Personalized pairing, guided onboarding

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.

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.

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.

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.

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.

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.

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.

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.

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.

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 clientsuccess@chatterboss.com. Our tech support team is also available Monday-Friday 9 am - 5 pm EST. You may reach out to tech support at assistant@chatterboss.com.

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.

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.

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?

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 finance@chatterboss.com.

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.

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.