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Scaling Beyond Startup Mode – Scaling Success Podcast


In episode 6 of Scaling Success, Sean Cantwell invites Andrew Waitman, CEO of Assent Compliance, to discuss his experience “operating at the edge of chaos” as he helped the business scale beyond startup mode into the elite, high-performing company it is today. Check out the full episode to hear Andrew discuss humility, hard decisions, and the grit it takes to win. 

About Andrew Waitman 

Andrew’s history of helping businesses succeed continues at Assent Compliance. Since becoming CEO, he has been integral to the company’s growth and helped it earn a spot on the Narwhal List for high-potential companies. Previously, Andrew was CEO of Pythian, overseeing its rise from a small business to one of Canada’s largest and fastest-growing global professional services companies. He also served as Managing Partner at Celtic House Venture Partners during its highest-performing years to date, when one fund produced one of the world’s top ten best venture fund returns ever. Andrew has served on the boards of more than 30 technology companies. He is currently a board member at Assent and Fidus Systems, and sits on Genesys Capital’s advisory board.

Scaling Beyond Startup Mode - Podcast

Scaling Beyond Startup Mode - Video

Full Transcript:

Sean Cantwell: Hi, guys, welcome to Scaling Success, a podcast geared towards entrepreneurs where we discuss a range of topics that contribute to building a valuable and long-lasting enterprise. Our goal is to provide our audience with access to experts on a variety of topics that are critical to scaling a successful business. If you’re new to the podcast, please go ahead and follow us on LinkedIn and Spotify. Today, I am thrilled to be joined by Andrew Waitman, CEO of Assent Compliance, a supply chain data management business headquartered in Ottawa and operating globally, and one of the fastest growing businesses in Canada. Assent also happens to be a Volition Capital portfolio company. So I have had the privilege of working closely with Andrew over the past five years and have had a front row seat to watch the company’s tremendous progress along the way. Andrew, welcome to the podcast.

Andrew Waitman: Thanks, Sean. Appreciate the invitation to join.

Sean Cantwell: All right, great. There are a bunch of topics we’re hoping to cover today, Andrew. But before we dive into those, I think it would be helpful for our listeners to know a little bit more about your background and the series of events that led to you becoming the CEO at Assent Compliance.

Andrew Waitman: Sure. So let’s start with Assent, so I’ve been here just over six years now. I was boxing with one of the founders, a young gentleman named Matt Whitaker, who was my boxing coach. I had previously taken a DBA services business, global DBA service business from about 40 people when I joined to about 400, about just under 5 million to about 50 million and Matt offered me an office. Because I said Matt I don’t want to jump into anything too quickly, but I would like an office to go to. So anyway, I joined in September 2014. And as you know, Sean, because you joined the journey in 2016, it’s been one hell of a ride and we’ll get into that. My previous background, I’ve kind of had multiple careers in some sense. I started off as a software engineer, writing software for telephone switches for Nortel. I then did an MBA. And so I ended up in investment banking and worked for Citibank on the derivatives desk, on the trading floor, and did that for a couple of years. Then I was really missing tech. So I became a tech analyst in a second tier boutique firm.

Andrew Waitman: And from there I met a billionaire who had founded Mitel and Newbridge, and he asked me to help him during one of the greatest venture times 1995 till, I guess I was there until about 2008. I ran a venture fund called Celtic House Venture Partners, so that was an extraordinary time to be a managing partner on an emerging stage. We had one of the best top ten of all time IRR’s. I think it was 110%. And it was a fabulous experience. And then from that, after the 2008 financial implosion, I got the chance to become an operator. I was invested personally in this DBA Services business, and the founder asked me to come in and help out. I volunteered and then he asked me to take over the company, which I did for five years. So it’s a bit of an eclectic mix. I’m formerly an engineer by original, but I do have a CFA and an MBA as well. So I had a lot of adventures, a lot of different adventures.

Sean Cantwell: It’s an amazing journey and thanks for sharing that with us. That’s not exactly the type of career that you can script, but I think speaks to your eye for opportunity and the ability to kind of assess the opportunities around you and step into those roles and create value. It’s a great story. I think one of the things that’s really interesting about your role at Assent Compliance is you stepped into the business while it was still a young company and there were three co-founders. You came in as the proverbial suit, if you will, to provide adult supervision. I’m curious, I think a lot of entrepreneurs experience similar situations when you step into a new environment as the outsider. I’m curious just how you approached that role and how you were able to so successfully integrate with the team.

Andrew Waitman: Yeah, that’s an excellent question, Sean. So you are right and a couple of points I would make, my experience as a board member, I’ve probably sat on 35 boards over my venture career and still sit on some tech. So when you sit on boards, and you know this Sean, you do get an appreciation for founders and there’s lots of good in founders and then everything from the new shiny thing. So there’s a yin and yang to founders. That experience allowed me to work with the founder at Pythian, which was prior to Assent, and then these three founders. The other thing being an early stage venture capitalist was you get really comfortable with risk and you get really comfortable with what you would call chaos, OK? Because I had cut my teeth in this DBA Services business, I really found my sea legs with regards to an operational role. I had never really held a senior operational role before I took over Pythian. So I did a lot of learning in real time. But when I came into the Assent context, I was much more confident. But also I understood the role of humility. I really did, Sean. When you come in with three guys, it’s their baby. They have been running it for several years. So you really have to kind of be careful not to move too quickly. Find out where people are at and frankly, as a volunteer, it’s a good way to do it because if the marriage doesn’t work, it’s no harm, no foul.

Andrew Waitman: I was literally just using an office and giving them advice, but we started working together fairly intensely. And so I think part of the first thing to your question is what is the chemistry? Who’s doing what and what are the big gaps? One of the first things that Matt’s mom was helping them with recruiting and that wasn’t going well. She wasn’t that happy about doing that. So it was one of the first tasks. I think when you kind of roll your sleeves up with founders and show that you will go in and do anything, go through 75 resumes and find somebody who can help recruit, which is the first thing I did, you build trust fairly quickly, like, hey, this isn’t a guy who has a suit and only sits in his office. I was in there. One of the first things I was quite proud of was Matt was very, very tight on money. Nobody could spend money. I was like, you know what, I think we should feed this crew. It was about 15 people at the time. I said, look, I don’t want to go argue with the guys about this is a good use of money. I’m just going to go, and it was a subway right across the street, I went and negotiated with the guy. I got extra cookies, but I said, I don’t want you to tell them where they’re coming from. I just want you to bring food on Monday.

Andrew Waitman: I missed a few things, like you got to tell people not to bring their lunch. Right? Duh. But anyway, so the food starts to arrive the first Monday for a month. And then everybody was thrilled. And then I went to Matt and I said, Matt, what do you think that was worth? Oh, because it was fantastic. I said, What do you think it cost me? And he goes, I don’t know. And I told him and it was like $800. He said we should do that. I said, yeah. And that got started the Food Mondays. I got reimbursed, but it’s one of those things where sometimes you do show as opposed to try and debate the merits of various things and you just try and build trust with both kind of formal things and informal things. In the early days, there was a lot to be done. I arrived first and left last. I did that at Pythian as well. So I’m a bit of a grinder and that builds trust and they see how your style is. Obviously I brought structure fairly quickly because of some of the models that I used at Pythian and over time they were just very happy to go from a place that was fairly growing quickly and hence the chaos to a place that was fairly organized and where we were going.

Sean Cantwell: That’s a really interesting point. You’ll oftentimes hear entrepreneurs and investors talk about startups operating right on the edge of chaos. I think perhaps your experience sitting on many boards gave you a comfort of stepping into that situation and perhaps knowing what needs to take place to bring some order to that chaos. It’s interesting, your anecdote about the subway leads to another question I’d love to get your perspective on, which is just building a culture. Is it an intentional thing or is it the product of the personalities of the leaders, an extension of the leaders? I know you are a student of business, Andrew. For those of you watching on video right now, Andrew is sitting in front of his bookshelf filled with business literature. I’m curious, when you were stepping into that CEO role for the first time I can only imagine just knowing you like I do, that you try to do everything you could to to kind of prepare. I’d be curious if you have any advice for folks who are stepping into that role for the first time. What did you do to prepare for it? Are there any books that you might recommend to kind of provide the blueprint?

Andrew Waitman: It’s a very good question. So first of all, what I would say, I was teaching in an MBA program for 15 years, and when I first was asked to teach on venture, I was very new to venture capital. So I was actually educating myself as quickly as the dean who had asked me, presumed I knew far more than I did. When you teach, you get asked a lot of questions so it can really test whether you have the depth. So I had to educate myself on venture capital very quickly. Then, Sean, what happened was in my journey in venture, I started to absorb a lot of the founding stories of Google, the founding stories of Facebook, the founding stories of YouTube, the founding stories of PayPal. I started kind of absorbing all these contexts through reading. Peter Thiel, I think everybody knows who he is, but he’s written a great book on startups. The title eludes me, but just read anything by Peter Thiel. But I think a lot of biography company biographies. I’m reading Jeff Bezos the book he just published on every single letter that he wrote to investors from day one. So I think studying the patterns is really important. Then there’s so many opportunities to teach. One way to learn and really absorb is to know that you’re going to do a lecture on X, Y or Z. OK, so one of the big topics that was talked about a lot was why was Silicon Valley so dominant in a global context? But even in the United States context, obviously Boston and New York have really emerged.

Andrew Waitman: But for a while, Silicon Valley kind of owned the podium. And so studying what it was, I used to joke with my students, it’s the water in California. But what was it about it? What was it about the money? What was about risk taking? What was it about entrepreneurs? Why were these companies from Salesforce to, you name it, succeeding so often? And I was a great student of that. So to your question, I’m a student to this day. You know Mark Roberge? I consumed Mark Roberge like a master class. I think he’s at Harvard now, but he was HubSpot’s CRO and CEO maybe I can’t remember if he was the CEO or CRO, but he drills in. The one thing I love about Jason Lemkin and SaaStr is they share, they cause the whole ecosystem to share and the insights. So even literally an hour ago, I’m absorbing Marco Roberge talking about some of the science and the patterns of sales. I think this gets to your question to me is no matter what context I’m in, I’m fascinated with what is going on in the current context and what is best of class look like and who’s doing that. So today I’m studying snowflake, crowd strike, these companies that are doing extraordinary success, Black Line, Kupa. And I’m trying to understand, you know, every context is different. Every single company has different context.

Sean Cantwell: Context matters, as you like to say.

Andrew Waitman: Exactly, context matters. But what can you learn from those? Let me just give you one anecdote about Amazon which fascinates me. Amazon has never, even from the day they started to Amazon Web Services, has never had a demand problem. OK? They have always had a fulfillment problem. That’s an interesting place to be. I’m a big patterns guy and I’m always looking for what pattern. Like as an example, you’re seeing some really interesting success around the Shopify ecosystem. I call that the caboose issue, which is you attach your caboose to this company that’s just building like crazy and you can be successful. PayPal on eBay. PayPal was made by eBay customers. You’ve got to go back to the Origin story because PayPal has evolved. But the origin story was that PayPal did not have a business without eBay and eBay tried to put them out of business until they eventually bought PayPal. So when you absorb hundreds of these startup stories, you start to see the common patterns and then you understand how to apply in the idiosyncratic kind of situations.

Sean Cantwell: But it strikes me that you are really kind of leveraging the experiences you’ve had as a CEO, an investor, also trying to complement that with use cases of best in class companies and really trying to kind of diagnose the situation you’re in and apply best practices to try and optimize for success, which I think is a great lesson for entrepreneurs that leadership perhaps can be learned if the right focus and attention and effort is put to it. I’m curious now that you’ve been a CEO for 15 years, I’m sure your role has evolved and your priorities shift based on where the company is and its stage of development and what the top priorities are. I’m curious what you consider to be the top priorities of a successful CEO. What are the primary objectives and responsibilities of a CEO?

Andrew Waitman: Yeah, it’s an excellent question. And I’m going to tie it back to your previous question, which I didn’t address as well, which is the culture issue, because I think it’s high. So ultimately the the CEO’s responsibility, and it does change in different phases and we should talk about that because you’ve lived through some phases of Assent. And Assent is now going from the 50 million to 100 million phase and the CEO does need to adapt. So the CEO is working in the business in the early stage where he’s finding the right players, the leaders. He’s helping identify the priorities and where the real puzzles are. But then eventually when he gets into the stage I’m at, I’ve got an exceptional leadership team now and the CEO goes from working in the business to on the business. You have more of a communicative and priority and external facing addressing various constituents. But back to your question. I think culture is one of these. And we could spend an hour speaking about culture. I do think that is one of the most important and priority responsibilities always for the CEO. I think who he selects, the systems of recruitment, I think every CEO, when you think about culture and you think about recruitment, as you in your question asked, is it the people you hire or is it other things? And it is both. But how you decide, if you study a lot of the CEOs of successful startups, they very much talk about their values and they talk about whether they’re articulated on their website.

Andrew Waitman: They talk about what they stand for, their purpose, and they talk about the system they created to ensure that after they’re not interviewing the people, that the system continues to reflect those values. Whether it’s Mr. Levin at Box or some of the more successful, they really kind of put a lot of energy and effort into that recruitment and cultural fit. I think more and more the world is around this idea that values matter as much as technical competence. Back to the roles I would say number two after creating the systems and the culture and contributing to that culture with energy and enthusiasm, I would say number two is accountability. This is where founder CEOs are challenged because you’re in different phases and you have loyalty. That’s one of the toughest things, is to make sure your team at the top level is driving the culture so you don’t have silos, you don’t have politics and so on. So I would say accountability, which is identifying where you have these challenges and then acting on them. On my 360 that I did about six or eight months ago, the one strong area of feedback to me was you didn’t address some of these troubled areas as soon as you should have. It is true. Partly it’s because we’re human beings and we have affinity to the people who got us here. But partly it’s a tough thing to kind of go and fire individuals who have contributed to your company to that point.

Andrew Waitman: So I would say accountability is number two. Then number three is the obvious set the goals clearly and the vision clearly and communicate and communicate and communicate. I think that as the company gets bigger, it gets more important for the CEO to make sure that the goals of the company are clear for the whole company, and not just the financial goals. What are the two or three themes, and there shouldn’t be more, for this year that we all get around? The go-to-market team get around, the product team get around, and the customer success team get around. Those goals are then tied into, and I think this is really important, is there’s three strategies in every company and Sean, I think everybody knows there’s a product strategy and everybody knows there’s a go-to-market strategy. I don’t think everybody understands there’s a customer strategy. What I mean by that, and you see this in all your portfolio companies, what is your customer success strategy? What is your customer experience strategy? This has to do with are you a managed service company with a SaaS platform? What are you, just a SaaS platform and doing tech support? What is your customer strategy? And I think as a CEO, getting back to these priorities, culture and recruiting, accountability and then communicating the vision, part of the objectives and vision is about these three areas of strategy. What is our product strategy? What is our go-to-market strategy and what is our customer strategy?

Sean Cantwell: You started on culture, which I find interesting, I agree it’s critical. In my role as an investor in the pre-Covid days, I would spend a few days a week on the road flying around, meeting companies. Culture in many cases is that type of thing that you just feel when you walk in the door. I liked being able to walk in, you see the logo on the wall and feel the energy of the place, that gut instinct would be like, wow, there’s a lot of motivation, energy, hard work, commitment, alignment. You can sense by people being in the office. My question is, as you well know, the move towards distributed teams was in the works before Covid. That’s certainly accelerated. And I think there’s questions about what the workplace looks like post-Covid. But my question is, how do you maintain the culture in a distributed environment when you can’t walk in the office and feel the energy? I’m curious just how you’ve thought through that and kind of taken steps to maintain that alignment amongst your team?

Andrew Waitman: Yeah, it’s a great question. I think terminology is so important in business, Sean. I really like that. You use the word distributed and not remote. Remote is kind of almost a pejorative. You’re remote, we’re over here. You’re there. Distributed is exactly what the future is. As you said, as you articulated, that’s the way the world was going. It was accelerated by Covid. Now we’re all thinking about hybrid. So we’re thinking about that cultural shift. So the value of proximity is not zero, OK, and particularly towards culture and engagement and and just connected ties between people, teams, and groups. You’re right. You have to be thoughtful. You have to be purposeful. For example, we are redesigning. We literally gutted our office, we literally have gutted the entire office and are redesigning the entire office for team engagement. Those teams can be 4 people are coming in or those teams can be 200-300. We thought about that. So part of the future is the space anticipation for being distributed and bringing teams together. I think one of the big things in the future is how do you find the balance? There’s no question that distributed is going. So we are hiring people now in different cities, which we tend to be biased towards the Ottawa headquarters. We were biased towards our American headquarters, our European headquarters. We’re less biased now. We definitely are more distributed. Now what you think about is, Andrew, how do you get some of those cultural benefits of proximity is how you design when you come together as teams and how. There’s inter-team get togethers, but there’s intra-team get togethers which are equally important.

Andrew Waitman: So think about an obvious one. Think about your sales QBRs. We have QBRs in all groups, but think about the annual sales meeting and the QBRs. Those are great meeting times and there is a lot of launch energy because obviously the product team is presenting to the sales team about what’s upcoming this year and so on. So what you’re going to do is you’re going to take those get together times and events by quarter, by year, And obviously by month sometimes. And you’re really going to invest in making sure that the energy time for both the formal presentations but there’s events for informal. And that’s what I think is different about the past world where some of that stuff just happened naturally. But now you’re going to be much more prescriptive about having the party, having the sports event, having the fun things, and actually really kind of driving the times in which we’re going to get together proximity. There’s going to be some coordination issues and there’s going to be some learning. But you’re absolutely right. It can’t be left to chance. Just as one example, because I think there’s how you organize, but there’s also what tools you use. So we just introduced, literally Monday, a tool called Officevibe. I don’t know. Have you heard of Officevibe?

Sean Cantwell: I’m not familiar with Officevibe.

Andrew Waitman: Officevibe is quite a clever tool. The idea in a distributed environment is it sends periodic questions to your entire team. We’re over 600 people now all around the world and there’s a set of like 120 questions. It’s very science based and it basically helps you understand where and how people are feeling. It takes people less than two minutes. They get asked one or two questions a week or every two weeks, depending on what you set. It’s all configurable, but you get a pulse of your organization, where people are feeling good, there’s an enablement of dialogue between managers and it complements, it doesn’t replace, but it complements one-to-ones and face-on-face with managers. A lot of where culture happens is the rock face or truth, what I call between the face-to-face, between people and their managers. Sean, you’ve probably heard this many times. People don’t leave companies, they leave their manager. That’s because somehow there’s a disconnect between expectations, communication and just feeling good about what you’re doing and the recognition you’re getting for it.

Sean Cantwell: Good. That’s really helpful perspective, I’m sure, for our listeners. One thing that I have really admired about what you’ve done at Assent Compliance is managing the competing priorities within an organization and what’s required to lead. We talked a little bit about alignment, recruiting, motivating culture. The other piece that I’d love to get your perspective on is maintaining equal focus on sales and product. Sell what you have today while continuing to build and expand upon your product to ultimately, in your case, create a platform which creates a stickier solution with up sell. And perhaps this is a good point in time to just hear your description of the evolution of Assent Compliance and how Assent has really evolved and expanded its offering over time. Then I’ll dive in with a couple specific questions.

Andrew Waitman: I think that’s an excellent point. And we really haven’t talked about what Assent does. So let me just cover that. So Assent started out serving a specific area of regulation in the United States, something called conflict minerals, which there was a piece of legislation requiring public companies to determine where they were sourcing gold, tin, tungsten and tantalum from and ideally not the DRC, Democratic Republic of Congo. And so the company started out as kind of a tool. There was no legislation. There wasn’t an incumbent. So it started out helping relatively large public companies with how to get this data out of your supply chain and get it into the SEC. New requirement, which is often good for startups, no incumbent and tedious task to do. Go out to your supply chain, get this information and then produce a report. But we had a much bigger vision. And the vision was that the requirements of engaging with your supply chain, we’re going to grow and those requirements were going to require a relationship with your suppliers that you didn’t currently have. Your suppliers are often just invoiced and they ship you “X” and then you’re done. There’s not really a discussion about ethical and environmental practices. As you know, Sean, because you’ve been on this ride, the zeitgeist has shifted enormously with regards to ESG and risk in your supply chain. So the vision for Assent is we feel we are the durable goods manufacturer transparency company.


Andrew Waitman: According to research, 85% of your business risks are actually in your supply chain, things that are ethically questionable or environmentally questionable going on in your supply chain and embarrassing you or preventing you to ship products. So we provide all the data. We provide the engagement with your supply chain, the education with your supply chain, the expertise for your supply chain, for what rules they’re under and what they must do in order for the end customer, the big OEMs to be compliant. To your question of evolution and managing the priorities of product versus marketing, it’s every company when you think about the great SaaS companies, Black Line, Kupa, Pro quo, these companies have to start off somewhere. I call it their first lilypad. They have to be able to sell something. And that gets them some customers. It gets them some credibility, but it’s often not enough a point solution to get them to increase their TAM, increase their footprint. And the real navigation is what is the next thing? How do you jump from lilypad to bigger lilypad to bigger lilypad? And you know, Sean, I think there’s a lesson even if you go back to books and Amazon. Amazon didn’t start out selling two hundred million SKUs. They started selling books and they had to make decisions along the way of what was obviously additive.

Andrew Waitman: And so if you remember, they did CDs. They did CD ROMs next because you can put them in the mail. They’re easy. They have a million SKUs just like books. I think every company, whether it’s Black Line doing finance, whether it’s Pro quo with us doing compliance, it’s about navigating what’s the next important area and how is it complementary. So you’re not talking to different people, you’re not having to convince different stakeholders and decision makers. So Assent’s journey was about navigating how what what group of companies. So who’s your target? So for us, it’s durable goods manufacturers, medtech, electronics, automotive, what their needs are and what their hotspots are. Trying to anticipate that, but also getting them to tell you. One of the dangers for small companies is they get pushed around by big companies saying do this or this, and you have to make your own judgment, whether that’s a broad issue or that’s an idiosyncratic issue to that large company. That’s where a lot of small companies fail, is they become custom shops, not configuration shops. And Sean, when you provided us the Series A, the reason I needed the Series A was to build out enough functionality so that we weren’t viewed as just a niche point solution. The whole platform that we talked about and you and I had a lot of conversations about how is your next thing getting better, right.


Andrew Waitman: You were OK investing in conflict minerals, but you needed to be more than that. And you saw our plan and our vision and you invested and then you wanted to see how the numbers and as the years went, I think we were both pleasantly surprised that you guys have navigated you still sell lots of conflict minerals, but now you’re doing product compliance. Now you’re doing trade compliance. You’ve really kind of, I call string the pearls together. But if you over-torque on the new pearl and you don’t nurture the existing, some competitor may take you away. So I always talk about first you take Manhattan, then you take Berlin. And that applies both from a marketing perspective, but it’s also a product perspective. You better dominate one before you get too far over your skis doing others. And the money that you and the other investors provided us helped us defeat time. Time is a big issue is you need to provide more. You’re often overselling what you have because you’re trying to paint a bigger picture. And so whether you’re selling a security platform or a finance platform or procurement platform, the customer wants more to engage with you. And it’s often a race to demonstrate that you can do that more.

Sean Cantwell: I think there are some some great lessons in there. I can recall. It’s interesting taking that walk down memory lane to the days when Assent was focused singularly on conflict minerals and there was always a risk or a thought of what happens if legislation changes. I think the team has done a really good job of starting there and now you look, it’s really an end to end supply chain transparency solution. I think there’s probably a few things that contributed to the team’s ability to get there. Different folks and organizations are motivated by different things. They think differently. I think you are a strategic thinker and I think perhaps you saw the vision of where it could go. I’m curious if you could just share with us perhaps like the push and pull of priorities whether it be amongst a management team or a board about really setting that vision and rallying the company and all stakeholders around a plan for something bigger. Because when you’re a $5 million company, you’re looking six inches in front of your face, then you’re $20 million and you realize that gives you the right to think bigger. But many companies, as you know from your days as an investor, stall out at $5m or they stall out at $10m or they stall out at $20m. And I’m curious how you think through the various checkpoints you reach and how that influences your longer term goals?

Andrew Waitman: It’s an excellent question. I would say it does start with ambition. So it’s an interesting perspective. But a lot of people, Sean, just want lifestyle businesses. I’m talking about the founders and the people who control the business. They just want a lifestyle business. When I came into John Hughes, Matt Whitaker and Robyn Beau, I said, guys, if you just want to sell this company for $10 or $20 million, I’m not your guy, OK? My first milestone is $100 million dollars. I remember when I told them that they’re like, “huh?” And I said, I’m not going to do something, unless I can see that I can get to $100m. Now, as you know, conflict minerals was not going to get us to $100m, but I was convinced after I’d spent four months because of the complexity of the business, because investors had kind of shied away, that I was convinced there was a space that was not well seen and we’ll get into category creation. But I think first is ambition. Second, and this is a really important point that I remind the founders, I often remind my leadership team and I often remind people that I’m helping out, is you have to look at the end of every month and you have to look at the end of every quarter, are we making progress? Because during the journey, there are times where you feel like you’re in the abyss. Because things aren’t always going well.

Andrew Waitman: Executive didn’t work out or this happened or this happened. Customers cause a lot of issues. And I would say to people when they question their nerve, I would say, are we farther today towards our $100 million goal or $50 million goal, whatever it is, than we were six months ago, a year ago? And everybody would always say, yes. I said, OK, well, we’re making progress, OK? And we see where we can go. To your point, just to go back to Amazon, I think Bezos is just brilliant. But when he started building books, he knew that he had a greater vision. But if he didn’t get books done and right, he couldn’t go to the next step. The AWS one is fascinating because it’s a B2B business and he was in the B2C business. So not many companies can do that. And we can talk about that in a second. But I think back to your question about scale and growth is it is about kind of making sure that the whole team is making progress every time frame. And then I would say, Sean, there is an element of luck and you saw this with us. Do you remember when Trump got elected like it sent a nerve through all of us going like, oh, my God, they’re probably going to kill Dodd-Frank.

Sean Cantwell: I remember there was like a good three or four weeks where I did Google searches on Dodd-Frank regulation multiple times a day. And I think in week one, he said repealing Dodd-Frank was priority number one. Now granted conflict minerals was buried in Section 10, letter J of there. And thankfully that endured. You have to take those challenges as they come.

Andrew Waitman: One of the founders, I won’t name who, called me up after the election night and said, “We are F*’d”. And I said, John, things don’t always go exactly as they seem. And so let’s see where we’re at. And we were already working on big vision, we were already working on product compliance which we knew had veracity but that could have been a really big air pocket. It wasn’t as bad as we thought. And when you hear companies pivoting, it’s usually some dynamic has changed, either competitive or structural in the industry such that that conjecture, that thesis is no longer sound. And so, Sean, this is back to your question about ambition. Sometimes the dynamics, the context does shift sufficiently that they have to consider their thesis is no longer sound. Think about what happened when Covid occurred, whether you were starting, I don’t know, whatever business you were starting, maybe it has got a tailwind or maybe it got a headwind, OK? And every single leadership team after Covid had to re-evaluate in the new information and decide what their pivot was or not. OK, for us, as you know, we did a bit of a shrink. I would say we got a bit lean in anticipation of some tougher times ahead.

Andrew Waitman: And then we went through one quarter of a bit of a lull and then, as everybody knows, SaaS just kind of took off if you were in the right space. I think serendipity, both poor, bad luck and good luck, does play a role. And in our world, you have seen regulations take skip. The recent one, the European skip that we didn’t talk about, we don’t even know about. So if you’re in a general flow and you’re paying attention, there’s often a thesis that their thesis is that this environment changes and those environment changes require solutions. We can’t even know or see what all those requirements are. So anybody in regulation or taxes or whatever just knows this stuff always gets more complicated, not less. That’s our general thesis.

Andrew Waitman: Now, how do we leverage what’s going on in real time in markets is how you navigate. And that’s part of the luck and combination of skill. As you’ve grown up with Assent, you could sit there and go we didn’t even know about some of those things, but you guys have navigated to them in a proactive and sometimes reactive way. We can talk about agility. Aaron Levin started out B2C and then his customers became enterprise and he’s like, hey, forget that B2C stuff is B2B stuff. They’re paying more, less pain in the ass, etc, etc. and they pivoted to where the market took them. And so I think the cleverness, PayPal is a good example of this, the cleverness of great executives is they’re always paying attention. And while they have a vision, if some huge gold thing, the gold bundle happens over here AWS, they’re not like, oh, that’s for IBM and HP to do. Let’s see if that cloud infrastructure thing takes off. And then they nurture it when it does. I think one of the big things, Sean, on this is you always do need to be running some experiments on your product side. I think that’s the big, tangential and related to your area. You always have to be kind of floating some experiments and seeing because if you get over-torqued, this is what the last 50-70 years, the innovator’s dilemma is you get fat and lazy on your success and you don’t start to see. We can talk about the Apple iPhone versus the BlackBerry and so on, but you get a little bit too arrogant that the platform shifting from a device to a platform and that’s where Android and iOS became the dominant. And it really wasn’t about the device anymore.

Sean Cantwell: I want to go back to a comment you made, because I think it’s really interesting and probably relevant to a lot of our listeners. You certainly need folks within the organization that see opportunity and set the strategy and then you got to bring the organization along. And I think your point about kind of intermediate wins and making progress along the way is a really interesting one. One thing that I think you’ve done that I admire and I’d love to get your perspective on is you strike a good balance of creating a culture of accountability while also providing folks autonomy. And I think you can go long either one of those at the expense of the other and you end up in a bad place. I’m curious if that’s something you intentionally think about and how you manage those two where you’re creating a culture of achievement and accountability, but people are also motivated on that path and don’t feel like they’re being micromanaged.

Andrew Waitman: I think it’s an excellent thematic area and I’m glad you raised it. So there are so many paradoxes in business, so many. One of the biggest ones is a business is not a democracy, and neither is it an autocracy. How you are successful in managing between control and accountability and autonomy for people to rise and fly. I’ll recommend one book which is sitting right beside me because I’ve been recommending this. So this is Julie Zoo and I think she’s from Google and she wrote The Making of a Manager. One of the challenges when you go from an individual contributor to a manager is that anxiety over I don’t control. And a lot of managers fail. This is where they do by overcontrol. High need to control. High need to be to be in the loop to approve. And it’s interesting, Sean,  I do reflect on this autonomy control because there are times and this is where a lot of founders fail because they believe that it was a few of them that got them there. And so they believe they have to be involved in every decision. There is anxiety when it’s like, I would do this, but you can’t tell people, you can’t dictate. We’re in a knowledge workforce. You can’t tell people what to do. This is not a factory. This is not a blue collar pull that lever every four minutes, OK? And so it is one of the great, fascinating things about a great leader is walking that line between having the systems and the measures.

Andrew Waitman: This is why a lot of people talk about the importance of OKRs and metrics and so on, because ultimately the metrics are how you get the accountability and you need high functioning individuals, super leaders and leaders to be able to be given the room. But you also need them to work together. And yes, Sean, I use the word magic because there are so few leaders, there really are, that manage this balance between the need to control where the entity’s going and provide the team the autonomy they desire so that it’s not complete chaos. It’s a real paradox. I’ll just give you one other example. The people who run processes in your business don’t want anything to change. The people who run innovation want to do the new shiny thing, and you have to do both. OK, that is a similar paradox of this control, decision making and autonomy is these tensions are real in businesses and success at every stage of a company is how you manage the tension between control and autonomy, between process and repetition and individual autonomy and choice and decision making. And it is real fascinating the companies that get this well achieve both. I would obviously say Amazon has done an extraordinarily good balance of achieving both. Part of it is leadership and culture and how you do experiments, how you trust people and how you learn. Ultimately, it’s how you learn from your mistakes and enable people be willing to make those mistakes.

Sean Cantwell: I think that leads to another topic I’d love to get your perspective on. And it’s a question we get asked a lot from entrepreneurs. And it is how do you bring together perhaps best in class external talent and meld that together with your existing folks? And you obviously want to create a platform where people can grow and develop within your organization. And there’s a lot of institutional knowledge there that you can’t get from an external hire. But there are points in time where companies reach an inflection point and they might say there are some things in our organization that we are lacking and we might need to go external for that. And I’m curious about how you think in your role as a CEO of managing the talent within the organization and creating opportunity for people to grow within the organization, because that obviously drives a lot of fulfillment. But then there are times where you have to recognize that you have to go external. And I’m curious how you balance those two.

Andrew Waitman: Again, it comes back to paradoxes. So tribal knowledge, as you recognize, is crucial because every situation is idiosyncratic and very path dependent. Assent is going through this right now where we’re hiring architects, we’re hiring really senior developers, and they’re coming into our existing framework. Some of them are bringing state of the art knowledge around SaaS and around data and so on. And your question is absolutely valid because what is the alchemy of that alloy? The people who have been with you for a while with their tribal knowledge, and this is why we did these things, but how do you improve your whole thing with state of the art? And as you know, state of the art is moving at quite a pace. And part of state of the art is we shouldn’t be doing this. There’s third parties to do this. There’s tools and so on and so forth. And often you’re hiring people who are well aware of what the state of the art is out there. And so back to your question about how do you bring those two groups together, we’re in the middle of this right now, both in our product team and in our go to market, where we’re bringing in some really kind of scaling up people because we’re looking to the $100 million and the $200 million. So we’re looking at folks who understand what that takes. And I would say, Sean, it starts in your hiring process, how do you get to the values of how people treat people? It is ultimately about people trusting people and therefore listening and therefore being open to ideas and therefore, are you bringing in people who are coming in curious and willing to ask and then sharing their knowledge or just coming in with a blueprint and telling you what you should be doing?

Andrew Waitman: We hired a CMO, she started in February. She’s just got such great cognitive models. But she also understands there’s a lot of things that we do in the ways we have done them, which she needs to understand because she doesn’t know the supply chain or compliance industry. So there’s this pacing of her trying to figure out not to be too forceful. And she’s looking to me as well to guide her. Am I moving too quickly or am I not moving fast enough? And I’m helping with that speed of implementation. These things ultimately, Sean, do come down to culture to people to trust and are the people you’re bringing in of the right kind of mindset, empathetic mindset, learning mindset. I was talking about Mark Roberge and I just wrote an email to my team. And I said, one of the reasons I really like Mark is because he’s got this predisposition to teach. And if you were to deconstruct Andrew Waitman, CEO style, most of my leadership team would say, well, he’s a teacher, CEO. He loves to, not lecture, but he loves to learn and then play back. He loves to share knowledge. I think if you hire experts who have been there and done that and they come into your organization in a positive way where they share knowledge and your people grow, then I think your people who have been there for a while, embrace that and recognize it’s going to take them and you to the next level.

Sean Cantwell: Now, that’s great. And a perfect segway, Andrew, to a couple of quick rapid fire questions as we wrap up this discussion. In your role as teacher CEO, I previously referenced that you’re a student of business, as I talk to entrepreneurs, they will often ask, what are some good books you’ve read? What would you recommend? As I think about scaling the business, and I know I will occasionally send you an email and ask for your Amazon book list because you always have a good recommendations. So any any quick recommendations? I know you already made one.

Andrew Waitman: Make you the manager. So there’s four that everybody gets recommended. Communicating as a Leader. They are right behind me. I’m just going to grab one of them. Obviously, I referenced this one. Everybody knows this one. The Peter Thiel. I would say if I had to choose one, this one, Sean, because as a CEO and a business leader, you do need to be foresightful. And you may think foresightfulness is an art. It’s not. It’s a science. And this book is about the deconstruction and understanding of those who become better foresightful people within two years. Nobody is better than monkeys throwing darts after two years, which this book talks about.

Sean Cantwell: For those listening not on video, Andrew is holding up Super Forecasting: The Art and Science of Prediction.

Andrew Waitman: By Philip Tetlock. So I think every leader needs to up their game of foresight. Because that helps them navigate rocks and opportunities. The captain, the CEO, his job is to avoid hitting rocks and to navigate to gold.

Sean Cantwell: That’s great. Last question for you, Andrew. What’s next for Assent Compliance?

Andrew Waitman: So what’s next is we use our scale to continue to bring substantial value. We have some of the most impressive names in business. The top brands. Our job is to be lifelong partners with these companies. And so what’s next is to continue to expand how we bring value for them to engage with their supply chain. That value comes from efficiency, comes from effectiveness, comes from building stronger relationships with their supply chain. So it’s execution, Sean. Continue to kind of create the category, evangelize the category and bring the value that our customers seek from us every day.

Sean Cantwell: Terrific. Andrew, thanks so much. You’ve had an amazing career as an engineer, a banker, an investor, an entrepreneur, a teacher, and a CEO. And I know our listeners will appreciate a lot of the wisdom you shared based on your experiences along the way. Speaking for Volition Capital, we’ve been thrilled to be along for the ride over the last five plus years. So, again, thanks so much for taking the time to share some of your experiences.

Andrew Waitman: Thanks for having me, Sean. I love sharing. And I think it’s one of the great things about the United States is how they share the knowledge and help build a bigger ecosystem.

Sean Cantwell: All right. Terrific.

Volition Capital

Sean Cantwell

Managing Partner

Sean Cantwell

Managing Partner


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