Exploring Life & Business with Scarlett Ross of WillowTree Virtual Assistants

Today we’d like to introduce you to Scarlett Ross.

Hi Scarlett, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
WillowTree Virtual Assistants started as a way to use my unique skills to create ease in the world both at home and at work. I enjoyed the challenge of learning new processes or software as my clients’ needs increased. I started working with selected clients part-time, but as our relationships grew, so did our businesses. The increase in hours was great, and I realized I might need help. While I was having fun solving problems and making things happen, it was important to me to keep my own flexibility.

I’ve always been a teacher and working in an administrative role, I saw an opportunity to help my clients and to build up other people. I wanted to build a company that reflected my vision of creating collaborative success, community focused work, and an inclusive workplace. I started taking on assistants who needed skills, schedule flexibility, or work experience. As part of their work with WillowTree, these assistants learned on the job and through special training with me. I enjoyed teaching and the assistants provided great service for my clients. I loved that these really dynamic needs between clients and assistants could work together and make everyone stronger in the end.

As my clients have grown, so has my team and my company. We worked hard through the pandemic when the rest of the world suddenly joined us in working from home. Today there’s a small, dedicated team and we support each other by encouraging new talents and experiences. We work mostly with mental health providers, continuing education providers, and solopreneurs. I choose to work with these groups because they share my commitment to dynamic, diverse, inclusive, and balanced work – and because what they do in the world matters.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
The road has been interesting and not always smooth. I was very lucky to have a friend and fellow virtual assistant guide me for the first couple of years. I learned the reality of being in charge of everything as well as being self-motivated (even in the mornings). What started as a flexible way to use my skills became a real business with real stakes when I went from part-time to full-time. Learning to trust myself and my instincts was its own challenge and a leap I made with determination.

Running a business has financial complexity, and as a contractor the ebbs and flows of client work forced me to understand how to survive slim times. Things like managing taxes, irregular income, and prioritizing among clients kept me researching systems to customize my work and my client relationships. I decided early that my assistants would get a heads-up on these challenges. I talked openly with my team about the financial realities of contract work. This was important because I believe in building a workplace that actually takes care of people.

Two things changed for me over the last 15 years that helped me evaluate the road and make it work for my needs. I navigate life with chronic illness and my days have opened up with less demand from my family. Chronic illness was definitely a bump, but it’s taught me about what’s valuable in work and work relationships. I learned to manage my own energy as well as looking at my assistants with a thoughtful approach to task management. My family changes meant more time to focus on my work load, which smoothed out my schedule. Between them they taught me to build systems that are flexible and sustainable.

The best way to find the smooth road is to constantly show up and be ready to navigate and build it.

Thanks – so what else should our readers know about WillowTree Virtual Assistants?
WillowTree Virtual Assistants is a small, queer-owned virtual assistant business based in the Atlanta area. Our clients are all over the world. We work behind the scenes so that therapists, continuing education providers, and solopreneurs can focus on the work only they can do. We take the to-do list and collaborate to get things done.

We specialize in administrative support, program coordination, scheduling, client communications, and the kind of organized, thoughtful systems that keep a small business running smoothly. Our clients tend to be values-driven — people doing meaningful work in mental health, education, and community — and we show up for them as a real partner, not just a task-taker.

What sets us apart is simple: we operate based on the needs of the client, not a cookie-cutter experience. Our team is built around flexibility, lived experience, and genuine care. Many of our clients are solopreneurs who have never had support before and aren’t sure they can afford help. We built our Gentle Start package specifically for them — a low-barrier, three-month onboarding experience designed to show what’s possible when you don’t have to do everything alone.

What I’m most proud of is the culture we’ve built where our small team learns together, supports each other, and brings real warmth to every client relationship. Our culture honors the center of that need for clients are tired but driven.

If there’s one thing I want readers to know, it’s this: if you’ve ever thought “I could really use some help but I don’t know where to start,” then you’ve got a place to start now.

Any big plans?
WillowTree is in a growth season and I’m very excited! We’re actively expanding our client base — particularly among therapists, sex therapists, and continuing education providers who need consistent, values-aligned support. We recently launched our Gentle Start package as a way to specifically lower the barrier for solopreneurs who’ve never worked with a VA. We’ve seen people light up at the idea that they don’t have to do everything alone, and I love that.

I’m also looking forward to creating partnerships with other entrepreneurs and professional educators in the Atlanta area. We’ve already made some connections, but growth is coming. Collaboration is at the core of how we work. I believe we’re all stronger when we’re building together rather than alone. The collaboration between a VA and the client is essential and to help that relationship we’re planning an introduction program for how to work with a VA. The hope is that clients get up to speed with less stress.

On a personal level, I’m looking forward to growing my team’s skills so that clients get the kind of attentive, trained, personal support that makes us stand out. Every time an assistant on my team thrives, our clients feel it and they grow too.

In the future, WillowTree Virtual Assistants will be looking for ways to advocate for workers that do not fit the traditional 9-5 idea. Our world constantly changes and our ideas of who is valuable as a worker should too.

Pricing:

• Gentle Start package – $500 for 3 months, support calls, onboarding experience
• Packages scale with your needs
• Primary assistant plus a back-up assistant; no dropped balls when vacation happens
• Tier pricing from 10 hrs/mo ($415) to 130 hrs/mo ($5,000)
• Custom packages and non-profit discounts available

Contact Info:

• Website: https://www.willowtreeva.com
• Instagram: https://www.instagram.com/willowtree_va/?hl=en
• Facebook: https://www.facebook.com/WillowTreeVA
• LinkedIn: https://www.linkedin.com/company/willow-tree-virtual-assistants/?viewAsMember=true