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Scaling Revenue Teams & Rebuilding Sales Processes - Adam Kay’s Playbook for AI-era Sales

from Making The Grade

34m 49s

Scaling Revenue Teams & Rebuilding Sales Processes - Adam Kay’s Playbook for AI-era Sales

Adam Kay, a seasoned CRO, emphasizes designing sales processes that align with real buyer behavior rather than rigid methodologies. He believes in building repeatable, predictable processes that deliver value at every stage, especially during initial discovery calls where he uses personalized market reports to educate buyers on hidden pain points. His approach is deeply rooted in buyer-centricity, recognizing that modern buyers are more competitive and skeptical, requiring a compelling narrative around problem-solving. Kay leverages AI not as a replacement for judgment but as a tool to validate hypotheses and measure process effectiveness, ensuring human insight remains central. He champions innovation through quarterly commercial hackathons where sales teams build prototypes in a fun, low-stakes environment, leading to practical improvements like real-time cold-call personalization. A recurring theme is the importance of accurate ICP definition—often misaligned with legacy assumptions—and the need to translate nuanced buyer needs into actionable data. Ultimately, Kay urges new CROs to embrace vulnerability, critically assess their own assumptions, and foster team collaboration, arguing that true scalability comes from humility, adaptability, and a willingness to learn from others.

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(upbeat music) Welcome to Make In The Grade, the podcast for founders and go-to-market leaders, building and scaling some of the most ambitious B2B tech businesses. This season, I'm gonna be talking to CROs about what it actually takes to lead a revenue function right now, from navigating more competitive markets, evolving by behavior, and how the CRO role is changing in an AI-driven world. Expect candid conversations, hard-won lessons, and practical advice from leaders who are in the seat right now, grappling with the real work of scaling a business. Adam Kay has spent his career building sales engines at early stage SaaS companies. But here's the thing, he's not a methodology guy. He doesn't just copy and paste playbooks that may have worked for him in the past. Instead, he obsesses over one thing, mapping your sales process to how your buyers actually buy. And in this episode, we dig into why most teams get this wrong, how he's using AI to validate thinking rather than replace it, and how a go-to-market hackathon is changing how his team at good fit think about innovation. So if you're interested in designing a sales process that actually improves your win rates, this one's for you. Adam, welcome to Make In The Grade, how are you today? - I'm very well, thank you, very well. What's the most important hire for the most impactful hire that you've ever made? - I think the most impactful hire that I've ever made is probably when I was at play role, which was an early stage employer of record business, typically founder, I mean, I always joined a family business, but it was a head of revenue operations. Happy to name him as well, 'cause it's an absolute superstar's name's Daniel Lam. If you're listening, Daniel, I'm still hoping you come and rejoin me one day. But it was, I mean, he's obviously a superstar in himself, but the role itself was not, you know, just a sales force admin. For me, this was a shift in the way I wanted to run the business being very data-led, very data-driven, rather than just kind of a quantity-led or gut-driven. Love that. And I'm a big believer in the value of wherever I'm up. So a strategic level, not, as you say, just a tactical level can be super impactful. So I'm really glad you caught that out. You're the first one on this season. So yeah, it's awesome. And then what's the hiring decision that you'd make differently today? - It's a decision that I always say, I'm gonna make differently, and I keep falling for the same one. And again, it's no reflection on any individual, but it's about stage fit. I get a bit dazzled by people with great CVs and great brands, but not necessarily have had that experience of working in that chaos and early stage and uncertainty. And they interview really well. They are smart, articulate, but they always struggle. And so I've made it a hard and fast rule. It's like, you know, something I remind myself of every morning is unless somebody has worked in this environment before and has thrived in it, doesn't matter how impressive they are in an interview or on their CV, it doesn't work out. That resonates a lot as well. - And then what's something you believed about scaling sales that you no longer believe? - Yeah, I mean, it was a lesson I learned when I first moved from AE into management, which was I was a successfully. And I thought, hey, if I can make a team of Adam Case, then it'll be a really successful team. That's my job is to make a team of my clone. And guess what, there is no one else like me. I'm not saying there aren't people better than me. There aren't many sales people better than me. But it was a lesson about scaling sales, which is, or perhaps scaling sales teams more importantly around embracing the strengths of the individuals in your team and working towards them. And actually recognizing that a team with diverse skills and experiences and opinions is a stronger team. This has really humbled me because it's allowed me to say, my way isn't always the right way. And we know there's more than one way to win a deal to run a process, et cetera. So it's recognizing that and understanding my shortcomings and compensating for that in terms of the team constitution that I'm building. Clearly, God, I've been guilty of trying to clone me as well. And it doesn't work. You're right. And then what's the metric you check first, every Monday morning? Monday morning should be go time. I should be really clear on a Monday morning, what is the metric we are trying to impact and what is the plan to impact that metric? So I will always end my week looking back at some of the key metrics, be that top of funnel. It can be quantitative, have we done the activities we needed to do? It can be qualitative, have we kind of learnt more about the type of accounts we're targeting and how we engage within them. Or it can be more bottom of funnel, which is has anything changed in terms of the pipeline constitution, the deals, et cetera. But that means myself and every member of my team should come into that Monday stand up with a clear plan of action of what's the metric we are trying or they are trying to move. And if I'm just looking at it on Monday, then we're already behind the curve and chasing it. We're going to dive into a topic which I know is close to your heart. The times that we've interacted over those years, you've always come across the someone that is a very process-led sales leader. Like I just imagine that you, you know, I don't know, where you're a lawyer or a mathematician or something in your lawyer. Yeah, that's right, that's right, that's right. Yeah, you just struck me as someone that would be super process-led. But I know that you look at sales process in a particular way. And when you join a business, you're not looking to copy and paste what you've done before or inherit the playbook that's already there. And I suppose just with that in mind, give us a sense as to kind of how you think about sales process and what you're trying to work out when you join a business. Yeah. And again, I have to qualify. This is always through the lens of the type of business and stage of business I join, which is early stage transitioning typically away from founder or one AE2A's in the team there to build a sales engine as it were. And I think about it in the way of what's my objective in scaling an organization. My objective is to scale the organization in order to scale it successfully. I need to become predictable. I need to know that a pound or dollar in at the top be that higher, be that initiative, be that a channel, et cetera, what it was likely to yield at the bottom. That's great, but in order to become predictable, I need to first be repeatable. I need everyone not being homogenous clones, but following the same process over and over. And I'm not expecting that process to be the home run out of the box, but it's a structure I can follow so that I can start moving on to predictability and I can scale with confidence there. So that's kind of my guiding principle when I'm thinking about when I'm going into an organization there. But again, I'm never, apart from my own failed startup and probably the less said about that, the better. But I've never been the first one bringing a product to market. It's typically been a founder or a couple of AE's doing that already and have had enough traction to generate a series of funding around. So I think there's a lot of learnings on what's happened before. Even if it has just been exclusively founder led to say, well, what's worked and what's not worked with the caveat and I always have to manage expectations of my founder, typically my CEO, which is no one's ever going to do this as well as you do. So don't be frustrated. You are clearly a founder because this is a passion and a problem that you have been kind of hoping to solve and hence the reason you launched the business. But when we hire people, that's not necessarily the reason they're getting up every morning. So you've got to understand that we've got to kind of build a process that not just reflects what you've been doing, but people can adopt and reflects a process that builds that kind of objective of repeatability and predictability. And then how do you go about, actually, as we're deciding on what that process needs to be, like what are the kind of key things that you're asking questions about or diving into in detail? - Yeah, I'm a big believer that, you know, obviously a sales process is very helpful because it helps us achieve this objective of a repeatability and predictability. It also helps us determine what do we do at every, what's the next stage. But I think the one thing people often miss is that it's got to be a good buying experience as well. And it's not just a selfish objective for the business to achieve our goals. It's really got to be a pleasure. And I think more today than ever, where you can't just turn up, show a demo, people think, brilliant, I'll buy it or not. So it's, you know, in my experience of sales, it's never been more competitive. The build versus buy argument has never been more prevalent. And so there's got to be a well factor or, you know, imparting a value at every stage of the journey. And we know that the winning by design framework of kind of the buyer journey around awareness and engagement decision, et cetera, understanding where your buyer is on the journey will actually impact the process that you're building out. So I think it's about considering all of the reasons you're building a process, not just for the sake of the business, but so that you can build a really pleasant experience and a reason for the buyer wanting to engage with you as well. That's great. Yeah, I love the way that you're optimizing for the buyer. And we obviously all talk about mapping our sales process to the buying process. And everyone's goal is to try and do that. But how do you, how do you ultimately get to the truth of how customers do buy? Yeah. And again, I think the key part is a little bit of patience. Like don't look for that home run because you're never going to, unless you're very lucky, going to actually design the most perfect process. And things always change. Markets evolve, your brand evolves, buyer awareness changes. So again, and good fits a great example. I've joined the business in October last year after the back of the series A. It's a data for go-to-market teams. Now, hasn't the world got enough of these right now? That's a real problem for us because we like to say we're tarnished by our predecessors in terms of how the market thinks about us. But we are very, very different. We have a very different proposition. We have a very different methodology. And our product is very, very different. But that's the hardest part for us in terms of educating the buyer, not just on the pain they're having, but on why we're not just another data vendor that they've tried 15 before us and they've all failed, anarchy difference there. So I think it's about recognizing your place in the market, both in terms of competitive landscape, but also kind of timing in that market, your brand awareness, et cetera. So that you can really think about what do I need to optimize for based on all those circumstances as well. Yeah, it's interesting what you're saying here is, as you say, it's market dependent and competitive dependent. But it also sounds like there's a degree of learning and iteration over time around what that buying process is and therefore how our sales process should map to it. Are there kind of key things in that buying process that you're looking to uncover that will then map to your sales process? How do you think about the key stages and things like exit criteria, which obviously we talk about a lot in sales in terms of forecasting? But how do you think about mapping it as well? So I think a special people have been in sales for a while, we've typically all been schooled in sales process, sales methodology, entry and exit criteria. Whatever your naming terminology is generally they follow a very similar process. But I think as you get more familiar with your market, you understand the use cases a little bit more. You understand the personas you're selling to a little bit more. And again, I'll kind of point it good for you and say, we sell to revenue leaders. Now, again, what's a revenue leader? You know, we'll think about the concept of champion, economic buyer. But for us, we try and translate this into actual language that revenue leaders we sell to revenue organizations understand. So for us, the most important person we're trying to sell to is who determines your go-to-market strategy? Who selects the accounts your teams are working? I don't know, that's always the economic buyer, the champion, et cetera. So again, it's about allowing yourself to depart a little bit from the structures that have kind of been instilled in us in the past and reflect the reality and what you've got right now. Now, we have two use cases, a good fit, typically actually one and all the other. The first one being companies cannot accurately map every account in their market, either because they are unable to do so. Because of technology or their definition of ICP, et cetera. Or because they've got a really, really niche market that's very, very hard to find. The other one is, we know all the accounts in our market, we don't know which ones to grade and prioritize. And so for us, understanding what the pain is in terms of those objectives will actually impact the process that we are running. Now, the stages are going to be the same, but the gates will be use case-dependent in terms of understanding that narrative there. As will be the business case that comes later on, because each one will carry a different objective and criteria there. Super interesting, and can you maybe bring it to life for us in terms of what does your sales process, therefore, look like today? Because as you say, we all get schooled in medic and, you know, millahiamen or, you know, whatever it might be. It sounds like you're not necessarily copying, pasting those, but yeah, give us a sense as to what the sales process looks like. So, again, the other variable to consider is channel, channel which the engagement was sourced. Is this somebody who's come cold outbound? Is this somebody who's inbound? Is this somebody who's come through our VC networks or my personal networks because they behave very, very differently? I think one of the imperatives I insist on at every stage of the process that I said earlier is that we're imparting value at every stage. Part of that value is going to be around educating the buyer on who we are, just so that they can understand differentiation. But I think a lot of what we're doing is really trying to open the buyer's eyes to a problem that they didn't necessarily think was present there because it's such a basic problem. Mapping your market, everyone thinks they've done it, and the reality is as we found 60% of a B2B SaaS companies market is hidden from them. They don't have it in their CRM. I've announced buyers, for example, have you ever got an inbound lead that you'd be happy to work that wasn't in your CRM beforehand? Most people say yes, I think that's an absolute catastrophe. I'm not saying it's going to be your best lead or your best account, but you should know every account in your market. So having these impact statements where we can really kind of get the buyer on the same page. And that's stage one of our process. We call it the initial call. It's not a qualification call because we have this concept of most pain that we are engaging is nascent. It's not expressed for our buyers. They don't actually know not just that they have the pain, but the impact of that pain downstream. So often, and it's been really interesting thinking about how we structure this. Because again, offer cold call. Somebody giving you 30 minutes of their time. That's a real privilege. And so if you just go into heavy pitch mode about why good fit will help them? Or heavy discovery mode where I'm just asking you, you know, 30 minutes worth of questions. There's no value in it for the buyer. So we've actually developed some collateral where we can actually walk people through and personalize. And again, this is, and I'm sure we'll come on to something about Gen AI and tooling today. But using some sort of tooling to really help us build what we call a market report, which is a personalized report based on our understanding of that company around the unique and bespoke data points that we would use to map their ICP. And use that as a source of conflict in that first call to say, you probably define your ICP by industry X company size Y location Z. But actually, your ICP is very, very different. What would that mean for you downstream in terms of understanding your entire market and how you grade there? And that always yields a very, very healthy conversation. Nine times out of 10 goes over 30 minutes because actually it's that a hard moment where revenue leaders like maybe I, maybe my problem isn't about better enablement or better product or hiring. I mean, those are all relevant and valuable problems to solve. But actually going back to those foundations around the start of any go to market motion is understanding your market and everyone in it and where those accounts are. That's great. And it almost sounds a little bit challenger sale-esque. That kind of commercial teaching pitch, I think they call it in challenger sale, where you're educating the market on the problem that they didn't really know that they had a bit delivering real value around that as well. Do you adopt any, like, you know, you talked about winning by design earlier, do you adopt any frameworks, whether it be bands or spin or winning by design, or is this all, like, purpose custom built for you based on what you've seen in the buying process to be in your market, in your context? I've never adopted a methodology. I've been trained and enabled in several. And as a seller, I think they're very, very helpful because they give you a clear guideline on how to sell, what to do next, et cetera. My experience, and hopefully, I do attribute this part to the kind of successful journeys I've been on, is that ability to critically look at several methodologies and say, "Well, what's relevant from there for this specific company, this specific product, and go to markets?" And I think being able to cherry pick and develop your own, you know, we've got some strange acronyms in terms of our executor, good fits. But actually, it's very, very relevant for us to think about in terms of that imparting of value, but also looking further ahead in the process, which is, at some point, I'm going to have to build a demo here. And that demo is meant to absolutely wow people, because we don't do generic demos. Good fit is not a generic data platform. Everything is very, very white glove highly customized. And if I can't show that in the sales process, then how are people going to trust me? They're absolutely trust Harrison, because he's a go-to market guru, which is why he was so successful. But I'm hiring reps who don't have the reputation, who don't have the experience. So I need to build a process where I know some of these challenges and reservations are going to come up later on in the process, so that I can get ahead of them. So yeah, in answer to your question, I think being privileged enough to be enabled in several different methodologies has given me this broad view of saying not relevant, relevant, and really building our own. That's not original in terms of there's nothing really new and unique, but it's original in terms of it's never been put together with those types of components. Love that. Scalwise helps founders and CEOs get the right sales and marketing leadership in place. Whether that's a fractional leader when you need someone fast or a permanent hire when the brief is clear. My co-founder Gavin and I have both been CROs and VPs of sales, so we understand the function from the inside, and we can have the kind of honest conversation about the hire that most recruiters can't. No fluff, no short lists, padded to look impressive, just the right person, faster. To find out more, visit scalewise.com or feel free to drop me a message on LinkedIn. Do you have a view on where most sales processes kind of drift away from, you know, how the buyer actually buys? Like, you must have seen or come into businesses where they're selling in one way and you've uncovered the fact that actually that is going against the way that a buyer would typically buy or do you have a view around where that misalignment typically occurs in a sales process? Yeah, and again, I don't think it's a static point. I think it's something that changed. I mean, I think we all can sympathize at the end of the quarter. Everything goes out the window, you know, we've moved from consultative sell to high-pressure tactics and get deals over the line there. That's not a pleasant blot buying experience, even if they are getting the 40% discount. They still don't enjoy the process. So, and I'm not saying one shouldn't do that. Right, you know, we've got to hit our targets. We've got to hit our great goals. I'd love to be this kind of hire my team, never go into that mode. But I think it's really, again, about probably the most important skill in sales, which is listening. It's really, and actually, something that I'm very passionate about, especially in demos and discovery calls, which is never going on them alone. Having a solutions consultant or sales engineer with you there, even if they're not adding value, somebody there to read the room so that you can actually monitor how somebody is engaging as you speak. Because if you go into your spay, and how great my product is, and all the customers we've helped, and you see them writing emails, you've lost it. And a salesperson who's talking often doesn't register that, because they're in the flow, they're focusing on their on their script or their pitch, whatever it might be. So I think it's really that awareness of are we engaging? here? Have we got the attention? And you touched on earlier, of course, we can't have this conversation without talking about AI. How has AI, I suppose, changed how you think about a sales process, how you design a sales process? Yeah, what impact does it have for you and your team? I mean, it's been immense. Firstly, it's helped me question everything I know, and I still do. I think, you know, AI has been the great leveler for people. Previously, my 15, 20 years of sales experience was my differentiator. And suddenly, actually, you know, people can achieve expert level very, very quickly there. I also think it's a dangerous storm. It's a dangerous resource for people to over rely on it and to stop thinking. I mean, we use it religiously. We are part of the kind of Claude generation. We've got everything hooked up there through the MSP in terms of every analysis that we do. Great, very, very efficient. But even when we're looking at bottlenecks in our sales process, I can see people, especially people who don't have a lot of context on the business or don't have a lot of experience, they are 99% reliant on the output from Claude. And it's very, very helpful, because it's able to amass a lot of data and to organize it in a structure in a way. But again, what makes the difference, and this, I think, starts from BDR all the way through CRO between good and great. A good and great is the difference from being able to feel and trust what you're thinking. Be that feel and reflect on what the buyer's thinking and saying or really to kind of trust your gut. It's actually a lesson Jimmy Fitzgerald told me when he came into to Paddle as COO back in 2020-2021, Paddle was the epitome of a data driven organization obsessed with data. And I understand why Harrison and Christian were very very inexperienced as founders, as leaders. And so they had to rely on data to tell the decision. But everyone's heard of analysis, paralysis. And we often found ourselves in that situation where the data wasn't telling us a story. And Jimmy came in and said, "Sometimes you've got to trust your gut. Sometimes you've got to trust that actually you've got to where you are because of your ability to kind of understand and read a situation even if you can't articulate it in the numbers. I'm talking about shooting from the hip to make every decision. But where there is no data, sometimes you do have to rely on that." So I think that's where that kind of overlap between AI and human experience is still vital. But for us at Goodfit, as I said, it's really helped us validate. And that's where I think it's most impactful. I will come in, speak to Harrison, speak to Alex, our other co-founder, speak to people have been selling the solution and Jam with them on what we think the entry and exit criteria should be. We'll obsess over certain stages. We'll take two to three weeks to really determine what does Good Discovery look like and how do we know we've done it. That will be based on expertise. Now, what we'll then do is we'll set up AI to make sure that have we achieved this in every discovery call we have. But also, what is the impact of those discovery calls that AI is saying are good versus bad downstream in terms of our win-racing conversion through the rest of the stages there. So I don't like to rely on AI to give me the answers. I would like to kind of give me the insights and then to validate our hypothesis, though. And what are some of the key insights that it's given you? What are the key lessons that is taught you around your sales process and how is it shaped your thinking in GoToMarket? I mean, some of them are really obvious ones that I'm ashamed that AI, a surface demand loss, like when you don't have the engagement of a senior person, a economic buyer, guess what happens to that deal? I mean, this is stuff that we were taught in sales school back in our early days. But it's really helped sharpen that again in terms of understanding what we need to do at what stage there. And often, we will talk, as I said, we typically sell to the senior revenue leader, but our tool is typically operated by a revenue operations leader, or not even a leader, a revenue operations operator. And so they might be blown away by it. And we are happy years prick up and we're like, hey, they get it, they're educated, that we can measure the impact. And we're like, does your CRO know you're talking to us? They've never heard of you. So again, that's a really basic example, but it's something that I think has slipped because we were just kind of really geeking out on those good vibes there. That's great. And sticking with AI, when we did our prep call, I think you were planning for or heading to a GoToMarket hackathon where you were getting the teams to kind of run experiments. And this evening. Yeah, this this evening. That's great. Tell me more about that. How long have you been doing that for? What, what, how does it work? Yeah. So I rolled it out last quarter. So we're doing it, hopefully quarterly. This is only the second quarter, but the role is no engineers allowed engineers are, you know, their hackathons are great. I remember at paddle, like, sitting in on these hackathons and, yeah, blessing they were trying to involve the commercial team, but I would be like, we have an idea and they'd say, great, now we'll go and build it, go away. So this is a commercial hackathon. This is for SDRs, salespeople, solutions consultants, AMs, sales management, marketing, and everyone is given lovable credits because really I believe enabling people and AI being able to prompt and use is a really vital skill, not just in sales, I'm actually pushing my children's school to incorporate it into their education as well, but it's it's it's again part of the not just the skill, but the culture I'm trying to build, which is when you join a series a business, there are some certain downsides. You could go and work for a very large established business, have a much more comfortable life, maybe predictable life, maybe even be better paid, but what you get at a series A is exposure and experience that is unrivaled, and I don't want those to be words I use in a job interview to attract talent. I want people to feel a sense of ownership. So I divide the teams into pairs, never the same, so I never put two SDRs together, it's always kind of cross pollinating the teams, and the objective is to build something that can improve our go-to market or the buying experience. And it's a pleasure. Why? Because we start at 4.30 in the afternoon, we go until 8.30, people have got two hours to build, they should have ideated beforehand, so we announced it a few weeks back, the teams, etc. They've got two hours to build the product, or the prototype of the product, and a presentation, and then they pitch back to a panel of judges their their tools and again the scoring criteria about clarity of presentation, impact of the product, etc. And there's some really awesome ideas. And again, I'm not saying that I shut people down when they come to me in daily business life, but often it is, like that's really cool, but I've got a million and one other priorities, whereas this is time ring fence to really let people shine. And I think that sense of empowerment and ownership is really great, and it's also just a bit of a laugh. We don't take it too seriously, in fact, we have pulled in and productized some of the ideas from the first hackathon, but it's also a chance for people to say, all right, 4.30 on Thursday afternoon, I'm not going to be going till 6 o'clock making cold calls or you know, pushing deals, I'm going to do something a bit different. So yeah, we bring the pizzas in, we bring the beers in, it's a bit fun, so it's a bit of team building, it's a bit of empowerment, but actually there's some really good outcomes based on the last one. I'm really excited for this one as well that we can actually bring in to our sales process to really enhance our our go-to market. That's awesome. Are you able to share maybe one or two things that made it to production? Yeah, absolutely. So the last one we built was, so we're very big on cold calling as a channel, got quite a large market, and we use, I don't know, they're called power dialers anymore, I think. You're nooks or something? You use nooks. So it's an awesome tool. I actually wish I had this one, I was still cold calling, in fact, guilty confession, I still jump in on the cold calling session sometimes, because I actually really enjoy it. Me too. Yeah. But it's a bit blinding, because you don't know who's going to answer. Suddenly someone picks up the phone, and at the same time you've got to figure out like, who's this company? Like, who am I talking to? What do I want to say? What's the script? And of course, it's a cold call, so they're like trying to get you off the phone as quickly as possible. So we developed a product that actually enables us to integrate with the good fit database, so that when somebody picks up the phone, we're not just able to pull out the most relevant data points that we think will turn their heads, but also customer use cases that are most relevant to them based on our answering that company. And that's in real time. So I can open a call saying, look, I'm working with this company X that was facing this problem, and it looked like from the outside, you were as well. You've got 30 seconds, I can just talk you through a proposed solution, and it's impacted our connect to conversation rates massively. I mean, it's pretty ugly, but it's effective. And so yeah, we are, again, I'm pushing our CTA to say, hey, put this in the roadmap. Come on, because this is going to impact revenue. So yeah, and it came from a BDR who had this idea, so it was really, really good. That's great. Any advice for other revenue users that are looking to replicate this type of commercial hackathon thing, things that have worked well or things that you would do differently if you were to run it any key learnings? Yeah, I think setting the criteria is really important, because if you just give people lovable credit and say, go build something, you know, who knows the relevance? Like, again, it depends what your objectives are. My objectives are to have this sense of ownership as the primary objective. This is not an atom-k problem to solve. We are all in this boat trying to solve this problem of how we sell better, how we scale faster. So if I'm thinking about that as the objective that people feel a sense of ownership, I want to tie it to an outcome that we are seeing in our in our day-to-day. So I'm putting some guidelines there around what you should be building for, as opposed to how do I build an app that takes my shopping list and converts it to the Tesco check, I'm like, that's really cool, but that doesn't help us sell better. So yeah, it's setting those guidelines, but also really trying to inject a sense of fun rather than pressure. This is a chance for you just to take off your corporate attire for a day and actually kind of bring yourself to work and have a bit of fun there as well. So I think setting the example, getting involved with the the team, mixing things up, but being very, very clear on how you're. measuring success. I guess with any part of go to market, that's always the same thing as well. And now we, I know we've not got a huge amount of time left, but we can't not talk about ICP. A topic that is really close to my heart, I know it's really close to yours as well. Such a critical thing to nail down and get right and we see so many businesses that don't do it well and don't nail it down. Where do you see most teams go wrong when it comes to really nailing their ICP? I think there are two major limitations, possibly three. Let me start with the first one which is the emotional one which is vulnerability about saying maybe I don't have this right. You've made it to CRO, you've grafted away for 15, 20 years and for you to admit the most basic principle and concept I haven't nailed, that takes a real degree of vulnerability and humility and it takes a really strong person to say that, especially when you don't want to show that necessarily. That aside, I think the two limiting factors we have seen in the market are two fold. One is they haven't accurately defined their market and there are probably two reasons for that. One is because they've never really thought about it and everyone's just been brought up in this legacy way of defining market in terms of my market is my industries, these industries, these countries and these company sizes and that's just become the norm. It's really interesting, I kind of made this objective when I joined GoodFit to speak to 100 revenue leaders. Yes, I'd love to sell to them but really I want to see how they define their ICP and it was about 90% I'd define their ICP in terms of industry, company size and location. But when you look at the company itself, that's not what it means. I mean, again, I use an example of one of our clients Trasky who sell GDPR data compliance solutions to companies who have a lot to lose as a result of mismanagement and personal data. That's the definition of their ICP, companies who manage personal data and have a lot to lose as a result of the breach. That leads to the second limitation which is, okay, I might have to find it well, but how do I convert that into data points? If I'm using with your respective legacy providers like Apollo or Cognism or Zoom info, they don't have that granularity to say, find me companies who manage lots of personal data who have a lot to lose as a result of a breach of that data. So even if they can define it accurately, there's no way to translate that into tooling that can scrape all the data for you. Well, I said we could talk about ICP a lot longer, but we are going to wrap up the show with our final closing question. We like to kind of pay it forward or help out, you know, other revenue leaders that are coming up maybe behind us, maybe a few years behind. What's one thing you'd tell a CRO want to two years behind you? What's the big bit of advice that you would like to give them? I think it's about trusting yourself. I think when you move into a CRO role, there's a lot of pressure. There's a lot of expectation, you know, I call it the Messiah complex up. Adam's going to come in and solve all of our problems. Like, I can't. I can't do all of my own. I'm part of a team and my job is to get the best people in the right positions and get the most out of them. And so I think recognizing that even if something's worked for you all the way up till now, your ability to look critically at a problem with fresh eyes is probably your biggest strength. And part of that is being vulnerable enough to say, I don't know the answer. Ask for help. So I think that kind of, I've reached the summit. I am the guru. I am the, you know, the source of all knowledge challenged that because yeah, you're great. You wouldn't have got to where you are if you weren't. But actually things change very, very quickly. The market has changed. The competitive landscape has changed and you can't do it on your own. So, you know, adopt a mentality where you're actively seeking help. Not just because you're going to have more. It's actually a really good management tactic to get to show vulnerability and to get people to open up to you. And don't feel that you've got to prove yourself as the kind of single point of success or failure in an organization because you'll never scale the organization if that's the case. Great way to finish. And I love that you again brought it back to critical thinking and challenging things with the fresh pair of eyes because that's been a through line through everything we've talked about today and clearly a big part of why you've been successful in your career. Adam, thank you so much for your time. Really, really enjoyed today's discussion. Thanks for having me on. Thank you for listening to Making the Grade. If this episode resonated, we'd love to hear about it. Feel free to leave us a review. Of course, share it with another revenue leader in your network and don't forget to subscribe so you never miss an episode. So see you again soon for more practical lessons from people shaping the future of revenue leadership.

Podcast Summary

Key Points:

  1. Adam Kay prioritizes building repeatable, predictable sales processes rooted in buyer behavior rather than copying existing methodologies.
  2. He emphasizes creating a positive, value-driven buyer experience by educating customers on problems they didn’t previously recognize.
  3. Sales processes must be tailored to specific use cases and buyer personas, such as revenue leaders, with dynamic gates and criteria that evolve with market changes.
  4. AI is used to validate and optimize sales process design, not replace human judgment—particularly in assessing discovery call quality and its impact on win rates.
  5. A commercial hackathon fosters innovation by empowering sales teams to build prototypes in a low-pressure, fun environment, leading to practical, revenue-impactful tools.
  6. A major misalignment in sales processes occurs when teams ignore buyer psychology, leading to high-pressure tactics that degrade the customer experience.
  7. Accurate ICP definition is often flawed due to over-reliance on legacy criteria (industry, size, location) and lack of granular data tools to validate it.
  8. Kay advises new CROs to embrace vulnerability, question their assumptions, and actively seek input—recognizing that effective scaling requires diverse perspectives and humility.

Summary:

Adam Kay, a seasoned CRO, emphasizes designing sales processes that align with real buyer behavior rather than rigid methodologies. He believes in building repeatable, predictable processes that deliver value at every stage, especially during initial discovery calls where he uses personalized market reports to educate buyers on hidden pain points. His approach is deeply rooted in buyer-centricity, recognizing that modern buyers are more competitive and skeptical, requiring a compelling narrative around problem-solving.

Kay leverages AI not as a replacement for judgment but as a tool to validate hypotheses and measure process effectiveness, ensuring human insight remains central. He champions innovation through quarterly commercial hackathons where sales teams build prototypes in a fun, low-stakes environment, leading to practical improvements like real-time cold-call personalization. A recurring theme is the importance of accurate ICP definition—often misaligned with legacy assumptions—and the need to translate nuanced buyer needs into actionable data.

Ultimately, Kay urges new CROs to embrace vulnerability, critically assess their own assumptions, and foster team collaboration, arguing that true scalability comes from humility, adaptability, and a willingness to learn from others.

FAQs

Adam focuses on mapping the sales process to how buyers actually buy, emphasizing repeatability and predictability rather than copying existing playbooks. He prioritizes creating a pleasant buyer experience and ensures the process reflects real market dynamics and buyer needs.

He believes that candidates must have worked in chaotic, early-stage environments and thrived in uncertainty. This experience ensures they can handle ambiguity and adapt, which is vital for building effective sales processes in fast-evolving startups.

He checks the key metric the team is trying to impact and their plan to achieve it. This ensures alignment and proactive action, preventing reactive chasing of goals and fostering clarity in daily operations.

AI helps validate hypotheses and analyze data, such as measuring the impact of discovery calls on win rates. However, Adam emphasizes human judgment and critical thinking, ensuring AI supports rather than replaces decision-making.

The hackathon empowers sales and marketing teams to generate innovative ideas in a fun, low-pressure environment. It fosters ownership, creativity, and practical solutions that improve go-to-market strategies and buyer experiences.

Many teams rely on outdated, surface-level definitions like industry, company size, and location. Adam highlights that buyers often define their ICP based on actual pain points and risks, which are harder to capture with traditional tools.

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