Valerie Trapunsky


ChatterBoss is the brainchild of Valerie Trapunsky, who founded the company in 2017 after a decade spent working as a top-level assistant for A-list celebrities and as the Chief of Staff for high-net-worth individuals and CEOs. During that time, Valerie developed a passion for effective problem-solving, and became committed to bringing the same level of excellent service to solo entrepreneurs, business owners, and executives ready to scale.

At ChatterBoss, we strive to solve customer needs through a combination of intelligent technology, intelligent systems, and most importantly, intelligent people. Together, the whole team has built a product that clients can trust to deliver personalized, reliable, and thoughtful service.

We have been working hard to change the landscape of what relationships between entrepreneurs and VA’s look like. Previously, it has been common for assistants to be thought of as just task doers. In our case, our assistants are thought partners, dedicated in the success of our client’s business. Getting to this place required a lot of focus and work on our culture, as our product is our PEOPLE.

Our core values (which have been co-created by our teams) really sum up who we are in terms of our culture:

  • We Do The Right Thing: We are fierce advocates for what is fair, in the best interest of our people (clients, partners, employees, contractors) even when no one is looking.
  • We Take The Lead: We are passionate thought partners committed to finding holistic solutions with confidence and humility.
  • We Care: We are empathetic listeners deeply invested in the relationships and success of our community

Valerie has appeared on numerous podcasts, webinars, and is always open to making a new connection!


  • How to communicate to achieve success with your teams
  • Hiring the right person for the right job + the future of hiring
  • How to show your team you appreciate them
  • The power of focusing in on your zone of genius
  • How to save time, meet your financial goals, and avoid burnout
  • Creating “whitespace” + the impact of it
  • The Work/Life Balance and personal joy
  • The art of delegation, how to over-communicate in a remote world to achieve success with your teams


  • How to create whitespace for yourself as an entrepreneur
  • How to troubleshoot miscommunication
  • How to show your team that you appreciate them
  • ´╗┐First time delegation techniques

Interested in this guest? Drop your info below!