We're Actively Hiring For These Remote Business Support Specialist Positions
Executive Assistant

Bilingual Executive Assistant (English/French)

Administrative & Marketing Assistant

Legal Assistant

We're Actively Hiring For These Internal Positions
Full Cycle Sales Account Executive (Remote, 3/4 time to start)

About Boldly

Boldly is an award winning executive assistant company hiring talented individuals who want a rewarding long-term career making a difference at companies they are passionate about. Boldly employs senior, experienced, and highly-skilled remote staff across a variety of disciplines like executive assistants, marketing, project management, and more. All our positions are 100% remote.

Here’s how it works: as one of Boldly’s team you’ll support 1-3 of Boldly’s executive clients on a long-term basis, usually 2-3 years each. You are a Boldly employee and team member, and while you are assigned to work closely with the business leaders at the companies you'll be assisting, you are still very much a part of the Boldly team, supported by your team leader and our culture of caring, camaraderie and team spirit.

Our approach is highly personalized, carefully matching team members with companies and nonprofits based on skills and personality for a winning long-term relationship.

You get to choose the companies you work with, and enjoy the variety and continual learning that comes from working with successful growing businesses and organizations. We believe in creating a win-win relationship for both client and team member so that it is a rewarding relationship for both of you.

View our open positions


Thanks for asking

We’ve collected some of the most popular questions asked by applicants as a resource for you.

About Boldly

  • What is subscription staffing?

    It used to be that to get the most talented people to work for them, companies had to find, recruit, and employ talent directly, with the myriad complexities hiring entails, from legal to payroll to HR administration.

    But now a change has happened. Just as many of us subscribe to services like Netflix, or Amazon Prime for the convenience they offer, companies are now subscribing to the things they need to run their business. That includes subscribing to highly-qualified long-term staff, rather than employing them directly.

    Instead, subscription staffing company Boldly employs a team of world-class marketers, project managers, executive assistants, and more—and makes them available on a long-term basis, allowing businesses to quickly get hand-matched remote talent for the exact number of hours they need each month with the convenience of a simple monthly payment.

    Subscription staffing isn't just good for businesses, it's great for employees too. Boldly is a remote-first, employee focused company, offering our talented team the freedom to build their own schedules, work remotely, and contribute to amazing businesses while developing their own fulfilling careers.

  • How is Boldly different from a virtual assistant company?

    Most VA companies will recruit you as a contractor/ freelancer with no benefits and no guarantee of work. You are usually part of an impersonal platform and put on a roster of available bodies to assist companies with random tasks. You never get to meet with the companies you support beforehand and there is no guarantee of the hours or the work that you’ll do. It’s hit and miss to say the least.

    At Boldly you are a W2 employee. This means our company works just like any other high performing company with the added benefit of being 100% remote with flexible hours. The companies that you support are committed long-term and you get to meet with the executives you'll be working with before you decide to work together, so that you can be sure it's a good match.


  • What level of experience do I need?

    Boldly team members all have at least 7 years of experience in their field of specialty. You are welcome to apply if you’ve had a gap in your career as long as overall, you have at least 7 years of professional experience.

  • How many hours a week am I expected to work?

    Boldly team members are expected to work a minimum of 20 hours a week (which is 4 hours a day) during business hours. If you are looking to work for less than 20 hours a week, unfortunately, you will be automatically disqualified.

  • When can I become full-time?

    Boldly has both full-time and part-time open positions. Please indicate which type of employment you are seeking on your application form and you’ll be able to discuss this further if selected for an interview.

  • I already have a full-time job. Can I work for Boldly for just a few hours a week?

    No. Boldly is a career choice in and of itself. We only accept candidates who are available daily during business hours, and who are able to dedicate at least 20hrs/week to work with Boldly.

  • I currently work freelance. Can I supplement that by working for Boldly?

    Yes, as long as you are available to work for Boldly for a minimum of 20 hours per week during business hours.

  • Where do I need to live to qualify to join the Boldly team?

    We're currently hiring in the following 48 States, as well as the United Kingdom: Alabama, Arizona, Arkansas, California, Colorado, Connecticut, Delaware, Florida, Georgia, Idaho, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana, Maine, Maryland, Massachusetts, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska, Nevada, New Hampshire, New Jersey, New Mexico, New York, North Carolina, North Dakota, Ohio, Oklahoma, Oregon, Pennsylvania, Rhode Island, South Carolina, South Dakota, Tennessee, Texas, Utah, Vermont, Virginia, Washington, West Virginia, Wisconsin, Wyoming.

  • Why are you only hiring in certain US states if the job is remote?

    Even though the job is remote, employment is based on the location that the work is performed, and as an employer there is a significant amount of administrative complexity and cost involved in managing employment in each state. As such, we have chosen a select number of states to hire in, which we review periodically. (Active duty military spouses may elect to use either their domicile address or their current residence as long as one of them is in a state that we are hiring.)

  • I live in a state where Boldly isn’t hiring but will be moving to a hiring state soon. Do I need to wait until I move to apply?

    Yes, please wait until you’ve settled in one of our hiring states to apply.

  • Are all of Boldly positions long-term?

    Yes. Please only consider applying if you are interested in joining our team for the long-term. Boldly is all about creating long-term and rewarding partnerships and our team make Boldly their career choice for years to come!

  • Can I work for Boldly as a stop gap while I look for a “permanent” position?

    Boldly is a career choice in and of itself. We are not a “freelance platform” and working for Boldly is not a “short term gig”. Please only consider applying if you are interested in joining the Boldly team for the long term - just like you would for any traditional W2 position.

  • What are the technology requirements to work at Boldly?

    Along with reliable, high speed internet you'll need up to date anti-virus installed on your computer and up to date software (i.e. Windows 10 or macOS and a recent version of Microsoft Office.)

  • What online tools do I need to be familiar with?

    Although tools will vary from client to client, you should be familiar with and easily able to learn the most commonly online tools used to work remotely, for example Google Workspace, Microsoft Office Suite, LastPass, Asana, Trello, Zoom, etc.

  • Where can I find the Business Support Specialist role?

    If you follow us on LinkedIn, you may have noticed that our team members' title is Business Support Specialist. Because the work our team of highly experienced Executive Assistants, Marketing Assistants, and Legal Assistants does is so varied and complex depending on their specific clients' needs, we use the title Business Support Specialist to better reflect the breadth of responsibilities our team holds. If you're interested in becoming a Boldly Business Support Specialist, we'd love for you to apply to one of our open roles!

The Application Process

  • How does the application process work?

    Please watch the video below in the 'Why Military Spouses Love Working with Boldly' section, titled "What happens after I submit my application?" Within 10 days of applying, we'll get back to you. If your application is selected, the process takes an average of 3 weeks to complete and includes 3 video interviews, reference and background checks.

  • Is there a fee for applicants to join Boldly?

    Absolutely not! You will never be asked to pay any fees to apply for a position at Boldly and you will never pay any fees once you are accepted as part of our team.

    Boldly is NOT a job platform. If your application is successful, you will be employed by Boldly, supporting Boldly's clients.

  • Will I hear back from you if my application is not successful?

    Yes, we'll get back to you within 10 days to let you know whether or not you'll move forward to the interview stage.

Getting Started

  • What's Boldly's onboarding like?

    Once you have successfully completed the interview process, including references and background checks, we will formally offer you a position with Boldly. After you have accepted, onboarding takes an average of 3 days to complete. It comprises of hands on/live training by video conference to understand our company culture, values, and best practices to succeed in a remote environment. It also includes access to our digital vault with hundreds of case studies, videos and guides. And of course, we’ll review practical information such as your benefits and how you’ll get paid.

    During this time we’ll also get to know you and your preferences better so that we can suggest companies for you to support that are a good match with your interests and availability.

  • Will I get trained?

    While we expect our employees to be trained in their area of expertise, we’ll provide training in how to work remotely and best practices to succeed working with multiple companies in a remote environment.

    Once you get started, you’ll benefit from working with your Team Leader which includes ongoing training and learning opportunities to help you succeed.

  • How soon will I start work with companies?

    Typically, our team get started supporting companies within 1 to 2 weeks of onboarding.

  • How do I choose the companies that I support?

    While we are a 100% remote company, we take great care to get to know you, your preferences, your availability, your skills, etc. We will suggest you for new client opportunities and you’ll get a chance to meet with the companies that you are interested in, to verify that it’s a good match. It’s always your choice whether to support a company.

  • What types of companies does Boldly work with?

    Boldly works with a variety of companies and organizations of all different sizes, from solopreneurs to start-ups to larger companies. We also work with companies in many different industries, including tech, science and medicine, design, finance, nonprofits, marketing, and many others! Though we work in many different industries, often the executives' needs are similar. Regardless of the industry, you will always have the opportunity to review information and meet with the client to confirm your interest in working together! Here is our customers page for a very small sample of the customers, companies, and organizations you might be working with!

  • Will I work directly with the companies I support, or through Boldly?

    You will work directly and communicate directly with each company, as a member of the Boldly team.

Working for Boldly

  • How many hours a week can I work?

    Our team works a minimum of 20 hours a week. Positions start at part-time with the opportunity to become full-time in due course based on performance. We’ll assign you to work with companies whose requirements match your availability.

  • How much will I get paid?

    Your pay as a Boldly team member starts at $23 an hour (£18 in the UK) with regular pay raises throughout your tenure at Boldly.

  • How will I get paid?

    You will be paid directly to your bank account.

  • Is this a W2 position?

    Yes, in the United States you will be a W2 employee.

  • What benefits will I receive?

    As a part-time employee in the United States, you will receive paid time off, and as a full-time employee you will also receive medical benefits and life insurance coverage.

  • Can I choose when I work?

    You can choose when you work during business hours. Keep in mind that you will need both morning and afternoon availability. So for example, if you are working with Boldly for 25 hours a week, which is the equivalent of 5 hours a day, you can choose to work 3 hours every morning and 2 hours every afternoon. These hours can be flexible day to day as long as you’re able to plan and organize your work according to the needs of the companies you are supporting.

  • Are the hours flexible?

    Yes as long as it’s during business hours both mornings and afternoons.

  • Is work consistent?

    Yes. Most of the Boldly team have worked with the same companies for over 2 years. If a client needs to make a change to their subscription, you'll be offered opportunities with alternative companies.

  • Will I have a supervisor?

    Yes, you will receive direction from the executive at the company you are supporting, and you will be assigned to a Boldly Team Leader who serves as your supervisor providing mentorship and support during your tenure with us. Your Team Leader is always available for questions and to meet face to face - which you’ll do very often!

  • Do you conduct regular performance reviews?

    Yes, just like any high performing company, we conduct performance reviews. In addition, your supervisor will provide ongoing feedback on a month to month basis. Your performance review is a way to recap and look forward to new opportunities.

Company Culture

  • What’s the company culture like?

    Boldly is an employee focused company, and we foster long-term partnerships, open communication, and transparency with our team. We have a “virtual” open door policy, which means that everyone has access to our managers and leadership team, and is encouraged to speak up, and connect with them directly, no matter what the issue. We believe that everyone deserves to enjoy a rewarding and fulfilling career, and like you we want to work with kind, friendly, positive people who go to great lengths to support each other, and make it a pleasure to work together!

    Expect lots of communications with company news, team shares, quizzes, prizes, company-wide charity events, and celebrations.

  • What is Boldly’s approach to diversity?

    Boldly’s number one value is kindness, and we place the highest priority on treating each other with kindness and respect, and on creating a culture where everyone feels welcome. To discriminate against anyone because of their age, race, color, national origin, ancestry, religion, sex, sexual orientation, gender identity, pregnancy or childbirth, physical or mental disability, veteran status, uniformed service member status, or for any other reason is not only flat-out wrong, but it goes against everything we believe in.

    Boldly’s hiring process focuses on skill and experience and is based on a written process and documented criteria that removes unconscious bias from our screening and selection process. What matters to us is that you have the required skill and experience, that you are friendly and care deeply about doing a great job, and that treating others with kindness and respect is fundamental to you.

  • Do I get to work with others on the team?

    Your primary contact will be your team leader who you'll meet with and speak with on a regular basis. We also work closely as a team, supporting each other, so even though we all work from different places, you'll “meet” team members as you share client projects, or as you provide vacation back up for each other….you’re never alone!

Meet Some of Our Team As They Live Life While Working At Boldly

Work and Thrive

Boldly is a remote-first, employee focused company, offering our talented team of W2 employees positions with the freedom to build their own schedules, work remotely, and contribute to amazing businesses while developing their own fulfilling careers.

100% Remote

We believe the best work is done when you feel best, in an environment that suits you. Our culture and values are all about creating rewarding partnerships for distributed teams, and focusing on performance, not time spent working at a desk!

Flexible Workday

We believe the 9-5 schedule is outdated. We empower our team to work closely with the companies they support on a schedule that yields the best results. Create a schedule that fits your lifestyle, and manage your hours in our proprietary dashboard.

Ongoing Mentorship

From onboarding to your first meetings with companies you'll be supporting and onwards - our Team Leaders will work with you to ensure that you are setup to succeed from day one. We insist on providing our team with a rewarding and empowering work experience.


We are a tight-knit distributed team! Expect lots of communications with company news, team shares, quizzes, prizes, company-wide charity events, and celebrations. You may also get to collaborate on different projects with your fellow team members!

Learning & Development

One of the perks of working with growing businesses is the ongoing opportunity to learn new skills, and to experience working in different industries. We promote from within and 100% of our Executive Team and Team Leaders are former team members.

Paid Holidays & Parental Leave

We encourage our team to take time off to rejuvenate at various times of the year and we welcome new family members! Benefit from paid holidays and vacation, parental leave, and other contributions so that you can love your job even more!

Apply to Join Us

Be part of something amazing.  Don't settle for work as usual.

Boldly’s team of talented professionals has left behind the daily commute for the advantages of working virtually. For some it's about having a more flexible schedule, or the freedom to spend winter somewhere warm, or the variety of working with multiple clients. As a world-class business support specialist, you’ll play the rewarding role of supporting entrepreneurs, small business owners, and executives with a wide range of tasks, helping them to succeed, and freeing them up to focus on growing their business.

Sound appealing? If you have a strong professional background in administration, customer service, marketing, or project management, an interest in learning new skills, & a stable home-office environment we'd love to hear from you.


How Working for Boldly Works

  1. Apply for one of our W2 positions

    Representing Boldly and supporting top companies from your home office means you’ll need to show us that you’ve got what it takes to uphold Boldly's reputation for premium service. If you are successful, you'll open the door to a job that most people can only dream of.

  2. Finish onboarding and choose companies to support

    Boldly has a waiting list of businesses eager to work with us. After your initial onboarding we'll suggest clients for you to work with that are a good match for your interests, and availability. You’ll speak to them to verify that it's a good match, before you start supporting them.

  3. Enjoy Boldly’s team culture while doing work that inspires you

    You'll soon get started supporting one or more of Boldly's clients and building a long-term working relationship with them. You'll always have a team behind you, with your Boldly team leader on hand to support you, as well as being part of Boldly's vibrant team culture.


Hours worked
by Boldly Milspouses


Boldly's Managers
That Are Milspouses


Boldly Team Members
That Are Milspouses

Is This For Real? Watch Our Team Tell Their Stories

Why Military Spouses Love Working with Boldly

For some it's taking their job with them wherever their latest posting takes them. For some it's maintaining their own career in a role that fits their flexible lifestyle. For everyone it's the competitive pay, the flexible schedule and work focused on their area of expertise: executive assistance, book-keeping, marketing, project-management etc. The Boldly team understands family commitment and values the skills you have to offer.

what we expect from our team:

  • A can-do attitude and a proactive outlook
  • At least 7 years of work experience within your professional industry or field of specialty
  • Reliability, trustworthiness and discretion
  • Strong time management and efficiency
  • Professionalism in all communications
  • Steadiness and dependability with great flexibility
  • A high level of internet knowledge and a solid understanding of cloud-based technologies
  • Quick to learn and grasp new concepts
  • A fast and reliable internet connection
  • Friendly!
Apply to Join Us

MilSo Success Stories

What first interested me in Boldly was the flexibility of location (we've moved 7 times in the past 4 years!) and the flexibility of schedule. But it has also been the ability to support my husbands career whilst still carrying on my own! The stability in both your hours and your paycheck, and the team collaborative environment are hard to beat!”

virtual assistant photo Jenna B. United Kingdom

Thank you for everything that you have supported me with and guided me through over these last 3+ years. I am truly grateful that for the first time in 12 years of moving with the military life, I will not be providing my notice to a job I have grown so fond of because of our move. I am so incredibly blessed to have found Boldly!”

virtual assistant image Nicole W. United States
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