Homebase's Oliver Fisher on leading high-performing teams

00:00:00:12 - 00:00:25:02

Ben Hillman

It's been a long season. The championship is on the line. For the sake of our metaphor, pretend that's your favorite sport. Hockey, basketball, football of any kind. The captain breathes deeply. Their heart rate is lower than the rest of the team. They've been through countless battles and fit naturally at the center of the team, huddle. They've reached the pinnacle of success with this team and others many times over.

00:00:25:04 - 00:00:46:11

Ben Hillman

So much so that the weight of the trophy is familiar when the final chance to score fives, will they take it themselves or pass it to a worthy teammate? This is the kind of leader that every team desires, the kind of leader who makes victory possible. Much like the world of sports, the B2B SaaS industry thrives on strong leadership.

00:00:46:15 - 00:01:08:03

Ben Hillman

The ability to navigate the complexities of software development, manage the first teams and keep a keen eye on the ever evolving market landscape is a testament to the prowess of those who stand at the helm in this fiercely competitive world. The guidance of an experienced leader can make all the difference between championship glory and entering a rebuild. Enter Oliver Fisher.

00:01:08:05 - 00:01:35:13

Ben Hillman

He may not be the LeBron James of SaaS or even the Wayne Gretzky of SaaS, for that matter. I mean, he is Canadian after all. But he is a man who knows more than a thing or two about leading teams of various sizes. At the time of the interview, Oliver was the chief technology officer of FreshBooks. Currently, he's the CTO of Homebase and he's had in-depth stops with the likes of Microsoft, Google and Shopify, all places where he was integral to early product initiatives.

00:01:35:18 - 00:02:02:16

Ben Hillman

In today's episode, we will delve into the valuable advice Oliver Fisher has to offer on what it takes to be a successful team leader and B2B SaaS. Join us as we explore the human aspects of leadership, the importance of structure and how to foster an ownership mentality among team members. Don't miss this opportunity to learn from a seasoned veteran of SaaS who has navigated the challenges of leadership and emerge victorious time and time again from battle.

00:02:02:16 - 00:02:27:21

Ben Hillman

It's Protect the Hustle, where we explore the truth behind the strategy and tactics of B2B SaaS growth to make you an outstanding operator. On today's episode, Oliver Fisher talks to Andrew DAVIES about the aspects needed at various steps of the leadership ladder. They talk about turning dreams into reality with folks who sell their time being integral to early Microsoft, Google and Shopify product initiatives earning mettle from excruciating leadership opportunities.

00:02:27:22 - 00:02:46:02

Ben Hillman

What aspects leaders need to build in at each step of the career ladder, and what to look for in acquisitions from a technological perspective? After you finish the episode, check out the show notes for the key skills leaders need to steer high performing teams. Then, while you're leaving your five star review of the podcast, tell us what resonated most about Oliver's advice.

00:02:51:11 - 00:02:57:01

Ben Hillman

First up, Andrew and Oliver talk about turning dreams into reality with folks who sell their time.

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Andrew Davies

Hello and welcome to Protect the Hustle. My name is Andrew DAVIES, Chief Marketing Officer of Paddle, and I'm really excited to be joined by Oliver from FreshBooks today. Hey, Oliver, thanks for coming on and prompting. Give us a quick introduction to yourself.

00:03:13:05 - 00:03:50:02

Oliver Fisher

It's great to be here with you today. Andrew Thanks for having me. I'm really excited to be chatting about all sorts of interesting things wherever our conversation may take us. I'm CTO at FreshBooks. I've been with the company about five and a half years at this point. My career before that started as a software engineer, starting at Microsoft for a number of years, moved over to Google where I took on increased technical leadership and eventually moved to Shopify, where I really started my real journey into management and leadership across the technical team and then came to FreshBooks to lead the engineering team here and that's been a really, really fun experience as I as I

00:03:50:02 - 00:04:10:07

Oliver Fisher

continue to learn more and more stuff and about business and how to lead the organization and doing all sorts of weird things like acquisitions and of course getting through the pandemic. The pandemic is actually everyone catching up with me because throughout my career, all the way from back from Microsoft, I've worked remotely and have traveled a lot. So I when everybody else went home, I said, Welcome aboard.

00:04:10:09 - 00:04:11:12

Oliver Fisher

I've been here for a while.

00:04:11:14 - 00:04:29:13

Andrew Davies

Well, I did assume that because I assumed that the Facebook and Google sorry, that Microsoft and Google don't have local offices up in Ottawa, but we will definitely dig into a bunch of those topics. And absolutely your your journey has been a really interesting one. Progressing from staff engineer, director, VPNs up to CTOs. So we're going to dig into that today.

00:04:29:13 - 00:04:45:12

Andrew Davies

I'd love to get some insight from you of, you know, the levels and the steps and the thinking, the learning you had to go through at each of those stages. But I had a quick look at your LinkedIn profile earlier, and it says there that you lead the FreshBooks technical organization that turns dreams into realities. So I love a big, bold statement.

00:04:45:12 - 00:04:54:15

Andrew Davies

So perhaps you can give us a little bit more color on what the organization looks like, the size and shape of the technical organization, and maybe a few of the dreams you've turned into realities whilst at FreshBooks.

00:04:54:16 - 00:05:13:03

Oliver Fisher

Yeah, I mean, I do I do think of it as dreams turning into reality. Sometimes they're small dreams, sometimes they're bigger dreams, sometimes they're smaller dreams that all add up to a bigger dream. So we have a with the company is about 700 800 people at the moment. When I started, it was around 300. The technical organization is probably around 250 people.

00:05:13:03 - 00:05:34:02

Oliver Fisher

I lead the engineering organization and doing product development, and then I have a couple of peers who lead our product organization and our Chief data officer who leads our data engineering and analytics organization as well. We have a very strong relationship because she handles all of the internal technology and I handle all of the external technology, which is, which is great.

00:05:34:02 - 00:05:55:09

Oliver Fisher

And we know where to sort of draw the line between what we do. Yes, I try and make the things that that go out to our customers and have them love and use every day. We started out as an invoicing company, but have now turned into North America's second largest online accounting service provider for small and medium sized businesses.

00:05:55:09 - 00:06:15:11

Oliver Fisher

So we focus particularly on people who sell their time. My wife is a lawyer. She runs a small her own small law practice. She keeps track of her time in FreshBooks, sponsor invoices out in FreshBooks gets paid, and FreshBooks is able to just push a button and send all of her records to her accountant at the end of the year instead of handing over this giant shoebox of paper.

00:06:15:11 - 00:06:41:18

Oliver Fisher

So she ends up saving money with her accountant. She gets as we start to do more and more data analytics and understanding the type of business that she's running and other people who are running similar types of business, we get to give her insights as to how she might be able to do things better. One of the great ones that we actually had come out of what we call innovation days, which is sort of the free time that we give our engineers to come up with brand new dreams to try and turn them into reality.

00:06:41:18 - 00:07:00:05

Oliver Fisher

One of the really interesting things there was about using some machine learning to figure out how much you should bill your time for, because you start out as doing your own business as a consultant, a lawyer, a I.T, professional, whatever. And of course you're undervaluing yourself and saying, I brand new to this. I should only I need to just get people based on price.

00:07:00:05 - 00:07:16:18

Oliver Fisher

Inevitably, you start out too low and then a couple of years in, you have no idea and you're scared whether you could really raise your price or not. We can give you some interesting insights in that about people like you actually charge twice as much as you do. Maybe you should have more confidence and really understand your value and get out there.

00:07:16:18 - 00:07:36:19

Oliver Fisher

So those are the sorts of things that I think are really useful and exciting to give people to really help them, you know, change their life. And that's why I think I love this this customer in this SMB space, they're really, really relatable to us, real, real human beings. They're not giant mega corporations. And they and you can have an impact on their life and deeply profound ways.

00:07:40:08 - 00:07:46:10

Ben Hillman

Next up, Olivia talks about being integral to early Microsoft, Google and Shopify product initiatives.

00:07:49:23 - 00:08:09:06

Andrew Davies

I love seeing and hearing a few of those stories of dreams that turn into reality, and we'll come back to that in a bit. So now if we reverse back 20 years, you joined Microsoft. I think you were working on Net Docs. Talk to me a bit about SEO, the world you entered. I think it was just out of college was that you joined Microsoft and it seems like you've worked for several different product areas there.

00:08:09:06 - 00:08:11:23

Andrew Davies

So tell me a bit about that experience and what you learned.

00:08:11:23 - 00:08:30:07

Oliver Fisher

That I ended up at Microsoft just by accident. I was at the University of Toronto doing a computer science degree. A friend of mine who had graduated a year or two earlier was working at Microsoft, and he came back and I ran into him some event. He I said, I don't want to this was in the mid nineties or late nineties.

00:08:30:07 - 00:08:49:18

Oliver Fisher

And so I said, I don't want to work for the evil Empire. And he said, Just send me your resume and you'll get a free trip to Seattle. I did, and I got a free trip to Seattle. And then sheerly by accident one afternoon I was talking that afternoon in the course of the interviews was with two people and they were just asked really interesting questions that I just really liked them.

00:08:49:18 - 00:09:11:10

Oliver Fisher

And they were working on this brand new thing that at the time was called Net Docs. It never really got another name since about a number of years later it ended up being canceled. No one's really seen it, but it was a tremendously exciting project and I and it was really these two people who I think really motivated and just gave me this insight of the things I could learn and the exciting things I could do at Microsoft.

00:09:11:10 - 00:09:31:12

Oliver Fisher

So when I talk to people about interviewing other engineers, I really point out to them that you might be actually changing someone's life in that interview because that decision that I made that afternoon to go and work with them is really shaped the next 25 or 30 years of my life in terms of things I learned. I mean, I sat down at the keyboard on the first day and just tried to figure out how to program.

00:09:31:12 - 00:09:52:18

Oliver Fisher

You know, I knew it from university, but programing as a professional, as a professional in a professional environment is is very, very different. And so just learning the mechanics of that is it was a tremendous learning experience at a company like Microsoft, which is one of those world class companies and is a really a machine that knows how to bring people along with that and help train them.

00:09:53:01 - 00:10:08:10

Oliver Fisher

If you're early in your career, I can't say enough about if you have the possibility of going into one of those places like that for a couple of years. So just learn how to do it is is amazing. I ended up by accident staying for, I think about nine years. A lot of life seems to happen by accident.

00:10:08:10 - 00:10:23:16

Oliver Fisher

But yeah, so I worked on that docs doing a bunch of internet technologies, but back then it was like the stuff I did then was about how are we going to get this software into this box that we're going to ship out to people once every few years? Then we won't know anything that they're actually doing with it.

00:10:23:16 - 00:10:42:15

Oliver Fisher

And it's so radically different now with everything that's online. The core skills of writing the program are the same, and the core values that you do are the same. But the feedback loop and the pace at which you can move now is so radically different than what was around then when you were trying to fit it all on to a CD.

00:10:42:19 - 00:10:46:02

Oliver Fisher

Not even a DVD. A CD that you would send out to people.

00:10:46:02 - 00:11:06:04

Andrew Davies

You spent 8 to 9 years there and you said a big first, big learning step was going from being a college engineer to being a professional engineer and reloading and loading that. Then we took we see the jump to Google. So what was the reason for that jump? Yeah, What was the step up or the leveling up that you had to go through as you took on more responsibility in some of their teams At Microsoft?

00:11:06:04 - 00:11:31:08

Oliver Fisher

I had dabbled with management, but for a variety of reasons. I actually, after about three years at Microsoft, ended up working remotely. And so I spent most of my career working remotely since then. And I was so I was doing team leadership, let's call it, and influencing our product organization, which was, I don't know, I'm well, I mean, I ended up on the Shell team at Windows, for instance, and worked on some some a couple of products in office as well.

00:11:31:09 - 00:11:48:01

Oliver Fisher

I moved around over a number of things, but was leading, you know, as part of an organization and helping to lead, let's say, a group of 10 to 15 people as part of a larger product unit of a few hundred. I was just getting tired. Just after nine years is a really long time and I wanted to do something different.

00:11:48:01 - 00:12:04:11

Oliver Fisher

And there was this amazing thing called the Internet that had come along somewhere in the course of all of that, and I could see a number of people who I knew who would move to Google, which was one of the leading Internet play places. They seemed to know something about the Internet and they were working in very different ways.

00:12:04:11 - 00:12:23:02

Oliver Fisher

And it was sort of exciting to figure out how to move over there. And there was also this really interesting possibility of being able to do more and more leadership. So I was living in Ottawa and working remotely and it happens that I happened to see that Google was hiring people in Montreal, which is about 2 hours just down the road.

00:12:23:02 - 00:12:57:15

Oliver Fisher

And so I emailed my friend John and said, Hey, did you know that you're hiring people in Montreal? And he said, No, I had no idea. We had an office in Montreal and it turned out it was three Icelandic employee people that that Google had bought from some company and put in Montreal. And so I ended up as employee number four in Google's Montreal office and the first non Icelandic employee there, which was exciting and that was really then became a journey about building something and building the team there, both in terms of building the office but also in terms of building a new product that I happened to stumble, stumble into again by accident,

00:12:57:20 - 00:13:18:14

Oliver Fisher

working on Google's anti-malware product and helping co-found that team in Montreal and grow that organization there. And so I think when I eventually left a number of years later, the Montreal had grown to about 50 people and the anti-malware team is now literally protecting billions and billions of people every single day. And I think their team is on the order of two or 300 people.

00:13:18:14 - 00:13:28:01

Oliver Fisher

Now, this is many, many years later, but it was it was a very exciting time. And so that was really the appeal was about building something not just a product but an organization and a group of people.

00:13:28:01 - 00:13:36:12

Andrew Davies

Being part of one of many hundreds and becoming part of a group of four initially that grew to 50. I love that. How's your Icelandic as a result? Have you learned any Terrible?

00:13:36:12 - 00:13:50:01

Oliver Fisher

Although I did one year at the Toronto Film Festival, I did go and see an Icelandic movie and then went back to the office and said, Oh, I saw this Icelandic movie. And one of them piped up and said, Oh, my brother was in it, and another one piped up and said, Oh, it was filmed in my cousin's house.

00:13:50:10 - 00:13:53:11

Oliver Fisher

So that's the sort of thing that happens when you talk to Icelanders.

00:13:53:11 - 00:14:12:11

Andrew Davies

But you use the word co-founder there, which I it was very interesting to hear. We'll come back to that a couple of times. I think talking about the the anti-malware engineering team building that out and protecting billions of users. And then I think I'm right in saying that you helped research or led the research and design of the first ad exchange, Google ad exchange forecasting system as well.

00:14:12:11 - 00:14:21:01

Andrew Davies

Very interesting to see working within those teams then in a team leadership position, but very involved in, you know, co-founding entirely new product paths.

00:14:21:01 - 00:14:40:15

Oliver Fisher

I will say I did not actually found that that was a product we inherited, but I think it's safe to say that the team that took it on at this point, I was working with a team in Chicago. We did take on this incredibly hard technical challenge and that was a really there were some really interesting moments in that because it was, again, a small team in Chicago that had taken taken that on.

00:14:40:19 - 00:15:02:19

Oliver Fisher

And we were trying to essentially forecast how many people between the, you know, males between the ages of 18 and 34 were going to be looking at the new york Times website between 3 a.m. and. 4:45 a.m.. Who also smoked and we were going to do this next december at wanted to understand that so that we could see how that inventory was going to get played out.

00:15:02:19 - 00:15:25:20

Oliver Fisher

So that forecasting problem was incredibly tactically complex and the team there at that point, I was again leading leading some of that team. And I there's a distinct moment in that where I realized what my job actually was as a leader on this team. And it was simply to say, yes, I joined this video conference meeting and it was and there were three or four engineers sitting there, and I said, Oh, hi, what are we going to talk about?

00:15:26:03 - 00:15:42:16

Oliver Fisher

And they started to outline this idea they had, and for whatever reason I had it in my head that particular week that I was just going to say yes to everything. And so they presented what I thought was a terrible idea just terrible. I thought it was going to go nowhere. And but for whatever reason, I said, Yeah, you should go give it a try, see what happens.

00:15:42:16 - 00:16:02:23

Oliver Fisher

So two of them went off and then came back a few weeks later and said, It seems to work. Can we get a couple more people? And at that point I said, Sure, find four people and they ended up finding a whole bunch more people. And it eventually completely revolutionized the product. And this again was just an accident of I happened to say yes, but that was this really interesting moment of understanding.

00:16:02:23 - 00:16:27:13

Oliver Fisher

A I really do not know everything. And B, there was nothing really stopping them from doing it. But they came to me just to sort of get permission, even though they didn't really need permission. And that seems to me to be in many situations of like the power of a leader being able to just trust your team and understand that sometimes your job is to just say yes and let them go do the thing that they want to do and you're good.

00:16:27:13 - 00:16:33:17

Oliver Fisher

And if you don't, that's the thing that's holding them back is just your sort of approval, even if they don't really need it.

00:16:33:17 - 00:16:49:02

Andrew Davies

You've now been a techie to Google in a couple of different products and you now step up to director of engineering at Shopify. And again, this co-founder word comes back. So I understand you helped found the Shopify Capital products within Shopify and that was a bit of a shorter tenure. But tell us about that step up and what you learned.

00:16:49:02 - 00:17:07:00

Oliver Fisher

That this was my attempt to try and not work remotely. I live in Ottawa. Shopify is based in Ottawa. I had known Cody, who was the CTO. Our kids go to the same school and so we know each other through like our our spouses friends. And we've been the two technical people who showed up at Christmas parties and so on and sat in a corner talking about things.

00:17:07:00 - 00:17:26:01

Oliver Fisher

So we talked for a number of years about maybe joining Shopify, and I was at that point I realized that I had maxed out what I was going to be able to do with Google in terms of leadership while working remotely. Shopify was here and I came over to to join Cody and I was think I was probably the first director of engineering to come into Shopify who had sort of grown up elsewhere.

00:17:26:01 - 00:17:47:21

Oliver Fisher

The company was it was pre-IPO, it was about 700 people at that point. And I joined, as you said, to help lead this idea that they had of of being able to basically cash advance money to merchants because we had all this data about we knew how how well merchants were going to sell things. We knew that there are swimsuits store we know you sell a lot of things in the spring.

00:17:47:23 - 00:18:11:23

Oliver Fisher

And interestingly, you also sell a lot of things in Canada in February because everyone's buying a new swimsuit to go on vacation to the Caribbean. We knew these two things, but in between you have dry spells, and if we could predict your sales, then we could maybe help smooth out those those humps in your revenue and get you through, maybe help you buy even more inventory that you know, in December or January so that you can make even bigger sales in February.

00:18:11:23 - 00:18:41:10

Oliver Fisher

So we started that team and that eventually grew into what we ended up calling. I'm not sure what it's called anymore, but at the time it was called the Merchant Services Division, which included additional things that merchants could come along and do, like shipping, doing payments. And so that was a really exciting time and was really about that was really the the first thing where we were given the latitude to just go and build the team in whatever way you needed to find the right people working with the recruiting team or just yourself, put together whatever you needed to.

00:18:41:10 - 00:19:01:12

Oliver Fisher

There was all sorts of technical problems and there was one weekend where everybody was telling me we just couldn't do this thing. I just sort of refused to believe it and sat down and wrote a prototype because it was raining. One weekend and came back in and said, Look, we can do it. Let's let's go do it. So there was just that little sort of additional level of ownership and commitment to what we actually needed to do.

00:19:01:12 - 00:19:07:20

Oliver Fisher

And the realization started to realize that no one else was going to do it if I couldn't get the team to do it was was very interesting.

00:19:11:10 - 00:19:21:03

Ben Hillman

And now Oliver talks about earning metal from excruciating leadership opportunities and how it's actually a little bit more rosy of a picture than you might realize.

00:19:24:21 - 00:19:38:10

Andrew Davies

And then we have this move to FreshBooks and a clean run from VP, engineering, senior VP, engineering to CTO. So talk to me a bit about that. Step up on each of those steps in the journey and perhaps the increase in ownership or responsibility that came with them.

00:19:38:10 - 00:20:01:19

Oliver Fisher

I joined FreshBooks as a VP of Engineering reporting into the CTO at that time, and that was just about a personal relationship that we had. We just got on the phone together the very first time, again as an accident. We just really liked each other. I actually had dinner with with Warren, I don't know, three weeks ago, five and a half years later, Warren was looking to grow that organization as as the CTO and I was coming in as VP and I was looking to learn more.

00:20:01:19 - 00:20:25:02

Oliver Fisher

I had this really strong flavor of leadership and growing a team at Shopify and that was looking to take on even a larger level of leadership there and wanted to learn from Warren. And I did. That was great. And it went well enough that Warren and I talked about it at the beginning of maybe, maybe you take this on as I go off and do something else because he'd been at FreshBooks about five years at that point and about six months in he did do that.

00:20:25:02 - 00:20:43:08

Oliver Fisher

I thought I was going to have about two more years. That's when I took on the role of senior vice president leading the entire team without the CTO and reporting directly to Mike, who was our co-founder. I will say that was a traumatic event. I remember when Warren phoned me and said, I'm leaving. You're in charge now. Being absolutely and utterly terrified.

00:20:43:13 - 00:21:03:16

Oliver Fisher

And I think with good reason because I realized I did not know what I was doing. But we survived and learned a lot. And I think, you know, then eventually growing into the chief technology officer role was an interesting thing and that along each way, I think going from that VP to SVP level was about it's with me now, there really is no one else.

00:21:03:16 - 00:21:20:21

Oliver Fisher

And I can remember some very, very difficult moments where the site is down, our product is down, we're having some problem. I absolutely rely on my team. It's not like I can go fix it, but if they're having a problem fixing it, I don't have a manager anymore that I can turn to what they're going to provide me cover.

00:21:20:22 - 00:21:37:21

Oliver Fisher

It's now me, right? And we were having some problems that at that point in time we went through about a year of we'd done a replatforming and we went through about a year of some very, very challenging uptime things. I ended up writing a couple of letters to our customers, apologizing and saying, Look, this is what we're going through.

00:21:37:22 - 00:21:53:14

Oliver Fisher

We're committed to you. Thank you for sticking with us. And we know that this deeply impacts you. And we are these are the things we're doing to help make it right. And so I think it was really about taking on that just a deeper and scarier sense of ownership, because there is there is ultimately no one else that was able to help out.

00:21:53:15 - 00:22:03:02

Andrew Davies

Let's talk a little bit more about that trauma where Warren, when Warren called you to tell me that news. So break down trauma for me. Like, what was that feeling? What was behind it and how did he resolve it?

00:22:03:03 - 00:22:25:12

Oliver Fisher

Oh, I mean, there were so many things behind it. I mean, I think in the moment, right, There were probably there was probably a little bit of a sense of betrayal. And this isn't what I signed up for. I'm not ready for this. But there was also I think the I don't know if I can do this, and I think that's a deeply challenging problem because I don't know that I can do it, but I have no other option because there's no one.

00:22:25:20 - 00:22:46:21

Oliver Fisher

I can't go and quit now and do something else and leave the team without without anybody leaving them. What do I do and how do I start to figure that out? There was also that a little bit of freedom there, right? Because before or if I wanted to do something, Warren and I worked really, really closely together, and if I wanted to do something, I'd sit down and I'd say, Hey, let's do this one.

00:22:46:21 - 00:23:16:10

Oliver Fisher

And I are very different people. Though he'd approach it from a different perspective, he'd helped shape it and change it, and he might even say, No, I don't think we should do that. All of a sudden I've lost that. I Or if I make a mistake, it's mine. And there's no one to help me make mistakes. What I did as quickly as I could, I will say I was about to say very quickly, but it was not very quickly, as quickly as I could, which is over a number of months, was to start to develop the right leadership team working with me to help give me that feedback.

00:23:16:10 - 00:23:41:04

Oliver Fisher

And I think the team that we've built now and have five years later, some of them have been there for almost as long as I have and some of them are much newer. But one of the key things that I'm always looking for is can you approach a problem from a different perspective than I have and then tell me that I'm wrong and one of one of the one of my peers, Stephane, our VP of product, tells me my superpower is that I can change my mind.

00:23:41:04 - 00:24:01:20

Oliver Fisher

I like changing my mind. I when I was at Microsoft, I was at Microsoft at this period of time where if you showed any weakness to the culture was such that people would jump on it. But it took me a long time to get over that. And I think Google really helps realize that I don't know everything and being able to change my mind, I now I actually got a little dopamine hit or something.

00:24:01:20 - 00:24:23:09

Oliver Fisher

Now, when I do change my mind based on somebody else giving me some feedback because I'm like, Oh wow, I did it again. That's amazing. But hopefully it's made the decisions better over time. But yeah, it is traumatic. I think as you're learning stuff, it is deeply traumatic because you don't understand that you're learning things. You just know that you're in immense pain and can't figure out what you're doing.

00:24:23:09 - 00:24:42:18

Oliver Fisher

And it's only months or years later that you look back and you say, Oh, that's what was happening. I was figuring out how to do that. I was learning how to do that. But in the moment, very, very stressful, painful. And it's happened a number of times in my my journey at FreshBooks, where I'd gone through months of the simple term as imposter syndrome.

00:24:42:18 - 00:25:00:02

Oliver Fisher

But that makes it sound so much more simpler than what's actually happening. And it's very difficult to break down. But it's a if you're feeling that at any point in time, I think it's the only thing I figured out to help deal with it is to sort of embrace it and understand that that might be what's happening and that you will come out better on the other side.

00:25:00:04 - 00:25:06:06

Andrew Davies

So you're painting a really rosy picture for anyone who's looking up the ladder thinking, I want to go. One day, Oliver said.

00:25:06:06 - 00:25:23:14

Oliver Fisher

To me so and so it is it is a balance. So I think it is a rosy picture, actually, because that those painful periods are excruciatingly difficult. I'm not in one right now, thankfully, but you come out of it and you look back and you're like, Wow, I survived that. I have a look at what I can do now.

00:25:23:14 - 00:25:41:22

Oliver Fisher

And that to me is just incredible. And you're able to take on a different challenge. And it applies to, like everything in your life now. And as a result of this, like part of my more recent journeys has been really about figuring out some of my own core values and then how do I use them in what we're doing as an organization and helping to build that organization.

00:25:41:22 - 00:25:51:03

Oliver Fisher

And so ultimately, I think you become a much more complete whole person as a human. But turns out that that's difficult and painful as as anyone who's been a teenager will know.

00:25:51:03 - 00:26:03:20

Andrew Davies

Fortunately or unfortunately, I think we've all been a teenager. At one point you talked about growing a team internally that you rely on for feedback, but that being people externally as well, through some of those moments of moment, you've built as strong relationships.

00:26:03:23 - 00:26:29:05

Oliver Fisher

I'm always looking for people wherever they can come from externally or internally. Finding people internally is amazing who you can help grow into some particular role, but then going out and talking to external people, you know that inevitably there's far more people outside of your organization and company who can help you. I've been lucky to have worked with a couple of professional organizations over time who have lent me a tremendous amount of support.

00:26:29:05 - 00:26:52:12

Oliver Fisher

They've been sort of executive support groups where we've done some learning and also just support and being able to say, Hey, I'm facing this challenge, what do you think? And then get ten different opinions from other people who may have been in similar positions but have very different points of view as well? I do not have enough good things to say about talking to other people and getting their ideas and opinions and frankly, stealing them.

00:26:52:12 - 00:26:56:13

Oliver Fisher

Right. And then being being happy to have them steal your ideas and opinions as well.

00:27:00:04 - 00:27:05:15

Ben Hillman

Next up, Oliver talks about what aspects leaders need to build in that each step of the career ladder.

00:27:09:13 - 00:27:28:21

Andrew Davies

So as you reflect back then, you've clearly reflected a lot on the journey of FreshBooks. And now if we reflect back across all of those different steps coming in, grad in engineering all the way through to where you are now, are there any aspects of that journey that people, you know, looking where you are now won't have recognized and won't have seen in each of those steps?

00:27:29:02 - 00:27:40:11

Andrew Davies

So, you know, there might be team leadership that you build in. There might be the sense of ownership that you build in. It's on you. What are the other aspects or attributes of each of those levels that kind of ramp up or that you need to build into your skillset?

00:27:40:11 - 00:27:58:17

Oliver Fisher

I look at it as really about thinking about some people look at it as width, I look at it as depth and distance as to how far you can see. And so I think of it as when you start off in early in your career and we see this with engineers, you show up on your first day. We say, Great, here's a bug to fix.

00:27:58:17 - 00:28:13:00

Oliver Fisher

It might take you a couple of hours. Let me know if I can help. And that's about being able to see a couple of hours into it, into the future. If I fast forward all the way now, my job is to actually look five years into the future and say, where are we going to be and what are we going to do?

00:28:13:00 - 00:28:30:23

Oliver Fisher

And then how do we get there? What do we do today to be able to get there? But at every step along that way, it's about getting a little bit further along. After you fix that first bug, that 61 day there, we're probably going to give you a bug that might take two days for you to fix. And then we're going to give you a work item that might take you all week to actually accomplish.

00:28:30:23 - 00:29:01:03

Oliver Fisher

And then, you know, as you're moving into more senior, more senior engineering role, you're going to be helping the team plan out the sprint and then the whole quarter of what work you're going to be doing as a team. And ultimately, I'm, you know, asking our engineering managers to plan out two or three quarters in advance and our engineering directors to understand what's happening to the company over the course of the next year to 18 months and how we have to all work and try and build the organization and plan to do that.

00:29:01:03 - 00:29:23:05

Oliver Fisher

And then an engineering VP is looking at multiple years and what's going to happen and the other aspect that has been added in there. So, so I so I look at it as distance in terms of that distance of being able to see the future. And I mean, I don't know, like Elon Musk, for all of his peculiarities, is certainly someone who at least claims to be able to see far, far much further into the future than any normal human being.

00:29:23:09 - 00:29:44:07

Oliver Fisher

And so how can I tell him he's wrong? But yes, it does translate to some weird things in the short term. So that's that's how I sort of view view that distance. The other thing as you're going along is certainly never be afraid to go deep. And it is sometimes I've heard it phrased as you can never be too technical and it doesn't, I think, necessarily apply to just technical things.

00:29:44:07 - 00:30:10:18

Oliver Fisher

All right. If you're in marketing and doing online ad sales and so on, there is a discipline and a set of technical skills that you have there and you use every day. Never be afraid to to get too deep into those things just because it is so valuable to be able to understand what the experience is and be able to ask the right questions and then turn around to, you know, more junior people on the team and say, Oh, let me help you with that.

00:30:11:02 - 00:30:33:16

Oliver Fisher

But also, have you thought about this? And maybe send it in a different direction? And if you don't understand what your team's everyday job is like and what their experiences like, I don't think you're going to be able to lead them effectively because I think fundamentally they won't trust you. And to me, trust is just a huge, huge, important value for for everything that we do as human beings.

00:30:33:16 - 00:30:40:19

Andrew Davies

I love it. You've got distance, you've got depth. Even better. They start with the same letter. You're clearly a consumer communicator. Hey, Oliver.

00:30:41:04 - 00:30:46:13

Oliver Fisher

You. I obviously need to come up with a third D right to choose, not the right number.

00:30:46:13 - 00:31:04:02

Andrew Davies

We could. We could brainstorm with the Ed Diamond of dynamism or something like if we're just a distance, how do you help people who are reporting into your on your teams put on new sets of glasses or binoculars there any tools or techniques that you've used to help them see further on the horizon?

00:31:04:02 - 00:31:34:16

Oliver Fisher

I paint them the picture. I'm very transparent about everything that we're trying to do. And so I try and paint them the picture that goes out as far as I can see it and say, this is what the sort of thing that we're going to be doing all the way out to, let's say, three years. And now if I've painted that picture really well for you, you have a pretty strong sense of what we might want to be doing in a year to 18 months, which is maybe where where you're hoping to, where we're hoping that you're going to be able to plan things out if I've painted that long term picture.

00:31:34:16 - 00:31:53:11

Oliver Fisher

Well, now take that into your world. And can I draw some boundaries and give you a sort of a box that says, okay, look, you don't have to know what's going to happen in three years, but can you tell me what's going to happen in 18 months? And more to the point, that box is not just around time, but it's also I don't need you to know what's going to happen to the entire company in 18 months.

00:31:53:19 - 00:32:13:14

Oliver Fisher

I just need you to know what's going to happen to, let's say, our payment system in 18 months and give people that box and you're only going to have $10 million to do it or something. I think the more you can help people to find the box that they're in, the more comfort they actually have to be able to do this.

00:32:13:14 - 00:32:37:06

Oliver Fisher

I've seen this repeatedly where structure actually provides freedom to people and a lot of people, especially a smaller start ups, are there sort of at the start up because they want to be able to do anything and everything right. I still have people on our team. We program almost everything we do is in Python, but I still have die hard people, engineers on our team who desperately want to program in Rust or whatever other fun language they think is.

00:32:37:13 - 00:33:00:19

Oliver Fisher

And we have to just say no, like the structure is not everyone knows that language. Everyone here knows Python. That's what we're going to use. And so that's one very simple dimension of the box or constraint on people. But by giving them people that constraint, I think people are very worried about going too far. And if you don't if they don't know what decision they're allowed to make, then they actually become paralyzed.

00:33:00:21 - 00:33:25:23

Oliver Fisher

And so if you say you can spend as much as you want up to $100, that's great. They might spend 99, but that's fine. They know that if they need to spend 101, then they need to go talk to somebody else. And then defining who's the next person to talk to. And it's simple enough with something like money, but it's, you know, gets more complex when you get into more technical conversations and just truly the autonomy that you do want to give people.

00:33:25:23 - 00:33:47:19

Oliver Fisher

It's so, you know, define the limits. So the people actually can go up to the limit with confidence that they haven't gone too far and that you're going to pull the rug out from underneath them. That's been, I think, a big thing that I've only figured out, I will say in the past few years. And again, I think I figured it out thanks to other people on my team.

00:33:47:19 - 00:34:03:04

Oliver Fisher

It was not an approach that I was originally thinking of taking and it goes a little bit against my personality. But learning from others has been a tremendous opportunity to understand, Oh, that's how people's brains work and let's help the brain work as well as it can.

00:34:03:12 - 00:34:20:08

Andrew Davies

So one aspect we probably haven't discussed enough yet which changes as you go from stuff engineer all the way through to CTO is the importance of hiring, building a team, setting culture. Can you talk a little bit about, you know, how that's become increasingly important to you as you become more senior and how you've handled that?

00:34:20:11 - 00:34:38:21

Oliver Fisher

Yeah, I would be delighted if I could figure out how to actually change culture. I it is something that I just had a tremendous amount of time doing. I did it in something that I could influence, but I have not figured out the formula to truly change it. But I do know that it starts with the leadership team that you build.

00:34:38:21 - 00:35:07:05

Oliver Fisher

And so when I go out and look for that leadership team, either internally or externally, I'm really looking for people who can appreciate that. And understand that their job is really to profoundly affect the culture that we're building. And I think that comes back to the core values. And so I like to have a values Composé session with leaders about what it is that they're interested in, why they're doing things, you know, what are the non-negotiable things they might have in their life.

00:35:07:05 - 00:35:33:05

Oliver Fisher

And things that they've learned about about that. And fundamentally, I think, as I mentioned earlier, it comes down to a lot of trust for me. If we can build an organization and a leadership team, trust each other, and then we can extend that trust out to the rest of our team and give everybody a culture where they're able to talk really well to each other, express ideas, no matter how bizarre and weird those ideas might be and and wrong sometimes.

00:35:33:05 - 00:35:52:14

Oliver Fisher

Often they're wrong without too much of a risk because we trust them to be able to go and do things and then and then define we trust you to work inside that box in these limits to do things to me, something that is incredibly powerful at the human level. And ultimately we are humans as much as some of our engineering key would like to only begrudgingly admit that they're human.

00:35:53:00 - 00:36:21:12

Oliver Fisher

We are all humans in, and there's just some fundamental things in there that we as humans need and excel in environments where we can have that. So it's a committee that comes back to that trust. How do I make a, I don't know, a high performing organization or a one that committed to quality. It's by me and my leadership team and their leadership teams and every single person, but starting with me going out and saying I care about it and not the thing I care about it, but then demonstrating that and doing that, sitting down.

00:36:21:12 - 00:36:42:16

Oliver Fisher

And so as an example, right when you know about that year of difficulty with our uptime, I turn my pager on and I got paged for every single incident that we had. And I showed up in the middle of the night to every single thing. And often I was the first person there. That was just the way that we as an organization started to change what we were doing.

00:36:42:16 - 00:36:59:06

Oliver Fisher

It sucked when I had to sometimes get up at 3 a.m., but I'd come on, I'm the leader of this organization. Why am I the one waking up at 3 a.m.? Well, because if I don't, then how can I possibly ask anyone else to worry? But I will say I don't. I have a formula for how? I don't have a formula for how you can change the culture.

00:36:59:06 - 00:37:07:19

Oliver Fisher

It is something that and so far eluded me. I could influence it and puts it in a general direction. Maybe on my good day on.

00:37:07:19 - 00:37:23:06

Andrew Davies

The on the hiring point, you know, you must have gone through the journey of hiring solo engineers to, you know, individual contributors to hiring team leads to now having to hire organizational, you know, leads. What have you had to build into your skill sets to kind of up level yourself as as the hiring impact has changed?

00:37:23:10 - 00:37:55:05

Oliver Fisher

I think it's about understanding what you're looking for. And I think that comes back to one of the things we said at the beginning. I learned that at Microsoft, you fit on probably six months into my job. They found you on that. The technical interview interviewing program, and you learn how to interview other engineers. And that really comes down to figure out what you're looking for, figure out how you're going to evaluate people on that, and then then do it right now, looking for some very, very different thing they than what I would have been looking for, hiring an engineer back 20 or 30 years ago.

00:37:55:05 - 00:38:12:21

Oliver Fisher

But fundamentally, if I don't know what I'm looking for, then I'm probably not going to find it. Thinking about that and coming back to those core values and what you want in a leader and understanding them and then being able to articulate that, I think that builds a tremendous amount and makes you a more attractive employer actually to people because they know that you're looking for access.

00:38:12:21 - 00:38:32:20

Oliver Fisher

And I back and I want to work in an environment like that or they're not, and then they can go find another job somewhere else, which is great with somebody who's looking for something, something different. I think that fundamentally, though, it always comes back to that human experience. And so I'm looking for leaders who are humans, who understand they're humans, who understand that everyone around them is that human.

00:38:32:21 - 00:38:48:21

Oliver Fisher

Even if we're building technical things on machines, how can we help the humans do that? Bill Coren, who is a VP at Google, had a saying that it's the the computers are the easy part. It's the humans that are the problem. And it's an interesting problem. It's far more interesting computers in my mind.

00:38:52:11 - 00:38:57:14

Ben Hillman

And now Oliver talks about what to look for in acquisitions from a technological perspective.

00:39:01:05 - 00:39:23:14

Andrew Davies

Let's quickly switch topic before we finish. One of your responsibilities now as the most senior technical or engineering person in the organization is to be very involved in acquisitions. And you know, you've made a few acquisitions, FreshBooks made a couple of acquisitions recently. Factor Rama Foss Bill, what do you look for in those businesses from a technical standpoint, a team standpoint, And how do you think about the integrations of those products and those engineering teams?

00:39:23:14 - 00:39:46:05

Oliver Fisher

Yeah, again, it's funny because I think of an acquisition in a lot like just that extended interview with a larger group of people. And again, I think you have to know what you're going in and looking for. Why are we buying this company or why are we interested in buying this company? And I hope that hopefully the the acquiring company knows why they're trying to be bought and why they want to be part of this organization.

00:39:46:05 - 00:40:04:03

Oliver Fisher

And so it's figuring out how those two things plug together. And that might be we're buying that company because we see a talented group of people and we just want them to be part of our company. Or they might have a particular piece of technology or they might have a particular type of customers that we think would be would be great for us to be able to help out a whole variety of reasons.

00:40:04:03 - 00:40:19:20

Oliver Fisher

But I think having that clarity of understanding of why you want to do this in the first step and then that helps you go out and evaluate if this in fact what we think it is, can we do it? And then when you get burned, when you do complete the acquisition, how you're going to bring those people together.

00:40:19:20 - 00:40:40:01

Oliver Fisher

And again, it's the very human thing, right? I can I've bought companies where I've looked at companies at belief, where they have a giant monolith. I have no idea how I'm going to tactically integrate it. But there's something in there and I trust the people who at the very least the people who wrote it once, can go write it again if we need them to.

00:40:40:02 - 00:40:57:14

Oliver Fisher

Whereas, you know, some of the other acquisitions, they built it in a much more modular way. It's quick and easy to pick up and plug in, but it's a more challenging people thing. And I think in many ways that's a that's a much more difficult acquisition to do than than the other one where you're just faced with some technical problems as opposed to some people problems.

00:40:57:16 - 00:41:15:19

Oliver Fisher

And then the other part is like, if that was an acquiring company, you have to recognize again that on day one you own that you do something. In the course of the acquisition process or on the first day or on the first week or anything that alienates the entire team that knows how to run the thing and knows everything about it.

00:41:16:01 - 00:41:36:21

Oliver Fisher

You've made a fairly fundamental error. If they all wait on you, you're just. So what would that say? I think that you now up to run. I just can't say enough about the humanity of everything that we do in technology and and approaching it that way. It's very common, for instance, to find smaller companies where their compensation structure is very, very different than a more companies.

00:41:36:21 - 00:42:09:12

Oliver Fisher

You got to know that when you're going in and understand that that's something that people deeply care about as humans and we all eat. And the money that we earn to to to be able to eat, but also primates are very, very focused on fairness. And so if you've now got one group of people in this acquired company who are doing very, very similar jobs to the group of established people, you've got, inherently they're going to find out about that and they're going to experience that millions of years of evolution towards fairness, you know, emotional reaction of like, this is wrong.

00:42:09:14 - 00:42:18:10

Oliver Fisher

How are you going to deal with that and make that work for everybody? This is why I think the the human problems are so much more interesting than the technical one.

00:42:18:10 - 00:42:34:03

Andrew Davies

You've I've written down a bunch of things here, and structure is what gives freedom about the fact that you as a leader want everyone around you to change your mind. The ownership mentality. It's on me. I really appreciate you taking the time motivated. Go through this to step us through each of those pieces of your journey and the lessons on the way.

00:42:34:03 - 00:42:42:17

Andrew Davies

So thank you so much. Any final thoughts as you speak now to an audience of technical people who are on one stage of that journey and looking up at that CTO role?

00:42:42:18 - 00:43:03:04

Oliver Fisher

I think it's simply a you can't plan it. A lot of life is just accident. You can make your luck better, but ultimately luck is always involved and really don't be afraid. The worst that happens is you have to go find another job. And we're lucky enough in this industry that we can, generally speaking, find another job. Although I know that's more challenging at some point than other times.

00:43:03:04 - 00:43:14:01

Oliver Fisher

But the worst that happens and the best that happen is that you learn so much more about yourself and about other people and form incredible relationships and build something and turn turns of dreams into reality.

00:43:14:01 - 00:43:16:00

Andrew Davies

Thanks so much, Oliver. I really appreciate your time today.

00:43:16:00 - 00:43:16:21

Oliver Fisher

Great. Thanks for having me.

00:43:16:21 - 00:43:44:09

Ben Hillman

Andrew A huge thank you to Oliver for taking the time. Now, you know the key skills needed to lead high performing teams. Today we talked about turning dreams into with folks who sell their time being integral to early Microsoft, Google and Shopify product initiatives, earning metal from excruciating leadership opportunities. What aspects leaders need to build in at each step of the career ladder, and what to look for in acquisitions from a technological perspective.

00:43:44:12 - 00:43:57:20

Ben Hillman

Make sure to give us a five star review and tell us what lesson Oliver taught you from today's episode. Thanks for listening. Subscribe to and tell your friends about Protect the Hustle, a podcast from Paddle Studios dedicated to helping you build better SaaS.