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Wishup vs. Boldly: Get Ahead With The Best Premium Executive Assistant Service

A deep dive into the differences between Wishup and Boldly executive assistant, including pricing, features, and who each executive assistant service might be the best fit for.

Prachi Bisht

• 11 min read
Wishup vs. Boldly: Get Ahead With The Best Premium Executive Assistant Service


As a founder, you’re not just running a business; you are the business.

Every decision, task, and deadline falls on you. That’s why hiring the right executive assistant (EA) will help scale yourself and your company.

Both Wishup and Boldly offer executive assistant services, but the difference lies in the talent, quality of service, it's pricing, and overall value they provide.

Let’s compare.

Spoiler alert: There is no alternative for Wishup's executive assistant. Here’s why.

More Bang for Your Buck

Wishup's executive assistant service is more economical than a Boldly premium executive assistant, making it a smart choice for budget-savvy and fast-growing businesses.

Our EA Can Do More Than You Think. Sometimes Even Better

Unlike Boldly, every Wishup Executive Assistant brings expertise in 200+ skills and mastery in 70+ no-code and 50+ AI tools. Experience matters, but capabilities win.

EA Who’s Jack of All Trades and Master of Everything in Between

Your business is unique, and so are your needs. From simple inbox management to managing investor relations, our executive assistants handle whatever comes their way. Consider them as a part of your core team.

Much like Numbers, Skills Speak for Themselves

We understand that founders do not just run businesses; they are everything for their business.

While Boldly hires executive assistants based on a minimum of 7 years of experience as criteria, our EAs are selected through a rigorous 6-step hiring process where only the top 0.1% make the cut.

They are trained in:

  • Prompting and AI tools
  • Strategic decision making
  • Time and project management software
  • And the list goes on

Service Comparison: Wishup comes with more, so you can grow faster.

Before choosing the right executive assistant service, it is necessary to check the plan options and compare the services in terms of the significant features.

Here is how Wishup and Boldly executive assistants compare in terms of such essential service plan features.


Plan Features Wishup Boldly
EA Onboarding Time ✅ 60 minutes ✅ 1 to 2 week
Pricing Plan ✅ $999 ✅ $2520
Discount ✅ $100 OFF and free consultation ❌ No
Purchase System ✅ Monthly Subscription ✅ Monthly Subscription
Applicant Selection ✅ 0.1% ❌ Unclear
Working Hours Two options:

✅ 20 hours per week (five business days)

✅ 40 hours per week (five business days)		 Five options:

✅ 40 hours per month

✅ 50 hours per month

✅ 60 hours per month

✅ 80 hours per month

✅ 160 hours per month
Money-Back Guarantee for Unsatisfactory Service ✅ Yes ❌ No
Replacement of EA ✅ Yes ✅ Yes
Sign a Non-Disclosure Agreement (NDA) ✅ Yes ✅ Yes
Backup for EAs on Leave ✅ Yes ❌ Unclear
Use Your Own NDA ✅ Yes ❌ Unclear
Cultural Fit ✅ Yes ✅ Yes
Time Zone Availability ✅ Flexible ✅ Flexible
Task Management ✅ Using Free Employee Management App ❌ Unclear
Security, Privacy, and Confidentiality ✅ Yes ✅ Yes
Aptitude Test ✅ Yes ❌ Unclear
Personality Test ✅ Yes ❌ Unclear
Cognitive Test ✅ Yes ❌ Unclear
English Test ✅ Yes ❌ Unclear
Email Writing ✅ Yes ❌ Unclear
Training ✅ Yes ❌ Unclear
Dedicated Account Manager ✅ Yes ✅ Yes
Knowledge Transfer ✅ Yes ❌ Unclear
Health Insurance ✅ Yes ❌ Only to full time employee
Global Talent Pool ✅ Yes ❌ No
Expertise in AI Tools ✅ 50 + ❌ Limited
Expertise in No-code Tools ✅ 70+ ❌ Limited
Ongoing Assistant Training ✅ Yes ❌ No
Satisfaction guarantee ✅ Lifetime ✅ Yes
Contract Cancellation ✅ Flexible, no strict cancellation rules ✅ 30-day notice required

Wishup is the Only Boldly Executive Assistant Alternative Worth Your Consideration

EAs so Good… We Dare Them to Outperform Chief of Staff Executives

  1. Expertly aligned with 100+ founders in 2025 so far.
  2. 200+ high-ownership EAs to choose from.
  3. 5000+ tasks managed monthly.
  4. 99% reliability rate in meeting deadlines.
  5. 98.8% client satisfaction rate.

Choose Wishup and save 40 hours every week, guaranteed.

Service Offerings: Who Covers More Ground?

Wishup and Boldly both offer a range of executive assistance tasks, but Wishup provides more specialized services.

Wishup provides a wider range of services at no additional cost, while Boldly charges a premium for specialized assistance.

Wishup: A One-Stop Solution for Remote Executive Assistant

Our EAs are Trained in Tools that you Leverage

Boldly Executive Assistant: Limited Scope

Now, what kind of company is Boldly? Boldly is a 100% remote staffing organization, and all its employees are hired from Europe and North America. All assistants are W2 employees, not contractors. They receive paid time off, paid holidays, a 401(k) match, and other employee benefits just like Wishup employees.

  • Boldly primarily focuses on executive assistance.
  • It offers marketing, project management, and customer service at higher rates ($79/hr).
  • Their executive assistants have no AI expertise or training in modern digital tools.

Wishup gives you a complete remote virtual team, while Boldly limits you to executive assistant tasks.

Pricing: Cost-Effective Plans with More Value at Wishup

For businesses looking for affordability without compromising quality, Wishup provides superior pricing compared to Boldly.

Wishup Executive Assistant Pricing: Budget-Savvy Plans

At Wishup, the cost of hiring an executive assistant starts at $9.99/hr. Plus, enjoy our virtual assistant management productivity app (worth $299/month) for free.

  • Kickstart Plan (4 hours/day) – Starts from $999/month.
  • Growth Engine Plan (8 hours/day) – Starts from $1,799/month.
  • Month-to-month flexibility—no 30-day cancellation notice required.
  • Free access to the Wishup App for workforce management.

Our budget-friendly and transparent pricing structure is ideal for small businesses and startups.


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Boldly Executive Assistant Pricing: (Over 5x More Expensive Than Wishup)

How much does it cost to get an executive assistant from Boldly?

Boldly is a US-based premium executive assistant company providing services such as administrative support, project management, customer service, bookkeeping, personal assistance, multilingual support, and marketing & social media management.

According to the latest information on their website, Boldly offers two types of pricing pages. The first pricing page is not restricted to any location, but the second pricing page is dedicated to New York City.

For most of the United States, plans start at $2,520 per month for 40 hours of support. You can also choose 50 hours for $3,150, 60 hours for $3,780, or 80 hours for $5,040. If you need more hours, they can create a custom plan for you. In New York, the prices are slightly higher, starting at $2,595 for 40 hours, $3,244 for 50 hours, $3,893 for 60 hours, and $5,190 for 80 hours.

Additionally, customers receive a small discount of 2.9% if they choose to pay by ACH. For specialized tasks such as web design, blog writing, or advanced technical work, Boldly charges a separate rate of $79 per hour.

Here's the breakdown of the Boldly premium executive assistant pricing:

Hourly Plan Monthly Pricing Monthly (New York) Pricing
40 hour plan $2520/mo $2595/mo
50 hour plan $3150/mo $3244/mo
60 hour plan $3780/mo $3893/mo
80 hour plan $5040/mo $5190/mo
Bigger plan to 160 hours Ask for pricing Ask for pricing

No matter which plan you choose, Boldly provides you with a skilled executive assistant. You even get to meet them before you decide to hire. They offer a free introductory meeting to help you get started. You can choose someone based in North America or Europe, and they will become part of your team.

Why pay more for less? Wishup offers premium service at a fraction of the cost.

Onboarding & Matching Process: Faster and More Flexible with Wishup

Hiring an executive assistant shouldn’t take weeks. Wishup provides the fastest onboarding experience.

Wishup: Matches You With a Virtual Executive Assistant in 60 Minutes

  • Match with an executive assistant within 60 minutes with our 3-step onboarding process.
  • Dedicated client success and an executive assistant manager for ongoing support.

Boldly Executive Assistant: Have a Lengthy Matching Process

  • Requires a multi-step consultation before matching an executive assistant.
  • Onboarding can take days or weeks.

We understand that time is money. Instead of waiting days to find a virtual executive assistant, you can start working with a trained professional in an hour.

Hiring Process: Selective vs. Experience-Based


The right virtual executive assistant isn’t just someone with years of experience. It’s someone with the right skills, adaptability, and problem-solving mindset.

While both Wishup and Boldly offer experienced assistants, their hiring approach makes all the difference.

Here’s how Wishup and Boldly's premium executive assistant compare:

Wishup: Hires Top 0.1% of Virtual Executive Assistants

  • Rigorous 6-step screening process, including aptitude, personality, and cognitive tests.
  • Only the top 0.1% of candidates make the cut.
  • Hire EAs with a minimum of 5 years of experience.
  • Extensive training of all our virtual executive assistants in 200+ skills, 70+ no-code tools, and 50+ AI tools before deployment.
  • Ongoing upskilling to stay ahead of industry trends.

Boldly Premium Executive Assistant: Experience-Based Hiring

  • So, now let's get an answer to the question: how many years of experience does Boldly's executive assistant have? As per our research, Boldly hires executive assistants with 7+ years of experience, assuming experience alone guarantees success.
  • They don't have structured training on AI tools or modern software.
  • Limited focus on ongoing upskilling.

Wishup doesn’t just hire experienced executive assistants; it trains them to be the best.

Check out our in-depth review of remote assistant companies: 

  • Wishup vs Athena Executive Assistant: Which is the Better Choice?
  • Bench vs. Wishup—Which Online Bookkeeping Service is Better?
  • Zirtual vs Wishup: Which Virtual Assistant Service is Better?
  • Wishup vs Belay Virtual Assistant: Who is Founders First Choice?
  • Wishup vs. Wing Virtual Assistant: The Raw, No-Fluff VA Comparison Every Founder Needs
  • Wishup vs. HelloRache Medical Virtual Assistant
  • Why Wishup is the Best Alternative to Time etc Virtual Assistant?

Why pay a premium for a Boldly executive assistant when Wishup gives you the top 0.1% talent, pre-vetted and trained by ex-entrepreneurs at a startup-friendly cost?

Training & Upskilling: Keeping Up with the Future

An EA trained in the latest technology and tools gives you a competitive edge. Wishup ensures continuous training in AI and automation tools, while Boldly relies on prior experience.

Wishup: Future-ready Premium Executive Assistants

  • Conduct ongoing upskilling to keep EAs updated with the latest industry trends.
  • We train our virtual executive assistants in 70+ no-code tools and 50+ AI-powered tools like ChatGPT, Bard, and automation platforms like Zapier.
  • We also provide continuous training to bridge the skill gap of the specific niche business needs.

At Wishup, we ensure your virtual executive assistant is always ahead of the curve.

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Boldly's Executive Assistants: Stagnant Skill Development

  • No structured upskilling beyond initial experience.
  • Executive assistants may struggle with modern business workflows.
  • Offers assistants with general administrative knowledge but limited exposure to new-age tools.

Future-proof your business with Wishup’s AI-trained executive assistants.

Communication Channels: Wishup Adapts to Your Needs

Clear, timely communication between founders and virtual executive assistants is necessary for the smooth running of operations.

At Wishup, we understand that an EA is more than just support to founders. They're an extension of you.

That’s why we offer communication across multiple channels, ensuring instant collaboration. In contrast, Boldly restricts interactions to scheduled meetings, video calls, and emails, limiting real-time responsiveness.

Wishup: Flexible, Multi-Channel Communication

  • Communicate via email, calls, texts, video chats, or WhatsApp.
  • Use the Wishup App for real-time task tracking and approvals.
  • Assign tasks through your preferred platform for seamless collaboration.

Boldly Executive Assistant: Rigid and Limited

  • Communication is primarily through email, text, video calls, and scheduled meetings.
  • There is no centralized platform for task tracking.

Get adaptive co-working with Wishup. No more delayed responses or communication barriers.

Technology & Workforce Management: A Smarter Approach



You're busy running your business, managing a distributed team, and understanding this need of small businesses.

We provide an AI-powered app that supports productive task-related discussions, file sharing, and instant communication.

We integrate technology to eliminate context switching and make collaboration and task monitoring way easier, while Boldly lacks a tech-enabled system.

Wishup: Integrate Technology to Eliminate Context Switching

  • We have a Workforce Management App to support productivity.
  • Track your executive assistant tasks, monitor progress, and get daily EOD reports.
  • Approve leave requests and assign tasks directly from your phone.
  • Get real-time updates on pending and completed tasks.

Boldly Executive Assistant Service: No Tech Support for Clients

  • There is no workforce management app for real-time visibility into your executive assistant's performance.

Wishup brings structure and efficiency with a dedicated app—Boldly does not.

Wishup: Money Back Guarantee for a Risk-Free Experience

  • Test the service before committing. If you don't like the service, we'll refund the amount, no questions asked.
  • Get firsthand experience of Wishup’s executive assistant talent with a 7-day no-questions-asked refund policy if it’s not working out.

Boldly: No Free Trial, Only Long-Term Commitment

  • There is no free trial, forcing you to commit without testing.
  • Founders must invest upfront without knowing the service quality.

Why take a risk? Try Wishup first and commit later.

Flexibility & Scalability: How Easy is It to Scale?

Scalability is at the core of any business experiencing growth. Wishup lets you adjust your EA support on demand, while Boldly requires advanced planning.

Wishup: Scale Instantly, Anytime

  • We provide on-demand scaling, allowing business owners like you to scale executive assistant support as you grow.
  • You can easily upgrade or downgrade the service plan based on your business needs.

Boldly Executive Assistant: Scaling Requires Advanced Planning

  • Requires adjustments to be planned in advance, making it less adaptable for fast-scaling businesses.
  • You need to give a 30-day notice period before canceling the service.

Stay agile with Wishup’s scalable solutions—grow at your own pace.

Which Executive Assistant Service Reigns Supreme?

The results are in, and we have a clear winner. 💪 

It’s Wishup! 🤩

Boldly brings experience, but Wishup brings so much more—elite executive assistants, startup-friendly pricing, 60-minute onboarding, and true flexibility.

Why overpay for limitations when you can have top 0.1% talent, AI-powered efficiency, and zero-risk hiring with Wishup?

Founders move fast, and your EA service should, too.

Ready to work smarter? Go with Wishup

👉 Book a Free Consultation Today and Hire Your EA in Just 60 Minutes!

Frequently Asked Questions

Is Boldly a Legitimate Company?

Yes, Boldly is a legitimate company, just like Wishup. They are a highly reputable remote staffing company that provides executive assistants and business on a subscription basis. Established in 2012, the company has earned a strong reputation for offering premium fractional staffing solutions to businesses of all sizes.

It has been featured on ABC News, Forbes, Real Simple, Military Spouse Magazine, and more.

How Long Has Boldly Been in Business?

Boldly was founded in 2012 (formerly known as Worldwide101), making it one of the most established premium remote staffing providers in the industry. With over a decade of experience, the company has fine-tuned its approach to providing highly skilled executive assistants and administrative professionals to growing businesses.

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