Jennifer Yousem
So let’s start with the basics. Who are you?
Darleen Priday
I’m Darleen Priday, and I’m the VP of Business Development for Peachtree VA.
Jennifer Yousem
Tell me a little about Peachtree and what you do for them.
Darleen Priday
We support busy leaders, entrepreneurs, and small businesses by providing highly vetted, U.S.-based virtual assistants. Our goal is really to fill in the gaps and give leaders time back in their day.
Jennifer Yousem
I can speak from personal experience about how great the process and overall experience has been. But for people reading this, there are a million VA providers out there, just like there are a million bookkeeping firms. So how does Peachtree differentiate? What’s the magic sauce?
Darleen Priday
I think it comes down to a few key things. First, we work with leaders who don’t just need task support; they need a thought partner. Someone who truly functions as part of their team, not just someone checking boxes.
The leaders we support know that if they had the time to figure everything out, delegate every task, micromanage the work, and then double-check that it’s done, they might as well do it themselves. They come to us because they want a true partnership and an ongoing relationship. That support has to go both ways; it can’t all fall on the leader.
They need someone who’s proactive, willing to step in, and actually take things off their plate. Our virtual assistants are seasoned professionals, they’re highly vetted, have transferable skills, and are committed to ongoing learning. Most importantly, they genuinely have a heart to serve.
We’re operating in a world where things change in the blink of an eye. We can’t promise that someone will be an expert in everything, but what we can promise is a willingness to learn, adapt, and jump in, whatever that looks like for the leader.
Another big differentiator is our intentional matching process. We don’t just look at skills and experience; we consider personality, company culture, what’s worked before, and what hasn’t. We’re very intentional about matching both chemistry and competency, so the leader feels confident and comfortable. That trust is everything, because if you don’t trust the person supporting you, you can’t truly delegate.
Jennifer Yousem
Yes, and I think that’s something almost everyone experiences. You know you need help, but the “how” can be hard, how to pass things off, what the most efficient way is. You’re right, it’s a learning and more importantly, a trust process.
When you think about your best-fit clients, who do you find yourselves working with most often? What’s usually happening in their business when they reach out?
Darleen Priday
Most often, it’s entrepreneurs and executives at a growth stage where they’re feeling stretched thin. Maybe they’ve tried delegating internally, or maybe they’ve just been doing everything themselves. There’s a lot of overwhelm, and they know they need help to scale without burning out.
Jennifer Yousem
That brings me to the matching process. We get asked this all the time, who’s going to be my bookkeeper? The answer starts with, “Who has availability?” But then there’s the next layer: personality, skill set, fit. So how did Peachtree develop its matching process? It’s been a while since I personally went through it, so I’m curious how that evolved.
Darleen Priday
That process is always evolving. We’re constantly looking for ways to improve and refine it. We have more tools now that help us narrow down strong matches, but even with technology and AI, there’s still a very important human element.
We have a team that listens to the sales calls and reviews detailed notes. Clients also complete a VA wish list that outlines not just the tasks they need help with, but the type of person and personality that would fit best with their team.
During the sales call, I spend time digging into whether they’ve had support in the past, what worked well, and what didn’t. That information is incredibly telling. It gives insight into the kind of support they actually need and helps us better understand their personality and working style.
Jennifer Yousem
So there’s a certain way you all approach this, and I don’t know if I can fully explain it, but if you’re new to the VA world, you tend to think very surface-level, right? Managing emails, managing my calendar. But you knew things I needed before I even realized I needed them. My VA’s role for me today is vastly different than when we first started working together. That’s been the real special sauce. So, are you doing all of the matching yourself?
Darleen Priday
I don’t do the matching myself. My role is to bring the clients in, and then I hand them off to our amazing team that is dedicated to matching. Of course, they use my sales notes and the sales call, things like personality fit and client needs, but they really know our VAs. They have relationships with them.
Our goal is a good fit on both sides. They understand what you’re looking for, and we want a VA who is just as excited to support you as you are to receive that support.
We never force our VAs to take on a client. Longevity matters to us. We want everyone involved to be happy, healthy, and set up for a successful relationship.
Jennifer Yousem
That makes a lot of sense. So once someone is matched, what does the first 30 to 60 days actually look like for a new client?
Darleen Priday
In those first couple of months, we really focus on onboarding and understanding the leader’s work style. That means shadowing routines, identifying priorities, and slowly taking on tasks while building trust. By the end of 60 days, the client often says, “I didn’t know I could delegate like this!”
Jennifer Yousem
How much time does a client realistically need to invest upfront?
Darleen Priday
In the beginning, it’s important to be intentional and share not only what you need, but who you are as a leader. I typically recommend a few Zoom calls and weekly check-ins during the first month, until you and your VA find a good rhythm. Then weekly zoom calls should continue to keep that relationship building. That said, it really depends on client preference. If you’re a verbal processor, more live conversations are helpful. If you prefer things documented in writing, fewer calls may be a better fit.
Feedback early and often is key. It helps your VA quickly understand what’s working for you and what’s not. While it can feel counterintuitive to slow down a bit during onboarding, once your VA is able to take ownership and truly pull things off your plate, the ROI is incredible.
Jennifer Yousem
And you mentioned the more typical things people come to you for, email and calendar management. That’s usually where everyone starts. But once someone reaches a certain point, whether they’re a business owner, an executive, what are some of the broader ways you all support clients beyond those basics?
Darleen Priday
Email and calendar really are the bane of everyone’s existence. People struggle with letting that go.
And I always tell clients: it’s not all or nothing. You don’t have to hand over the keys to the kingdom and disappear from your inbox or calendar entirely.
Most of our clients are high achievers. They overbook themselves. They say yes to too many things, and they’re juggling a lot of moving parts.
Entrepreneurs especially tend to have 50 irons in the fire. Even if they’re focused on one main business, they may also have rental properties, personal commitments, business partners, and so many things competing for their time.
Not everything on a calendar is created equal. Having someone who understands all of those moving pieces and can juggle them thoughtfully is critical.
Our VAs can help with meeting prep, document preparation, follow-ups; we work with a lot of coaches, for example. Clients often need to provide documents or access, and chasing that down can feel like herding cats.
Instead of you being the one constantly following up, your VA can act as a liaison, handling communication, tracking what’s outstanding, and keeping things moving. That communication is vital.
I always say, no news isn’t necessarily good news. We live in a world where outsourcing is common, which is great, but someone still needs to check in, confirm deadlines, and make sure things are on track.
Your VA can surface issues early, bring you in if a decision is needed, or flag delays. And you can feel confident knowing everything is being monitored, and the project is moving forward.
Jennifer Yousem
Agreed. If someone is on the fence, what’s usually holding them back, and what would you tell them?
Darleen Priday
Most often it’s fear of losing control or not knowing how to delegate effectively. I tell them: start small, pick one or two tasks, and let your VA show you the process. Once they see the relief it brings and the quality of support, that fear melts away quickly.
Jennifer Yousem
Something that I also think really sets you apart, though I haven’t worked with a ton of other VA services, so I can only compare my experience to what I hear from others, is the consistent check-ins.
You’re always asking, “Is this still working?” Because, like any relationship, it evolves. And ideally, it evolves in the same direction.
My relationship with my VA has evolved significantly. So, what happens if the relationship changes in a way where, say, the VA no longer has the skill set that’s needed? How do you handle that?
Darleen Priday
We have a relationship specialist who oversees each engagement. They check in regularly with both the client and the VA to make sure everything is moving forward smoothly.
One thing I’ll highlight is that we have a scalable model. You can start with as little as 25 hours a month, which is really appealing for entrepreneurs who know they need help but aren’t sure how to delegate or where to start.
It’s a manageable, bite-sized way to begin building support naturally.
To your point, if a client outgrows a VA or needs additional capacity, we don’t throw the baby out with the bathwater. The relationship specialist might say, “Okay let’s keep your VA focused on this area where she really excels, and let’s bring in an additional VA now that the roles are clearer.”
That way, you’re expanding thoughtfully instead of starting over.
Jennifer Yousem
Yeah, and in my case, this is a low bar, but my VA is far more tech-savvy than I am.
What started as more tactical support has evolved into so much more. She manages our social media, which is huge since I don’t have a clue.
For me, that’s been the real game changer. She’s not just a support, she’s a thought partner. She’s a true member of our team. Everyone on my staff knows if they need something from me and I haven’t got it done, they can go straight to her, and she’ll make sure I get it done.
Darleen Priday
Yes! I love that you’re bringing this up because I can really relate. I often say I become the bottleneck.
I never have to remind my VA to do anything. She’s the one reminding me: “Hey, you have this meeting,” or “You need to do X, Y, and Z,” because I’m moving so fast.
Sometimes I do things in my head and think they’re done, or I start them and get distracted. She really helps keep me on track and provides accountability.
And I always tell people: tell the good, the bad, and the ugly. Everybody has it, right?
Jennifer Yousem
Right, and I’m very direct with my team about this. I’m usually doing a thousand things at once, even if it doesn’t look like it on the outside.
We use Zoom chat, which is great for quick hits, but if I’m not in a position to act on something in that moment, it completely evaporates from my brain the second it comes in. What’s been really helpful, and this only came with time, is that my VA and I have developed a shorthand. She knows how and when to respond as herself and how and when to respond as me.
I get introduced to a lot of people, and the second step of every introduction is always, “So great to meet you. Let’s get some time on the calendar.” And I don’t need to be the one making that happen.
Darleen Priday
Exactly. It’s about preserving you, and your presence, for where it makes the most impact. That does take a little bit of time, which is why I always say the more feedback and transparency you give early on, the better. It’s like any relationship: the more you put into the beginning, the faster they really get to know you.
Jennifer Yousem
Absolutely. And I really think it depends on the right match, a level of trust, and developing that shorthand. My VA knows where all of my appointments are. I live in the middle of nowhere, so she automatically blocks travel time. Stuff like that, I don’t think I could have even articulated that need upfront.
Darleen Priday
And we live in a world now where some things are virtual and some things are in person. I always say I’m great at virtual, but in-person is what trips me up.
I don’t allow enough travel time. I don’t block my calendar properly. Knowing how to move between those two worlds is really important.
Jennifer Yousem
I think it really comes back to partnership and proactive thinking.
At this point, my VA and I have been working together for maybe three years.
She knows my downfalls, where I’m going to drop the ball. And even if she can’t do the thing, if it’s something only I can do, she makes sure to remind me in the best way possible.
Sometimes she works hours that I’m not working and will send messages. And we figured out together that if she sends me late-night Zoom messages, there’s a very low chance I’ll remember or act on them.
So, we adjusted. That’s something we came up with together.
I think as leaders, we often walk around with this “I have it all together” face, especially outward facing.
Darleen Priday
And having a safe space with someone who is genuinely invested in helping you not let things fall through the cracks, that’s incredibly powerful.
Someone who knows your faults, your hang-ups, where you struggle, and helps you work through those things so you can be your best self.
It’s empowering for a leader to say, “Okay, I have this one person who knows everything, and they’re here to help me show up better for everyone else.”
My job isn’t just to get people in the door. My job is to make sure they end up with the right support, even if that support isn’t us.
Jennifer Yousem
I love that. That’s so thoughtful.
Darleen Priday
You know, I really love what I do, and I care deeply about supporting our clients in a way that’s truly a win for everyone involved. Sometimes that means acknowledging that we’re just not the right fit, and that’s okay.
Jennifer Yousem
What you all do is actually very similar to what we do. We’re involved in very intimate parts of people’s lives, their livelihoods and their businesses. There’s a lot of emotion wrapped up in that, even when there’s no personal crisis happening.
I get asked all the time, and I’m sure you do too, about the sheer number of options out there, especially offshore options. One of the things I really love about Peachtree, and something that differentiates us as well, is that everyone is U.S.-based and experienced. We want folks for whom this is a career, not a gap filler.
Darleen Priday
Yes, and that’s exactly how we vet our team.
What I always say about offshore support is this: if you’re looking for simple data entry or very transactional tasks, and it’s working for you, then great, stick with it. I even have clients who use offshore support for that kind of work.
But when you use just 25 hours a month with a seasoned VA, it can elevate you as a leader by leaps and bounds. And it doesn’t translate to just 25 hours back in your time; it multiplies. When you free up your brain space from the minutiae, you’re able to think strategically again.
I have so many clients who are absolutely brilliant. They have incredible ideas, but there’s no one to execute them. So, they start to dumb things down. They make themselves smaller just to be manageable. And that honestly breaks my heart.
Jennifer Yousem
That’s the worst place to be. So, what do you do? How do you walk people through that?
Darleen Priday
I think I’m able to help because I genuinely relate to my clients. I’m not a natural delegator. I talk about it all the time. I see the results, but it’s not easy for me either.
I tell my clients that delegation is a muscle, you have to build it and most entrepreneurs are actually terrible at it. High performers can do things fast, and often faster themselves, but eventually they hit a ceiling and become their own bottleneck.
I always compare it to teaching kids how to tie their shoes. It’s excruciating to wait for them when you’re trying to get out the door, but if you never let them learn, you’re always going to be tying their shoes.
Delegation is the same way. It’s slowing down to speed up. It’s saying, “Yes, this will take longer right now, but once this is off my plate, I never have to do it again.”
Jennifer Yousem
Yes, and that’s where the thought partnership piece is so powerful.
People ask me all the time, “What does a fractional CFO even do for a small business?” And most business owners are solopreneurs. They don’t have a board of directors. They don’t have senior leadership around them. So even taking 10% of the decision-making or data processing off their plate creates an exponential lift.
For me and my team, that shows up in things like my VA reminding managers that one of their associates has a work anniversary coming up. It’s such a small thing, but it’s also something that can easily fall through the cracks and yet it’s a huge driver of culture.
Darleen Priday
Absolutely. In a world full of apps, workflows, tools, and automation, those intentional human touches make the biggest impact.
I try to be very intentional with our clients. We don’t just onboard them and disappear. You’ve done client spotlights; we do the same. We highlight our clients. We’re rolling out new initiatives for our client community in the coming year.
And my VA is instrumental in that. Like so many leaders, I have a lot of ideas, but I can’t implement them all at once.
She’s great at helping me prioritize. She’ll say, “Okay, let’s plan that for Q1. Let’s push this to Q2. Here’s what I can take off your plate now, and here’s what I can start researching.” Because by Q2, I’ll have forgotten I even said it, I’ll have another hundred ideas by then. And now that she knows me so well, she’s also really good at reining me in and saying, “That’s unrealistic. We already have X, Y, and Z we’re focused on through the end of the year. Let’s push that out.”
That kind of support really sets things up for success. Otherwise, it’s easy to get excited in the moment, chase an idea, and then have it fall flat because the timing is off or it’s not executed properly.
Jennifer Yousem
I actually find that human overlay is more important than ever.
We’ve had clients leave us for much less expensive, sometimes heavily AI-driven, bookkeeping tools and automations, only to come back later. Because very few businesses don’t have nuances that require a human touch. I see the same thing in the VA world. I can always tell when I’m interacting with something that feels more automated or “bot-like.”
Darleen Priday
None of my clients are simple or one-dimensional. Some even have full internal teams and still value having an outsourced VA, someone outside of the internal dynamics, someone who truly has their back. I know you experience the same thing.
Jennifer Yousem
Yes! Having a different thought partner. So, is there anything you want people to know about you or Peachtree that I didn’t ask, but that we should include?
Darleen Priday
I would say, first and foremost, I genuinely love helping people.
Jennifer Yousem
Yes, you do.
Darleen Priday
If you’re thinking about getting support, even if you’re not ready today, I’m not high pressure. Not everyone needs help right now, and not everyone needs Peachtree. I’m always happy to have conversations, offer perspective, and provide value, whether that’s for the future or by connecting someone with a different resource.
We truly care about our clients’ success. A win for us is supporting someone, even if they eventually outgrow us or their circumstances change. If we can play a small role in helping a leader move forward, that’s a win.
We’re a small, lean, hands-on team. We know our clients. We know our VAs. And we genuinely have a heart to serve, with excellence.
