How to Boost Productivity by Supporting Your Team’s Work-Life Balance

By Jason Swenk on October 20, 2021

Are you looking for ways to boost your team’s productivity while also improving your work-life balance? Jason Berkowitz was working as a personal trainer in NYC when he discovered SEO and decided to become a freelancer. He grew his business and started hiring and building his team to create a legit agency, Break The Web. Now that he has a team, he has been implementing a few ways to boost productivity and morale. In this conversation, he talks about the key roles he hired to start growing his agency, why offering unlimited PTO has worked for his team, and how a special summer schedule allows the team longer weekends.

3 Golden Nuggets

  1. On growing his agency. Jason found success learning about SEO practices and how to help people implement them in their websites. However, freelancers have to take care of different aspects of the business like admin, selling, project management, execution, client management. Some people are comfortable with that, but he wanted to delegate certain aspects of the business to increase his income. For this, the first strategic hire was an account manager, which was the first step to start building a legit agency. This way, he didn’t have to spend so much time speaking with clients, relaying information, and setting expectations and could focus on other aspects of the growing business.
  2. On unlimited PTO. More and more people are deciding to offer employees unlimited PTO. It is an ongoing debate and, in his particular case, Jason decided to do this at his agency. The main reason has to do with fairness. “If I wanted to take unlimited vacations, it was only fair to allow that as well in the team culture,” he says. But there was also the matter of allowing people to enjoy their time off and see how that affected the way they enjoyed work. There are still rules, it is based on performance, employees have to put in requests for PTO at least 10 business days beforehand, and it can be approved or denied. But it has been a success at his agency.
  3. Boosting his team’s productivity. Other than offering unlimited PTO, another strategy introduced this year at the agency to boost the team’s morale was working half-day Fridays in the month of June. It was a way of letting them enjoy their summer weekends, but it actually ended up improving team productivity from Monday to Thursday. Work was being executed much faster and more efficiently. It also helped Jason maintain a better work-life balance. Overall, it was a success for this team and something that they may continue to do every year.

Sponsors and Resources

Wix: Today’s episode is sponsored by the Wix Partner Program. Being a Wix Partner is ideal for freelancers and digital agencies that design and develop websites for their clients. Check out to learn more and become a member of the community for free.


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Growing Your Agency, Work-Life Balance, and Boosting Your Team’s Productivity

Jason Swenk: [00:00:00] What’s up, agency owners? Jason Swenk here and I have another amazing guest and, uh, his name is Jason. He’s also from New York. So don’t get confused. He’s probably better looking than me, but, uh, we’re going to talk about growing his agency, life balance, and a lot of cool stuff. So, uh, I’m excited to have him on. So let’s go ahead and get into the episode.

Hey, Jason. Welcome to the show.

Jason Berkowitz: [00:00:29] Hi! Thank you so much for having me, Jason. It’s a pleasure and, yeah, best name ever.

Jason Swenk: [00:00:34] I know. I was like, don’t get confused. You’re the newer and better version of me, I guess. But tell us who you are and what do you do?

Jason Berkowitz: [00:00:42] I am the founder of the search marketing agency Break The Web, and we specialize primarily in SEO and paid search.

We help in-house marketing teams, integrate SEO, which is always nuanced and confusing and annoying, into their existing marketing practices. So it’s seamless all around.

Jason Swenk: [00:01:00] Very cool. And so how did you get into this space?

Jason Berkowitz: [00:01:03] It was probably by accident. I used to be a personal trainer, way back when in New York City.

And I was tired of working for a gym and basically working off the leads that they gave me, which were new membership signups. And I had the idea of what if I can get people to come to me? Is there a demand? So of course people are going to Google typing in personal trainer NYC. Saw the acronym, SEO started implementing it on my website at the time.

And then I was like, screw personal training. Uh, this SEO stuff is fun. Of course, SEO was way different back then anyway, but it was kind of a paradigm shift. That’s where the journey started. I worked as a freelancer for a while, but that’s where it started.

Jason Swenk: [00:01:39] How long ago was that?

Jason Berkowitz: [00:01:42] Around 2009, 2010 is where I started actually getting into the practices of SEO what’s involved? What does everything mean? What’s the methodology? So about a decade now.

Jason Swenk: [00:01:53] Very cool. I remember when you could get right for any term by just putting that keyword in the background at the same color. So I might be dating myself on that one, but that was a really…

Jason Berkowitz: [00:02:04] The good old days. Oh yeah. One among the many different things that would work really well and really fast back then.

Jason Swenk: [00:02:13] What made you decide to go from a freelancer to hiring people?

Jason Berkowitz: [00:02:18] Yeah, I think I wanted to have a certain income. The problem with being a freelancer is that you’re managing everything. When it comes to admin, selling, project management, execution, client management. All these different aspects.

And some people are comfortable with that, but I felt like I needed to delegate certain aspects if I wanted to increase my own personal income. So then I started bringing on VAs to help with some of the smaller things. And then before you know it I’m like, wait, I can let go of this one thing too and not have to worry about it? And I can let go of this one other piece?

Then before you know it, you just look up, you’re like, oh shit, we’re a boutique agent.

Jason Swenk: [00:02:59] Yeah, it’s exciting to let go of the stuff that you don’t necessarily want to do anymore or have to do. And then other people actually start doing, you know, a better job. And I’m always curious, who was the first hire?

Not the person’s name or well, please list out their social security number. I’m just kidding. What was the role? What was the first role that you hired?

Jason Berkowitz: [00:03:23] The first unofficial, non US-based was a VA in the Philippines. That was to help with link building as one of the big, uh, time-consuming aspects related to SEO. The first US in which we officially, you know, start with like, hey, we’re going to be legit and grow a real agency was an account manager.

I found myself just taking a lot of time speaking with clients and trying to relay information, setting expectations. So the account manager was our first hire.

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Jason Swenk: [00:03:51] Awesome. There’s always a debate around kind of PTO. Well, there’s more and more people now kind of giving unlimited PTO. Why did you go to that?

Jason Berkowitz: [00:04:04] I think if I wanted to take unlimited vacations, if it made sense or just take off when I wanted to take off, it was only fair to allow that as well in the team culture. I think just people are going to enjoy work if they could also enjoy pleasure. And if you restrict them by X amount of time that they have for that pleasure, they may not enjoy work as much.

So if they just needed an extra three or four days on a certification or an extra trip. Or maybe they were capped out throughout the year for the amount of days, that just gives them a bad taste in their mouth. So we’d rather if you’re doing great work, if things are looking good and we won’t be set back, if you take an extra couple of days off by all means, go for it.

We just care about the output more.

Jason Swenk: [00:04:48] Yeah. Some people are always concerned about can people take advantage of it? Like, have you ever had anybody try to take advantage of it?

Jason Berkowitz: [00:04:55] No. They still have to put in requests for PTO at least 10 business days beforehand. And they still could get approved and denied. I don’t believe I can recall offhand recently I have denied someone.

But we do have it in our knowledge base internally and our SLP is that it is based on performance. So yeah, technically, if you want to go ahead and request. One thing we’ll be looking at is how much time they’ve taken off previously, a culmination of hours. But also the performance and the output overall, as well as what things might look like around the time period in which you plan to take off.

But yeah, I don’t think I’ve ever denied someone and no one hasn’t taken advantage yet. Surprisingly, I find what might be, if you do have, for example, two weeks or 80 hours of paid time off towards the end of the year, people want it. So then you’ve got people taking off just for the health taken off and they may just sit on their couch.

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Yeah. You know, we had that in the very beginning of our agency where everyone, like, we would say, hey, it doesn’t rollover. You got to use it or lose it. And then they wouldn’t use it until the very end. Then literally right when all the clients want all the work they’re like, I’m taking time off. And it really screwed us majorly and it was pretty hard, cause sometimes we had to deny it.

I do like how you have, hey, we have unlimited PTO. But you have to put in like, and you’re a lot nicer than I would have been about 10 days. I’d have been like, at least give me a month. Or like, if, if there’s emergency, like your parents need you or something or kids or something like that, obviously go.

But if it was like, hey, I forgot to tell you about my Hawaii vacation. I’m gone for two weeks and it’s happening next week. I’d be like, well, you might not want to come back.

Jason Berkowitz: [00:07:37] Yeah. You know, I know we were just talking about New Yorkers and whether New Yorkers are mean. And I guess that’s, you’re in New York attitude right there.

Jason Swenk: [00:07:45] Yeah. Well, I think I was telling people, I was like, and I could say this cause I was like, yeah, cause we’re brutally honest and a lot of people do take that as mean. But you definitely know where you stand with the New Yorker. There’s no beating around the bush.

Jason Berkowitz: [00:08:02] No sugarcoating. No.

Jason Swenk: [00:08:04] Is there any other interesting things that you guys do around making your team happy? Uh, you know, incentivizing them or anything like.

Jason Berkowitz: [00:08:14] Yeah, we tested out in the month of June as the intro to summer half-day Fridays. And everyone loved it. So it’s just half the time you normally would be estimated for that hourly output of the day. I loved it. So I was happy with it. And after interviewing every team member, they loved it too.

And I think it’s something we might do recurring every June, maybe even possibly thinking about just doing four-day workweeks, the month of June. Just to see and everyone loved it because they were able to take, they didn’t need to put in for PTO or maybe half day PTO on that day. Uh, which was nice. And just having a longer weekend as the summer rolls in, especially after the last year and a half or so. It was nice to boost morale a little bit.

Jason Swenk: [00:08:55] Yeah, I see more and more people doing that. And actually, if you think about it’s probably should do it for the rest of the year, honestly, half day on Fridays, or maybe even one a month be like Fridays are completely off. I’ve seen some of our mastermind members actually do it on Monday because everybody hates Mondays and… right?

And it’s a little bit easier, but a lot of times on Friday afternoon, people are just messing around. I remember walking around the office, like they’re not getting shit done. Uh, you might as well, hey, here’s the benefit. Go home. But, uh, yeah, it’s, uh, it’s definitely pretty interesting.

Jason Berkowitz: [00:09:31] Yeah. I dunno if I will be able to do Mondays. I feel like Monday is like the first half that they are catching up from what you might’ve missed over the weekend. But good for them. I appreciate it.

Jason Swenk: [00:09:40] Yeah, well, they were just like, and how I do my schedule now is I don’t do any meetings on Monday, even though I’ll work Monday. And then I take off Fridays. I never work on Fridays. And just by doing that, it just eases you into that, that week. And it’s amazing how much more you get accomplished in the shorter week, rather than just sitting around. Because I remember seeing some employees, they were just sitting around and they like, like looking at the clock.

Jason Berkowitz: [00:10:12] Yeah. Well that’s was one of the things we noticed with the half-day Fridays is that productivity during the week, Monday to Thursday was actually up. Deliverables and stuff were executed much earlier.

According to like our time tracker, which I don’t know how they gauge productivity, I guess, user movement on the mouse and stuff. Uh, productivity went up and everyone was saying that like, yeah, I was actually getting stuff done quite quicker and sooner and probably more efficiently.

Jason Swenk: [00:10:34] Yeah, exactly. Awesome. Well, Jason, this has been amazing. Is there anything I didn’t ask you that you think would benefit the audience listening in?

Jason Berkowitz: [00:10:42] I don’t think offhand. Um, maybe where to find us in case you’re curious about learning more about Break The Web, always a shameless promo, uh,

Jason Swenk: [00:10:50] Awesome. Well, what’s a website people can go in and check you guys out?

Jason Berkowitz: [00:10:54] Yeah, or you can just Google “break the web.”

Jason Swenk: [00:10:57] Awesome. Well, thanks so much for coming on the show. And you guys go check out their website.

If you guys enjoyed this and you want to be around other amazing agency owners that could really help you scale faster and share what’s working with you. So, uh, we all can grow together. I want you guys to go to the This is our exclusive mastermind. That’s only for a select few and not everyone gets in.

So go to And until next time have a Swenk day.

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