Managing Director of Siteimprove Canada, Mike Cart, speaks to how he built a revenue generating SaaS company in the Canadian market


In episode 1 of All About Revenue, we sit down with Managing Director of Siteimprove, Mike Cart, to discuss his journey to becoming a sales leader, and his strategy for building out a revenue generating SaaS company in the Canadian market.


Asad: Today’s All About Revenue podcast is with Mike Cart, the Managing Director of Siteimprove Canada. Michael, thank you for coming.

Mike: Thanks for having me. Excited to be here.

Asad: You and I have known each other since 2014. I think I’ve had a great first hand experience to how you manage and lead, and how you teach and coach. It’s been the backbone of your success in building out Siteimprove within the Canadian market. So, when we decided to do this podcast, I thought it would be a very interesting perspective to share with the market.


Let’s start with the beginning. They call sales the accidental career because, in school, no one teaches it. It’s very hard to find yourself in it. How did you get into it?

Mike: My dad was in the sales field, he worked for IBM and through different positions, ended up retiring as a VP of sales for IBM. When I was little, we traveled quite a bit and sometimes I’d go to work with him and I always looked up to him. There was always something about sales that I liked the idea of as I was going through university. When I thought about what I may want to do, sales was the first thing that immediately caught my eye. So, I never applied for any other job besides a sales job. It was one of those things where it’s like, “Okay, I think I might be good at this. My Dad made a career of this, and I want to try it.” Here we are today.

Asad: Wow, that’s really interesting. I had no idea that your Father was in sales.

Mike: Yes, for 30 years with IBM. He spent his whole career with IBM.

Asad: When you were choosing how to get into it, was he the one that advised you in joining a firm like Canon at the earliest stage of your career?

Mike: No, not at all. That’s one of the things I really respect about my Dad, he would give me advice but he wouldn’t try to push it on me. He wanted me to make my own decisions which I really respect. When it came down to it that the photocopier office equipment industry was renowned for really good training, being able to develop your skill sets and in all honesty, make money. I was tired of eating Kraft Dinner and ramen noodles at university. So, the idea of being able to be a little more financially flexible was very attractive, that was the origin. Making me feel old now, it’s been a while.

Asad: Canon and Xerox both have training that probably laid the foundation of what we call solution selling, consultative selling, even the challenger sale, the backbone of the challenger sale are those two things, right?


When you think about having gone through a formal training program and you think of some of the people that you’ve met that haven’t done that, what do you think you got out of it that other people who bought a startup too early missed?

Mike: You’re joining a well-oiled machine that knows what they’re looking to do and has a proven model to get there. That doesn’t necessarily mean you’re going to fit or like it but based off of all those decades of experience and success, they are able to put a plan in place to do that. With office equipment, photocopier specifically, there’s a ton of companies and I can’t even imagine what it would be like now from the competitiveness, but there’s not much that separates them.

So, you have to be razor-sharp and on point when it comes to differentiators, value, overall solution, rapport, developing relationships, and so many other ways throughout the training. Looking back at it now, it’s one of those things where it wasn’t always easy all the time, but it really laid that foundation of the fundamental process structure.


What were the things you did to make sure that you would become a good leader?

Mike: I was fortunate enough to get an opportunity and when you take that first step, somebody is taking a leap of faith and betting on you. I was able to get that and I felt very fortunate as I was still relatively young in my sales career. I felt like a fish out of water because I had always wanted to be promoted and have that opportunity, but when you’re actually in that chair, you’re looking at things from the other side. You may imagine what it’s like, but all of a sudden, all those little pieces are becoming bigger and you’re looking at things differently. Instead of filling boots on the ground, you’re looking at things from 5000 feet up; the good and the bad. 

In all honesty, it was overwhelming at the beginning. I started to think, “Wow! what’s going on? Did I make a mistake trying to get out of sales?” That’s where I was fortunate enough to be surrounded by some really good mentors and have good Sales Managers while I was a Sales Rep. So, I really got to know my Reps in that first management job, it was an inside sales situation for a call center type. I really tried to understand them, their challenges, and work on things together.

As that kept on evolving, I was not trying to feel like I know it all because every day I learned so much from my Reps and my colleagues as well as other like-minded and more tenured and experienced people. It sounds good to get better every day and try to always challenge myself to see what I’ve been doing and make it work.

Asad: When you mentioned mentors, it seems to be the difference-maker between success and failure from the majority of people. If you have the right mentors and you are learning from people that have done it, they know what not to do and what to do. So, finding the right mentors and developing those relationships is important.


How did you go about deciding who your mentors should be?

Mike: One of them kind of fell in my lap and I’m extremely lucky, it was my old boss. She was very good friends with a third-party consultant that ended up being contracted at the company that I first got my Sales Manager role at. 

I knew her, but not really well. She was, I believe, an influence of getting the owner of that business to take a bet on me to fill that job. That was unbelievably helpful and very lucky. I had different ideas and I would always try to seek her advice to really see if I’m on the right track. Sometimes, I would think that I had figured it out and she’ll come back and say, “That’s not how it works and this is why” and really wouldn’t be afraid to challenge me. There were others as well but the reason why I’m spotlighting her is that she was there right during my first position as a Sales Manager. That was one of the longest years of my professional career because it’s shifting gears completely. It’s like graduating elementary school as the king of the castle, and then all of a sudden you’re in first-year high school and you’re at the bottom of the totem pole. That’s exactly what it felt.


Having now been a mentor to so many people, what have you gained from being a mentor?

Mike: It’s kind of surreal to be honest, thinking back to being the one that is seeking advice. But you’re always learning just like you said, regardless of what side you’re on. To be on the other side, where someone approaches you to ask for that advice, it’s very flattering and rewarding too. It’s humbling, but I always try to look at things from a customer’s perspective, my Sales Reps perspective, and my Sales Manager’s perspective. Depending upon what the ask is or what problem it is, It’s all based on their position and vantage point. What drives that? Getting back to the mentorship piece, it’s a matter of why those questions are being asked and from what circumstance, from what position of strength or challenge. Try to work with them as well as really understand and learn a ton from that. Everybody has skills; everybody has value. It’s just a matter of what you are really good at and what the areas are that you want to be sure of.

Asad: Do you still need mentors for you to continue developing? Do you have mentors and other differences to the ones you had before?

Mike: Yes and yes. I want to constantly continue to learn as I have time to learn. I mean, I am learning every day, as I mentioned, I’d be foolish to say that I even have part of it figured out. I feel like I’ve been able to make some adjustments and some strides, but everything’s changing, so many things are changing every day. In the technology software world, we always joke that years are like dog years. It feels like things are happening so quickly because they are. To be able to keep up with that, you have to continue to seek advice and continue to challenge yourself. But to the question, you said about types of mentors; yes, really trying to. That’s one of the things I’m currently doing. I do have some trusted sources all over the world that I’ve developed, but I’m fortunate enough to know them, to really pick their brain and really try to keep that network as fluid as possible whether it be advice or just different things from their perspective and their opinion. It’s something I’m constantly seeking out.

Asad: So, after Audibility, you joined Siteimprove, and it was a really interesting move because it was into SaaS, which was your first entry into that industry. Siteimprove is an established business that was doing really well in Europe and the US, but they had no presence here, so you had to build that market out.


What were some of those challenges that you had to deal with in building this market out and finding talent and acquiring revenue and maintaining revenue? What did you have to deal with as you took on this new role? 

Mike: It was a new frontier and one of those things where I took a bit of an educated gamble. I did some research in regards to the company and talking with different mentors and individuals that I trust in my close circle when making those decisions. I did my homework on the company, the competition, and the overall pros and cons list. I know a lot of people overthink things, but when it comes down to it, just use your judgment and trust yourself. After meeting the Executive Management, understanding the product and understanding the plan, it was enough to say “I’m in”.

I still remember the time when the CEO of North America and the owner from Denmark were in Toronto and I was with them looking at 15 different offices in one day. We had an idea where we wanted to be, but that afternoon was super busy going through the different spots. After we found one, we went through and took a look at what we wanted and said, “Let’s do it. Let’s move.” that was one of the things immediately that I think kind of set the tone for how things work at Siteimprove in the sense that we are not afraid to make decisions that make sense. That mantra is something that is still consistent. I knew that my leadership had my back when going through things on the way down to tons of mistakes. First of all, new to SaaS, we didn’t even have an office, we had to go buy all the furniture. Even just on-boarding and training people when I’m doing the same thing, it’s a very unique experience.

Asad: When you think about Siteimprove, one of the things that you’ve mentioned that seems to be quite different is the speed of action. When you are a larger business, you have all these processes which slow down decision making and sometimes, when you’re building a market out, you need to have that entrepreneurial feel to the business where you can just move quickly. 


How did you qualify that this business would allow you to be fast when you need to be? Or if it will give you support when you need it, but will not stifle you with processes?

Mike: It’s a great question. I started over four years ago and at that point, we had a limited amount of data just because of what worked and what didn’t, but also from a reporting standpoint, we had little information. So, we would be using information from Copenhagen, where our headquarters is, in regards to different areas of opportunity throughout the world and where they made the decision to make investments. How they originally started, I’m not sure if you’re familiar; they started calling us into Canada for about a year and a half.

There were about two individuals that were connected because it was basically an area that nobody touched. Some people were like, “Okay, I’ll try to call in Canada.” and through some success, they understood that there’s enough of a market here and did a little more research to say yes.  So, in regards to the scaling, it comes down to the people. I was fortunate to have Sales Reps that hit the ground running. They did a really good job just because they’re very skilled and they were able to talk to the right people and be able to show the value. That success was able to garner continued optimism from Corporate to continue to add on to that. As success and productivity were continuing to be sustained, it was continuing to be able to garner that investment. 

Asad: When you look at the last couple of years, you built a team out yourself and you are leading them now. You were coaching them. You are hands-on with each person. 


You’ve now added a layer of management under yourself;  Sales Managers. How has your life changed?

Mike: Prior to last year at the turn of the calendar, that was true. I was the one throat to choke whether it be good or bad. To be able to look at the revenue, retention, and everything in between, we were getting to a point where it was just too much. I mean, there were a total of 15 to 17 people, it was just too much. There’s only so much you can do. So, the new Sales Manager that came on in February has been here for over a year.

It’s been an absolute game-changer, he is an unbelievably skilled individual and he has been able to handle the day to day with the account executives, the direct sales force, as well as our Business Development Representative. He is that focal point, that day-to-day. I’m still involved in different types of meetings and different types of conversations, but the day to day goes through him and that has made a massive difference. That has helped me step back and look at things from a bird’s eye view to really take a look and try to make decisions that are based on a bigger picture and not just on what is happening now. That was hard to do, to be honest. To be able to step back and look at things more strategically has been an absolute game changer and be able to trust myself because of the people that we have in place. 

They’re very good people and that’s the key to everything. If we don’t have good people, regardless of sales, customer service, or consultants then it doesn’t matter. You could have the best game plan or think you have the best game plan, but if you don’t have the pieces to execute, succeed and grow, it’s all for nothing. That’s really helped to look at the bigger picture and grow from that side.

Asad: It’s such a critical high if you get it right, it’s fantastic. You can be strategic. This person can be there to implement your strategies and you can trust this person.


What were you looking for and how did you decide what you’re looking for? When you knew that you wanted to bring the person for this particular position? 

Mike: That is probably one of the biggest decisions that I’ve had to make outside of work. You could look at it as a tipping point where that individual doesn’t pan out. Then what happens? Where if it does, then you’re able to really grow and catapult to another level. So, in the interview process, we had different stages which are just the standard questions, but we also want to see what they’re like in a boardroom, outside of a boardroom, maybe over an adult beverage, just to see that social connectivity as well. That was something that was an extremely extensive search. We wanted someone that had the experience of working with dynamic teams and working with a constantly growing company. 

Asad: Instinctive decisions are interesting because a lot of times people are scared of instinct. You develop a perspective on it and then you internalize it, it goes into your subconscious, and it’s very quick. A lot of people should be trusting themselves, but they don’t. In terms of this market, there’s high demand, there’s a low supply for talent. You are hiring, building out SaaS sellers, and everybody wants them. How do you go about finding great people in this market and then keeping them? Because it seems like when you’re going to find them, a thousand other companies are talking to them. Then you bring them onboard and a thousand people knock on their doors to poach them. 


In sales, the best salesperson closes 50% of what they’re working on. They’re going to have bad days and on those bad days, they might pick up that phone call from one of the people that are trying to take them out of your company. What do you do to keep them interested, happy, and engaged through this entire journey?

Mike: That’s the magic question. In regards to finding that talent to answer your first part, we’ve partnered with Sales Talent Agency for a long time which really helps to find our best Sales Representatives. In regards to keeping them happy and satisfied when things aren’t just sunshine and lollipops, I really feel one of the biggest game-changers has been being able to have more of that unbiased structure. So, we talked about the Sales Manager for the direct sellers, our Partner and our Business Development, but outside of that, we have a Manager of Customer Success with two Reps under her, as well as a Technical Support Engineer who was fantastic. We also have a team of Consultants, as well as Marketing that are on board too.

Building out more of the organization here, where it doesn’t necessarily feel like a satellite office or doesn’t feel like you are a second priority is important. It’s good to be more fine-tuned as a whole. We’re up to 21 right now and it’s not too big, we are still intimate. I mean, it’s not multiple floors.

I’m lucky in the sense that we’re pretty close and I truly believe that everybody enjoys everybody’s company. Not to be best buddies with everybody, but you’re going to be spending more time with your coworkers than you are with your partner. It’s extremely important, especially with more of an office role, to enjoy the vibe of where you work. We have music going all the time. We have different genres of days and that’s something that I think makes a huge difference if you’re new in sales. What is probably one of the most terrifying things, regardless of your experience, is making calls in front of your co-workers that you don’t know unless you are a select type of personality. It’s easier once you get comfortable, but it’s all about how you can create that environment that feels inclusive from day one.

It’s being able to look at all those little things that we’re constantly evaluating and looking to improve. How can I make this office and this environment constructive, successful and a place that people want to be. Because if you have that in place, it’s going to heighten the rest of your skillset. Everybody has to be able to know what they’re going to do, but if you feel good where you are, you are naturally going to do better.

Asad: This is all really complex stuff. Learning how to make this happen is a really difficult journey. Sometimes people get too focused on learning about sales or leadership, but it seems like the things that people can do outside of selling and leading that allows you to be able to create this culture.


What are some of the other things you do that enables you to do all of this better?

Mike: I try to stay connected with different networks. It’s something that I need to do more of, to be honest. So, whether it be sales meetups, technology meetups, or marketing meetups,

I enjoy the types of events that are hosted at other people’s offices because you can step in, even if it’s after hours and nobody’s there, you can feel what it’s like in their immediate space. Is that dark? Is that light? Is that loud? Is it based off what the desk looks like? Is this something where it looks like people are having fun or feeling that they can be themselves?

I’ve been able to do a ton of learning from that throughout the Toronto area. I’ve stayed with our close friends to be able to bounce ideas off of them. I’m always looking to question the status quo of my own judgment because if I’m trying to fool myself, it’s going to come out one way or the other, sooner than later. So, let’s take a look at that and see if there are things that can be improved.

Asad: Interesting. This has been great. Thank you for taking the time to sit down with us. 

I say I’ve known you, for five, six years and there’s still so much in this conversation even though we regularly meet and chat and try to share ideas with each other. There’s so much new stuff that comes out from this. It’s been great. Thank you for taking the time.

Mike: Thank you so much. Take care.


Are you expanding your sales team into a new market? Contact us today and learn how we can help your company grow.


Subscribe below to get the latest content delivered right to your inbox!