Boldly connects ridiculously talented US-based executive assistants to leaders in absurdly crucial roles.

Founded in 2012, Boldly serves established companies and nonprofits that require premium executive support. Boldly’s staffing model ensures clients can maintain compliance and work with trusted administrative professionals for the long term.

What sets Boldly apart is their team of W2 employees—unlike most firms who rely on contract-based virtual assistants.

By offering competitive benefits such as PTO, a matched 401(k), tech stipends, and a caring, supportive culture, Boldly has achieved rapid growth and astonishingly high retention rates among both clients and staff.

About Boldly

Boldly was born in early 2012, when Sandra Lewis and a group of experienced remote professionals began offering business clients a well-rounded range of services. Through their commitment to quality and reliability, word of mouth spread, and demand shifted from short-term projects to long-term, monthly tasks. Boldly took shape as we continued to add more and more professionals to the team who share the same values—friendly, skilled, responsible, and “can do” support all grounded in quality.

What became apparent in working closely with their first clients was that, while most tasks fell under “general admin support,” each business was unique, with very particular needs.

Today, Boldly remains committed to delivering a highly curated and personalized approach.

How is Boldly different?

• Boldly’s EAs all have a minimum of 10+ years experience and are highly invested in seeing you succeed.
• You’ll meet with your EA before you commit to ensure it’s a good match. 
• Boldly’s US team are employees enjoying the highest pay in the industry, benefits, and an involved company culture.
• All of this plus a dashboard for tracking work, an ironclad satisfaction guarantee, and fanatical customer service.

Professionals with a “why”

Boldly relentlessly seeks out the most experienced EAs who go all-in to help leaders succeed. Boldly EAs are driven by long-term partnerships and the opportunity for fulfilling remote careers.

Meet first

You want an executive assistant who’s passionate about your work, and who gets you. Meet your Boldly EA before you sign up, and both decide if it’s a good fit.

Enterprise ready – multiple EAs

Whether you’re looking for a single executive assistant or need to support your entire leadership team, Boldly can help you scale personalized, premium-quality support.

Skills and experience first, AI-enhanced

All Boldly EAs are fluent in a wide range of popular AI-powered applications. They can also seamlessly integrate your favorite tools into their workflow.

Fast, fractional, and compliant

Boldly has done the hiring—all executive assistants are US-based Boldly W2 employees, so they can get started in days and work long-term with no 1099 compliance risk. Choose full-time, quarter-time or anything in between.

Security and confidentiality

Boldly works with your systems, software, and/or VPN connections. Team members are happy to sign NDAs in addition to the standard confidentiality agreements they are bound by.

Note that Boldly was formerly Worldwide 101.

What Boldly’s Customers Say

Boldly’s Services

Finding reliable, trustworthy, and competent help has always been one of the foremost challenges as companies grow.

Whether you’re looking for a single executive assistant or support for your entire leadership suite, Boldly’s team of ridiculously talented executive assistants can help you scale personalized, premium-quality support.

Here’s a list of the common services offered by Boldly:

• C-level executive assistance
• Personal assistance
• Marketing and social media management
• Project management
• Bookkeeping
• Customer service
• Multilingual customer service and admin

All services include:

• Your staff integrated into your team
• Full support from Boldly’s client success team
• Personal onboarding to help you get started and regular check-ins to support your long-term success
• Client dashboard to keep track of your staff’s activity and manage your account
• A trained backup so that you always have cover during vacation or illness
• Ironclad satisfaction promise
• Access to extended team for design and web projects, and for access to additional resources when you need to scale.

How Boldly Works

Boldly’s process is highly personalized.

Unlike many of their competitors, who will simply assign the next available person, Boldly gets to know their clients’ unique requirements and suggests a staff member they believe will be the right fit both in terms of skill sets and personality.

Your executive assistant should be passionate about your work and a strong match both personally and professionally. You’ll meet your Boldly EA before you sign up, and both decide if it’s a good fit. The magic of the relationship between a Boldly client and their staff comes from the fact that both of you have chosen each other.

Basically, the company won’t let you pay unless you feel the match is right!

Here’s how it works:

1. Tell Boldy about the support you need. In a short, productive meeting, we’ll listen carefully to your requirements to ensure that we suggest the right EA to match the leader they will support and your company culture.
2. Meet your executive assistant first. You’ll speak to the person Boldly recommends to verify that it’s a good match before you sign up, so that you have that extra level of confidence in who you’ll be working with.
3. Start working together. Your Boldly executive assistant will learn about your business, how you like to work, and the tools you like to use. (They can also recommend collaboration and business tools.) You’ll see everything they do in an easy-to-use dashboard.

Boldly Remote Staff Recruiting

Boldly has a simple premise. They only hire people who are passionate about doing a good job and passionate about working from home–people who go the extra mile to retain that privilege.

They strongly believe that happiness at work is essential to providing clients with consistent, long-term support that truly drives business growth and momentum. Boldly goes beyond simply hiring highly qualified staff; they focus on cultivating a loyal, vibrant company culture where celebrating five-year work anniversaries is common.

If you’re seeking a proactive staff member who can handle significant responsibilities without the need for micromanagement—and who will genuinely save you time—choosing a premium service like Boldly can deliver far greater value than what you might find elsewhere. Additionally, Boldly’s staffing model handles all compliance matters, ensuring you’re not exposed to the legal risks associated with contractor-based solutions offered by other companies.

That, and most of their team have 10-15 years of experience in their area of specialty!

Founder & CEO Sandra explained: “We recruit people that have an innate sense of service, and we find that the motivation of continuing to work virtually from home translates into team members that shine. At Boldly ‘your success is our success’ is not a cliché. It’s true and we live by it. Boldly has the capacity to grow with your business, and respond to fluctuations in your staffing needs.”

VA Company Comparison Chart

*Specialist services are available for an additional charge.

(In this article, Boldly explains why they’ve chosen not to offer rollover hours or a free trial.)

Who is the Perfect Boldly Client?

Boldly is a higher-end alternative to virtual assistant staffing agencies. Companies turn to Boldly when they need highly experienced, long-term support on a fractional or full-time basis.

The average customer signs on for around 60 hours a month, but a wide range of customizable options are available starting at 40 hours per month.One thing I found interesting was that many clients turn to Boldly after a less-than-ideal experience with a lower-cost VA service to see if a premium executive assistant can make a difference. If you’ve tried outsourcing overseas before and weren’t happy with the results, perhaps it’s time to try a higher-end service.

Boldly Client Case Study

Boldly Plans and Pricing

In terms of pricing, Boldly has package rates of $59/hr for admin services and hourly rates of $79/hr for more specialized services such as project management, web development, blog writing, and design.

And again, per Boldly Founder & CEO Sandra Lewis, the 3 areas that set Boldly apart from the competition:

1. Our People.

Reliability and quality are EVERYTHING.

We recruit people that have an outstanding professional background and a great attitude – executive assistants that have made the transition from a corporate career to working from home, and who bring a wealth of Fortune 500 training and experience with them.

Clients get the best of both worlds – a team member with extensive experience, available to them when they need it.

2. A Personal Service.

We really get to know our clients and assign a remote staff member that will be a perfect match. We stay attuned to clients needs so that we can grow with them, and are flexible enough to adjust as needed.

3. A Hybrid Model.

Many providers offer either a team-based service, or a dedicated service. We offer a hybrid model where clients can have a dedicated assistant and take advantage of an extended team for additional services.

Boldly Alternatives

For European (UK) assistants or US-based support, the closest competitor may be ClearDesk, Prialto, or Time Etc. All well-rated alternatives that operate on a similar model.

Time Etc may not match the level of experience or training of Boldly, but if budget is a concern, the rates are slightly lower.

If you have a specific skillset in mind, you might consider posting the job on FreeeUp to see what comes back. I like to cast a wide net and compare candidates in trial tasks and interviews to see who might be the best fit.

Your Turn

Have you worked with Worldwide101 or Boldly? If so, please take a moment to share a review of your experience below to help others with their decision.

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