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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 executive assistant 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 fractional 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 assistant?

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 an assistant 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 fractional executive 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 executive assistants, our ChatterBoss team will teach you how to make the most of our service, so you are sure to maximize your use of an 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 fractional 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?

At ChatterBoss, we are fractional executive assistant experts. We bring top-tier US-based support that A-listers enjoy to high performers, entrepreneurs, and executives.

Where are ChatterBoss assistants located?

Our 200+ fractional executive assistants are located throughout the US to ensure that we provide the highest level of support for US-based entrepreneurs and businesses. Meanwhile, most of our admin assistants are located in South Africa, supporting low-intensity process fulfillment. This unique combined offering allows ChatterBoss to provide a primary US-based assistant with affordable and dependable admin support.

What is a Fractional Executive Assistant?

A ChatterBoss fractional executive assistant is a highly skilled professional who provides top-tier administrative support to executives and businesses on a part-time basis. The fractional approach allows you to benefit from their expertise for a fraction of the time and cost compared to hiring a full-time employee, while still giving you access to a dedicated team member who learns your business, workstyle, and preferences over time.

Furthermore, ChatterBoss provides a two-assistant fractional team to offer the benefit of the support.

How does the two-assistant model work?

ChatterBoss packages offer a two-assistant model which includes your US- based Executive Assistant and your South Africa-based Admin Assistant. You will be carefully paired with a US-based Executive Assistant based on your unique set of needs, personality, industry, and budget.

Your Admin Assistant works with your Executive Assistant to create a streamlined approach to support you. Our Admin Assistants have an average of 5 years of of experience and are ready to support project or task deliverables with defined and tested standard operating procedures or guidance. They provide lower-cost, admin-level support and allow for continuity when your Executive Assistant is away.

For example, in the event your Executive Assistant is out of the office, your Admin Assistant may be able to step in to provide backup support with specific tasks. To take advantage of the seamless transfer of responsibilities, we highly encourage you to review your SOPs with your executive assistant at least monthly to ensure all processes are up-to-date.

Does ChatterBoss offer specialized support (such as bookkeepers, web designers, social media strategists, etc…)?

Yes! We have experts that span many different skills and industries. Your Executive  Assistant will be a professional, career EA who will be your right hand and has access to 30+ experts with niche skills and talents that are available to further supplement your team on an as-needed basis.

What is the process to be paired with my assistants?

ChatterBoss is a leader in the entrepreneur/assistant pairing space. This is at the heart of why we do what we do – guided by our mission to create balance and meaningful connections in the lives of everyone we touch through a systematic approach at the intersection of human behavior and science

The pairing to your assistant team is a carefully curated 2-step process.

Step 1: Match based on basics such as listed needs, availability, time zone, skillset, software requirements, and industry experience. 

Step 2: Utilize our proprietary character assessment pairing algorithm which is proven across the industry to have the highest levels of accuracy for success. All of our assistants take the character assessment to incorporate more matching parameters and is highly encouraged (while not mandatory) for clients for increased pairing success. When taken by both, additional parameters are unlocked so we can pair you with an assistant based on cognitive ability, motivation, and personality.

You can learn more about our unique commitment to optimal pairings in our best-selling book, Delegation Nation, written by our Founder & CEO, Valerie Trapunsky.

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 ask you to allow 5-10 business days depending on your specific needs.

What is the screening process for ChatterBoss assistants? 

ChatterBoss has a uniquely designed multi-step recruitment process to thoroughly vet candidates to ensure we're selecting assistants who have the skills, experience, work ethic, and commitment to provide the excellent support our clients expect and deserve. New assistants joining the team are also required to complete a background check and provide proof of professional liability insurance.

When are assistants available?

ChatterBoss Fractional Executive Assistants are independent contractors who set their own availability. If there is a specific need for time zone, availability, or expectation for response time, please let us know during your onboarding call to ensure we identify the best-fit assistant who can meet those needs. We highly recommend establishing response time and task turnaround expectations in your first call with your assistant. Open communication around these expectations aids in relationship growth and success.

What is a Relationship Manager?

Your relationship manager is committed to the success of your relationship with your assistant team every step of the way. They will onboard you, aid in relationship building, growth, troubleshooting, and serve as a delegation coach for you. Unlimited access to your dedicated Relationship Manager is included for all of our clients. The Relationship Manager team is available Monday - Friday 9 am - 5 pm EST. Contact your Relationship Manager at [email protected]. Our tech support team is also available Monday-Friday 9 am - 5 pm EST. You may reach out to tech support at [email protected].

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

Anyone who tells you that working with an assistant is foolproof hasn’t done the real work. The executive assistant function is one of the most complex in your organization by its very nature because it does not have templates, rather it is custom-built around your skills, personality, delegation style, industry, and more. Our unique pairing approach is designed to control for many of the important matching factors to maximize success. We know that there are some points of friction along the path of any relationship, and we are experts at helping you navigate those moments and come out stronger together with your fractional assistant team. Our relationship managers and delegation coaches have helped hundreds of executives and entrepreneurs to build lasting and productive relationships with their fractional executive assistants.In the rare occurrence of friction, we will explore your perspective, strive to identify the source of any friction, and support you in troubleshooting through our relationship expertise. We will facilitate re-pairing to a new assistant whenever necessary. You can learn more about our unique commitment to optimal pairings in our best-selling book, Delegation Nation, written by our Founder & CEO, Valerie Trapunsky.

How long can I expect to work with my Fractional Executive Assistant?

ChatterBoss’ vision is a world where every entrepreneur has their dream team. Our goal is to create long-lasting relationships that enable success and growth for both clients and assistants. Our average assistant retention rate is 96% month over month, and we see 90% of our assistants have a relationship with their clients for over a year. Once paired with your executive assistant, our aim is for you to continue with that assistant for the lifetime of our partnership, unless otherwise requested. Please read our FAQ question on subscriptions to learn more about how you can extend your relationship with your assistant for even longer through our volume-based discount commitment packages.

What does ChatterBoss onboarding look like?

With a one-time onboarding fee of $499, you will receive a personalized kickoff delegation strategy session, a custom scope of responsibilities for your assistant team, a 6-month Roadmap to Success, and your character assessment summary. The character assessment and interpretation are explained in the earlier question, What is the process to be paired with my assistant?

How does billing work?

Our team of experts has identified monthly support plans that entrepreneurs have found to be successful and are designed for you to get the most out of your Executive and Admin Assistant support. This team dynamic provides the perfect combination of thought-partner collaboration and low-intensity support, ensuring you receive optimal support from both assistants. During your strategy call, we’ll do a deep dive into your specific goals, and timelines, and suggest a package that would best fit your needs.

Billing processes automatically on the 1st of each month for packages, and weekly on Mondays for hourly billing. As billing is processed, you will simultaneously receive a receipt outlining the charge details and the total amount. No need to lift a finger! Please note that sales tax may be applied based on your location. If you ever have billing questions, our Finance team is here to help. They can be reached at [email protected].

What if I am not interested in a plan?

ChatterBoss support plans are ideal for consistency and multiple areas of support. We provide an hourly alternative option for entrepreneurs interested in a single area of support or short-term, one-off projects. The hourly option requires a 5-hour per month minimum.

How do assistants keep track of time?

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

Does ChatterBoss offer an Affiliate Partner Program?

Yes! We are proud to have grown organically over the last seven plus years because our clients continue to recommend us to their friends, colleagues and networks. Our affiliate partnership program includes a $150 payout for each new client that you refer to us. If you’re interested in becoming a partner, sign up in Rewardful directly here to track your referrals and payouts.

Does ChatterBoss service clients outside of the US?

Yes, ChatterBoss is happy to work with clients based outside of the United States. Most of our assistant team is US-based, so please be aware assistants are available within US time zones. We suggest discussing any time zone considerations during our consultation call to ensure we can find the right match for you.

Do you have access to my credit card information?

When payment information is provided through the ChatterBoss app, we partner with a third-party payment processor, Stripe, 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 we take extensive measures to ensure you're always protected. Our team of assistants have all signed confidentiality contracts and are provided with data security best practices. Should you request additional protection for your business, you can request for your assistant to sign a company-specific NDA and we recommend having your legal counsel draft an agreement that covers your specific needs.

How does ChatterBoss ensure that my private information is not
lost or leaked?

At ChatterBoss, we make data security a top priority and provide ongoing guidance to both clients and assistants to ensure private information stays protected. We encourage best practices like using password managers, frequently resetting of passwords, avoiding public Wi-Fi, and keeping devices password-protected. We also advise clients and assistants to openly discuss expectations around safeguarding sensitive information. While we cannot guarantee perfection, our focus on education and open communication promotes doing everything reasonably possible to prevent loss or leaks.

What can I expect during the consultation call?

In your initial consultation, we will get to know more about you, your business, and your pain points that are taking away from your “zone of genius”. This call will introduce you to our model, and pricing, and we will answer any questions you may have regarding ideal pairing with your fractional executive assistant team.

What is the breakdown of hours between the Executive and Admin assistants in the different packages?

Through carefully reviewing years of client success patterns, we've structured our package offerings to focus on consistency, accountability, and cost-effectiveness. Each package level includes a set number of hours between two assistants– your executive and admin.  This optimal combination of an executive assistant and admin assistant team ensures your needs are met efficiently and effectively while enforcing knowledge transfer and continuity.

You benefit from your executive assistant’s subject matter expertise, strategic insights, and ability to address complex issues proactively. Simultaneously, your admin assistant provides tested process and recurring support under the mentorship, allowing for a more cost-effective solution without compromising quality.

You can view our pricing page to learn more about the package options and breakdown.