Rob Rawson on Future-Proofing Your Startup by Solving Hard Problems


Today, on the Early-Stage Founder Show, I’m talking with Rob Rawson, the CEO and Co-Founder at Time Doctor and

In our chat, Rob shares the strategies he and his team used to build a multi-million dollar SaaS business, but where we really focus is on the future.

So many companies forget the problem their software is ultimately trying to solve for it’s users. Rob’s customers don’t just want time tracking tools, they want to be able to measure and improve their team’s productivity. To truly provide that solution for them, Rob and his team need to solve some hard problems, and today he shares how they are doing that.

If you’re worried about increasing competition in your space, then this is the episode for you.

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Topics covered:

  • (00:06) – Rob’s background leading up to where his company is today.
    • (00:19) – How Time Doctor and came about.
      • (01:17) – The difference between the two startups.
        • (02:02) – The kinds of employee behaviour that tries to predict.
          • (02:03) – When a person might quit.
          • (02:23) – Whether they may be management material.
      • (02:40) – When Rob branched off from Time Doctor and started
        • (03:09) – The drive and intention to build
          • (03:19) – Customer requests, and Rob’s intuition that it would solve a key problem for people.
    • (04:40) – Where Time Doctor and are today.
  • (05:07) – Growing the business
    • (05:10) – The major turning points for Time Doctor and
      • (05:34) – Performing split-tests.
        • (06:33) – The effect the tests had in developing the unique website design for Time Doctor.
        • (09:54) – Why the same tests don’t work for
    • (10:19) – The major drivers of customer growth so far.
      • (10:47) – Rob’s use of his own products, which led to problem solving.
      • (11:39) – Content marketing.
      • (11:47) – Focusing on the product.
        • (12:25) – Hired a development team to improve the products.
      • (13:28) – Properly assessing competition in the market.
    • (15:04) – What gives Time Doctor and their competitive edge.
      • (15:31) – Focusing on a specific and narrow niche.
  • (18:09) – How Rob plans to tackle the core issues of employee accountability and assured productivity.
    • (19:02) – The inherent complications of productivity.
    • (19:34) – How and if productivity can be measured.
    • (25:01) – How the competitive SaaS arena affects product development.
    • (26:14) – How Rob allocates the resources to solve these core problems.
      • (26:37) – Confidence in their project manager.
      • (27:11) – Listening to customer requests and feedback.
      • (27:18) – The factors for prioritization.
        • (27:41) – A detailed look at how Rob prioritizes development at Time Doctor and
        • (28:50) – Simplicity versus complexity in project management software development.
  • (30:20) – The biggest obstacles and challenges to success that Rob sees moving forward.
    • (31:22) – Distraction of focus.
  • (32:51) – Parting advice to founders.
    • (33:09) – Interview your customers.
    • (33:14) – Fully develop a clear problem statement.
      • (33:33) – Don’t work on anything else until you’ve solved that problem.
      • (34:27) – The problem statements for Time Doctor and

Rapid-fire Questions:

  • (36:02) – What do you spend too much time doing?
  • (36:31) – What do you not spend enough time doing?
  • (36:52) – What are you hoping to accomplish in the next quarter?

Where to learn more:

If you want to hear more from Rob or see what’s happening at Time Doctor and you can contact him through the contact page at Time Doctor or the via the same page at


Andy:  Rob, thanks for coming on the show.

Rob:  It’s great to chat with you.

Andy:  0:00:06.8  So, you’re the cofounder and CEO of Time Doctor and  To get started, why don’t share what those companies are, what they do, and how they all came about.

Rob:  0:00:19.3  I actually started initially, because I had a team in the Philippines in an office, so I had over 20 people working on various internet marketing businesses in the Philippines, and I actually wanted to leave the office.  I kept getting drawn back to coming into the office, even though I was only there one day a week kind of thing.

0:00:41.3  But I would keep coming back, and I actually wanted to leave the Philippines.  So, I’d traveled to the Philippines so I wanted to leave.  So, I had this idea of wanting to have everyone work from home, so I developed some software that would actually work and allow me to have everyone working from home and have confidence that everyone was working effectively and productively while working from home.

0:01:03.8  So, that’s how I created the software.  Really for my own need in the beginning, and then it was also a need that a lot of other people had that I also realized they needed it, so I started to sell it to other people as well.

Andy:  0:01:17.0  And what is the difference between Time Doctor and Staff?

Rob:  0:01:22.0  The difference is that Time Doctor is aimed at remote companies and it’s all activated and controlled by the user.  So, if you’re working remotely, you need to be able to say, “Look, this is my personal laptop, I’m turning it on, I’m turning it off, I completely control it.” is different.  It works for office computers.  It’s for larger companies.  It works in the background, and has an option of background.  So, it’s a bit closer to employee monitoring software,  0:01:51.9  But it also has these features for machine learning for predicting behaviour, as well.  Which is an interesting kind of slant.

Andy:  0:02:02.2  What sort of behaviour is it trying to predict?

Rob:  0:02:03.4  It can predict things like, when the person is going to quit their job.  So, if the person starts their job, you can predict within a few months of the person’s likely to quit their job.  So, in a call-centre for example, one of the big problems is churn.  You have people that start, and then three months, six months, they quit their job.

0:02:23.8  And if you can identify that really quickly, that’s a huge benefit for the organization.  So, those are the kinds of things – you can actually also predict if the person is more likely to become a management material within six months, if they’re going to be on that track.

Andy:  0:02:40.4  And when did you branch off?  Because I know, at least in its current form today, hasn’t been around since the very beginning.  Or has it?

Rob:  0:02:49.3  Yeah, no it hasn’t.  We actually had another version of before that, which we shut down.  And we evolved it into this version, which is kind of similar to Time Doctor, but aimed at a quite a different market.  0:03:05.8  So, it’s more recent.  It actually launched only less – about one year – less than a year ago.

Andy:  0:03:09.9  And did that come about just by listening to the customers and some of the requests you were getting at Time Doctor, or was there something more to it?

Rob:  0:03:19.1  It was partly that, and partly my own intuition of knowing what people need in an office situation versus in a situation where they’re working from home.  So, the way that Time Doctor works, is it’s time tracking software and also productivity, so that you know when your staff are working, and you know if they’re working productively, and that is all controlled where they click to say, “Yes, I’m working on this task, I’m working on that task, etc.”

But for large companies, who’ve got thousands of people, then it’s kind of hard to get people to change their behaviour in that way, to actually get them to start actively tracking time.  0:03:59.0  So, that’s why the idea of came about.  It’s just a different market really, a different kind of segment.

Andy:  0:04:06.5  No, that’s interesting because in that market, you’re going to have people coming from all sorts of different backgrounds.  A lot of times, with a time tracking tool from own experience, you’re going to have people who are looking for something just to keep them off Facebook, and you’re also going to have people like you’re saying, who run an office and want to make sure that their staff is, not just productive, but looking to get some insights to really optimize the behaviour that they’re getting.

0:04:34.6  And trying to do that all within one tool, within one marketing site even, is really difficult.  0:04:40.4  So, I think the split makes a lot of sense.  But, I’m curious, where roughly – roughly where is the company at today?

Rob:  0:04:48.0  In terms of size, we have over 70 people in 28 countries all around the world.  So, we’ve got seven figure revenue, so it’s a software as a service model.  So people pay us every month.

Andy:  0:05:07.8  And, you started back in April 2012, and I’m guessing it wasn’t just this overnight success, and immediate hockey stick of growth, so looking back on those five years, what do you see as the major turning points in your company’s history?

Rob:  0:05:26.2  There’s a lot of improvements, there’s not really one specific turning point where everything hinged on that point.  0:05:34.0  I know that there was some split tests that we did for conversion optimization that actually made a big difference, so we found, discovered something that helped a lot to get more people to sign up.

0:05:45.2  Because in the beginning, we were finding it difficult to actually get people to sign up.  So, I think there’s a lot of different things.  At the moment, we’re working on improving the design, so I think that right now that’s going to lead to quite an increase in the way that the business is going.

But, I can’t say that it’s always one thing right.  It’s just constantly working and it’s just diligence of improving, improving, improving.

Andy:  0:06:11.1  Exactly.  It’s just kind of moving the ball forward and steadily making progress.  And that’s the thing that so many first time entrepreneurs, people who get into startups, I don’t want to say the wrong reasons, but for maybe naive reasons, they don’t see just how much work over such a long period of time, is needed to really get to success.

0:06:33.8  But one thing I do want to talk about, is that – some of those split tests that you run.  Because if you go to, you’re going to see a website that is much different than a typical SaaS website.

0:06:50.5  So, how did this come about?  Was this just a test – and to describe to the listeners, basically, if you go there right now you’re going to see the logo in the top left, but you can’t click it.  It doesn’t bring you anywhere, and it just says, “Answer three questions to see if Time Doctor is right for you.”  0:07:06.1  First question is do you manage other people, and then there’s a yes or a no.  There’s the three questions, and that’s it.

Rob:  0:07:15.1  There’s actually no option.  There is a kind of hidden option at the top right, which is to sign in.

Andy:  0:07:19.8  I see it.

Rob:  0:07:19.8  You can almost not see it, and it’s only there for the people that have deleted their 0:07:23.8 [Inaudible] … they’re still users and then they need to sign in and they don’t want to have to go through the three questions.

But, basically, this three question approach is something I came up with because I was thinking that people are in this mode of just looking when they go to the web.  They just, “I’m going to look at this and have a look at that and then I’m going to…that’s it.”  They don’t do anything.  0:07:46.7  So when you start to actually click and you start to go, “Oh, I’m going to click on something” it gets the person in an action mode, where they’re starting to take action rather than just – and be proactive rather than just passively reading material.

0:08:01.3  So, I think that makes a difference in the psychology of the person as they’re going through the website.  And we have split tested that versus without the three questions, and it has won.  That doesn’t mean that we’re always going to continue with that in the future, because there are disadvantages to those three questions.

0:08:18.6  I don’t think it would work for the majority of businesses.  For example, it does really annoy people.  They don’t want to actually click on those three questions.  And that’s something that some people have said, “Oh how can you do that?  It’s annoying people, what’s going on?”

But, I think the thing is, if the person is so annoyed that they’re not willing to even answer three questions, the chances of them buying the software is almost nil.  0:08:45.4  The type of person that’s not willing to answer three questions, is also the type of person that is never going to buy our software, so it doesn’t make a difference to us in that perspective.  0:08:53.6  But, it’s something that we were looking at again.  We may change that.  You might see that go away in the future.

Andy:  0:09:01.1  Yeah, because it’s funny that you mention that the type of person who would be annoyed by that.  And obviously, at least from my perspective, many people will be slightly annoyed, because it is – if I’m in the mindset of, “Alright, I’m going to figure out these different options, evaluate them, check out the website, get some features, get this and that,” this is different.

0:09:22.4  And it’s like, “Ah I don’t want to go through this.”  But, if I’m someone who is really trying to solve a painful problem, it’s going to be worth the time.  You say it’s only three questions, I can tell that the questions are pretty simple, I’ll do it.  It’s not probably going to be a big enough roadblock to get me to go away entirely.

Rob:  0:09:39.0  It’s extremely simple to click on three questions, and it’s also a bit of a novelty factor, “Oh, this is a website I haven’t seen before,” so that’s a positive as well.  So there’s positives and negatives basically, and so we’re kind of playing with that to see what the best option is still.

Andy:  0:09:54.6  Have you tested a format like that at

Rob:  0:09:58.7  No, I think we haven’t tested that.  The traffic is a bit lower at at the moment, so – and because it’s aimed at more enterprise, and also because we have more of a sales model for  The traffic to the website is not something we can split test as easily, and it doesn’t make so much of a difference.

Andy:  0:10:19.7  Interesting.  And, we had talked about this a little bit before the call, but you had mentioned how you’ve gotten to where you’re currently, 70+ people, doing seven figures a year in annual recurring revenue, what do you see as – I know it wasn’t a major turning point, but what were some of those actions that you took consistently to help get to that point?  What have really been the drivers of your customer growth so far?

Rob:  0:10:47.2  So the first thing was actually using the product ourselves.  I would say that’s possibly the most key – important key factor in our success in the beginning.  Because, the fact that I was using it and that our team was using it, means that we were constantly looking for problems.

0:11:05.2  And with, especially desktop software, which they say it is a software that is on the desktop, it has to be on the desktop, it can’t be just web-based, and that kind of software has multiple small issues.

0:11:16.7  So, there might be a person, 1 in a 1000 person, people have this specific issue with the software, so you have to fix that issue.  But you really need to fix all these tiny issues in order to gain enough momentum in order to make sure that people are not annoyed and there’s not constant problems.  0:11:36.9  And that’s a key factor obviously.

0:11:39.2  And then, it’s content marketing.  Working a lot on our content marketing, getting some traffic and growth from that, 0:11:47.3  and then it’s the product.  I think focusing on the product is really, really key.

And I’ve heard that from many different software as a service founders.  It’s just make a product that people love, constantly listen to the customers, try and improve the product, and I’m not saying that we’re perfect, I think that we were probably not as good as companies like Facebook in how they do things or we’re definitely not – we don’t have the resources of a company like Facebook or some of the very successful SaaS products that are way more successful than us, but we had something that we have focused on.

0:12:25.6  We hired a big development team, we constantly worked on improving our product and that has paid off.

Andy:  0:12:33.7  It’s – when I talk to early stage founders, I’ve been doing this for awhile, and startups have always been something that have really interested me, and the ones that get successful, the ones that kind of break out of those earliest stages and get some traction, they get to the 10K, 20K+ MRR a month, they’re doing something.

When you talk to them about what it was, it’s almost never some marketing strategy or anything, like a growth hack or whatever, it’s always, “We just had to keep working on our product, improving it, because there was so much low hanging fruit, there was so many feature requests, there were so many bugs we had to tighten up before it even made sense to really start pouring in the effort on marketing.”

You got to make sure the product is there, and it seems like at those very earliest stages, just getting the product to be good enough is a pretty big challenge.

Rob:  0:13:28.5  Yep.  It doesn’t mean that marketing is not important, and I think it depends also on the competitiveness of the product, the type of product.  It’s becoming more difficult because there’s more products out there that do everything, so you – there’s probably a competitor.

When we first started, there wasn’t as many competitors, or at least when people came across, or they’re looking for a product that did what we do, then they probably didn’t know of any other competitors, so they didn’t, they hadn’t found anything else that could do what we could do.

0:13:59.3  So, that’s helpful as well.  To be in a market where you’re not saying, “Oh, here’s ten competitors, which one am I choosing.”  Because if you’re a startup and you’re in that situation where there’s too many competitors and they’re going – you’re choosing one versus ten, you’re going to be really stretching to be able to compete with nine other guys who have been there for a few years and have – probably some of them have 10 million dollars funding.  You know what I mean?

0:14:27.8  It’s really, really difficult.  If you go in a very niche – what I’ve seen some startups do, is actually just same product, but in a different niche, so that different, kind of – we’re actually for lawyers, we’re for accountants, and then they – it may not be that the product is dramatically different, but the very fact that they are marketing it for lawyers will make a difference.

Andy:  0:14:47.9  Right.  If I’m evaluating ten different solutions and one of them says they’re specifically for someone like me, that just answers all of my questions.  I’m almost taking a chance by going with someone else when it seems like this one product is going to serve my needs exactly.

0:15:04.8  And so, I’m curious though, there are a lot of competitors out there, I had told you before that I had actually worked with Hubstaff for quite some time, and they’re competitors as well.  How do you stand out in the competitive market like that.  Because, right now, if I were to look for time tracking deals, I can’t even imagine how many would come up.  So, what do you think it is that gives Time Doctor and a competitive edge?

Rob:  0:15:31.1  For Time Doctor, we are – firstly, we are focusing on a specific niche, which is people working from home, and our very specific niche is people that are tracking the time of somebody in a really actually a – it’s similar to a kind of an Upwork thing where they have somebody who might be in the Philippines, they’re tracking their time and they want to see screenshots of that person.

0:15:56.1  So that’s a super narrow niche.  But our software can also do the same function as other kinds of software like, I don’t know if you’ve heard of Toggle, for example, which doesn’t do that kind of screenshot thing at all, it just does time tracking.

0:16:13.4  So, by focusing on the narrower niche, we’re able to get that market more completely and really serve the needs of that market.  But I would say actually, what we’re trying to do at our core, is to have a software where you know if your team is really working.  Like, you can be sure that you know your team is working even if you’re not there.  And that you can have confidence in their productivity.

Now you tell me a software where that’s the case, because it doesn’t exist actually.  0:16:46.8  There is no software that can do that.  There – even our software, we’re only just touching it on how to do that.  So, actually it is meeting the core need.  And that’s the core need.  The core need is how do we know that our team is really productive, they’re really working even though I’m not in the office.

So, I had that need, I had people in the Philippines, I didn’t want to go to an office, I didn’t want to have to check up on them, I just wanted to make sure that everyone is really, really productive.  And so, as far as I know, there’s no software which actually can do that effectively.  I could go into that in many details.  0:17:24.8  It’s a very hard problem to solve, and that’s why nobody does it.

Andy:  0:17:30.1  And I think that makes a really, really good point because so many people forget that customers aren’t looking for another SaaS tool to add to their growing list of software that they need to use to run their business.  No one wants a time tracking tool just for its own sake.  They want it because of what’s going to help them do in their business.  And a lot of times, that’s going to be bringing accountability to a remote team.

0:17:59.5  And, you’re not solving a time tracking problem, you’re solving that accountability problem.  You’re solving deeper issues there.  So, I do think it would be interesting to go a little deeper on that.  0:18:09.2  Like how are you planning on tackling that core issue of what your customers are really looking to solve?

Rob:  0:18:17.5  Well, you want, as the the owner you want to be able to see very, very quickly.  So you want to go and say, “Here’s my team, I can see in a report that I know they’re productive based on that report.  I know if they’re slacking off, or if they’re on Facebook all day.”

Telling someone’s on Facebook is not a full answer, because they might be doing social media, they might be on another website, it might be the case that somebody who is on Facebook actually is productive, it’s just that they’re relaxing a bit in their own Facebook.

0:19:02.1  So, it’s a lot more complicated than that, than just saying, “Hey checking if my team’s on Facebook.”  So, it’s looking into all the details of that.  We actually use machine learning to, kind of, try and determine what is the factors that actually are associated with productivity, but it’s a complicated answer and it’s something that we’re still figuring out.

And we’ve got a tool which works, and people are really happy with it, where it is now, but we want to take it to another level of being able to do that to a better degree.

Andy:  0:19:34.4  What metrics do you use to, I guess, measure productivity.  Because that’s something that in itself, seems like a really difficult challenge of trying to figure out the right way to measure that, because with all machine learning, with anything else you try to apply to the problem, you still have to answer the question, alright, how do we actually measure what is productive work and what is not.

Rob:  0:20:02.5  Yeah.  I mean that’s like a core – that’s the core problem.  Is like, is this person – there is no one single thing that you can say that this one thing is productive.  Because people talk about this quite a bit.  They talk about the story of the person working two hours a day and it’s the same productivity of somebody working eight hours a day.  And that can be true.

0:20:26.9  I would say it’s not true.  I would say most of the time, people who are working harder are more productive.  0:20:33.1  But it’s interesting that just working harder doesn’t make you more productive.  So, it’s like a – it’s a really interesting puzzle.  I’m not sure I can answer it on this call, because it’s still something that we are getting the full – we’re still putting the picture together.

0:20:50.5  We have the software which works reasonably well, but I’m just admitting to you, there is, in my opinion, no software out there which fully solves that issue.  But I believe it is solvable.  I believe it’s something that we can solve, and we can find out indicators of what a person, when they’re becoming less productive.

0:21:09.0  One of the things that actually, for people that are working from home, they can really kill productivity is if they have young children.  And I know that, because I have young kids, and I could not possibly work at home when I have young kids.  It’s just a nightmare.  It’s absolutely insane.  I would be in the room, like a separate room right?  So, I’m in the room and then my two year old will be knocking on the door for 15 minutes right.  Not just for a minute, but for 15, “Daddy, daddy, daddy, daddy, daddy.”  So the idea that you can be productive when your two year old kid is knocking on the door for 15 minutes is insane right.  There’s no way.

0:21:47.1  So, remote — productivity for a remote team, it’s a tricky equation.  Now for other people, they do manage to solve it, even with those young kids.  All the kids – people in our team that have older kids, we have mums, and they seem to be able to manage it.  Usually they have a nanny.  They’re in the Philippines, and nannies are a big thing over there.  So they’ll have a nanny looking after the kids while they’re working from home.

0:22:13.6  But I believe that there are indicators.  The simple ones are just, does the person – were they working eight hours a day and did they suddenly now only working five hours a day, or four hours a day with lots and lots of gaps because they have to constantly get up.  That kind of thing.  But that is too simplistic, and it’s not going to give you the answer, because there maybe people that are working the five hours and being just as productive.  0:22:45.7  It’s complicated.

Andy:  0:22:47.3  Yeah, it’s a hard problem.

Rob:  0:22:49.2  It’s a hard problem, and that’s why I think this is going to be an amazing market for us, because we already have quite a lot of people.  Obviously it’s a need.  There’s a huge need, and we have a lot of people that are seeing that it’s working for them.  But, I’m admitting that we can do even better.

0:23:07.2  We are not fully solving this problem.  I don’t see any software on the market that is fully solving the problem and I think that we can solve it.  0:23:14.2  And I think it’s also contentious.  I think the interesting thing about this is that there are people who really love our software, and there are people who hate it.  That’s an interesting thing as well right.  Because people hate the idea of the concept of being monitored or that sort of thing.

0:23:34.0  And so, I think it’s actually good to be in a market where there’s a love hate relationship.  It’s something that we are also working on, but we can’t desire to be loved by every single person out there, because if everybody just likes us, then we probably don’t have a market.  We have more of a market by the fact that some people love us and some people hate us.

Andy:  0:23:58.2  You need strong opinions to motivate action.

Rob:  0:24:02.0  Yes.  Yeah.  But that also doesn’t mean that we want to create bosses that are, kind of, basically nasty bosses.  We’re not like that, we’re very relaxed about our team and I like to think that we’re quite – I’m a good boss, and if you look at our team, we have almost nobody who’s left our team or went early.  So, that’s an indication that obviously people are pretty happy if they’re never left.

Andy:  0:24:37.1  Right.  You touched on a lot there, and one of the things that I really want to stress, is that as SaaS gets so much more competitive, because it’s so much easier to build tools today, you’re in a slightly different spot because of the desktop software component of it.  That is a bit bigger of a burden to entry.  But, it still hasn’t prevented you from having dozens of competitors.

0:25:01.4  But as things get more and more competitive, it seems like you can’t just be a pack of features anymore.  You really need to solve that underlying problem that your customers are having.  And to do that, it is usually going to be pretty hard.  It is usually going to take a lot of work and that’s why other people haven’t done it, but I feel like you’re right on in that in the long run, to really thrive in the competitive markets, you have to solve some of those hard problems.

Rob:  0:25:30.0  Yep, yep.  And I think even at its core, you look at probably the most competitive area in SaaS, it would be project management software.  There’s so many project management software out there.  You’ve got Asana, you’ve got Basecamp, and they’ve got a lot of funding, they’ve got huge number of users, and they’re trying to solve the issue of collaboration and how to get teams to collaborate better together.  But within that, have they really solved it?  No.

0:25:55.3  I mean if you look at people that are using Basecamp, most of them are not using it properly, or they haven’t – they still use emails and the communications are still all over the place.  So, they haven’t solved the issue, because it’s an extremely hard problem to solve.

Andy:  0:26:14.7  Right.  And so, I’m curious, how do you allocate your resources in terms of developers, in terms of your internal team.  How are you allocating resources to work on these hard problems.  Because you can’t just put all of your developers on these, not necessarily moon shop, but on these bigger projects that aren’t going to pay off for quite some time?

Rob:  0:26:37.9  That’s an allocating – we now have a product owner, product manager who allocates the resources and says this is the product road map and we’re going to work on these things first.  So, we work on that with a combination of what people want, where our vision is for the product, where we think it could be, and then try to focus on this core issue of how do we solve that.  How to make sure that you know that your team is working.

So, focusing on that and we put all of that together, synthesize it, and it’s a judgement call really at the end of the day.  0:27:11.4  But some – if you’re listening to your customers, there are some things that will come across very strongly.

0:27:18.7  So, you’ve got to take into account, is it an easy thing, you might do that quicker because it’s an easy thing to handle.  How many people are asking for it?  How does it fit with your vision, are you just distracting yourself by going in 50 different directions or are you still at the core?  So, you want to try and keep the core of the product.  So, you put all of these factors together, and then you decide on where to prioritize based on that.

Andy:  0:27:41.1  And to go a little bit deeper, because it’s like there’s going to be bug fixes, there’s going to be those low-hanging fruit types of requests, types of things that are on the roadmap that you can say, or the product owner can say with pretty reasonable accuracy, “Alright, if I put a few developers on this, they can knock this out in a week or two.  In this next spring” or however you have it structured.

But like, how do you fit in, “Alright let’s develop a machine learning algorithm to measure true productivity.”  Like, how does that, kind of, fit into the more traditional prioritization charts of priorities on a roadmap?  Do you break it down into pieces, or is this something that you have a few people just continuously working on, or…

Rob:  0:28:29.4  Yeah, we just have one person who’s a machine learning expert who’s working on that.  So it’s not really a distraction for the rest of the team.  It’s not an expense that is something that we’re particularly worried about, so it’s just something that we’ve identified as an opportunity, so that’s what we’re working on.

0:28:50.0  In other areas, it’s the more resources the better, in some ways.  I think that if you look at different models, it’s interesting, because you hear a lot about simplicity and keeping the products simple.  And for example, Asana is like that, and Basecamp is fairly simple.  They try not to build too many features.  And then you look at Atlassian and Jira, you’re familiar with Jira?

Andy:  0:29:17.9  Yes.

Rob:  0:29:17.5  Incredibly complicated product.

Andy:  0:29:20.8  Yeah, they have an entire industry of consultants just to get it set up for you.

Rob:  0:29:25.2  Yeah, and Salesforce 0:29:24.9 is even more complicated.  Salesforce is the original SaaS product and it’s probably the most complicated SaaS product around.  I just, I would hate to set up a Sales Force account, it’s just so complicated.

0:29:37.7  It’s like, it’s interesting that this simplicity thing, well there’s a certain truth to it, but there’s also a truth that the enterprise customers, the bigger customers in particular, they need all these features, they want these features.  And I think the part of the success of Atlassian and Salesforce is that they have all of these features that do all of these things, and it satisfies the needs of more enterprise and larger clients.  And that’s part of their success.

Andy:  0:30:07.2  That’s really interesting, because there is so much difference between the small-medium business market, the pro 0:30:16.0 [Inaudible] market and the enterprise market, and you can see it a lot in how you split up your business.

Obviously, there are a large businesses on both ends, but dividing the products into two different brands that are going to tackle different segments, it seems like a way to, kind of tackle that, but those enterprise clients, those enterprise deals are an entirely different ball game, in my opinion.  And I would have loved to have another hour to talk with you to really dive into how you’ve made some of those adjustments as you moved upmarket.

But, unfortunately, I can’t steal of your time this morning, but what I do want to ask though, to start wrapping things up, is it seems like solving these hard problems, finding a way to really stand out in the crowded market, is one of the bigger challenges that you’re facing.  But you’re willing to tackle it going forward.  What do you see as the biggest obstacle to success?  The biggest obstacle that could get in the way of actually achieving some of those loftier goals that you’ve set up?

Rob:  0:31:22.2  Distraction of focus.  So, I think that that is something that I’ve constantly had a problem with, and it’s something that I personally made many mistakes in.  Because as I’ve built the product, and I was the product manager for many years, until fairly recently, we brought in a product manager, so I was actually making the decisions about where we were going to build the next feature.

0:31:48.2  And I think, quite honestly, I built a lot of stuff that we didn’t need or that was only a small percentage of people were using.  So I made these classic mistakes, that I think if you read a lot of startup stuff, they talk about again and again, is to focus on the core need and to solve that really well before going on to something new.

0:32:08.4  So, that’s the mistake that I made in the past, and I’m going to continue to make sure that we don’t make that mistake in the future.  Focus on the core need and don’t go in multiple different directions.

0:32:21.9  I know I just said that Atlassian does that, but they are doing it – I think they’re doing it after they’ve solved the core need, or at least it certainly also in proportion to the size of the business.  So, if you’re a ten million or a 50 million dollar business, it’s quite a different equation.  At that stage, you could go ahead and build lots and lots of little features, and that’s fine.  So…

Andy:  0:32:47.7  Especially if you’re a billion dollar business.

Rob:  0:32:50.4  Yeah, exactly.

Andy:  0:32:51.6  But so, for founders who are at that point where they haven’t quite solved that core need yet.  They’re making progress, what advice would you give to them to keep that focus and to not get distracted by some of those shiny objects that may pop up?

Rob:  0:33:09.1  Interviewing customers definitely will help, but I think the problem statement is something that’s really helpful.  So you have written down what is the problem that you’re solving, and make sure you write that down.  Because if you write down the problem statement, then it will always bring you back.

0:33:33.8  And don’t keep – basically have a philosophy of not to work on anything else until you’ve solved that problem.  And you’ll know that you’ve solved the problem because the business will start to take off and people will be rating you really highly and it will be, I think it will be reasonably obvious that you’re on a good track at that point.

0:33:57.7  Unless you’ve solved a problem that’s not a big enough problem for people.  In which case, you’ve made the wrong decision in the first place about the business.

0:34:08.5  But, I think it’s just having in your mind that you’ve got to focus on the problem and the problem statement.  What is it?  Have we solved it?  Do we need to keep working on that?  What else can we do to solve that?  Keep – your mind is such a powerful thing, if you keep focusing on that, “How can we solve it?  How can we solve it?  How can we solve it?” eventually you will come up with a way.

Andy:  0:34:27.6  And how would you put into words what the problem statements are for Time Doctor and Staff?

Rob:  0:34:34.9  So for Time Doctor, the problem is that when you have a remote team, you don’t know what they’re really doing.  You don’t know if they’re productive, if they’re really working, if they’re slacking off.  And you want to know, are they actually working, are they being productive right now.  What are they really working on?  How can I see in one glance that I can be sure that they’re working.  Even if they are working productively, sometimes there’s a nagging doubt for the owner and they need to be reassured that the person is working productively.

0:35:05.9  So, it’s even if they are working productively, the person needs to be reassured that they are working productively so they don’t have to constantly ask them questions.  0:35:14.7  You know some business owners are like, “Oh what did you do today?  What did you do today?  What are you doing?” and then the employees are probably pulling their hair out because, “Can’t I just do my work?”

Andy:  Let me just focus and get things done.

Rob:  0:35:29.2 …tells you that, and gives you that analysis and gives you very, very quickly and easily in a succinct format, and then the owner doesn’t have to go back to the team and constantly ask them to try to follow up.  They feel reassured, that’s the problem.  And that’s the problem that I believe, in my opinion, nobody has fully solved yet.  0:35:49.2  There’s a lot of people attempting to, but nobody’s really fully solved.

Andy:  0:35:54.0  And then Rob, before we wrap up, I like to ask all my guests a few rapid-fire questions, so I’ll go through them quickly, but your answers don’t need to be short.  0:36:02.0  And the first one is just, what do you currently spend too much time doing?

Rob:  0:36:05.2  I have been spending too much time creating accounts, because it’s crazy, as a software, as a sort of business, we have 50 – it’s maybe not that much, but it’s at least 30, 40 different pieces of software, and I’m sometimes creating accounts for people.  So, I’m starting to, basically outsource that to someone in the team.

Andy:  0:36:31.2  And then what are you not spending enough time doing?

Rob:  0:36:32.8  Actually communicating with the team via video.  Because we’re remote, the team needs to feel connected with me as the founder and then also to just communicate the vision.  So those sorts of things I have been a bit slack in doing.

Andy:  0:36:52.7  And then, what are you hoping to accomplish in the next quarter?

Rob:  0:36:57.7  In the next quarter, we are building out the next versions of our desktop software and improving the design of the product.  And we’re also doing a lot in terms of marketing, improving our social media marketing, improving our content marketing.  So, there’s multiple fronts that we’re working on.  Split testing.  So there’s a lot of things coming down the pipe.

Andy:  0:37:24.4  Awesome, and Rob, again I want to say thank you so much for your time today.  It was a lot of fun chatting, but before we do say goodbye, if listeners want to hear more from you or just see what you’re up to at Time Doctor and, where are the best places for them to go?

Rob:  0:37:39.8  Yeah, you can see at the Time Doctor, you can basically go to the contact us page there, you can have a look at our blogs, you can do the same for and if you want to get in touch, I think you can send a message through the contact us page on Time Doctor, is probably the best way.

Andy:  0:38:05.3  Awesome!  Well Rob, thank you again so much for your time.

Rob:  Ok, great to chat.