The Trusty Oak Blog

Trusty Oak By the Numbers: Celebrating 7 Years in Business

VA Map

It’s one thing to simply connect entrepreneurs with freelancers. That’s the basics of what we do here at Trusty Oak, and have been doing now for seven years. But our team takes it much further, developing a values-based culture, a strong network of interconnected, collaborative virtual assistants, and a commitment to transparency and accountability.

Trusty Oak’s motto is “keep growing,” and we’re celebrating seven years of that motto coming to life this month. Our support has helped hundreds of entrepreneurs become empowered leaders, better delegators, and more successful business owners.

Giving Small Businesses the Tools to Succeed

For the past year, we’ve been working hard to better support small business owners and entrepreneurs’ with an improved matching process and more education and connection. We started holding monthly public workshops to teach how to best work with a Virtual Assistant and show how a virtual assistant can be a smart investment for a small business owner. We also launched our Trusty Oak Academy – a new platform to house educational content catered to the needs of our clients – and we have big plans for future courses

Our Client Success team has done a tremendous amount of work creating a new Client Success playbook, and rethinking how to provide support to growing small businesses.  

Trusty Oak prides itself on its goldilocks approach to matching small businesses and entrepreneurs with a virtual assistant.  On one extreme, some platforms ask exhausted small business owners to do the work of vetting and hiring themselves, reading through work samples, resumes, and reviews for hours before trying someone out; the other extreme matches within minutes of applying or lets users “try out” a random assistant for free for a period of time. Both these approaches fall short of a great long-term relationship with a virtual assistant.  

Our extensive experience shows that the key to success is relationships – relationships with our clients and with our virtual assistants.  We partner with small business owners to help ensure they match with a virtual assistant who will not only ease the work of the everyday, but grow with them long term as they build their business. 

This is why our Client Success team takes care to truly learn the needs of our clients, asking not only about the tasks they’d like to offload, but also about their work style, communication habits, challenges, and goals. We take the results of this questionnaire and use it to find the perfect-fit VA. 

While the entrepreneur has filled out a simple questionnaire to get started, the behind-the-scenes work is where the true magic of our platform happens. Here’s what we mean: 

  • The best of the best virtual assistants: Each VA who joins our team is strenuously vetted with assessments and interviews. Our vetting process takes weeks and whittles down hundreds of applicants to only a few qualified candidates. Only the best are given a coveted spot on our highly-connected team.
  • Team approach: When you hire a Trusty Oak VA, you get a team. This is the Trusty Oak difference that has become so many entrepreneurs’ secret superpower: their VA is their ticket to a pool of qualified freelance rock stars who can help as their needs evolve and scale. Many of our clients start with one VA and expand quickly as they realize the potential for more help, better outcomes, and faster scalability. 
  • A culture of growth: Trusty Oak believes in values-based leadership, which means we are committed to collaboration, transparency, and follow-through. Our unique virtual assistant mentorship program helps us ensure we’re staying true to our values in every interaction with our clients. 

Trusty Oak in the News 2022

Welcoming New Team Members

This year, we’ve welcomed several new team members, promoted others, and built the corporate team to help us better support our Virtual Assistants and Clients. We have hired 38 new virtual assistants this year and three new employees. Welcome to the Treehouse! 

New Team Members: 

  • Kristine Rego – Client Success Coordinator
  • Ana Pardick – Client Success Assistant
  • Annika Kalac – Social Media Coordinator and Graphic Designer
  • Jamie Williams – Executive Support Specialist 


  • Maribeth Fura – Director of Culture and Learning 
  • Bex Howell – Director of Client Success 

23,846 and counting: 

The number of hours Trusty Oak virtual assistants saved their clients this year so far

108 and counting:

Entrepreneurs currently being rescued from small-business burnout by their virtual assistants

64 and counting:

The number of virtual assistants currently redefining work/life balance and doing what they love with Trusty Oak


The average number of hours our clients save each month by delegating

A Message From Our CEO, Amber Gray

Trusty Oak is seven years old this month, and I love to get a bit nostalgic when celebrating anniversaries. I will always remember and thank the early, more humbling years for teaching me patience and fortitude and showing me that I can do hard things. Today, I am enjoying celebrating continued personal and organizational growth and the opportunity to impact even more people. 

We have over 73 teammates in 25 US states, more than a hundred inspiring clients across the country, and dozens of our colleagues and peers collaborating with us and cheering us on. We are better together, and our network just keeps growing and getting stronger. Some years have bigger challenges than others, but each year has gifted us with the opportunity to level up as human beings and as an organization.

In 2021, we defined our company’s core purpose:

Purpose-fulfilled people change the world.

In 2022, we landed on a powerful Big Hairy Audacious Goal (BHAG) which has provided us with a renewed vision for the incredible legacy we want to create together.

Trusty Oak’s BHAG is to:

Contribute to the sustainable growth of every small business through education and connection.

And that’s why we host monthly educational webinars for our VAs and entrepreneurs, and we are launching Trusty Oak Academy in Q3 2022. 

We want to see the success rate for small businesses and freelancers increase significantly and we believe that virtual assistants, effective delegation, and high-trust relationships are the key to seeing this shift

Yes, we are a virtual assistant company, but we are not just a virtual assistant company. We’re here for the longrun and we do this because we want to change the world – one small business owner at a time! Freelancers, solopreneurs, entrepreneurs, startup founders, authors, and creatives – we invite you to join us on this incredible journey. 

Let’s #keepgrowing together,



Maribeth Fura

After graduating with a B.S. in English Education, Maribeth Fura started her career in Human Resources focusing on Training and Organizational Development. She spent 13 years at a fast-growing and competitive manufacturing organization and learned the importance of hiring great people to build a successful business. She is the gatekeeper of Virtual Assistants at Trusty Oak and is committed to hiring top talent to serve our clients. Maribeth loves helping people grow and watching organizations succeed because of their amazing people. She is passionate about designing straightforward and sustainable business processes and believes that organizations excel when communication is clear and simple. Maribeth resides in State College, Pennsylvania and loves going on adventures with her husband Scott and their three young children. She spends her free time cooking, camping, reading, making fun mixed drinks, discussing the merits of the Oxford comma, and starting new DIY projects on her mid-century modern home.

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