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How it works

Personalized pairing, guided onboarding

Our sophisticated onboarding process will pair you with an assistant you're sure to love, and we'll help guide the way to VA success.

Getting Started

Follow these 7 easy steps and you’ll be up and running in no time:

1
Sign Up

Sign up here on our website or download the ChatterBoss Android or iOS mobile app to sign up from your phone.

2
Complete Questionnaire

Complete a sophisticated questionnaire that helps us assess who your remote executive assistant will be, based on the skills you need and the personality type that best suits you.

3
Pair Up

Onboarding call with Client Success Team for strategy, roadmap development and custom pairing.

4
Schedule

Schedule a one-hour Kick-Off Call with your executive assistant.

5
Get to Work

Your assistant will guide you on handing off your first few tasks.

6
Follow the Roadmap

Get started on the 30-60-90-day roadmap your ChatterBoss executive assistant has devised for you.

7
Hit Your Goals

Start achieving your business objectives!

graphic of arrows in bullseye on target
“ChatterBoss has been a tremendous resource to me personally and professionally. The team of rock stars goes above and beyond to provide exceptional services and make my life easier in all aspects. I'm so grateful to have found this service and their team and refer people to them regularly.”

-Peter Stuart, CEO Outlier Capital

Examples

What kind of tasks should you give your VA?

Below are just a few examples of tasks that your ChatterBoss executive assistant can help you with:

Business

Services

Process creation and testing
Project management
Client management
Staffing and recruitment
CRM support
Pitch deck/presentation help
Social media management
Calendar and Email management
Lead generation
Call monitoring
Custom research
Business travel planning and booking
Automation
And much more!

Personal

Services

Restaurant recommendations
Gift buying
Travel concierge
Personal shopping
Event planning
Scheduling and appointment bookings
And much more!
✅ Learn how a VA can help you! 
Schedule a Consultation

The perks of working with experienced assistants

Here’s what you can expect when you sign up with ChatterBoss:

Peace Of Mind

ChatterBoss executive assistants have three years of directly relevant experience at a minimum, so they are trained in industry best-practices—and further trained to meet ChatterBoss’ rigorous standards.
The ChatterBoss administrative & backup team is highly responsive: you can expect to hear back from our team in the ChatterBoss app usually within minutes, and always within an hour.

We recommend setting response and turnaround time expectations with your dedicated assistant during your onboarding call.
Our remote executive assistants are US-based, so you won’t ever have to worry about a significant time difference.
ChatterBoss executive assistants have access to an extended team of specialists and our experienced Client Success Team who are masters of delegation and outsourcing.

Highly Effective Systems

By the end of our onboarding process, you will have a clear set of goals, a pragmatic list of priorities, and a strong strategy for your outsourcing plan.
ChatterBoss executive assistants are not only efficient task doers, they are also effective thought partners, helping you both accomplish your goals and set new ones.
If you are new to the world of virtual assistants, our ChatterBoss team will teach you how to make the most of our service, so you are sure to maximize your use of a virtual executive assistant.
Live time management enables you to track the status of your tasks in real time.

An extension of your team

Our onboarding questionnaire ensures that your dedicated executive assistant is compatible with your personality and communication style.
Your ChatterBoss executive assistant is trained to adopt your company voice when communicating with clients, safeguarding the continuity of the client experience.
Real-time communication makes dedicated ChatterBoss executive assistants feel like a full-time addition to your staff, without the overhead costs.

The perks of working with experienced assistants

Here’s what you can expect when you sign up with ChatterBoss:

An extension of your team

Compatible

Our onboarding questionnaire ensures that your dedicated executive assistant is compatible with your personality and communication style.

Adaptive

Your ChatterBoss executive assistant is trained to adopt your company voice when communicating with clients, safeguarding the continuity of the client experience.

Immediate

Real-time communication makes dedicated ChatterBoss executive assistants feel like a full-time addition to your staff, without the overhead costs.

Highly effective systems

Strong Onboarding

By the end of our onboarding process, you will have a clear set of goals, a pragmatic list of priorities, and a strong strategy for your outsourcing plan.

Thought Partners

ChatterBoss executive assistants are not only efficient task doers, they are also effective thought partners, helping you both accomplish your goals and set new ones.

Guidance

If you are new to the world of virtual assistants, our ChatterBoss team will teach you how to make the most of our service, so you are sure to maximize your use of a virtual executive assistant.

Time Management

Live time management enables you to track the status of your tasks in real time.

Peace of mind

Experienced

ChatterBoss executive assistants have three years of directly relevant experience at a minimum, so they are trained in industry best-practices—and further trained to meet ChatterBoss’s rigorous standards.

Responsive

The ChatterBoss team is highly responsive: you can expect to hear back from your dedicated remote executive assistant usually within minutes, and always within an hour.

US-Based

Our remote executive assistants are US-based, so you won’t ever have to worry about a significant time difference.

Extended Team

ChatterBoss executive assistants have access to an extended team of specialists, ensuring that most tasks are completed within a 24-hour period.

Get Started Today!

Let our team of best-in-class remote assistants help you take your business to the next level!

FAQ

Any questions?

Below are some of the most common questions we get asked. If you can’t find the answer you’re looking for, please contact us!

What is ChatterBoss?

ChatterBoss is a company of dedicated executive assistants that curates custom-built teams for busy entrepreneurs.

Where is ChatterBoss located?

Our headquarters are in NYC and our team of dedicated assistants is located throughout the US. A portion of our amazing back-up assistant team is located in South Africa.

Do I get a dedicated assistant?

Yes! Your dedicated assistant is a high performing assistant who will integrate into your business and become a true member of your team. In addition to that, you will also get access to a dedicated back-up assistant. This second assistant is also a part of your team and will be responsible for supporting your workload, as well as providing coverage in case your dedicated assistant is sick or is away.

Does ChatterBoss offer more than just dedicated assistant support?

Our support network is here for any additional specialized and project-based needs. You may see a full list of our specialists here. You will also get access to our suite of over 200+ assistants for additional support or if you want to grow your team.

What is the process to be paired with my assistant?

ChatterBoss has two options for pairings: standard and advanced. 

If you select our standard pairing, you will be paired with your assistant based on an onboarding strategy session to identify your needs, availability, time zone, skillset, software required as well as industry experience.

If you select our advanced pairing, we take things a step further. While we will consider all parameters listed in the standard pairing, we will also share a detailed character assessment with you. It is the same assessment we use when hiring our assistants. Using our proprietary pairing model, we will match you to an assistant based on cognitive ability, motivation, and personality. This option includes an interpretation session with our founder to coach you and your assistant on the best ways to work together based on your unique characteristics.

How long does it take to be paired?

ChatterBoss takes pairings very seriously as it is our goal to find each client and assistant their best match. With this in mind, we never want to rush the process, so we allow up to 5 business days to collect all of the information shared in the onboarding, outline the roadmap, and identify the best fit.

When are assistants available?

ChatterBoss dedicated assistants are independent contractors who set their own availability. If there is a specific need for time zone or availability, please let us know during your onboarding call to ensure we identify the best fit assistant who can meet your availability needs. Your assistant’s availability is listed in the ChatterBoss app once your pairing is complete.

What are ChatterBoss' hours?

ChatterBoss Client Success and Administrative teams are available from 9AM to 5PM Eastern Standard Time.

How does back-up support work?

ChatterBoss provides two levels of back-up assistant support. The first level provides back-up administrative support for limited periods of time when your dedicated assistant is unavailable.

The second level of back-up support is our client success manager, who oversees our app communication and is always in the app with you. If your dedicated assistant is unavailable for a short period of time and you are in need of a higher level of support, please do not hesitate to reach out.

How long can I expect to work with my dedicated assistant?

ChatterBoss’ vision is a world where every entrepreneur has their dream team. Our goal is to create long lasting relationships which enable success and growth for both clients and assistants. Our average assistant retention rate is 93% month over month. Once paired with your dedicated assistant, our aim is for you to continue with that assistant for the lifetime of our partnership, unless otherwise requested.

What if things aren’t going well with my assistant?

Our Client Success Team is here to guide you and your assistant to a successful relationship. Part of your ChatterBoss support includes unlimited access to our Client Success Team for delegation coaching and tips, strategy, troubleshooting, and mediation. In the instance we are not able to come to a comfortable way forward, we can re-pair you to a new assistant.

How do I access an Admin Assistant?

Our dedicated assistants are uniquely matched with their own Admin level assistant for seamless internal delegation. They're also available to you, upon request, for low intensity process fulfillment/turnkey tasks. Your admin assistant will be automatically paired to you upon the start of your relationship within the ChatterBoss app. Some clients prefer to have more interaction with their admins and others prefer to do everything through their dedicated assistant. We encourage you to communicate your preferences to your dedicated and admin assistants.

What is the response time?

ChatterBoss administrative & backup team is highly responsive: you can expect to hear back from our team in the ChatterBoss app within an hour.

Similar to your availability needs, we request that you share your expectations for response time from your dedicated assistant during the onboarding call so we can ensure we find an assistant who aligns with your workstyle.

What does it cost to get started?

ChatterBoss has a one-time onboarding fee which varies depending on the type of onboarding selected. The standard onboarding fee is $399. This includes your customized onboarding strategy session, as well as the creation of a 6-month roadmap. Handpicked pairing to your dedicated assistant, and unlimited strategy and coaching. 

The advanced pairing onboarding fee is $550 and includes everything in the standard onboarding, plus the character assessment, and interpretation explained in the earlier question What is the process to be paired with my assistant.

What are the ongoing costs?

Outside of the onboarding fee, you decide how much you want to spend with ChatterBoss. During your strategy call we’ll recommend a suggested budget to start, based on your goals, timelines, and level of support selected, but it is your choice. The best part is the budget is flexible. If some weeks you need to do more than your budget and other weeks, less, that’s no problem. You’d just communicate those needs to your dedicated assistant week to week and they would operate within that temporary budget as requested.

Is there a minimum commitment to use the service?

ChatterBoss has a small 5-hour monthly minimum commitment. This time is only billed to you if you use less than 5 hours per month. The purpose is to create continuity and retention of high-quality dedicated support, and to encourage consistent delegation as studies show delegation and outsourcing is the fastest way to grow your business.

How do assistants keep track of time?

Assistants track their time by the minute, down to the second. Within our app, you are able to see in real time what your assistant is working on, how long it is taking, and what was done during that time.

How does billing work?

Our billing is automatically processed each Monday for work completed the prior week. As billing is processed, you will simultaneously receive a receipt outlining the hours billed and the total amount. No need to lift a finger! If you ever have questions, our Finance team is here to help. They can be reached at finance@chatterboss.com. Please note, ChatterBoss internal team follows the federal holiday calendar. Therefore, on any Monday that is ever a federal holiday, billing will happen the next business day.

Do you have access to my credit card information?

We partner with a third-party payment processor (e.g., Stripe, Inc.) to manage credit card transactions and do not have access to your full credit card details.

Is my personal information secure?

Absolutely! We consider all information related to your account as private as you do; and take extensive measures to ensure you're always protected. Our team of assistants have all signed confidentiality contracts and are provided data security best practices. Should you request additional coverage from ChatterBoss, we have a standard NDA we are happy to sign with clients. For NDAs with your dedicated assistant, we recommend having your legal counsel draft an agreement that covers your needs, specifically.