Ten years ago this month, Andrew Waitman was at a career crossroads. The veteran venture capitalist and tech executive had just left IT and data analytics firm Pythian after a five-and-a-half year stint as CEO and was looking for a new challenge. Waitman, a self-confessed “workaholic,” had a couple of potential irons in the fire. […]
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Ten years ago this month, Andrew Waitman was at a career crossroads.
The veteran venture capitalist and tech executive had just left IT and data analytics firm Pythian after a five-and-a-half year stint as CEO and was looking for a new challenge.
Waitman, a self-confessed “workaholic,” had a couple of potential irons in the fire.
One was commercializing an idea for an app that connected customers with professionals such as plumbers. Then there was the possibility of joining the executive team at electronic product development firm Fidus Systems, where his longtime friend Mike Wakim was chief executive.
In the end, however, Waitman found his next calling in the most unlikely of places – the boxing ring.
Waitman was among the business leaders who took part in the Fight for the Cure, a charity boxing event that raised money for the Ottawa Cancer Foundation.
As it happened, he trained with the event’s co-founder, Matt Whitteker, a young entrepreneur whose company helped manufacturers ensure that materials such as gold, tin and tungsten used in many electronics were ethically sourced and complied with regulations governing environmental, social and other factors.
Intrigued by the small firm then known as Assent Compliance, Waitman moved into an office at the company’s headquarters. In September 2014, he agreed to become CEO of the organization, which had about 25 employees and annual revenues that barely cracked the seven-figure mark.
A decade later, the firm now known simply as Assent helps some of the world’s largest manufacturers ensure their suppliers are complying with an ever-growing list of government laws and regulations on everything from human rights to health and safety standards.
Fuelled by hundreds of millions of dollars in venture capital, Assent employs in excess of 1,000 people and has seen its annual recurring revenues more than double in the past three years.
But Waitman, who earned a bachelor’s degree in electrical engineering from the University of Waterloo in 1987 and an MBA from the University of Western Ontario’s Ivey Business School in 1992, is hardly satisfied.
In June, Assent announced it had officially achieved the coveted “centaur” status, hitting US$100 million in annual recurring revenues. But even as the company crossed a threshold that Waitman had been relentlessly pursuing for years, he was already plotting how to lead Assent to US$200 million in ARR and beyond.
Today, the man who returned to his hometown in 1996 to work for the legendary Terry Matthews as managing director of Celtic House Venture Partners is a celebrated tech leader and much sought-after mentor and investor in his own right.
For all those accomplishments and many more, Waitman is the 2024 recipient of the CEO of the Year Award from OBJ and the Ottawa Board of Trade. OBJ’s David Sali recently sat down with Waitman to discuss his career. Here is an edited transcript of their conversation.
OBJ: What was it about Assent that really grabbed your attention and why did you decide to take the leap at that point?
AW: I was boxing with Matt every Wednesday, and Matt heard that I was leaving (Pythian). I said, ‘Well, I could use an office.’ He was like, ‘Sure, we’ll give you an office.’ And I said, ‘In return, if I can be helpful to you, I will.’ In the end, I was impressed with (co-founder) John (Hughes’) and Matt’s energy and enthusiasm. Conflict minerals were really starting to get traction (after the U.S. Congress passed the Dodd-Frank Act in 2010 requiring public companies in the U.S. to disclose their use of tin, tungsten, tantalum and gold). Matt was the quintessential entrepreneur and John was the quintessential salesman. And both of those (qualities) I resonate with. They were getting customers that didn’t make sense to me for a startup that had raised no outside money – I’m talking about brand-name, big companies. I was like, how are they doing this? That curiosity drew me in. I’m a guy who wants to be helpful. They needed some assistance with some hiring, with some organizing, and so I rolled up my sleeves very quickly, even though I was looking at these other projects. I’m a bit of a workaholic, so I just got involved. And then it became clear to me that there was a big opportunity there with what I call large, real customers. Customer acquisition is one of the toughest things for every business. I was impressed that at that point, their challenge wasn’t so much customer acquisition, it was more handling the fulfilment (of contracts). This is where I thought, ‘Wow, I can help them.’ They needed to do a bunch of work on the product side, on the customer success and go-to-market side.
OBJ: When did you first start to realize that Assent could potentially become a centaur?
AW: I had every intention to take Pythian to $100 million (in ARR). I’ve always been fixated on that (number). It really started to form in years three and four that we absolutely could get to $100 (million in ARR), and obviously now my aspirations are a lot bigger. But when I first joined, it wasn’t clear to me whether that was possible. If there was anything that caused me pause about joining, I would say that I wasn’t sure whether it was just a niche software that you would sell to some industrial software company or whether I could build a real business around it.
In the period from 2010 to 2020, there were a bunch of rules created that were applicable in our world. From 2020 to now, there are a whole bunch of new laws. You could see it coming. You don’t learn about legislation the day it’s published. You are aware through your subject-matter experts that the European Union is working on this, the (U.S. Environmental Protection Agency) is working on that. There was a tailwind every year, and you start to realize, this isn’t going to stop. I was starting to realize in 2017, 2018, 2019, ‘Hey, if we navigate this well, we can build a real complementary platform business.’ And platform businesses are much more valuable than niche tools. It’s not a big ‘Aha,’ like when ChatGPT dropped and the world shifted dramatically. Sometimes these homogeneous tectonic shifts are massive. But we’re in a much more complex, niche market where you realize over time that companies need a new system.
OBJ: Now that you’ve set your sights on $200 million in ARR, what’s keeping you up at night?
AW: As you grow to $100 million (in ARR), you have to move from heroes to systems. The heroes are all these critical team members who do extraordinary things and help you win deals and develop products. Heroes matter, and we’ve had many. But as you grow, you can’t rely on heroes. You have to have systems. Your sales process has to be systematized; your marketing programs have to be programmatized. Meaning that you could take different people and insert them and it still works. This is one of the most important things as you’re going from $100 million to $200 million, is how to move with agility from heroes to systems that work successfully. That requires SaaS tools that often need to be co-ordinated in some functional way. And then, do you have the telemetry to give you the feedback to improve those programs?
And then I would say No. 3 is team development and new recruiting for (experienced staff), so that we don’t have to make all the mistakes that every other executive team made. The executive team we have today is very different to what we had five years ago and what we had 10 years ago. I would argue many entrepreneurs and founders do not make those changes along the way, and that’s what holds them back. Part of the responsibility of the (investment) firm is to change the jockey if the jockey can’t scale. And the responsibility of the CEO is to make sure the team is capable. That team may need to be complemented or you may need to replace them. That’s not to say the people you’re replacing are bad people. It’s just that they may be inexperienced (in dealing with issues) at that scale and therefore with the speed at which you have to make these decisions. You can’t (wait) for them to learn on your time. Part of my responsibility over the next couple of years is to (build) a leadership team to make sure we’re able to go to $200 million and $400 million (in ARR).
OBJ: How would you assess yourself as a CEO?
AW: I am an uber-collaborator. I don’t think I have it all figured out. I’m an educator CEO – I’m a big reader and I’m trying to always share (knowledge). But I’m also a big synthesizer – I’m listening to everyone a lot of the time. I want everybody’s perspective. I do understand that decisions need to be made in a timely manner, but I also think voices need to be heard. In a highly complex environment, you need somebody who encourages all the voices to come together and make good decisions as a team. John Hughes is a founder here; he still works intimately with me and is still the major non-institutional shareholder. And I listen to John even more deeply today than when I first met him, because John has excellent entrepreneurial instincts. Those instincts help me gauge the commercial likelihood of whether we should do this or that. The hardest thing as a CEO is there are always opportunities put in front of you and you’ve got to choose which ones (to pursue) because you can’t chase them all.
Business is a set of tensions. And one of those tensions is in a complex, dynamic environment, you need to get other input, but you also need to make decisions. I think I walk that balance of listening to the folks around me very well while ensuring we are making timely decisions and we are ambitious. I’ve always been ambitious. I’ve always been competitive, but not obnoxiously competitive. I’m what I would call quietly competitive. People often don’t see me coming. But I want to be (in the) top quartile. And I think that requires an ability to work with other people, synthesize what they’re saying and then make sure we’re making decisions in a timely manner, moving forward and learning from those decisions.
This is an abridged version of the Q&A. The full version will appear in the next edition of the OBJ newsmagazine that will be published later this month.
