly. This episode covers everything from compensation structure to health benefits and paid time off.
Episode 4 covers:
- How Boldly’s pay is structured (and if there’s any flexibility)
- How raises and pay equity are handled
- How PTO and paid holidays work (yes, even for part-time team members)
- What health benefits are offered and who’s eligible—including coverage for dependents
Listen to Episode 4 on YouTube or read the transcript.
Episode 5 – Boldly’s Clients
Curious about the businesses Boldly supports? Hollie and Devin dive into our diverse client base and explain how we match you with clients based on your experience and availability.
Episode 5 covers:
- The types of clients Boldly works with (hint: it’s a wide range!)
- Why time zones don’t limit your client opportunities
- How we match you with clients based on availability and fit
- Why most team members stay with their clients for years
Listen to Episode 5 on YouTube or read the transcript.
Episode 6 – Reapplying To Boldly
In this final episode, Hollie and Devin provide guidance on how to reapply to Boldly if you weren’t selected the first time. They discuss when and how to reapply and how to improve your chances of success.
Episode 6 covers:
- Why Boldly can’t provide feedback on every application
- The importance of meeting Boldly’s experience requirements
- How to improve your chances for future applications
- The best way to approach reapplying after not advancing
Listen to Episode 6 on YouTube or read the transcript.
Want To Learn More?
We are building the most ridiculously talented executive assistant team out there, and we’re looking for those who strive to share their unique skills, talents, and extraordinary level of care with us.
To learn more and apply, please visit our Careers Pages.
