Beyond Founder-Led Sales: Why Your First Sales Hire Keeps Failing | Ep. 3

So many portfolio companies still have the one rainmaker, the one founder that is doing predominantly the largest amount of sales. The issue is though, is that as the business scales, how do they move beyond the one guy? They are often unsuccessful. The founder is still heavily involved. And if you're going to really scale your business, you've got to do that better. Hi, everyone, and welcome to The Rule of 40, the show all about Australia's tech scale-ups, founders, operators, and investors. I'm Josh Ascoff, and with me is Jason Serta. Hello, hello. This is our first episode with a guest. This is going to be fun. Big welcome to Jonathan Staff, Chief Revenue Officer of AAC Tech and Executive Director of WinDC. Jono has spent more than 20 years running high-performance sales teams across Australian IT through AC3, Dimension Data, Macquarie Cloud and now ASE Tech. He also hosts Things Reasons, the independent show for IT leaders. Today we're getting into go-to-market and sales, what we typically see from founders, what good looks like across enterprise and mid-market and how to move from founder-led sales into a sales team that can carry the number. Welcome, Jono. Thanks for having me, guys. This is pretty good. Somebody told me it's called a pod swap. Yes. First time I've heard that today. I know. We are pod swapping, and thank you for having me on Things and Reasons last week. I'm very excited about that episode coming out. So I guess we are sister podcasts. Is that a thing? It is now. Yeah. I'm pumped. This will be a good conversation. There's a lot to unpack here, right? Absolutely. You know, Jono, I have been talking about... the struggle around moving beyond founder-based sales. We see so many portfolio companies that, you know, they still have the one rainmaker, the one founder that is doing predominantly the largest amount of sales or all the sales. And I think that the issue is though, is that as the business scales, we're seeing this so often, Josh, right? Like, how did they move beyond the one guy? Because often they are often unsuccessful, like really struggle to move beyond it. There's either they may hire a guy, you may cover his wage, but doesn't go very much beyond that. But at the end of the day, you know, the founder is still heavily involved. And if you're going to really scale your business, you've got to do that better. Right. And just for the founders out there, you know who you are. Yeah, you know who you are. We want to come and try to surround you with clever people that can help you solve this problem. And can I tell you, there is very few people that I would go to. I count Jono in this list of people that know how to build both the strategy and the execution around sales and knows how to move people beyond founder-based sales. So I think this is a bigger problem than all of us. acknowledging if that makes sense very kind of you to say Jay it's no wonder this is a struggle because sales is actually really bloody hard and it's getting harder yes so you got to get smarter so should be a good conversation for your listeners today we've got it we've got a lot to cover some really exciting things but before we get into that tell us one thing that the listeners should know about you Jono one thing they should know about me for a long time I thought sales was Bullshit. Yeah. Yeah. So I started in IT as an engineer and still am, I would say, dangerous enough. I've been off the tools for a long time. Yeah, before I became a business guy and deeply interested in B2B tech sales, but sales in general. And there's so much to study and learn. And it wasn't until almost a third, maybe a half of the way through my career, I really embraced sales for what it is, but also the magic that it can bring if you can unlock sales for a business. It's incredibly rewarding. So that's... People might not know that about me. It's a weird thing for a chief revenue officer to say that there was a long time where they thought sales was BS. So there you go. I think as well, you need to know who your client is and how to access them. How do you get at the right type of people that you are going to sell to? And a lot of portfolio companies don't know who their client is, for one thing, let alone how to get access to them, right? Absolutely. There's a, there's a very long list I've accumulated. And it's, and it's a funny thing too, because once it's, it's a, it's a moving feat. You've never really got it a hundred percent right. That's also part of the magic too, is that just when you think it's working, you got to change. Yeah. Because there's a lot about sales that you can't control. 92% of B2B buyers start their journey with vendors already in mind, right? So just at the start, right? So how do you get in their sphere of influence is an interesting question nonetheless. Right. And, uh, so these are, these are real big challenges. They're getting harder, I think. Yeah. So I think John, let's, let's go to a macro level. So the, the Australian buying landscape in 2026, what does a buyer look like in the Australian scale up? enterprise space you know what are they what are they generally looking for what's what's changed what have you seen yeah there's some there's some actually some good research that's come out this year from adapt shout out to our friends at adapt around the b2b sales landscape in australia particularly but also across apac which a lot of our audience will be interested in there's a dynamic whereby there are now more buyers involved in a decision to buy for a large contract and by large contract that's anything over a million dollars of total contract value um most of the audience here will be in b2b tech land so they're interested in mrr tcv so anything over a million dollars there's upwards of 10. wow buyers who are involved and the sales cycle has now officially approaching 300 days. So these larger transactions in Australia are more scrutinized. There's a lot more due diligence. And what that means is you need to have stamina in your sales org to be able to maintain good quality engagement in those deals and stay on the right track and keep all of the relevant stakeholders aligned. to the ultimate goal, which is to do the deal for a much longer period of time. It's super interesting because I think if you imagine that they're the kind of averages and the numbers we're working towards, that's going to be businesses that have really well-oiled sales machines, demand generation in place, really well-experienced individuals running those. So if you don't have that in place and those are the kind of the market averages, you could be in for a time much longer than that and may not be successful if there's... up to 10 buyers in that conversation. That's right. I think that's where the science of sales really starts to come into play. If you don't have a deliberate approach to how you're going to manage your way through that complicated transaction over a sustained period of time, if you're just winging it, I think it's going to be very, very hard for you. I think it's also, you need to be narrower. You need to be more specific to be relevant. in order to get the right conversion economics. You've got to really narrow in on what your ICP is and know that very well. And then, you know, have a very clear hypothesis and kill criteria and how you're going to close, you know. You're making a really good point there. I think by extension, how we would frame that from a sales leadership perspective is... about qualification so what these stats are telling us is that the cost of poor qualification now is much higher you need to you need to be able to be much more surgical with the way you deploy capital and resources into pursuing a deal because it's more costly to do a deal it takes longer and you've got to engage with more people So you can't afford to be spraying and praying and playing the numbers game or all of these analogies where if we just put enough in the top of the funnel, some will come out the bottom. You got to be really deliberate and clever about how you manage your funnel and be selective about your pursuits. Never let go of the pipeline. Sorry. No, it's a great point because I think in the context of our Rule of 40 podcast where we think about these two core numbers in year-on-year growth rate and your EBITDA profitability, these things are much closer than what people may think. Running a profitable sales engine and considering those metrics and the investment in time, even if you are successful in winning the deals, if you're... not meeting your kind of profit targets or you're overspending in that process, you haven't qualified well, the list goes on. It can affect you on both sides of our rule of 40 equation. Put you into the burn, right? Well, that's exactly right. And it gets worse as you scale. This is one of those weird things, right? So if you don't do this right from the start, and then somehow you manage to stumble across a seam of gold from a demand gem perspective, and all of a sudden you're working on 3x the number of deals that you were before it's going to make your problem 10 times worse yeah right so the better you get at generating demand the the better you need to the more discerning you need to be about which deals you work on and deliberate about how you're moving through the funnel and so i think you know everyone's acutely aware there are cost pressures there are pressures on all organizations from a systems and buying perspective how are you seeing that in the market right now is that is that pressure coming out in the sales cycle immediately is it still to flesh out yeah i i kind of struggle with this one because um having done this for a long time when you're in the trenches everyone's always talking about market conditions is the market good is the market bad are buyers in a hurry to buy Or are they slow to buy? Are we in a recession? Are we in a downturn? I think we're just, I think we're in a now perpetual age of buyers are incredibly educated and discerning. Yeah. And I think, um, I think, I think there's no such thing as it's, it's just raining deals. Like it's always hard. Just a question of how hard. We see the same thing when we see organizations come in wanting to get funding and we talk about where a target's been missed. And Jason and I have been doing this for a number of years now. So we've actually seen businesses come through the cycle. We looked at them at their seed stage and they've come back for a seed extension or a series A. And we can go back and look at your numbers and say, you said you were going from one to five. It's been three years and you've gone from one to 1.5. And the biggest red flag for us in that process is we hear these kind of macro. Oh, the market's been in a downturn. You know, buyers have pulled budgets out of programs like this. Most recently, people are paused because of AI. I just don't see that. It's always something, right, Josh? Like, I think that's true. I think the key thing is you're always going to have some kind of external stimuli on your plan, right? But I think that it's a 70-30 strategy to execution where I think founders have it the other way around. You know, they just do stuff. You know, when they're not necessarily on strategy. This is an interesting thing. Like I went through a time now. 15 years ago, you know, I started my career in sales, going out and kind of almost doing door-to-door sales in the health space. And you've got a big playbook and, you know, here's the science of selling. Here's what you say. Here's how you introduce yourself. Here's how you try and get to questions and yes questions versus no questions. And I think, you know, if you go online, you can find hundreds of thousands of hours of people talking about the science of sales and what to do. Great foundations. I think there are a lot of founders that will have done that because it's their first time selling. Jono, tell us a little about the difference between the science of sales and then the art of sales. Yeah, I'm glad you brought this up. This is like a passion topic for me. Call it, Jono. Call it. Okay. What I've learned about sales, having studied it, lived and died by whether or not we make the number every month, every quarter, every half for a long time. and then helping other people do the same thing which is what sales leadership is what i've learned is that it is a science and an art good sales good sellers are performing artists kind of in the same way as sometimes i talk about if you ever watch a great comedian and but if a different comedian told their joke it wouldn't be as funny yeah it's the same joke so there's a there's a there's a truth to that with science and art or playbooks I can give you a script and I can have two BDRs do 100 calls a day. One's going to get more appointments than the other, but it's the same script. What are they doing differently? And that is like a, I'm constantly curious about that. I'm constantly curious about what are these high performers actually doing differently? What makes them influential? Are they students of their craft? And they are. They're actually studying their craft. they're watching micro body language they're adjusting they're trying to do better next time they're constantly uh figuring out how to make the script more effective how to unlock how to get some competitive edge on this science because if everyone's doing the same thing how why is someone going to buy from you over somebody else yeah so there is a performing art to sales absolutely now um some people will be listening to this going okay um That's bad because how do you teach the art? The good news is you can be successful if you religiously apply the science and you're disciplined and you can do that and be okay while you develop your art, which will make you exceptional. You need to be relentless though. Absolutely. So the best people I see, the high performers I see are students of their craft. They see it as a craft. They're always honing their craft and they are ruthlessly disciplined about the application of the science. Not scared of getting a no, not discouraged by getting a no. They keep going. Yeah, they have an abundance mindset. Yes. There's always another conversation and another deal. We can get it like there's a lot to unpack there, but I agree with you. It is a science and an art. You can learn the science and you can teach the science. That's how you scale, but you've got to develop. The art, I mean, it's a nice segue because for founders out there that have an existing sales team, you know, might have some BDRs or, you know, something in that space to go and look now at or what are my high performers doing? differently I think we put a lot of emphasis operationally in trying to support or manage the underperformers with potentially not as much curiosity around you know Jono's knocking it out of the ballpark I should go and listen to what he's saying because I think the script looks like this but Jono's a high performer and he's saying things slightly differently and maybe we need to we need to roll that out or there's something we haven't considered I've seen scenarios where you'll have founders or senior leaders in a business and they've developed the best playbook the process the brochure looks amazing they're they're almost they're so committed to the product market fit and the features and it's the their baby and then you go out and ask the top rep why they're successful and they're like oh i just chucked all that in the bin it was all i think it'd become and they're doing something complete no one knows no one ever thought to ask them yeah that doesn't work i don't do that why aren't you teaching the others well why would i teach more deals for me right they've come back in from hunting and look how good i am yeah yeah i'm not going to tell you my secrets right so they're that it's such an important question to ask you're right um there is a tendency if if you have scaled to a small sales team to be performance managing the ones who aren't making it and never really being or Probably not, it's not about not being curious, but probably just making assumptions that the person who's doing well is actually doing it your way. More often than not, it's probably not. I think the challenge is though, is that the strategy hasn't been designed. So in that circumstance, you are relying on amazing, resilient, relentless people and it's people dependent rather than systematic and... and strategy driven. And I think part of that is like I was saying, like the real issue is that the strategy was never designed. So they are not clear on who their client is and how to get access to those clients. And what is the strategy around? There's just more execution on top of weak strategy that will just burn cash faster. Yeah. Yeah, I think so. Yeah. Throwing good money after bad. For me, if you, if you think like the way that most businesses evolved and maybe a lot of your portfolio companies or potential portfolio companies have a rockstar owner-founder doing founder-led sales. Before they think about their first hire, they often have never sat down and really asked themselves or spoken to somebody who's going to get it out of them, what is it that you're doing that helps you close a deal that makes you successful? If I said to you, Here's your new target. Explain to me how you're going to make it every month and convince me. And often they've never really thought about that. They've never had to carry a quota. They've never had to worry about losing their job if it doesn't work. They've never had to really, really sit down and reflect and extract their process into something that they can repeat because it's so intuitive to them. But it won't be that doesn't scale. It's super interesting because, Jason, you and I are going through the investment conversations with founders. We're effectively asking them the same questions because they're putting in front of us numbers and things that this business is going to hit and they're wanting to take investment on the basis of hitting those numbers. And we end up stress testing in our questionnaire or in the investment process. How are you going to get there? What are the channels that you're going to go through? Who is your ICP? You know, so often we see investment not make it through our process because we get a really beautiful slide or a few pages on our ICP and how we're going to get there. And when you go looking through their customer base, it's someone completely different. It's knowing how to get to these clients and understanding your strategy and doing that and then having a systematic process that you can drive to drive that. Like we sat down recently, Jono, you actually made this comment to me once, you know. Like we were talking about referrals is one of the largest that bring in deals in a particular business that we were talking about. And you said to me, you know, Jay, I have a process where my team will go back on a two month rotation and ask the question of the clients, please rate me from zero to 10. And if they score me an eight. or a seven we ask for a referral if they score you a low score then you know to put it into a recovery program and make sure you address the fundamental issues as to why the client is is unhappy but at the end of the day on a two-month rotation a you know where all your clients are and you are optimizing for referrals and you will get referrals on that basis if the customers love you right i think that's true that's a again it's about being proactive and deliberate and having a plan a lot of founders are probably intuitively getting referrals from their warm market when so okay take that signal and then build a plan and how do i scale that why why do i get a referral i get a referral when we do a good job how do i know when we've done a good job well i need to go and meet the customer how often do i want to get a referral now i need to meet them what so you and now this becomes a kpi So it's all up there, but how do you extract it out and build it into a plan that you can execute on? It's surprising how many companies don't ask their clients where they're at. And so it may go a year. Maybe they do annual survey of clients or something. I think there's a lot of lip service paid to customer experience surveys and different metrics and NPS and other things. My view on that is to keep it very simple. And that is how do I earn the right to get a referral? okay have i got have i got a repeatable way to to do that how am i then getting the signals from the customers so i can measure that well i've got to ask them questions so i need to meet them and talk to them do i even have people who can go and do that do i have a system of record that can support them to do that at scale can i report on it but these are now things that when you're shooting from the hip none of these things are happening Utility, we focus a lot and we look a lot at this kind of misunderstood middle, these businesses that are beginning to scale and find product market fit, but don't quite understand which elements are scaling and what's going to work. So there's still some things that they need to uncover and work out. So true. One thing that you talked about earlier, which is a key reason we wanted to bring you on today, Jono, is this concept of moving from founder-led sales. We talk a lot to founders. These things are growing. integral to that process uh you know as investors we say well what what next who who's coming how is this going to go from three to thirty and thirty to three hundred um and we get remarkably shallow answers what's your view about moving from founder-led sales to something that scales um recurring revenue business yep so i'm assuming here we've already got some revenue yep so the founder's done a good job and there's a book of ar here yep the first thing is is my house in order do i have a handle on my customer base and churn have i got stability so is my house in order before i scale and by that i mean are my customers having a good experience with me do they acknowledge that their solution is fit for purpose and do they feel like they're getting a good deal i.e do they want to go somewhere else or do they want to stay and if they want to stay do they want to do more business with me so do you have a handle on that You don't want to bring them in the front door and then go out the back door. Right. There's no use winding up and spending money on acquiring new logos if you're losing them as fast as you can bring them in. 100%. So step one, really answer those questions about your current book of business. Do I have a handle on that? And probably my first hire would be somebody who can get a handle on that. Yeah. Right. Now that doesn't mean you can't also hire a growth person. or a salesperson in parallel. But my suggestion would be really get your house in order. And it doesn't actually have to be complicated. Customer success manager, account manager, but whoever, call them whatever you want to call them, they don't have a sales target. They have a retention KPI. You're not the same people, right? Landing guys are very different personalities to nurturers. It's a huge mistake, in my opinion, and a very tempting mistake to make when you've got limited capital to deploy into your sales org to try and hire a swiss army knife it it will not work different people it will not work a weapon growth person is a very different person to a highly strategic b2b retention relationship business person and so i think you know one experience that i've had in the past and kind of being an early stage employee when you're going to get that really great salesperson the one that's going to go and trying to build an incentive plan for that person when you know i sat there building that myself thinking okay well i know what i get paid uh and i'm you know bringing in this person and you know they might be starting on more than me and then there's sales and comms and what else that could be spent on in a business it's you know it's a confronting moment in a scale up yeah let's talk about that so so are you actually emotionally ready to make the investment that is required and if you're not it's probably because you're not convinced it's going to work and the reason you're not convinced it's going to work is because you actually don't know what's going to work You haven't figured out what it is that you do and how you're going to replicate it. It's a great description for something that is probably otherwise gut feel that you kind of sit there and you've written the job description. I'm going to put it up. You've maybe interviewed. Your first instinct is usually the right one. If you're feeling uncomfortable about spending a lot of money on a gun salesperson, it's probably because you're not convinced they're going to actually be successful. And you're not ready to do it. Right. So then you need to be focusing on how do I get ready? So I am so bloody comfortable that I can open my wallet and fork out a million dollars and now I'm going to get a return. That's how ready you need to be. And that's how ready I think your investors want you to be as well because it's their capital. And if your sales guys that come on are successful, and even if they are earning more than you, you are benefiting even greater because your business is prospering, right? Of course. I think there's a readiness that comes from a number of places. It's from understanding deeply what is going to work and having done your due diligence and built a plan and spoken to the right people and extracted all of that gold from your founder-led success into something that you can teach other people to do. Where you're confident then that you've given them everything that they need to be successful so that you can then be confident to performance manage them if they're not. Because the next big track is trap. is you hire them and then you you kind of knew in yourself you weren't ready to give them enough but you figure well they're weapons so they'll figure it out yeah it's going to be okay like i can just if they're weapons i mean they were successful at their last place they won all the awards they went to sales club the guy i spoke to that is their mate said they're awesome whatever right and then three months in you're going oh the deals aren't there and six months and 12 months now you don't know how to have a performance management conversation Because they're a weapon, they're going to convince you that it's your fault. So now you're stuck again. Right. And so I've seen, I've seen a mistake in the past with founders around, you know, the building of remuneration package and incentive plan where, you know, you just kind of feel the incentive plan is a way of performance managing them. If they don't sell, they're not going to get paid and, and that's going to motivate them and it's all going to work itself out in the end. But if you're talking about a 300 day sales cycle, that's a lot of time to be sitting and hoping that it's going to work itself. They need runway. So you need to do your diligence upfront. You need to be prepared for a performance management conversation. So you need to have absolute conviction that they've been set up for success. So is that you can come from a position of integrity and honesty and strength when you're having a performance management conversation. But yeah, this is a huge mistake that I've seen founders make. They try and manage performance through sales incentive plans. They're actually two very different things. You shouldn't need a sales incentive plan to be able to have a honest performance conversation with a sales person. I think that's, you're doing that because you know, in yourself, it's probably, you probably could have done more to set them up for success. I think as well, if you, if you separate out the landing team and the customer success side of it, the nurturers versus the landers, you know, your salespeople are more focused. the other thing as well is is that don't let the sales guys get distracted with busy work that yep that is contrary to where they're focused this is a classic trap of hiring the swiss army knife so when the account if you hire an account manager this is a classic and you give them a sales quota and you tell them to keep your customers happy when they miss their sales quota they're going to say they were busy keeping customers happy yes and when their customers are unhappy they're going to point to the fact that they made their number and you're always going to have this tension coupled with The fact that everybody has a happier place. They're going to have a natural proclivity towards one or the other. A good customer success manager probably is pretty uncomfortable with trying to carry a bag. Yes. And someone who's carrying a bag really doesn't want to deal with some delivery drama. Yeah, I mean, they're more egocentric, coin-operated type people that are landers, right? They want to hand over and move to the next kill. Yes. In some cases, yeah, you're going to have It takes all kinds, right? It's hard to, I don't like putting labels on people, but you're going to, in my experience, you're going to have types of people who are really, really driven. They get out of bed in the morning and it motivates them to know that they have to hit a target. Yes. Right. It drives them. Other types of people that the idea of that kind of makes you retreat or you're a bit, oh, that's uncomfortable. That's kind of what you're testing for. Yeah. i want to kind of pick on something i know you've said to me in the past jonno around for founders that are looking for some signs that there's something more to look at in the sales team or with your sales people so we kind of follow the performance management process i hear a lot from founders and and their teams around what really works is they've got really strong relationship-based sales they've got really good they're well respected in the market they've got a lot of friends and uh you know we've lost deals because someone's chosen to do deals with their friends or they're just really good at relation-based selling yeah what's your views on relation-based sales uh if someone says that to me this will this will like probably get out there with my interview if someone comes in an interview with me and says i'm a relationships guy or person i'm like i'm checked out immediately don't say that to me come on We're hiring them because they've got this book of business. They're going to bring all their customers. They know everybody. And then I've never, ever seen that work. Your best friend's not going to give you their money unless the product's good, it's value for money, you're competitive, you run a good process, you engage the other nine people that are involved in vetoing the buying decision. This is complicated. Now, not to say that you can't win deals like that. We've all got a really warm market that will follow us wherever every good salesperson has that. That doesn't scale either. So you're just hiring another partner. How many friends do you have? That's right. Eventually run out. That's right. Yeah. And because we're in the B2B tech game where we're in the business of stitching up take or pay agreements and other things like that, there's constraints. So yeah, they're best friend, but I need a deal now, not in two years when they contract with the other guy. None of that. none of that works it doesn't scale yeah i mean and they're easy pitfalls to fall into in that scale up phase you've you've got some traction you want to go fast feels so good they've got they can bring a deal i just need a deal yep but the problem is you do that one deal now your investors want more deals Absolutely. We want to keep seeing this. We want to keep seeing this. It's not an unfair expectation. Right. Right. So it might, you might survive the quarter because you hired a guy who can bring a deal. There's no longevity in that. I think people do, it's helpful. People do buy from people who are influential, that they like, that they trust. These things are important, but. They don't scale on their own. You can't necessarily transfer that from a previous transaction to a new transaction. They have to be able to bring that with every new transaction. And you've got to equip them with the tools and systems and knowledge to help them do that. So that's that getting back to extracting what it is that makes a founder successful into something that I would ask a founder, convince me. Yeah. Convince me why a customer is going to buy. I want to test whether or not I can repeat that. Yeah. Let's fire into Quickfire 3 on Rule 40. So Jason, Jono, jump in. One go-to-market decision that every scale-up founder should revisit in the next 30 days. What would you send them to go away and look at? This for me? Yeah, go Jono. Go to market decision that they can revisit in the next 30 days. It depends on the scenario that they're in, I think. But if I was going to say, let's just assume they've just made an attempt to move out of founder-based sales. They've hired a person. Maybe there's been a little bit of success. The first thing I would go and revisit is, do we have absolute clarity around what we're solving for and why anybody would care? And can we articulate that? That's a great one because mine's ICP. It's so easy to kind of creep out into our ideal customer profile is or start broadening it, which, you know, to your point, you need to be super clear on the problem we're solving and who for and what it's worth to them. Absolute ruthless clarity. What am I solving for and who are the people that will care enough to invest in the solution and why will they care? enough. If, if you hired me to come and sell something for you tomorrow, I need to understand those. If I, if you can't explain that to me, or if you do, and I'm not convinced you've got to, you need to work on that. You won't, you won't get the salesperson that you want to hire if you don't do that. And so funny if you're talking about hiring someone who might be coming with a book, if you're not clear on who that is and what your problem solves, you really pushing it uphill to work out of that person that you're hiring to help you is. really going to be able to help don't hope they're going to figure it out on their own um they're they might but what what you're you're risking it's a it's a really costly mistake i think from an investor lens as well like we refer to this as product market fit in a bigger degree but i guess it's the concept of you know like i was saying earlier you know knowing knowing how to get access to your clients and then you know know where to find them be specific enough that your value proposition is strong enough this is key metrics that demonstrate product market fit yeah product market fit is absolute gold when when i've seen product market fit that that is real the velocity through the funnel the way a deal moves through the funnel it'll send shivers up and from an investor's perspective right then you're ready to put fuel in the tank, to go harder, to go after more of them, whether that's, you know, conquering your local market and or internationalizing or taking that into new markets, right? That's, that's the stuff we get excited about. Yep. So before you, and demand generation and marketing is a whole other conversation that top of, like we could do a whole other pod on that. But I think before you invest in that or. bringing a salesperson on, or if you have already brought them on, course correct now, stop everything, answer these, answer this question with absolute clarity. Yep. Mark, the marketing side is, well, there's lots of verification points, but at the end of the day, before you even walk into a meeting, you know, you should be able to have landed in many validations of the service, the company, the product. successful case studies. All of those things should be happening before you even step in the room. And when the successful salesperson steps in the room with an ICP that's on point, you know, the chances of closure are highly increased, right? Yeah, because you're able to qualify. And then this all just comes back to efficient use of capital in go-to-market. So then question two, Jono, what's one piece of sales advice you think has aged badly? oh man love it so much um anything to do with uh you just need good relationships yep so our relationships build it and they will come yeah that's another one yeah yeah that's another one uh oh it's all about relationships it's really important our our relationships are great and but i think what's what's absolutely more important is credibility How do you very quickly establish credibility and trust? So relationships used to be a proxy for trust. I think it's more than that. Buyers are very educated. They've got a lot of choice. They are more inclined to buy from somebody they have a relationship with. But what we're really saying is they want to buy from an organization and by extension, a person representing that organization that has credibility. that they can verify so they trust them. Yeah. Jason, piece of sales advice that's aged badly. I mean, I think build them and they will come is a great one, but I think that buyers are liars in some circumstances and sometimes we believe our own rubbish. I think you just need to put yourself out there and just be open to the fact that if your strategy is not right, what are you going to do about it and own it? you know ask the right questions and ask the people around you and people that may be in the know because it's often a scenario where a lot of people don't have it right it's really you know i think that's a really good one um it's so true you can't put your head in the sand and and assume everything's if something's not working uh customers and prospects will tell you most people are just afraid to ask i think that's true i want to have an uncomfortable conversation i've spoken to a client and he told me it's fine you know like like there's i think part of it is you got to keep yourself honest and you know we have a concept of the zooed conversations right zone of uncomfortable discussion you know how do we actually sit down and have a real conversation of what's not working and i think sometimes founders are not willing or ready to do that you know what i mean agreed right so last question um what's the first sign the sales motion is is working so before you actually get to the signed contract and the deal when do you see something and go we're getting there this is working um velocity to me it and this this you have to have an actual sales funnel and a process right and a methodology but let's assume you've you set these things up and it doesn't even have to be hard for anyone who's listening you can use a bloody spreadsheet It doesn't matter how you record this information, but you need to have a simple funnel process that allows you to track and measure the velocity with which a deal moves through that funnel. So we're qualifying the deal. Now, how long did it take us to qualify it? Now it's qualified. And if we've qualified it, now we're investing some time and effort into developing a proposal. And when do we present that to the customer? do they want us to present yep we've presented it to the customer now we're now we're either going back and redeveloping the proposal or we're moving to now where we're going to enter into a contract negotiation or whatever whatever your process is but the velocity with which it moves through that process that funnel is a is a real lead indicator that things are starting to work we've got a good number of stuff going in and it's moving through And most of it's coming out the other end with a signed order. The other one is if you're qualifying well, things aren't happening to us. We're making things happen. If deals aren't making it through the funnel, it's because we exited the deal. So the reason for loss, did you qualify out or did the customer ghost you? I don't care if we're, clap it in if we're qualifying out, like celebrate that, right? So how quickly is it moving through and are things happening to us or are we making them happen? But you need to be able to measure these things. Brilliant. I always say never let go of the pipeline. You've got to be on it all the time. You just never let go of it, right? I think people do let go. Founders kind of, you know, they move between, oh, we need to really sell and then we need to deliver. And then we need to sell again and then deliver. And so the thing is, if you're not consistent on your pipeline, you will have absolute lulls in your sales. Yeah, it's a big flywheel. It takes a lot to get going. It's magic when it's, when it's going, but when it stops, bloody hell, it's hard to get it going again. That's right. It takes twice as long again. Truly. Right. So you got to, you got to keep that pipeline. So good. So good. Right. Well, that's all we've got time for today. John, thank you so much for joining us, sharing your insights. It's been fantastic to have you on and to be our first guest. What an interesting topic to go through today. Can I tell you, Josh, like, look, every portfolio company we meet needs more sales. but the art of the sales is is honestly not given enough attention and i i honestly believe i've been referring to this as how do you move beyond founder-based sales challenges but in order to truly scale right we need to help our portfolios address this problem head on and we often see it right that first sales guy hired and sometimes the founder says oh i don't want to sell and those type of scenarios are always a disaster right and i think that you know we need to help them lockdown on the strategy, right? The strategy is 70% of the, of the exec, the execution is 30, like, you know, it's so true. And it's, I mean, it's easy to forget sometimes in a scale up where, you know, you've got lots of challenges. You're trying to run an engineering team. You're trying to find product market fit in some stages, but sales independently is hard. Sales is difficult. You know, the science is, there's a lot to learn. The art is a whole nother area again, and then building a team. So for founders out there, this feels difficult. It is difficult. If it was easy, everyone would be doing it. But there are steps that you can take that are going to give you a chance and increase your chance of success. I think at the stage of businesses, we often start working with. they're all centered around founder-based sales. I think the next phase of that is to help them mature beyond that. They hire the first and the second salespeople in order to truly scale. And that's why there is a hidden ceiling around some businesses that really struggle to move beyond this. This is definitely an area that we've only just picked the surface of. But Jono is definitely one of those people that can really help us solve for this problem that has done it so well in so many portfolio companies. And I'm sure there are exceptions, Jay, but if I think about the businesses that we've looked at for investment, even some of our own portfolio, those that haven't ever gotten away from founder-based sales would definitely fall into the good little business category. They haven't scaled. They've not gone beyond that. Eventually the founder can only do so much. Only so many hours in the day. truly and i think that is currently one of the biggest challenges you know every one of them comes to us and say we want more sales we want more we want to grow we want to do this sometimes they don't realize that founders may be an obstacle in that process and um so i i think part of that is be honest embrace the fact that this is an area that really needs to be unpacked and uh and get on plan get on strategy understand those things because i think if we apply some of this knowledge, you will unleash yourself, right? And I really think this is a big area that doesn't get enough airtime. Yeah, brilliant. Well, I think that's all we've got time for today. Thanks for listening to The Rule of 40. If you enjoyed the conversation, follow the show, share it with someone who's building something as a founder or building something great. You can listen on Spotify, Apple Podcasts, watch the full episode on YouTube, breakdowns of each episode are on our LinkedIn and The Rule of 40 newsletter. And Josh, I had a good friend of mine who told me that, Jason, you know, there's a lot of isms that you're using. right um that we don't maybe don't understand so i know we're going to do some short videos that are going to try and explain some of our isms is that a thing we heard one today what was that that was uh what was that pod swap pod swap pod swap apparently is when you you go on to each other's podcast so we are pod swapping there you go and if anyone wants to do any more pod swapping let me know all right well um thank you everyone we'll see you next time yeah good on you Cheers, guys. Bye.

00:00 The founder-led sales problem
01:00 Welcome and introducing Jonathan Staff
04:00 Jono’s background: from engineer to CRO
05:00 The Australian buying landscape in 2026
08:00 Qualification and the Rule of 40 connection
12:00 The science and art of sales
17:00 Strategy vs execution: why execution on weak strategy burns cash
22:00 Moving from founder-led sales: what to do first
30:00 Why relationship sales does not scale
32:00 Quick Fire Three
38:00 The first sign the sales motion is working
41:00 Where to find Jonathan Staff


Australian enterprise deals over $1 million in total contract value now involve upwards of 10 buyers and a sales cycle approaching 300 days. If your sales motion still depends on the founder being in every room, you are building a ceiling.

Jonathan ‘Jono’ Staff, CRO at ASE Tech and Executive Director at WinDC, joins Jason Serda and Josh Ayscough for the first guest episode of Rule of 40. Jono has spent more than 20 years building high-performance sales teams in Australian IT, including at AC3, Dimension Data, and Macquarie Cloud Services.

What this episode covers:

• The 2026 Australian buying landscape: more stakeholders, longer cycles, higher qualification costs

• Why 92% of B2B buyers begin their journey with a vendor already in mind

• The science and art of sales, and how to develop both in your team

• Why ‘I’m a relationships guy’ is the wrong answer in a sales interview

• How to know when founder-led sales has become a ceiling

• The right hire sequence: stabilise before you scale, land before retain

• The first signs the sales motion is actually working

Subscribe for new episodes every two weeks.

Follow Jason Serda on LinkedIn here: https://www.linkedin.com/in/jserda/
Follow Josh Ayscough on LinkedIn here: linkedin.com/in/josh-ayscough/?skipRedirect=true
Spotify: https://open.spotify.com/show/44IVscPmz3sgMSmxEvk312
Apple Podcasts: https://podcasts.apple.com/us/podcast/rule-of-40/id1887992198
LinkedIn: https://www.linkedin.com/company/utiliti-group/

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