BOLDLY

Overview

Boldly is a premium virtual assistant company that has been operating since 2012, originally under the name Worldwide101. The company rebranded to Boldly in 2019 but kept the same leadership, talent pool, and service philosophy that built its reputation.

What separates Boldly from most VA providers is its employment model. Every team member is a W-2 employee — not an independent contractor. This is a meaningful distinction. W-2 employees receive benefits, professional development, and long-term stability, which translates into lower turnover and more experienced talent staying on the roster.

Boldly also sets a high bar for experience. Their assistants typically have 10 to 15 or more years of professional background in executive support, marketing, finance, or project management. You are not getting a junior hire learning on the job. You are getting someone who has spent a decade or more supporting C-suite leaders and managing high-stakes workflows.

The company is based in the US with a distributed team across the US and internationally, operating on a subscription model with dedicated team members assigned to each client.

Services

Boldly focuses on executive-level support, which is reflected in the depth and sophistication of their service offerings. This is not a company built for data entry or basic admin tasks — it is built for professionals who need senior-caliber assistance.

Executive Assistance

This is Boldly’s core strength. Their executive assistants handle:

• Calendar and schedule management — coordinating across time zones, managing complex meeting logistics, and protecting focused work time
• Travel planning — booking flights, hotels, ground transportation, and building detailed itineraries
• Email and inbox management — sorting, prioritizing, drafting responses, and flagging items that need direct attention
• Meeting preparation — assembling agendas, pre-read materials, and follow-up action items
• Board and investor relations support — scheduling board meetings, preparing materials, managing stakeholder communications

Marketing Support

Boldly provides marketing professionals who go beyond basic social media posting:

• Content strategy and blog management
• Email marketing campaign execution
• Social media management across platforms
• Brand voice and messaging consistency
• Marketing analytics and reporting

Project Management

For businesses that need operational coordination without hiring a full-time project manager, Boldly offers experienced project managers who can:

• Track deliverables, timelines, and dependencies
• Coordinate across internal teams and external vendors
• Manage workflows in tools like Asana, Monday.com, and Trello
• Prepare status reports and escalate risks early

Customer Service

Boldly’s customer-facing team members can manage:

• Phone and email support
• Client relationship management and follow-ups
• Help desk and ticketing workflows
• Customer onboarding coordination

One thing to note: Boldly does not offer specialized technical services like software development, advanced graphic design, or accounting. Their strength is administrative, marketing, and operational support at a senior level. If you need bookkeeping or financial management, a provider like BELAY may be a stronger fit for that specific function.

Pricing

Boldly uses a subscription model with three main tiers:

The per-hour rate drops slightly as you commit to more hours, but all three tiers fall in the $39 to $43 per hour range.

These rates are at the higher end of the VA market, and that is by design. You are paying for team members with a decade or more of experience, W-2 employment status (which means Boldly covers payroll taxes, benefits, and compliance), and a service model built around long-term dedicated relationships.

For context, offshore VA services typically range from $5 to $20 per hour, while other US-based premium providers like BELAY start around $2,100 per month for part-time support. Boldly’s pricing is competitive within the domestic premium tier.

If you want to estimate how much VA support would cost for your specific workload, our VA cost calculator can help you compare across different providers and price points.

Hiring and Matching

Boldly’s matching process is more selective than most VA companies, both on the hiring side and the client-matching side.

On the hiring side, Boldly only accepts experienced professionals — typically with 10 to 15 or more years in their field. They do not hire entry-level candidates and train them up. Every team member comes in with deep professional experience, and the W-2 employment model means Boldly invests in retention through benefits, paid time off, and career development.

When you sign up as a client, the matching process works like this:

1. Discovery call — Boldly’s team learns about your business, workflow, communication preferences, and what you need help with
2. Team member selection — Based on your requirements, Boldly identifies one or more candidates from their roster whose skills and experience align with your needs
3. Introduction and onboarding — You meet your assigned team member and begin a structured onboarding process
4. Ongoing relationship — Your assistant works with you on a dedicated basis, building institutional knowledge over time

The emphasis on long-term relationships is a defining feature. Boldly is not designed for one-off projects or rotating assistants. You get the same person consistently, which means they learn your preferences, your business, and your communication style.

If the match is not working, Boldly will reassign you to a different team member. But the goal is stability — building a working relationship that lasts months or years, not weeks.

Client Experience

The day-to-day experience of working with Boldly leans toward a high-touch, professional partnership rather than a task-based transaction. A few things stand out.

Communication quality is strong. Because Boldly hires experienced professionals, you are working with someone who can anticipate needs, ask the right questions, and handle ambiguity without constant direction. This is the advantage of the 10-plus years of experience requirement — your assistant does not need to be micromanaged.

The subscription model keeps things predictable. You know exactly how many hours you have each month and what you are paying. There are no surprise fees or per-task charges. If you need more hours, you can scale up your subscription.

Onboarding takes effort. Like any premium VA relationship, the first few weeks require investment on your end. You need to document processes, share access to tools, and communicate expectations clearly. Boldly supports this with a structured onboarding framework, but you should expect to spend time upfront getting your assistant up to speed.

Turnover is low. The W-2 model and benefits package mean Boldly’s team members tend to stick around. You are unlikely to lose your assistant to a competitor or have them disappear mid-project, which is a real risk with contractor-based models.

Who Should Use Boldly

Boldly is built for a specific type of client, and the fit matters. You will get the most value from this service if you are:

• A CEO, founder, or senior executive who needs a seasoned assistant capable of handling high-level administrative work, investor communications, and complex scheduling
• A growing company that wants dedicated, long-term support from someone who builds deep knowledge of your business over time
• A professional services firm (consulting, finance, legal advisory) where your assistant needs to communicate credibly with clients and stakeholders
• A leader who values experience over cost and would rather pay more for someone who can work independently with minimal oversight

Boldly is also a good fit if you have had bad experiences with junior VAs or contractor-based services and want a more professional, stable arrangement.

Who Should Look Elsewhere

Boldly is not the right choice for everyone, and being honest about that helps you avoid a mismatch.

If you are budget-conscious, Boldly’s rates are hard to justify. At $40 to $43 per hour, you are paying a premium that makes sense for executive-level support but not for basic administrative tasks. If you need someone to handle data entry, simple scheduling, or routine inbox management, a provider like Time Etc offers capable US-based assistants at lower rates.

If you need entry-level admin work, Boldly’s talent is overqualified and overpriced for that scope. You would be paying for 15 years of executive experience to do work that a competent VA with two years of experience could handle just as well.

If you need full-time support at competitive rates, Boldly’s model tops out at 40 hours per month in their standard plans, which is part-time. For full-time dedicated VA coverage, Stellar Staff offers full-time assistants starting at $1,599 per month — significantly more hours for less money, though with a different talent profile.

If you need specialized technical work like bookkeeping, graphic design, or software development, Boldly does not cover those areas. Browse our full reviews directory to find providers that match specific skill requirements.

How Boldly Compares

Here is how Boldly stacks up against two other well-known VA providers in the premium space:

Each of these providers fills a different niche. Boldly wins on experience depth and the stability of its W-2 model. BELAY is stronger if you need US-only talent with bookkeeping expertise. Stellar Staff offers the best value if you need full-time dedicated support and want rigorous vetting at competitive rates.

Use our comparison tool to see a detailed side-by-side breakdown of any two providers.

Frequently Asked Questions

Is Boldly the same company as Worldwide101?

Yes. Boldly rebranded from Worldwide101 in 2019. The company has been operating since 2012 under the same leadership team. If you come across reviews or case studies referencing Worldwide101, they are referring to the same company.

Why does Boldly use W-2 employees instead of contractors?

The W-2 model gives Boldly more control over quality and retention. Their team members receive benefits, paid time off, and professional development — which means they stay longer and invest more in client relationships. For you, this means less turnover and a more stable working relationship with your assigned assistant.

What experience level should I expect from a Boldly assistant?

Boldly requires a minimum of 10 years of professional experience. Many team members have 15 or more years supporting executives, managing marketing programs, or leading projects. This is significantly more experience than what most VA companies require.

How does Boldly’s pricing compare to other VA services?

Boldly’s rates range from roughly $39 to $43 per hour depending on your plan. This is higher than offshore providers ($5 to $20 per hour) but competitive with other domestic premium services. The pricing reflects the W-2 employment model and the experience level of their team. Check our VA cost calculator for a personalized cost comparison.

Can I change my Boldly assistant if the fit is not right?

Yes. Boldly will reassign you to a different team member if the initial match does not work out. Because they maintain a roster of experienced professionals, they can typically find a replacement without significant downtime.

Our Verdict

Boldly occupies a clear position in the VA market: premium talent, premium pricing, and a premium employment model. The W-2 structure, the 10-plus years of experience requirement, and the focus on long-term dedicated relationships make it a strong choice for executives and senior leaders who need someone capable and reliable at a high level.

The tradeoff is cost. At $40 to $43 per hour with a minimum of 10 hours per month, Boldly is not the right fit for budget-conscious buyers or businesses that just need basic admin help. And the part-time subscription model means it may not work for companies that need full-time coverage.

If you are a CEO, founder, or senior professional looking for a seasoned executive assistant who will learn your business and stick around long-term, Boldly delivers on that promise. If your needs are more general or cost is a primary concern, our reviews directory has options at every price point and service level.