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Valerie Trapunsky
CEO
Ready to get things off your plate?
We can help you strategize your most pressing needs.
ChatterBoss fractional executive assistants help you run your business and personal life more efficiently.
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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.
Follow these 7 easy steps and you’ll be up and running in no time:
Sign up here on our website or download the ChatterBoss Android or iOS mobile app to sign up from your phone.
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.
Onboarding call with Client Success Team for strategy, roadmap development and custom pairing.
Schedule a one-hour Kick-Off Call with your executive assistant.
Your assistant will guide you on handing off your first few tasks.
Get started on the 30-60-90-day roadmap your ChatterBoss executive assistant has devised for you.
Start achieving your business objectives!
Below are just a few examples of tasks that your ChatterBoss executive assistant can help you with:
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Here’s what you can expect when you sign up with ChatterBoss:
Let our team of best-in-class remote assistants help you take your business to the next level!
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!
At ChatterBoss, we are virtual executive assistant experts. We bring top-tier US-based support that A-listers enjoy to high performers, business owners, and entrepreneurs.
Our 200+ Dedicated Assistants are located throughout the US to ensure that we provide the highest level of support for entrepreneurs who are located in the US or whose business is in the US. Meanwhile, the majority of our backup assistants are located in South Africa, to support with low-intensity process fulfillment. This unique combined offering allows ChatterBoss to provide a primary US-based assistant, with affordable and dependable backup support.
Simply put, having a Dedicated Assistant gives you peace of mind, dependability, and the benefit of a team member who learns your business, workstyle, and preferences over time. Furthermore, at ChatterBoss we believe that it takes a dedicated two-assistant team to get the full benefit of the support. What does this look like?
You will be carefully paired to a US-based Dedicated Assistant based on your unique set of needs, personality, industry, and budget. In addition, you will get back-up support to provide lower-cost, admin-level support and continuity when your primary assistant is away. The goal is for your assistant team to integrate into your business and become true members of your team.
At times when your Dedicated Assistant is unavailable, backup support can be provided by your admin-level support assistant, or if necessary, it can be arranged for another Dedicated Assistant to step in temporarily if specific skills are required. To take advantage of the seamless transfer of responsibilities, your monthly review and updates of SOPs are highly encouraged to ensure all processes are up-to-date, documented, and understood by you and your Dedicated Assistant.
Yes! We have experts that span many different skills and industries. Your Dedicated Assistant will be a professional executive assistant 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 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. The character assessment is taken by all of our assistants 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 up to 5 business days to collect all of the information shared in the onboarding, outline the roadmap, and identify the best fit. If a unique pairing requires more time, we will reach out with an updated timeline.
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 Dedicated 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.
Unlimited access to your dedicated Relationship Manager is included as part of your onboarding fee. This means we are here for you to support you with things like growth, delegation coaching, and troubleshooting. The Relationship Manager team is available Monday - Friday 9 am - 5 pm EST and will respond to all of your communication within 1 business day. 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.
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 Dedicated 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.
Our Relationship Managers are here to guide you and your assistant to a successful relationship. Part of your ChatterBoss support includes unlimited access to our Relationship Manager 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.
ChatterBoss has a one-time onboarding fee of $499. This includes a customized onboarding strategy session to identify your 90-day roadmap to success, a dedicated Relationship Manager, a handpicked pairing to your Dedicated Assistant using science-backed character assessment and analysis, and customized delegation coaching.
The character assessment and interpretation are explained in the earlier question What is the process to be paired with my assistant?
Outside of the onboarding fee, you decide how much you want to spend with your ChatterBoss assistant. 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.
ChatterBoss has a 5-hour monthly minimum commitment to get started. However, we recommend starting with 5 hours per week in order to provide high-quality dedicated support and tangible results and to allow for consistent delegation. On average the client who sees the best results uses anywhere from 5 to 20 hours per week.
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.
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 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. Please note, that for any Monday that is a federal holiday, billing will happen the next business day.
We are committed to long-term relationships, and one way we aim to accomplish that is through our subscription product offering. While our model gives you access to your Dedicated Assistant with the flexibility of working as much as you need, our subscription packages with volume-based discounts create an opportunity for higher discounts based on your consistent needs. Schedule time with our Director of Client Success to learn more about subscriptions and whether it may be the right fit for you.
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.
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.
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.
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.
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 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.
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”. In this half-hour Zoom session, we will discuss the pairing process and how we can find you your ideal match in terms of a virtual executive assistant. This call will go over our model, the pricing, and onboarding fees, as well as answer any questions you may have in regard to bringing on an assistant to support you and your business.
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