E4: From Startup to Scaleup: How to Achieve 3X Revenue Growth and Deloitte Fast 50 Honours with Tony Simonsen | COO PayApps (AutoDesk)

Welcome to the Switch Gears Show. This is your host, Preet Sarkar, and I'm joined by Tony Simonson today. Tony, thank you so much for joining the show today.

My very great pleasure, Preet.

So, I've known Tony for a number of years, and he is a seasoned COO, having built revenue and teams across global companies like EMC, Avaya, Polycom, as well as scaling fast-growing Aussie software companies like Soprano Design and Payapps, notably leading them to the Deloitte Fast 50 list. Tony, I am so excited to have this conversation today and get into some of your stories from the trenches. And I guess first up, let me start with what was the transition like going from global tech companies to Aussie startup and growth-focused companies?

It was certainly interesting. When you work in those large multinationals, you've got enormous amounts of infrastructure around you that supports you in doing what you do almost every day. The challenge with that though is that it can slow you down at the same time. Lots of support, lots of infrastructure, lots of things going on, and sometimes lots of process. Transition that to very small companies that have none of that, and you find yourself very quickly rolling up your sleeves and needing to do a lot of the things yourself that perhaps others might have done for you. For those of us that love doing that, it's a fantastic transition where you get close to not just the customer, but also the people involved in delivering whatever it is you're delivering to the customers. For some, they don't get comfortable with it. For people like myself who enjoy that, it becomes a lot of fun, to be honest with you.

Yeah, that's fantastic. And just like you said, you can see the contrast or the advantages and the disadvantages. I feel the same way in that for the hundreds of conversations I've had with leaders at crossroads, there is the appeal of going to work for an Australian headquarters startup with local CEO, CTO being part of that team. But often the reality reality when you land is you realize that the infrastructure is missing or the big brand name is missing. And you've got a very different environment. And for those who've made it successfully, they don't want to go back to what was as well. Now, having done this twice over successfully, tell me, what are some of the key challenges that you encounter as you go beyond that startup phase into scale-up phase? Because now it's getting larger, it's multiplied, it's magnified. So, what are some of the challenges that you encountered?

Yeah, it's challenge and opportunity, right? So you've got to look at both equally. I think many of these organizations are founder-led. Many of them have the founder still in a senior leadership role who is driving that business. Many of them have been successful because of that founder and their sheer guts and determination to get them to wherever they need to be, typically based on an idea they had that they've brought to the marketplace and solved a problem that perhaps no one else can. So that founder's role in this transition is very important. The ones that succeed are the ones where the founder has made a decision that they are not the right person to take the business forward. And that founder then decides they're going to relinquish their overall responsibility and perhaps focus on the things they truly love. Often it is around product and what they sell in the marketplace often. They love being in front of customers, clearly, which is very important. So that transition from a founder-led organization to perhaps an executive-led organization where the founder plays a role is a really important one. And that's not one that should be treated lightly at all and can be the most challenging. Some founders choose that even though they think they want to make the transition, it's very difficult for them not to do that. Some realize that, you know what, I've served my time. I've done what I need to do with this business. It's now time to hand the reins to someone with a different set of experiences. It's not a better, it's not a better set of skills. It's not better anything. It's just a different set of experiences that perhaps can take their baby and do something more with it than they possibly could. And then allows that founder to really do what brings them joy. And I think the balance of those 2 in the early conversations you have with the founder or founders when you make these changes and move into these roles are really important.

That's very good. So now let's look at now that the transition or the decision has been made to have an executive-led team. And now you have a couple of key stakeholders. You've got notably the revenue side of the business, and you've got the product and the tech side of the business. I often hear that can be challenging between product-led growth and sales-led growth mindsets. So tell me, how— what are some of the challenges that one can expect to encounter and how to overcome them?

Yeah, it's an interesting question. It's almost a conscious decision as well. Product-led businesses, those that have born out of an idea to solve a problem where that founder perhaps has worked in an industry, saw a problem, decided technology could solve that problem, Product has been the key. Product has been the thing that they've positioned to solve the problem. And when you think about product-led SaaS companies, product is everything. People utilize free trials in early days to help them get familiarization with the product. They can see that it solves a business problem for them. They utilize it and product very quickly becomes a very big part of the conversation. The other way of looking at things though is where you've got sales-led activity, which is around sales teams that are helping to create opportunity, uncover the problems within the customer base and helping that customer solve that business problem using technology. Quite 2 different motions that are very important to understand. The conflict potentially and the tension does occur when you've got the perhaps the crossovers depending on the sort of market. that the organization might serve, where people who have very proudly built something in the marketplace that solves something unique, perhaps, and believe that is the solution to all problems, for example, for customers large and small. The reality is, my view is that you always need to put yourselves in the shoes of the person that has the problem rather than think about this great widget that I have that might solve your problem. And so, you getting a strong balance between the two is incredibly important. I find that getting alignment around the objectives that we want to achieve in the marketplace is often the best solution to any problem like that. And having leadership teams completely aligned around, let's, for example, revenue growth, around customer satisfaction, and around employee engagement, as an example, gets you all aligned around common objectives rather than perhaps has people working in different directions in the business. It serves to take away that tension that occurs sometimes between the product-oriented sort of businesses and the sales-oriented businesses and gets you focused truly on the thing that you must solve for, which is working with a customer to solve their business problem.

Yeah. One of the things that I hear again and again is that product-led companies, you've got the people who've created the product, you've got the people who are building the revenue engine and trying to meet what the customers are asking for. And then, you've got the investor who's looking for an outcome on a timeline. And often, just organic inbound acquisition is not going to be enough. It's got to be building a sophisticated revenue generation, a revenue ops engine.

Yeah.

So, RevOps becomes really critical to be able to hit those milestones where you build your marketing, sales, and customer success engine. So, Can you tell me a little bit more about how you've structured and built the RevOps engine?

I'm a bit of a passionate advocate for this because I see how it works and how successful it can be when implemented well, supported well, and driven in the marketplace. So typically, revenue operations frameworks are the combination of sales, marketing, and customer success functions. Underpinned by an operational part of the business that provides not just data, but great insight and has responsibility for the tech stack that supports all of those businesses. So if you think about the siloed view of life where you've got a sales organization who might have salespeople, lead generation type people, SDRs, et cetera, and they're underpinned by their sales operations teams, You might have marketing functions, again, doing all the things that they do from a marketing point of view, underpinned by marketing operations and customer success the same. You think about the overhead with that, where you've got overlap, duplication of effort, and no consistency of information and insight. I think you lose some real efficiency there, number one. Number two is often salespeople, marketing people, and customer success people aren't absolutely aligned around what they're trying to achieve for the business or in the marketplace. So bringing them all together under one banner and the sort of people that tend to lead those businesses are CROs, Chief Revenue Officers, for example, with singular goals. Revenue growth as an example is one very important piece. So everyone is aligned around revenue growth. They're all working towards one objective. But the other key is the piece that underpins it, which is around the operational side of the business. Where it's one operations function that serves all of those parts of the business with hopefully insight that is ubiquitous. So, the metrics you set up, be they sales metrics, marketing metrics, or customer success metrics, are all driven by a singular function and serve to those functions, not just to provide them with data, but to give them insight to make far better decisions around how they run their business, how they serve their customers, how they can course correct where necessary, somewhat proactively rather than reactively.

Yeah, that's great. And so as you are putting this together, what are some of the key metrics that you are measuring across marketing, sales, and customer success to ensure that you're on the right track?

Yeah, so I look at it from a lead flow point of view is the best way I would put that to you. When we think about lead flow, it starts with Either someone's found you or you find them. And those leads are often someone has a problem, they find you, they make a connection, they want to talk to you about that and how you might help solve their problem. Or the outbound world where we are reaching out to someone that may not know they've got a problem, but we help to uncover that for them. MQLs, marketing qualified leads, very important to understand that. And the balance between those that are driven by the outside world versus the inside world. Is also critical to understand. The conversion, the quality of those leads coming in as well, and the way we qualify them and very quickly either qualify them out or move them onto an inside sales force or an external sales force is really important. Rapidity, time to get information moving is also very important. And not just the volume of leads, the quality of the leads is important and the time it takes that information to flow to people and get it into the hands of people. That need to be talking to the customer, truly critical. From a sales point of view, we want velocity, we want volume, we want value. We want to see opportunities moving through our funnel as quickly as possible. So we're talking to customers, we're doing discovery, we're understanding their challenge, and if we can truly solve their problem for them, we're showing them how we might do that. And then we're moving to a phase where We're hopefully closing them and we're closing them more often than not, which is around our close rates, for example, where we're then transitioning that to our onboarding teams who take responsibility for onboarding the customer, not implementing, not installing, onboarding the customer onto our platform and doing that well and doing that quickly because that other metric is really important to us. We have the world of marketing where we're creating leads. We have the world of sales where we're closing opportunity. The next most important piece is to onboard those customers quickly, but with a level of satisfaction where they enjoy the process, which helps with not just their experience with us then, but also the retention of that customer. So we're thinking very clearly about the onboarding process before we're even closing the opportunity, and we're moving it into that onboarding phase. Then we're transitioning that to our support functions. We're transitioning it to ongoing management. And we're measuring and tracking along the way. So it's a cycle. And we're always staying in touch with our customer all along the way. I think that's very important. So the level of touch we have at different phases throughout the process to me is very important. And we need to be measuring that. So it's a cycle that is important. The smallest number of metrics is often the best way. We can, I can assure you that all of us can come up with hundreds of different metrics we might want to measure in businesses, but the reality is. If we can keep it to the smallest practical number, rule of 5, if you want to use it that way, with the most impact, will allow us to then have good observation of the business and how things are going. And we use tools to do that. I talked about the operations function and how important that is.

Yes.

They are the part of the business that provides that insight for us, whether it's the dashboard, the knobs and dials that allow us to change what we're doing in our business. But presenting that information as true insight that lets us make great decisions quickly with and for the customer is truly important.

Thank you. That's— and I can see how you have those 3 functions and then underpinned by this operational layer, which creates actionable insights in the form of the information that you bring back up.

It's a good term, that actionable insight. I like that, Pri. I'll put that one in. If I use that 3 times, I can call it my own. Absolutely.

Absolutely. Moving on to best practices. So now you've done this journey in a variety of companies with different challenges and stages, and it's almost always the same thing, whether they are obstacles to revenue growth. What are some of the best practices that you would share for another CEO who's at an earlier stage or companies that find themselves stuck? What are some of 5 to 7 things that you would do to ensure that there is cadence? There is— I like what you said, value and velocity. Yeah.

Yep. A lot of years ago, you used the word seasoned at the start of this conversation. I will say seasoned is experienced, not old. But a number of years ago, I had the great fortune to work for a CEO, a guy called Steve Smith, who ran Equinix at the time. And he gave me a piece of advice that I've never forgotten. And he said to me that I should listen, I should learn and then lead. Because if I go straight to trying to lead before I do the first 2, I'll fail. And you know what, I've carried that through my career because, and I've coached and mentored people on that. And I've used that in my own practices every single time because every company is truly different. I think we all have to understand that. We can fall into the trap of being experienced leaders who believe we've got our magic template that we apply to the business. It's going to solve all the problems, but it doesn't work that way. Sure, the model absolutely can be applied, but without really truly understanding the organization, who the company is, who the customers truly are, who the partners are, as an example, and who the people are, We can make mistakes early. So taking the time to listen, lead before leading, I think listen and learn before leading, I should say, is really important. I also overcaffeinate. So I spend a lot of time talking to employees. I talk to leaders, I talk to the board, and importantly, I talk to the customers and partners because I want to get a sense for that business, the opportunity, what's working well, what's not working well, and what corrective action needs to be taken quickly. versus not as we start to think about doing things a little bit differently. Because often we'll be brought in to solve a problem. Often we'll be brought in to take it from this stage to this stage. Often we might be asked to continue doing what's been done well, but there's always going to be things that need to be done a little bit different or a lot differently that we have to uncover relatively quickly. And so by asking those questions, and in the words of Ted Lasso, Be curious, always be curious and find out about people and find out about what makes them tick. For me, has worked exceptionally well. By driving in and going, I know boats and here's what we're going to do. You can get everybody offside and you can get a misaligned organization very quickly. And it takes a lot more time to realign an organization that you've lost than it does to perhaps get one That needs that alignment aligned, if that makes sense to you.

Yeah.

I spend as much time as possible externally as I do internally. The voice of the customer is really important and you have to feel comfortable and vulnerable enough to ask the hard questions of your customers around how they feel about you, what works well, what does not work well, how well do we serve you? Because we're there to serve you. We're there to provide a solution to a business problem. Our job is to serve you. So, if we're not doing that, please tell us and be honest about that and use that information to help us do whatever we need to do in the business differently to get a better outcome for them. And if you're— the third thing is then around the people. So, I've probably 4 or 5 times in my career, I've come into organizations where employee engagement has been quite poor, morale's down for one reason or another. People feel disempowered. People feel they're not aligned to the direction of the business. They're just doing their own thing for the sake of it sort of thing. And it shows. Attrition is high, satisfaction low. And I can tell you, I can tell you hand on heart that if your customers are unhappy and your employees are unhappy, your revenue is going to be unhappy as well. So that's why I spend a lot of time on both these things. And Again, I run a little process. I call it Workout. On this podcast, I won't use the acronym that I use normally, but it stands for WPMO. And it's loosely based on a process that GE used to run called Workout, where you bring all the employees together and identifying and uncovering the problems in the business, working on solutions to solve those problems, prioritizing around the things that are most important, and then empowering the people who came up with the idea in the first place.

Yeah.

To run the project to solve the problem and then making sure that you support them in doing so. So immediately what you've done is engaged your team in solving problems and/or creating strategy for the business. You've empowered them to fix problems so they feel part of the solution, not just peripheral to it. And quite frankly, you know what? Most of the answers live within the business anyway. So you've actually tapped into a base of knowledge That sometimes us experts seem to think we know, but the reality is we don't. And you got to look at this as a bit of a circle sort of thing. And I think that by getting these things identified from a best practice point of view early, work well, because the time you invest now will bring about the least cost at the end. The time invested now, and it's the overcaffeination, it's the lack of sleep, it's the Conversations you have will pay you benefits down the track. I can absolutely promise you.

That's fantastic. And I think the results speak for themselves, Tony, from what you've achieved. Yeah, that's very good. Thank you. Last question. And this is a little closer to home. Being a CEO, leading teams, high growth expectations, investors want an outcome. You're trying to move a bunch of people in a certain direction on a timeframe. How do you stay focused, sane, healthy, balance the demands of home life, work life, and stay motivated and pull it all together?

Yeah, it's a great question. My first boss at Cisco was based in Florida and he looked lovely, man. And we worked together for a long period of time, but he used to say to me, Sleep was overrated because I don't think the man slept. But the reality is sleep is completely underrated. I think sleep's very important and getting somewhere between 7 and 9 hours is hugely important. Getting good routine is hugely important. I think staying away from devices and those sorts of things close to bedtime, paging out your day, writing your notes perhaps prior to going to bed, those things are truly important as well. I stupidly am this late age triathlete as well, where I'm doing middle and long distance triathlon and I'm training 6, 7 days a week, ridiculous hours. But what I do is I get up early to do that. So it doesn't intrude on family time or work time. So I get up quite early. I get all my training done. And quite frankly, it starts the day off fantastically, but not everyone has to do that either. Simply going for a walk, experiencing the outside, experiencing the sunshine. Listening to podcasts rather than reading something, reading email or those sorts of things, just getting in tune with what's going on around us, I find very important as well. I rise things around training, around life, around wellbeing, around family. I make sure that there are things in my diary that let me achieve that balance. I'm not taking my— oh, my last daughter is learning to drive and making sure I'm helping her by driving to school with her and picking her up and taking her to work in the afternoon sort of thing. So we get those moments together. Making sure you find those little moments with children or other members of the family at times is also important. And then balancing that with the work life, which is no one can work 24/7. No one can be switched on 24/7 because you just don't have that capacity. Anyone that says that is probably a very tired person or they're probably fooling themselves anyway. And so finding that right balance is critically important. Leading from the front is my other thing too, right? If I say to you, Pri, if you're working with me, so it's really important to find balance, Pri, I want you to make sure you balance family time and work time and those sorts of things. And then I go and work 24/7. I'm answering email at midnight, 2 AM. I'm not leading by example either, right? So I'm, I think in all things, whilst it's overused a little bit, but finding the right balance for yourself is important. But if I summarize that with good sleep, time off away from screens and other sources of things that keep you awake and active. Time with family, talking, reading, listening, truly important. And I've worked hard on that. I worked really hard on that. I've focused a lot on being, and I listened to podcasts that talk to that. I'm always looking for what brings me happiness and what brings me joy. And I can say to you, being in and around teams brings me joy. My family brings me joy. My training and other endeavors brings me joy. And I wouldn't do them if they didn't. I wouldn't, I don't do them because I have to. I do them. Because I love doing them. Always find what brings you joy. And when you strike that balance, you not just become a happier person, but everyone around you is the same. Because if you're unhappy, it's contagious, isn't it? But if you're happy, it's also contagious. And it's not just about being happy for the sake of it. It's actually just truly being happy and relaxed. And I find that by, you lead teams and one of the things people will say is I always have a quite, not a relaxed view of life all the time, but Even under stress, you've got to maintain your role as leader. It's important to make sure you're leading from the front. So, if you're stressing and fretting about various things, whether it's numbers or whatever, people around you will do the same. And that's when we talk about culture, right?

Yeah.

Culture is simply how we act and behave, isn't it?

Absolutely.

Setting that tone, I think, is important, right?

Absolutely. I can tell you time after time when I look at— I've had the last 15 years working with very successful leaders, global companies, startup companies, scale-up companies. And one of the consistent themes that comes out from successful leaders is number one, self-awareness. Number two is self-care. And number three is a concern for others around them. And that's both at home and team. And if you can get your oxygen mask on first, because you're no good to others if you're Struggling, you are more likely to position yourself to actually make it through year after year, evolving with the business, rather than getting stressed out and burnt out quarter in, quarter out, because it will do that to you as well. So—

It will.

I am very grateful myself, going back when I stepped into leadership, I think about 20 years back. That was a time when I worked at FedEx and VPs would send out emails at 4 and 5 in the morning. I think that was before even auto-schedule us to either demonstrate that they were working that early. But there's enough evidence from science to sell us that you do need sleep. You need exercise.

Absolutely.

Because if you're not doing that, you're not being good for yourself, your family, and the mission that you've taken on with the company that you're at. So—

Correct. Absolutely correct.

Tony, thank you so much. This has been an outstanding conversation. You've given a lot, and I appreciate you so much for doing this. So, thank you for this time. And take care.

Thank you. It's been my pleasure, Perry.