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From Executive Virtual Assistant to CEO: How Sadie Prestridge Built a VA Agency in Three Months

Case Study

From Executive Virtual Assistant to CEO: How Sadie Prestridge Built a VA Agency in Three Months

Sadie Prestridge left her corporate job as an executive assistant team lead and transitioned to online executive virtual assistance in 2018. Very soon after this career shift however, she was able to generate such great demand for her services she decided to seize the opportunity to set up an agency. Let’s take a look at how Prestridge and Co. was built in such a short time frame, the unique challenges encountered along the way and how Prestridge managed them. Don’t forget to check out the end with a summary of Prestridge’s Productivity Stack Quick Reference and her Watch-Listen List!

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Challenge 1: From Corporate Executive Assistant Team Lead to Virtual Assistant –  How to choose a niche

Prestridge’s goals when she left her corporate job were fairly simple. She wanted to stay at home while still contributing to her family’s finances.  “My plan was to pay my mortgage and be at home.” 

She started working as a virtual assistant (VA) in 2018 with no idea what niche she wanted to focus on. She offered any services that people would pay for such as making graphics and managing Pinterest boards as a general VA. She didn’t realize what she did in her corporate job is also sorely needed in the online world. 

Solution: A Facebook job posting for an executive VA (EVA) was the flash of inspiration she needed. “When I read it, it just felt like exactly who I was meant to work with and what I wanted to do.” 

Prestridge sent a video application, had a great interview and got the job in late 2018. This became her first big client, a high-level business coach in need of executive virtual assistance. By 2019 she was able to release her general VA clients and fully step into the EVA niche.  

What is the difference between a general VA and an EVA? Prestridge describes an EVA as a right hand person, a forward thinker who can anticipate the needs of the CEO and step in to take care of them. The EVA asks “How can I support you and take things off your plate so you can be the CEO and stay in your zone of genius?”

Prestridge contrasts this with a general VA who would be very task focused and will rely on instructions on what needs to be done. An online business manager (OBM) on the other hand, focuses on higher strategic matters like financial forecasting, hiring and organizing work charts. “So the EVA manages the CEO, while the OBM manages the business.” 

People: Prestridge, first big client/business coach

Systems: Online freelancing – looking for and applying to VA job opportunities online

Tools: Asana, Slack, Graphics software like Canva, Pinterest, Facebook, Loom or other video software to submit her application to first big client

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Challenge 2: How to keep a solopreneur business running while taking a maternity leave

Through referrals from her first big client, and her own networking and marketing, Prestridge was soon fully booked. She had 6 retainer EVA clients and was very comfortable with where she was. “I had no thoughts of setting up an agency or anything. I had thought about doing a little bit of coaching. But then I got pregnant in the fall of 2019.” 

She didn’t want to release any of her clients but had to figure out how to take a maternity leave and then have time with the baby when she went back to working with her clients.

Solution: Through the suggestion of her business coach client, she hired one EVA to handle all of her client work in the months leading up to and during her maternity leave. Prestridge made her first hire in January 2020, and trained her for four months before stepping back. She assigned tasks on Asana, made detailed loom videos for each task, reviewed the work and wrote up standard operating procedures (SOPs) as they went along. She also had the new EVA sit in on all her client calls.

By April, one month before she was due to deliver, she fully handed over all tasks and observed how work flowed without her. From there, she made more adjustments to their process.“I kind of tweaked and did a lot of Loom video trainings and separate calls with her just to make sure that everything was going well and feeling really good for both parties” 

People: Prestridge, her business coach client, one EVA 

Systems: Intensive training and handover to newly hired EVA

Tools: Asana, Loom, Slack, Voxer, Dubsado, Google Chrome, Google Calendar, SOPs

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Challenge 3: Too many referrals – Stay a solopreneur or scale up?

When Prestridge hired one EVA at the start of 2020, there was no commitment to building out a full agency. The conversation with her business coach was “Let’s hire one person, have them support these clients while you’re on your leave, and then let’s decide what you want to do after that.” 

But by June 2020, just a month into her maternity leave, she already had a lot more referrals. COVID had pushed a lot of businesses online that needed the support of skilled EVAs. Prestridge faced the dilemma of going back to her solopreneur set up or to continue the mini-agency to serve more clients.

Solution: Prestridge said ‘yes’ to the challenge of taking on more clients and just figured it out along the way. “We went from that team of one to a team of 6 by August of 2020.” And so Prestridge and Co. was born.

People: Prestridge, additional EVAs to build a team of 6

Systems: Self-belief in her abilities to level up to the next stage. This no doubt was affirmed by the high demand for her services, in the midst of the COVID lockdown, while she was away on maternity leave!

Tools: Asana, Loom, Slack, Voxer, Dubsado, Google Chrome, Google Calendar, SOPs

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Scaling & Success

Challenge 4: How to build an agency in 3 months

Juggling the challenges of having a newborn baby and a newborn business was a stressful time. The agency had quickly grown into a 6-figure business, but they had no systems or processes in place. Her EVAs were overwhelmed and clients were not happy. 

Solution: Prestridge dove into creating the systems and training that were needed to support her team of EVAs and enable them to serve clients better. “Because I am very systems-focused, I thought about how I could do that without me training each individual VA.” 

She created training courses covering the whole range of tasks the EVAs need to perform with and for clients – from how to lead a client on their client calls and how to communicate on Slack to how to put your to-dos in Asana. She prepared similar training material for the clients too, including SOPs and Loom video trainings to smooth out onboarding and interfacing between the EVAs and clients. 

People: Prestridge, her team of EVAs, one tech EVA

Systems: Documentation of SOPs, scaling up training by shifting from one-on-one approach to creation of training courses

Tools: Asana, Loom, Slack, Voxer, Dubsado, Google Chrome, Google Calendar, Zapier, SOPs

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Challenge 5: How to set up EVAs and clients for a successful, systematized experience 

As she built and ironed out processes within the agency, Prestridge realized clients themselves did not have properly set up or documented systems and processes. “I could train the VA really well and teach them how to use all these systems. But these clients were coming to us without their own systems and processes.” This added to the friction in onboarding and getting to that optimal point of collaboration between client and their EVA. 

Solution: Prestridge changed the way she worked with clients. Instead of simply assigning them fully trained EVAs who are left to figure things out by themselves, she included a process of first setting up a system for how the client is going to work with their incoming EVA. This streamlined and organized the whole onboarding process by first getting a clear understanding of how the client’s business works and then how and where the EVA can come in and best provide support.  

The client system and process audit also includes a review and analysis of their other software or system needs, recommendations and cost analysis. When client systems are fully set up, then the fully trained EVA’s can step in. Meanwhile Prestridge continues to provide support to the EVA on the back end.

People: Prestridge, her team of EVAs, one tech EVA

Systems: Systems audits, doing pre-work with clients before they onboard their EVA

Tools: Asana, Loom, Slack, Voxer, Dubsado, Google Chrome, Google Calendar, Zapier, SOPs

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Challenge 6: How to hire and train EVAs, and ensure the right workload 

With the success of her agency primarily resting on how well her EVAs performed, Prestridge needed to ensure the right fit when hiring and continuous training to maintain their high standard of service. She also needed to ensure proper workload management because each EVA handled multiple clients. Some in fact had their own one or two personal clients (not through Prestridge and Co. agency), so managing their assignments is necessary for sustainability.

Solution: Prestridge laid out a clear hiring policy: they hire only experienced EVAs (at least 6 months) who are detail oriented, can work with systems, and are willing to learn and grow. They supplement with comprehensive in-house training – ranging from productivity strategies, to the use of Chrome profiles, setting up ideal schedules in Google calendar, how to set up, and manage inboxes, file and organize things. “We go piece by piece on that front because they need to be able to do that for their clients.” 

In terms of workload management, Prestridge limits agency-assigned clients to 3 to 4 per EVA. She makes sure each EVA has a good mix of low, medium and high-needs clients so they aren’t overwhelmed. 

She highlights how helpful it is to assign one customized Google Chrome profile for each client. This minimizes confusion and mistakes for the EVA, and overall just makes them more efficient as bookmarks and other relevant settings are set up for each client’s profile. Working within one Google profile for each client also helps protect sensitive information and access to documents. 

People: Prestridge, her team of EVAs

Systems: Clear hiring policy, continuous training, creating training courses covering various tasks and skills EVAs need to master

Tools: Asana, Loom, Slack, Voxer, Dubsado, Google Chrome, Zapier, Google Calendar, SOPs

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Challenge 7: How to shift to a CEO mindset

Prestridge’s transition from solopreneur to agency-owner happened within a matter of months. She admits that sometimes she is tempted to jump right back into the day-to-day operations and put on her old hat as an EVA herself. But she understands that she needs to reprioritize now as CEO  – “How do I move the needle without feeling that urge to work with the clients?” 

Solution: Prestridge, with the help of a team member, created a “strong routine” for herself, or a CEO schedule that will keep her focused on managing and growing the agency instead of going back to directly work with clients. 

The daily schedule starts with checking emails and Voxer, then revs up with time for reading blogs, listening to podcasts and preparing for meetings. Next come time blocks: for marketing, systems, finance, teams. “I have all of this mapped out on my Google Calendar with descriptions of what I should be doing with each block.”

Prestridge’s EVA and OBM also help her stay focused on her CEO role when she gets distracted by client issues. They remind her, “No, ma’am, you need to go network and market.”

People: Prestridge, her VA and OBM

Systems: Time blocking, Creating and sticking to a strong routine that helps her focus on her CEO role.

Tools: Slack, Voxer, Google Calendar, Apps for listening to podcasts such as Apple Podcasts

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Challenge 8: Work-life balance: How to step away the end of the day feeling good

As a CEO and founder, Prestridge wants to avoid feeling perpetually stressed by tasks left undone or a feeling that she is not on top of things. “I know a lot of entrepreneurs, they shut down, but they don’t actually shut down. They’re stepping away, and they’re still thinking about business.”

Solution: Prestridge ends each day by doing a review of the day’s to-do lists, email, Slack and Voxer. “Did I get everything I wanted done for that day? If not, do I need to shift what’s coming up for the next day?” This end-of-day ritual allows her to end each day feeling confident that everything has been attended to and things are on track. And she doesn’t have to worry about surprises or “fires” the next day from something that was overlooked.

People: Prestridge

Systems: Daily “last minute check”, shut down ritual

Tools: Slack, Voxer, Google Calendar

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Hindsight: What Prestridge would have done differently

While she appreciates that she learned so much during that summer of 2020 when her mini-agency quickly scaled up, in hindsight, she wishes she had better systems in place, had spent more time creating systems to train the EVAs, and had known how to hire better.

“There were a lot of instances where the hire was bad, but there were other times when the hire wasn’t bad, but the training was bad. And so it was my fault that they didn’t work out. So I do wish that those pieces would have been stronger.”

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Favorite Tools

With Prestridge’s systems and productivity-focused mindset, we had to ask what other tools she recommends (or does not). In terms of e-commerce platforms, she prefers Thrivecart  to SamCart as she thinks it is easier to use. She recommends Kajabi over Teachable for selling online courses, for ease of use as well. She admits Kajabi can get expensive but it allows for a lot of integration. Last on her list of recommendations was ActiveCampaign for email marketing over MailChimp. “I have been a diehard active campaign fan since I started my business. I just feel like it has more capabilities than some of the other ones.“

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Prestridge’s skills in setting up systems and SOPs made her an outstanding Executive Assistant, and were also key to her rapidly scaling up to a full agency. Her success is also driven by her ability to take quick, decisive action and the flexibility to add or adjust processes as she learns along the way. Today, as CEO, she uses the same tools and routines her agency provides their clients so she can focus on working on, not in, the business and provide strategic direction. 

Prestridge and Co. may be a young agency, but its team of dynamic and high-level executive virtual assistants certainly have plenty of opportunity for growth especially in the ever-expanding digital economy.

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Prestridge’s Watch-Listen List

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Prestridge’s Productivity Stack Quick Reference

Starting Stack

Growing Stack

Scaling & Success Stack

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More about Sadie Prestridge

Sadie began her online business as an Executive Virtual Assistant in 2018, and now runs a team of highly-trained EVAs. In the beginning, still working her corporate job, Sadie quickly found her stride and was able to quit her full-time job only three months later.

With her client roster full, she had surpassed her previous income by June of 2019 and kept growing! Training and building up a team of highly skilled women, Sadie created Prestridge and Co. to be a leading team that knows how to support and take initiative in leveling up business operations. Prestridge and Co. provide systems, structure, and day-to-day support that helps CEOs and Founders manage themselves, their busy schedules, and their visionary companies that are changing the world.

You can find her on:



Are you wondering how an Executive VA can support you? Prestridge and Co. lists 172 ways:

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