Creating a Space for VAs to Thrive: A Case Study

Nathan Lippi on Finding and Nurturing VAs with Limitless Potential

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Nathan Lippi is the founder of, a tool that teaches agencies how to optimally use for their own business and their Clients’. 

“ is a tool that helps people do automated outbound email campaigns that normally a salesperson would have to do; but it helps you do it without a person being involved. And we train people how to use this tool in a six-week boot camp.”

How did you get started?

“I decided at some point I wanted to do my own thing and be my own boss…Eventually I landed on the idea of starting an agency. At first we had no leads…and then very suddenly, we got too many.”

Nathan realized he needed help with the influx of clients, so he turned to

“I’m very happy with the person I [hired] on, and we’re actually hiring another very soon.”

After his first hire, Nathan’s work as an agency began shifting into something new. 

“During my agency work, people start asking me, “Hey, can you teach me to do what you do?”  After saying ‘no’ many times, “it suddenly became very obvious that there was an even bigger opportunity to train people–and so we pivoted the business.” 

That’s when was born.

“There’s a lot of demand for Clay experts that can help companies set up automated outbound campaigns and if you’re interested potentially and becoming an agency owner or if you’re already an agency owner, can set your agency apart.

And can help you get there in 25% of the time that it would take you to learn skills on your own.”

What does your Filipino worker do for your business?

“…her name is Flori and she worked in Qatar for 8 years as an executive assistant. Then she moved back home to the Philippines because she wanted to spend time with her family and have a remote job. Originally I brought her in because I wanted someone to become an expert in so she could help set up more clients in the agency.”

Tell us more about your hiring process

“As part of the hiring process… I had her and other people do a test where they actually worked with and she passed with flying colors. I was very happy to hire her, taught her to become an expert in the tool, and she helped me.”

“But when we pivoted the business, suddenly I needed people to do different things. And because she was so smart and had great habits [and] a great attitude, she was able to pivot along with the business.”

What qualities do you look for when hiring?

“John Jonas has this course, ‘One Va Away’…It’s $99 and it was really worth it.”

Based on John’s advice, Nathan decided to forgo a face-to face interview, which gave him time to really consider the questions he asked and evaluate the responses he received. 

He took note that Flori’s reasoning qualities were above average. She was thoughtful and timely in her responses. Her conscientiousness also made her stand out.

 She also had a “rave review” from her former employer, which Nathan found valuable. 

“And then, at the end of the hiring process, like I mentioned, she passed the actual work test with flying colors.”

Nathan included that the right “attitude” is critical for a good hire and company fit. He specifically observed that you can tell a lot about a potential hire’s personality and attitude from their writing and response style during the interview process. 

He suggests looking out for some the following when hiring VAs: 

  • Do they get defensive when you give them feedback? 
  • Do they respond stiffly or overly formally? 
  • Do they include emojis in responses that give you a sense of their personality?
  • Do they come across as friendly?
  • Do they seem more playful or more business-like?

Different personality qualities are valuable in different work roles–staying alert to these nuances during hiring creates an advantage for the employer. While evaluating personality traits, it’s important to remember that you’ll be spending a good amount of time training and working with your new Filipino virtual worker. 

“…we’re trying to select people that are going to be effective, but also be fun to work with in our culture.”

How long has Flori been with you and how has it affected your business?

Flori has been with the business for 3-4 months and Nathan says they are “definitely seeing a lot of results.”

“When I was by myself I didn’t have anyone to take the tactical client work off my plate…Flori came in, built up the skills really quickly, and she’s able to turn around stuff probably faster than I can, to be honest. [She’s a] very focused, very hard worker, and just really analytical.”

“And because she’s able to turn around the client work, I don’t feel like I’m behind…I can trust her…and it frees me up to have time to focus on the strategy. If I hadn’t hired Flori, it’s very unlikely we would have pivoted to another business model that’s much more lucrative.”

Flori’s training has also directly impacted the trajectory of their business.

Nathan’s original objective when he hired Flori was to make her a expert. In a turn of events, came from the original training that Nathan built for Flori. 

“It was a very simple training on how to use She’s the first person I really trained on And when people started asking–‘hey, can your agency train us?’–we just built on that training and that experience that I had teaching Flori. The entire pivot of the business was based on [Flori’s original] training.

Tell us more about how you train Flori.

“…since we’re a fast-moving business, I like to meet every day for half an hour with the two people on my team.”

Nathan also makes time for weekly one-on-one meetings that last about an hour.

“Not everyone does this, but for our business, it makes sense…we talk about questions she has, her growth and so on. And she’s coming to each meeting with all these questions and she’s very eager to grow and learn.”

“I’m recommending books to her. I’m giving her feedback and advice, and also connecting her with people who can help her grow.” 

Nathan is also sure to take time during the one-on-ones to let Flori know how much he appreciates her work.

Do you have specific software that you use to communicate with your team?

  • Slack for daily communication 
  • Clickup to track tasks 
  • Google Docs to share, save and access information

What else should employers look for when hiring?

Look for a worker with great habits. “[Flori]  used to be an executive assistant; she had to develop really good habits. Even though she’s doing a different type of work, she can apply those to her current work.”

Nathan also cites the importance of looking for workers with a warm personality. “Warmth…is very important, and now I’m looking for that in every person we hire that’s going to be part of the core team.”

What can you look forward to or spend more time doing now that you have a VA?

“My wife and I want to go to Japan in June or July. And right now I’m working very, very hard to get the systems in place and to allow that to happen. Flori is a huge part of that.”

Do you have any special methods or approaches for motivating Flori that are particularly effective?

  • Treat your Filipino workers as equals and recognize their potential.
  • Create a company that’s really warm and growth-oriented.
  • Work to make sure your workers understand what’s going on in the business. Be transparent.
  • “Celebrate when people are doing well and give very specific feedback to people so that they can grow as fast as possible.”
  • Cultivate a warm and non-toxic work environment. 
  • Show interest in their personal interests–have fun with them.
  • Be invested in your workers as individuals.
  • Encourage your workers to come to you with questions
  • Create time for one-on-one trainings and check-ins.

Do you have specific tips for entrepreneurs who are considering hiring Filipino workers?

  • “I would not make people work the graveyard shift…it’s not healthy for relationships, for mental health or for physical health…it’s another perk of the job that’s meaningful and helps you attract talent.”
  • Workers from the Philippines tend to be averse to confrontation, so Nathan recommends “making extra space” and remembering that as the boss, your actions and responses can be a “loaded gun” and you may not realize it. Be warm and gracious with your communication and always watch for things you may be doing wrong. 

How can people connect with you and follow your business?

Find Nathan Lippin on LinkedIn or visit the website

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