Boldly Reviews: What Clients Should Know Before Hiring

You’re looking for Boldly reviews because you need to find an assistant, and you want to know whether this company can deliver. Handing over your calendar and your inbox (and probably your credit cards down the line) is a big step.

Boldly has been around since 2012. It hires its assistants as employees and posts its prices online. Those are all good signs.

The rest takes some digging. How many hours do you get each month? What happens to the hours you don’t use? When can you reach your assistant? How many other clients do they have?

We cover all of it below, along with what Boldly costs and who it suits.

TL;DR – Should You Hire Boldly?

The short version, in case you’re between meetings.

Boldly is a good fit when:

• You want a US or Europe-based assistant employed on a W-2.
• Your workload is predictable and fits inside 40 to 100 hours a month.
• You’re okay with the pricing and month-to-month terms.
• You need bookkeeping, marketing, or paralegal help, along with admin work.

Look somewhere else when:

• You want one person who learns your business deeply and answers fast.
• You need coverage outside Monday to Friday business hours.
• You’re buying support at the chief of staff level.

What Is Boldly?

Boldly is a remote staffing company based in New York. It matches experienced assistants with executives. You pay a monthly subscription to get the service.

Sandra Lewis founded it in 2012 under the name Worldwide101. She changed the name around 2019, after a prospect said the old one sounded like a cheap offshore call center. The company has been fully remote from day one and now employs over 100 people.

Boldly calls its service “premium subscription staffing.” That sits somewhere between an hourly VA agency and a full-time hire.

If you’re looking for an executive assistant (EA) and evaluating Boldly as an option, you should sort out the difference between a virtual assistant and a remote executive assistant first. It helps you decide what you should be paying and which option you need.

What Assistant Support Does Boldly Offer?

Boldly’s service list is broader than that of a typical executive assistant firm. Whether that helps you depends on what you need.

You can hire an executive or personal assistant here. Boldly also staffs separate specialists for marketing, social media, bookkeeping, project management, customer service, and paralegal work.

The regular plan starts at 40 hours a month. The average client buys around 60 hours.

Each client gets one dedicated assistant and a trained backup for vacations. A wider team handles specialist projects. You also meet your assistant before you sign, which many competitors skip.

However, three limits are worth knowing before you go into the sales call:

• Assistants work Monday to Friday during business hours. No nights and no weekends.
• Each assistant supports up to 3 clients at a time.
• Boldly replies within a few hours on a business day. Anything sent after hours gets a reply the next business day.

Boldly Reviews Across Client and Employee Platforms

Boldly scores well on the major review sites.

Boldly Reviews Across Client Platforms

Public feedback from paying clients is scarce. Below is everything we could find:

• Clutch: An executive at a large media firm rated the work 4.5 overall, then marked quality at 2.5 out of 5. He credited the team for being stable and hardworking, said his staff could improve, and noted they were sometimes “hard to work with.” 
• Reddit, r/ExecutiveAssistants: A business owner who used a Boldly assistant for almost 2 years rated her highly, said onboarding went smoothly, and reported being matched within a couple of weeks. She later quit, and he ended the contract. Looking back, he wrote that he “didn’t like how little my VA actually made,” since much of his fee went to the company. His thoughts sit in this thread on Reddit.

Boldly has no profile on Trustpilot, G2, or the Better Business Bureau. So, unfortunately, that’s the whole picture.

For a company running since 2012, the independent client record is thin. Ask for 2 or 3 references in your industry during the sales call.

Boldly Reviews Across Employee Platforms

Assistants have left far more feedback, and it’s detailed and current:

• Glassdoor (4.8 out of 5 from 133 reviews): 96% of staff recommend the company. Work-life balance and culture both sit at 4.8, while pay and benefits score 4.4, the lowest of the set. The full review page runs to hundreds of comments.
• Indeed (5 out of 5 from 8 reviews): A Business Support Specialist posting from a remote role in February 2023 praised her team leader and the hiring process. Another said she assumed Boldly was “too good to be true” before applying, given how many remote job scams exist. You can browse them on Boldly’s Indeed page.

Assistants talk about flexible hours that let them care for kids or parents, careful matching between assistant and client, and a 401(k) match and paid time off that reach part-time staff too.

One reviewer with 25 years of work behind her called Boldly “by far the best company I’ve been a part of.”

However, there are a few complaints as well.

Work volume isn’t promised, and one assistant on the virtual assistant review page warned there is “no guaranteed work/client load.” Others say full-time schedules get heavy once you’re juggling several busy clients and their separate systems.

Hiring takes a while. Only 31% of candidates rate the interview experience positively.

When it comes to pay, Boldly’s own job listings for assistant roles advertise $25 to $31 an hour. Several experienced assistants walked away over it, including one who said the rate matched what she earned 15 years ago.

Plenty of others take it happily for the benefits and the flexibility.

All of this matters to you as a buyer. A slow, selective hiring process means the assistant you’re matched with cleared a high bar. Staff who rate their employer at 4.8 tend to stay, so you’re less likely to lose your assistant a year in.

The Pros and Cons of Using Boldly

Boldly gets some things right, and a few things might wear on you. Both are worth knowing before you commit.

Where Boldly delivers:

• W-2 employment keeps contractor tax questions off your desk.
• Assistants come with 10+ years of experience. Boldly pays 100% of their insurance premiums, which keeps turnover low.
• Pricing is published, with no setup fees.
• Terms run month to month and come with a satisfaction guarantee.
• Boldly also covers admin, marketing, and bookkeeping, so you don’t have to source 3 separate providers.

Where clients get frustrated:

• Unused hours expire at the end of every month.
• There’s no free trial.
• Coverage stops at the end of the business day.
• Anything outside executive assistance bills at $79 an hour, above your plan rate.

The hour balance causes the most friction. When you buy time by the hour, someone has to track it, and a beginner may bill more hours for the same work.

That’s why hourly part-time executive assistant support disappoints executives. They wanted a partner, but what they got was a timesheet.

Want to know how top performers get the most from an assistant? My wife, Stephanie Bull, and I (we’re the founders of ProAssisting) wrote ‘The 29-Hour Work Day’ to answer that. Grab the free PDF and audio version.

When Boldly May Not Be the Right Fit

The reviews above tell you what working with Boldly feels like. However, everyone’s needs are different. 

These are the 5 situations where we’d steer you elsewhere:

• You want one person who knows everything: Boldly’s assistants say their work isn’t guaranteed. Boldly decides which clients they’re assigned. If things change on their end, they start over with someone new. Deep knowledge of your business is what makes an assistant faster at understanding your needs. Boldly’s model can disrupt that.
• You need someone at 9 p.m.: A $10M prospect emails on a Sunday. However, since Boldly doesn’t offer after-hours support, you end up answering it yourself. But if you’re thinking that you’re already paying $2,600 a month and have other priorities, you may want to look at other options.
• You want your assistant to stay: Boldly doesn’t publish how much of your fee reaches your assistant. Their listings advertise $25 to $31 an hour. Underpaid assistants don’t tend to stay long. Every departure costs you the onboarding time, the context, and the months it takes a replacement to get useful.
• You’re a founder watching every dollar: Entry plans run $2,600 a month for 40 hours. This option is suitable if you only need simple tasks done. The 100-hour-per-month plan runs around $6,500.

Executives in the first four groups usually end up hiring a fractional executive assistant.

The Best Alternative to Boldly

We built ProAssisting around the parts of this model that frustrate executives most.

That pay split is why our assistants stay longer with you and learn your business deeply.

Beyond the model, we accept fewer than 5% of applicants. Every ProAssistant has 5+ years of experience supporting executives at Fortune 500 companies. 

You’re getting the support of such an experienced assistant with no onboarding fee, no long-term commitment, and no equipment or benefits cost on your side.

Book a free consultation to see whether ProAssisting’s flat monthly retainer model fits your needs.

Frequently Asked Questions (FAQs)

Below are the questions executives ask us most often about Boldly:

Is Boldly Legit?

Yes. Boldly has been running since 2012. 

It employs a real US workforce, publishes its terms, and holds a current Great Place to Work certification. We found no lawsuits or regulatory actions.

Are Boldly Assistants Employees or Independent Contractors?

Boldly hires its assistants as W-2 employees. They get medical, dental, vision, and a 401(k) match. 

The company also covers 100% of the insurance premiums.

What Does Boldly Cost Per Month?

The entry plan is $2,600 a month for 40 hours, depending on where you look. 

Work outside executive assistance costs $79 an hour. There are no setup fees. Paying by credit card adds a 2.9% surcharge.

What Is Boldly’s Contract and Cancellation Policy?

Agreements run month to month and renew on their own. Give 30 days’ notice before your renewal date to change or cancel. 

Unused hours don’t roll over, and there’s no free trial. 

Can You Request a Different Boldly Assistant?

Yes. If the fit is wrong, you tell your client success contact, and they look for someone new. You also get a trained backup who steps in when your assistant is on vacation or out sick.

Ask on the sales call how long a rematch usually takes. That answer varies a lot, and you want to hear it before you sign.

Final Verdict

If your hours are steady and you want one platform covering several jobs, Boldly is a reasonable choice. It is a well-run executive assistant staffing agency.

The trouble starts when your work won’t fit into an hourly bucket. Some executives need answers within the hour, chief-of-staff coverage, or an assistant who knows the business inside out after a few years. Those needs point to a different setup.

That gap is why we built ProAssisting.

Your ProAssistant is US-based, works your hours, and carries two other clients at most. You get top-level executive support for 50-80% less than hiring in-house.

Also, 75%+ of your retainer is paid straight to your ProAssistant, which is why they stay for years. Our ProAssistants have supported leaders at J.Crew, Fidelity, Oracle, and JPMorgan Chase.

If that sounds like what you need, book a free consultation. We’ll talk through your workload and what kind of support actually fits. If it’s a match, we’ll go find the right ProAssistant for you.