MBA953 Guest Teacher: Rob Rawson- How to Manage and Scale a Remote Team to Over 60 People
2 Feb 2026 · 3 min
Rob Rawson, founder of Time Doctor, built a remote team of 60+ people across 28 countries. He uses multi-stage hiring with paid tests, hires two people per role to find the best fit, and runs daily video calls plus screen-recording to keep everyone connected.
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Hey O. Welcome to the $100 MBA show where building a better business is our business. With our daily 10 minute business lessons for the real world. I'm your host, your coach, your teacher Omar Zenholm. I'm also the co founder of the hundred dollar MBA, a complete business training and community online over at 100 MBA net. If you're just and you want to make sure whatever you're building, your product, your business itself is actually what people want, then you're going to love our free seven part course on idea validation. In this seven part course, you're going to get seven specific videos and a workbook that goes along with it to make sure you nail your business idea, product, service, price, whatever it is. And it's absolutely free. All you got to do is go to 100 MBA net to enroll today. Today's episode is a guest teacher episode. On our guest teacher episodes, I bring on a guest to teach you their area of exper. Today we have entrepreneur Rob Rawson. Rob is the founder of timedoctor.com a huge app in the remote working space and he's going to be teaching you how to manage and scale a remote team over 60 people. Building a remote team is definitely an option and a lot of people are starting to see it as the best option, not just the most affordable. We run our team here at the $100 MBA and webinar ninja, our software company. Completely remote. That means we don't have one physical office where everybody works. Our team is all over the world. But how do you do this? How do you hire these people? How do you manage them? How do you make sure that the work is getting done well? That's what Rob Ross is going to be teaching in today's guest teacher lesson. He's going to break down what are the advantages of building a remote team, how to find these team players, how to hire them, how to make sure you found the right hire, how to create a strategy for hiring and how to manage them once they're on your team. The rules are a little bit different because you're not in a physical space together, but it's definitely doable and it definitely can be efficient. We got a lot to cover, so let's get into it. Let's get down to business. Today's episode of the $100 MBA show is brought to you by Microsoft Surface. When working on projects you love, you need a powerful laptop that hustles like you do. The new Surface Pro has a fast processor and all day battery life so you can run the programs you need when you're on the go. It's light enough to take anywhere and works with your iPhone, so it's synced with your life. The new Surface Pro is the lightest, most powerful Surface Pro ever. Rob Rawson is the founder of timedoctor.com, a great app that tracks the time that your remote workers work to make sure they're actually doing their job. It also makes sure that you're paying them fairly. It's one of the most popular apps for remote teams. His website gets millions of visitors every month, and it's for good reason. Rob knows what he's talking about when it comes to building and scaling a remote team. I met Rob in Sydney, Australia. I got to know him this past year and he's a very interesting guy and he's got a lot to offer when it comes to this topic. I'm gonna let him take over now, but I'll be back with my takeaways on this topic. But for now, take it away, Rob.
So this is Rob from Time Doctor and I'm going to cover how to manage and scale a remote team. I'm currently running Time Doctor which has over 60 team members in 28 countries. And it's a software company for productivity and remote teams. So remote has actually been a key factor to our success because we can get more affordable team members who are also amazing. And it's a lot, lot easier to find great people. So even if you're not going for the lower cost, it's actually easier to find great people remotely because you've literally got the whole world to choose from. You don't have to focus on only your city. You can hire people from anywhere. So here's what we're going to cover. The keys to finding great people, how to improve communication and systems in your business, and making systems to scale that remote team. So how do you find great people? First of all, you want to post in some key places and you want to make sure that you're usually getting hundreds and hundreds of applicants. So, for example, for a developer position, we post in Stack Overflow. Also, you can post in WeWork remotely, Upwork, and in the Philippines, there's online jobs. There's a lot of different locations. LinkedIn is another great location to post in. So you should always put the word remote in the job title. Or we hire from anywhere. This is really critical. And then evaluating the talent is the next step because you're going to get a lot of poor quality applicants when you're hiring from all around the world. That's just the reality of the situation. There's a lot of people who are not that great who are going to apply to your job. And, and so you need a process that works for literally hundreds of applicants. You need to start with a simple test. So I always try to make a test that is very, very matching the work that they're going to do. So it can't be a test that's not related to what they're actually going to do. It has to be exactly matching what they're going to be doing in the job. So, for example, if they're a developer, they need to develop actual code on the test, and it needs to be related to the type of code that we're doing in the job. If they're a recruiter, ask them to do a mock call with the candidate. Or if it's sales, you ask them to sell you something in the test. And you can actually use video software to get them to record and sell to you in a video so that it streamlines the process. Because you were trying to interview hundreds of salespeople, you'd have no chance. You would only be able to do it if you get them to video interview first so that you can listen to hundreds and hundreds of videos, actually quite quickly, and you can sort through them and see who you like. But if you try to evaluate people on resumes, you're really going to find that you don't get a great result because you're going to find people that are good at writing a good resume, but not necessarily good at the actual job you want them to do. So you need a scalable process, something that can work for hundreds of people. And if you're not getting hundreds of people, then there's probably something wrong with your process because you're hiring from the whole world. You should be getting a lot of applicants to your job. And so it is much, much easier to hire remotely. And when you're posting a job and when you're getting referrals, then if you're not getting hundreds or even thousands of of applicants, it means that you are not posting the right places or you're doing something wrong. So also, how do you evaluate people if you're not a. If you're not a technical person? Well, another thing you can do is there's certain test sites like HackerRanks. So we use HackerRank. It actually was used by Facebook at one stage, and that tests their programming skills. You don't need to be a developer to use it, which is fantastic. We use an applicant tracking system and we use Breeze hr, which is amazing. It allows you to take videos and also have different questions as part of each stage so you can evaluate them through various steps and tests. So we do an easy test in the beginning that's critical because you don't want to put through people through a massive test right in the beginning, but then later down the process, if they pass that first step, you give them a more difficult test. And if it's long enough, then I actually pay for the test because it's not reasonable to ask someone to do a four hour test without paying for it. So I actually pay for the test. And that sounds like might be expensive, but in reality you're talking about a relatively low recruitment cost if you're getting five or ten people to pay for that test. So the multi stage process is really important. And then right at the end you want to hire two people on a test basis to see if who's going to work out because you don't know, even if you've gone through all of these evaluation steps, you still don't know who's going to be great. So it's better to hire two for each position so that you have a much better graded chance for, of finding the right person. So you want to look also for people that have shown that they done other projects that they're interested in, they're enthusiastic and they have a lot of self drive. That's a really critical thing that you're looking for. So if you're hiring the best people, then half your work is already done because that's really the most critical step in my view to hiring and scaling a remote team. You need to hire really great people, but it's not the only thing you need to do. Communication is another really important part of remote teams because when you're not there, you're not bumping into each other. What happens in an office is that you just tend to bump into each other like oh, hi Bob, you know, I'm thinking about this, why don't you try this? And so when you're remote, you don't do that. And so you don't naturally communicate as much. And that means you need to structure the communication and purposely communicate more than you do when you're in an office. You actually need to make sure that you're communicating enough. So one thing that we do is daily meetings on video. And why video? Well, if you were coming into an office and you, you didn't even look at the person, that would kind of Be strange. So it's sort of similar when you're remote. You need to at least have a feeling of the person in the room. You have more connection, you have more experience of that person. Like you're really on a team together. When you're communicating in video, you also want to have a chat app such as Slack or Skype constantly open. So you're chatting to the person constantly. And there are other great tools like Jing or Snagit, which are for recording videos of your screenshots. So sometimes you might not be at a coordinated time to chat, but you can actually record a video of your screen. So it's just like you're sitting next to somebody and you share that video with them, or you share a screenshot of your screen and you can visually communicate even though you're not in the same room. These tools make it so much easier. Also, when you're scaling, you need to use a project management tool. And there's so many of those like Basecamp or Asana. But if you're trying to do everything via email, you're really missing out on a more productive communication method because email, a lot of things get fallen through the cracks and you can't track things in projects effectively. So a project management tool is really important. Systems is the last thing that I want to talk about. They're really necessary for scale. So for example, in our hiring process, we have an exact step by step process process for every job. So this is step one, this is step two. And in the software that we use, it actually is in that software. It's, it's clearly delineated who's responsible for this step, who's interviewing on this step. And if there's a problem with the hiring process, we can see that and we can fix the process. And it also makes it that we're improving it. Every time that we do a hiring process. We're improving each time because we're seeing what worked the last time and then we're making adjustments. So this process driven approach is really critical. When you're starting to scale. Maybe it's not so important in the first one or two people that you're hiring, but when you get to 60 people, it's absolutely critical. Also, our software Time Doctor kind of holds it together because you're making sure that everyone's productive and it's tracking their time and making sure that they're actually working and not seeing, spending all day on Facebook. And so it's really, really powerful to do all of these things. I know this is A really brief overview of how to do it, but I just can't state enough how effective it is, how amazing it is to build a remote team and how much this can be by itself a huge competitive advantage. Just think about if you're trying to build something, something in an office and you're in a city that has 4 million people, so you're super limited in terms of the number of people. And now you can go to the entire globe. So your ability to hire is much greater, your ability to find amazing people or to cut your costs. Like, if you want to focus on the lower cost but still effective people and hire from the Philippines, hire from Ukraine, you can do it that way as well. So you have a lot more and you don't have to go for the low cost. You really can go also for hiring just great people remotely. And that's also a very, very effective strategy. Thank you.
Support for today's show comes from Microsoft Teams. Microsoft Teams is your hub for teamwork. In Office365, we run a remote team with teammates all across the world. And things can get really, really hectic if they're not organized. With so much to look after, wouldn't it be great to just have one place to look? Microsoft Teams is that single workplace where you can work, share and connect with the people in your work life. Teams brings together your chats, your meetings, your files and your apps all in one place. Take Teamwork, where you work with apps for mobile and desktop. So whether you're sprinting towards a deadline or sharing your next big idea, Teams can help you and your team achieve even more. Microsoft Teams in Office 365. Visit office.com teams to learn more. What a great lesson by Rob Ross and founder of timedoctor.com I found that everything he said today was just spot on. A lot of the things he mentioned I learned the hard way, especially when it comes to the hiring process. You got to put them on a trial project to make sure they can do the job that they're being hired for. And I love the idea of having two hires get hired at the same time to see who does a better job and who gets the job. You need the best talent. And this is why I love the idea of a remote team, because you have again, all this selection from around the world of great professionals. Now, having said that, you do have a lot of selection, which means you have a lot of great people, but you also have some duds. And the number of duds you have to sift through are going to be more than the ones if you're just hiring locally. So just keep that in mind. Yes, you're going to have more access to better talent at a better price. But you're also going to get a lot of people applying that are just not good enough. And you got to be able to understand that a lot of the people that are going to be applying for the jobs you're posting are not going to be slam dunks. I would say most of them are not worth even an interview. But that's okay. It's a bigger pool of candidates. You're gonna have a lot of great candidates that you can actually hire. The one thing I would add to Rob's lesson, Rob mentioned this about communication. Making sure that you communicate over communicate with remote teams. But when you come to hire remote players, I always look for people that are great communicators, people that communicate often, that can communicate with the team. So when they're in that trial project, I'm looking at how they communicate with everybody. And if they are actually keeping us up to date with everything they're doing and they're not afraid to ask questions, questions are a good sign. When people join your team and ask a lot of questions, that means they're actually interested in doing a great job. I get really worried if I hire somebody and they're not asking questions. It makes me question if they know what they're doing. Questions mean they want to know more about what you do, your product, your service. So they can be able to help you in a specific way, in a better way rather than just listening and not adding their take to the whole thing. You want somebody to come in and add their talents to your team. Thank you so much Rob for that awesome guest teacher. If you want to check out time doctor so you can track how much time your remote workers are working, go to timedoctor.comcoupon and use coupon code 100 MBA to save $100 your first first month. Again, that's taimdoctor.comcoupon use coupon code 100 MBA and save $100 your first month at timedoctor.com alright, that's it for me today guys. But before I go, I want to leave you with this. One of the great things about having a remote team and being able to hire around the world is that you can get coverage pretty much 24. 7 in your business. You can have people working on your business 24, 7. Talk about getting ahead when other small local based businesses only work nine to five. Or let's say 10 hours a day. You can have your team working 24 7. Pretty cool. So just another plus for remote teams. Alright, I'll check you in tomorrow's episode where I discuss how to create an effective morning routine. How you start your day is so important. It sets you out. It's. It sets you out for a great, productive day. It sets you up for success for even a productive week or month. And making a habit of that morning routine is really something I want to talk about. So make sure you tune in to tomorrow's episode. Subscribe so you don't miss it. Alright, I'll check you in tomorrow's episode. I'll see you then. Take care, Sam.
