Become a VA

Virtual Assistant Careers at Trusty Oak

Ready to join a team of rockstars as an independent, freelance virtual assistant?

We’re glad you are considering a career as a virtual assistant, and we hope you will take a closer look at joining the Trusty Oak team. Being a VA has both challenges and rewards, and here at Trusty Oak, we strive to make the rewards outweigh the challenges by providing our team with everything needed to be successful.

Our VAs are independent freelancers, so they make their own schedules and choose which projects they want to take on. It’s a pretty sweet gig, perfect for individuals with a professional background who want a flexible alternative to traditional employment.

Watch the video to meet some of our VAs

Our Application Process


  • Apply and submit your video introduction
  • Complete a Zoom screening


  • Complete an admin or marketing assessment
  • Complete a Zoom interview


  • Background screening and contract
  • Trusty Oak starts promoting you
  • Land your 1st client

We’ll be honest—our vetting process can be strenuous.

We mean it when we say we’re rounding up the best virtual assistants in the country and matching them up with motivated entrepreneurs. We offer spots on our tight-knit team when they become available.

We often accept applications even when positions aren’t open immediately to make sure we’re always poised to meet client demand, and we keep in touch with you throughout the entire selection process.

Benefits of Joining Trusty Oak

We have a team of experienced assistants who have skills ranging from data-entry and bookkeeping to writing and marketing so we are able to pair up our clients with a perfect assistant for their business.

  • A brand that is a trusted, reliable resource for business owners seeking assistance

  • Access to software programs such as Canva Pro, Grammarly, HubSpot Meetings and CRM, and more

  • One-to-one professional development and mentoring to help VAs succeed as freelancers

  • A personal page on the Trusty Oak website each VA can use to promote themselves

  • Free professional development opportunities and resources

  • Camaraderie with other like-minded, hard-working people

  • Competitive pay and the opportunity to earn commissions

  • Targeted outreach and digital promotion for each freelancer to get to their ideal workload and ideal clients fast

  • Weekly direct deposit paychecks

Minimum Requirements to Apply

  • At least two years of experience as an executive assistant, project manager, office manager or similar role
  • A nerdy obsession with getting the details right the first time
  • A dependable computer (Mac or PC) with Microsoft Office
  • Access to high-speed internet and a dependable phone
  • A work environment conducive to working distraction-free
  • A desire to build a business as a virtual assistant (30 hours per week) without doing it alone
  • A commitment to never, ever “ghosting” a client or Trusty Oak — a cornerstone of the Trusty Oak difference
  • A positive attitude during challenging situations

Experience we’re looking for

We’re looking for assistants with experience in:

  • Marketing

  • Project management

  • Social Media

  • Managing calendars

  • Content Writing

  • Quickbooks

  • Email Marketing

  • Customer Relationship Management software

Advanced experience that can be beneficial:

  • Graphic Design

  • Advanced Excel

  • Ghostwriting

  • Bookkeeping

  • Web Design

  • WordPress and Squarespace