The Trusty Oak Blog

3 Questions to Ignite Business Growth

As we head swiftly into Q4 and our third year of business at Trusty Oak, I’m feeling a strong urgency to take a pause and evaluate some of our successes and failures so we can keep the positive momentum-swinging as we enter 2018. We’re identifying the strategies that are working, moving some back-burner projects to the front, and dropping some systems that haven’t served us well or that we’ve outgrown.

This process of evaluation has been insightful and exciting, and in this, I’m reflecting on some sizable changes we made (or are in the process of making) that are both contributing to and helping us manage business growth. In order to grow, things must change. We have to be willing to make a constant choice to change the way we work and think, or we risk being left behind.

Asking ourselves these three questions changed how we are operating and growing our business, and (hopefully!) also prepares our team to sustain continuous business growth.

Are the tools and software programs you use daily still serving your needs?

As a completely virtual team, we depend heavily on technology and software programs for nearly everything we do. We use G Suite, Slack, Trello, Quickbooks, PayPal, Zoom, Canva, Passpack, MyHours, Hubspot, etc., etc. This list goes on for a while, especially when we look at the various tools we also learn and use for our clients. Even though most of these tools serve a basic need and nothing more, it’s worth taking some time to review how well they are handling the day-to-day workflow.

Pain Point #1

Through this review, we identified that our time-tracking software is slowing us down and we need to completely change programs.

When we had just a few virtual assistants and a few clients, the system we were using was working well. We were able to organize it in a way that made sense to everyone. The basic features we needed were there and we had figured out a workaround using a Google Sheet to make up for a missing budgeting feature.

Trusty Oak Grove Map.png

Then we doubled our staff and our client base. Even though we were archiving some clients and projects in the system, overall the data (lists of projects and accidental duplicate names, etc.) in the system was getting sort of overwhelming. The Google Sheet was rudimentary and scaling it to work for 15+ users has been challenging.

With so many people using the program in their own way, things got messy. Plus, when I trained new assistants on the tool, I heard myself apologizing time after time that it was clunky and that I knew we needed to find a better way of doing things, but we just kept improvising with what we had.

I had to embrace the idea of changing software altogether, and I knew I had to do it fast. It will only be harder as we continue to grow, so we started the search for an awesome time-tracking program that had all of the features (including budgeting!) and have just landed on a decision to make the change.

Key Takeaway #1

In the moment, it’s easier to stick with what is familiar, but in the long run it will be worth shaking things up, working extra to manage the change carefully, and then go all in with a new thing.

Is your lead generation strategy still working?

When I started the company in August 2015, one of the very first places I put my money, time and energy was in joining a referral network. I was spending 8-10 hours per week networking, and driving to meetings. Many of these meetings were casual “get-to-know-each-other” meetings, and oftentimes they were meetings with people that someone else I knew set me up with. I’ve never been on a blind date, but I’d imagine it couldn’t be that different than many of these engagements with referrals. It felt a lot like playing the lottery – I bought a ticket with a glimmer of hope in my heart, but I never got disappointed if I didn’t walk out with a deal.


It wasn’t a bad way for me to gain exposure and get practice at pitching what we do. I certainly learned a lot from other more seasoned business owners and even made some new friends that I had a lot in common with. But after doing this for a year, I felt discouraged with the amount of energy and time I was devoting to conversations that were not affecting our revenue.

Pain Point #2

We were working way too hard for lower quality leads and our reach was limited to my own physical proximity. 

A personal goal of mine is to run my business in a way that does not tie me to a specific physical location. (It’s a virtual business, after all!) I also wanted to develop a sales process that I could easily duplicate as I added new team members who are interested in working on business development. In-person networking was not something we could expect from people who chose to be a VA so they could work from home.

So we shifted.

Amber working in Mexico

(Me on a video conference call while in Mexico!)

Instead of spending the bulk of our time and money on referral networking, we invested in online marketing software, advertising, and online tools to help us conduct business by phone or video conference. We collaborated to develop templates and workflows that we could easily duplicate and share across our team. We continue to work on creating engaging, helpful content for our clients and prospective clients. We research, experiment, and track.

Key Takeaway #2

With this change, we not only are seeing an increase in sales, but we’re also providing a better experience for our team, our clients, and anyone else that interacts with our brand. It’s targeted and planned, and at the end of the day, it’s much more rewarding knowing that our hard work is producing the results we want.

Do you have a hiring strategy to sustain your pace of business growth?

To this day, word-of-mouth referrals are the primary source for finding talented, professional virtual assistants to join our team. Many of our current team members know each other or knew me before I started the company. A large portion of the US workforce dreams of remote work, so there has never been a shortage of interest in working as a virtual assistant. We receive applications via our website on a weekly basis, even when we are not actively hiring. Awesome, right? Not completely.

Pain Point #3

The problem was that I couldn’t respond to everyone in a reasonable timeframe – many excited, qualified applicants were getting ignored and losing interest. Not only does that reflect negatively on our business, but it also resulted in stellar candidates getting hired somewhere else.

Additionally, when I did need to hire someone (and fast!) my calendar would be filled for two weeks straight with reviewing resumes, conducting interviews, and contacting references. We had to come up with a tracking system and a checklist that included reviewing every application and responding to every person that applied.

Many applicants for open positions didn’t hear back from us and we were missing out on hiring some serious talent.

We figured out a way to use our CRM to manage the applicant pipeline and keep track of every application that comes in. Instead of waiting until we need to hire, we’re vetting candidates and keeping notes so we can even more accurately match assistants up with business owners quickly and confidently. 

Another important factor in this change was that I began to practice delegation and lean on the experience and leadership skills within our current team. Getting some help and another perspective on candidates puts us in a better position to make solid hiring choices.

Key Takeaway #3

By creating a strategic plan for hiring, we balanced out our workload and created some space to help us ensure we were making the best possible hiring choices.

One thing I’ve learned above all else in my experience of starting a business is that no one does it big on their own. I have learned so much from other entrepreneurs and mentors along the way, so I would love to hear from you!

What decisions are you making to support business growth for your company? Let’s talk.


Amber Gray

Amber Gray is the founder and CEO of Trusty Oak, an Austin-based virtual assistant company providing administrative and marketing support to small business leaders, authors, and creative teams. A people-first approach to hiring, along with a scalable growth model have positioned Trusty Oak as a flexible, dependable, and affordable alternative to hiring administrative and marketing employees. In 2021 and 2022, Trusty Oak was named Freelancer Hiring Platform of the Year, and in 2021 Amber was recognized as Austin Business Woman of the Year.

Before founding Trusty Oak, Amber spent five years at a rapidly growing digital agency based in Austin, TX. Four of those years, she was responsible for hiring and leading both local and virtual teams while working closely with clients ranging from CEOs to bestselling authors to build their brand online. As VP of Operations, Amber helped lead the company’s growth to #15 on Austin Business Journal’s Fast50 List in 2014.

As a female founder and leader of a company that has quickly established a recognizably special culture within a non-traditional workforce, Amber has energized and empowered women from diverse professional and personal backgrounds to go against the grain of historically standard female roles in business, technology, and leadership. Trusty Oak provides an opportunity for experienced admin and marketing professionals to work independently as freelancers, but with a supportive internal network consisting of other ambitious and resourceful remote workers.

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