E72: I Collapsed My GTM Org Chart. This Is Why | Ian Tickle, CRO @ Freshworks

Ian Tickle is the CRO at Freshworks. Today, he manages a nearly billion-dollar ARR business, but he's also been through multiple successful exits, including to Adobe and Oracle. In today's episode, Ian walks through how and why he collapsed a split go-to-market org chart, bringing global sales and customer success under a single roof.

Customers don't care about my org structure. They care about dealing with Freshworks and is Freshworks going to look after them? That touchpoint is very much on my watch.

Also on the docket, how rapidly scaling enterprise software companies can end up suffocating under under their own bureaucracy, how poorly managed AI can quickly become a liability, and how to get ahead of both dangers.

If your systems aren't talking to each other, if they're not connected, then what you tend to find is AI is actually doing like a shit.

Your systems and org structure are the foundations that enable team performance. So if you want to learn how a 30-year SaaS operator thinks about these critical topics, this is the episode for you. All this and a lot more on the Revenue Leadership Podcast.

Today's guest is Ian Tickle, the Chief Revenue Officer at Freshworks, and Ian is a 30-year SaaS operator. He took Omniture through the Adobe acquisition, RightNow through the Oracle acquisition, and built Domo's, uh, EMEA business from scratch and ran it through the IPO before becoming their global CRO. Uh, then he joined Freshworks in 2024 to run, uh, the European market, and 20 months later he's now CRO of a nearly billion-dollar ARR business with sales, CS, tech support, uh, and customer experience all unified under him. And so today we're gonna talk about what that unified revenue org actually looks like from the inside, some of the trade-offs between having these teams reporting separately versus this unified, uh, structure. And then we're gonna hit a pretty interesting idea that, that I don't hear explored very much, which is, uh, how do you build simplicity into an enterprise or organization as it grows, because complexity isn't necessarily maturity, even though that is sort of the natural end state that many of us find ourselves in. And so we're gonna talk about fighting that, fighting that pressure and unpacking a bunch of cool ideas. So looking forward to it, Ian, thank you very much for joining.

Great, Karl. Thanks very much. Glad we could get the time together.

Yeah. So what did I miss in your bio that's really important for folks?

Well, I guess we could go back to the early days when I first started at business. I actually left school with very few qualifications. So I didn't go to college. I didn't go to university. So I finished school and my first job was actually working with NatWest Bank and putting checks into a check sorting machine and really starting to do those shift works where the checks would come in. I'd sort them in the machines and that was my life. And I loved it. To be honest with you, it was, it was, it was great fun. And then I had actually a bit of a serious illness, so I couldn't, I couldn't actually lift the heavy checks. So the, the bank who were brilliant at training, phenomenal at training, put me onto an assessment center and the assessment center broke you down into a couple of areas. It was either very programmatic and you move into more of the, the side of the business where you're doing the backend programming on the, on the hardware that they were using or more creative side and they put you more into the business. And for dramatic effect, because I can't actually remember, but you know, I kind of got most of the programmatic ones wrong and most of the creative ones right. And I remember saying to the bank, oh, so I'm not stupid then. They're like, no, no, no, you just think this way. And it just completely released me and really helped the way I think and the way I look at things. And I realized that I'm much more observant than a detailed reader and studier and things like that. And from there, I went into looking at business processes. Business challenges, started evaluating software solutions for business problems. Loved that. Um, got on really well with one of the software vendors who was talking to us about a particular solution that they had and, uh, ended up leaving the bank and going to work for the software provider and, uh, worked there in tech support. So I started tech support through into pre-sales, then into partner, partner sales, into sales, sales management, and then worked my way up there into general management. And ultimately, I guess, Chief Revenue Officer roles.

That's a very interesting and winding path to get to where we are today.

Yeah, I enjoyed it though. It was one of the things I think I realized as we look at some of the areas that I really like to focus on is that creative element. So looking at stepping back and looking at the business problem. And I think the bank was really strong in that business analysis world where I actually had to go and be the consumer. Like I was a person that people were selling to. So I moved forward with the understanding business problems, understanding the value. I learned what people like from software vendors, the stuff people don't like from software vendors. And I think that stood me in really good stead as I worked my way through, you know, the different phases of my career, because it gave me the grounding and the basis of when we do a big deal review, I still in my head have, I know what I liked and what I didn't like, but also what a business case looks like. And it's not all about just the core ROI, it's the cost of change, the cost of service and all those elements. So it really gave me a good basis for my career, to be honest with you. Very cool.

So I wanna hop into the first sort of big topic. You know, you've stepped into the CRO role at Freshworks, you've collapsed a formerly split go-to-market structure, you know, before sales was split from the customer growth, customer success orgs into this one organization. I'm curious to just walk us through the logic for Freshworks, and then I want to zoom out and talk about some of the, like, the core principles that people can use to evaluate that in their own business. So what was the rationale for you guys and what were the outcomes you were hoping to get?

There's a couple of areas that we really wanted to focus on as we looked at the business. So we had a relatively, well, we actually do have a relatively broad portfolio of customers. So we have a PLG motion for our SMB business. We have a very strong commercial business, mid-market and enterprise. And across those, we had different teams really focusing on the different size of customer. So we had an organization that focused on the 0 to 500 employees and 500 employees and above. And as you grow organically, you'll find that these, these teams and these environments just naturally expand. And as you expand, one of the things you start to see as you become a larger and larger organization. Is you see great post-process, you see great policies, but also you see those other areas where you suddenly realize that there's teams being built to do things that maybe you should be doing from a central focus. And it's all with the best intent and it's all with the desire to really drive business and make sure that we are effective to the customers. We support them, we look after them, but it also comes with complexity because it means sometimes people aren't necessarily fully aligned with the same objectives and goals that we're trying to set as a corporate entity. So when we looked at the, how do we optimize and how do we become more effective? There's a couple of things that really settled for us. One was, we were running some form of duplication. Not in the sales organization, but in supporting teams and supporting systems. And as you know, as you become a larger organization, those supporting teams are fundamental to what we do. But also, it's incredibly important to make sure you control that, that cost element as well. Fundamentally make sure you get the right message down to the teams the way that you need. And more layers that you put in, the harder it is to get that message down. So that was, that was the first one was like, it just made sense that we could optimize our systems and teams and become more effective in the go-to-market, become more efficient, not only in the selling, but also you'll hear I'm very passionate about the cost of service and how do we become as effective as we can be to serve the customers as well. The other one it creates all sorts of TAM issues. You can only imagine the parent-child discussions. You can imagine the conversations between reps and managers on who owned the parent, who owned the child, and this child was in a different region from that parent who was just a holding company based out the Netherlands. So there was a degree of just tension that we created inside our organization as well. Whereas if we collapse that, we could, we could manage that in a much more effective way. So there's a degree of, look, you can see that this isn't optimal. It wasn't slowing us down, but it wasn't optimal. And as you look at where we are as a business, it is about making sure we're cash efficient with what we do, making sure we're increasing our efficiency of the people that we're working with, but also making sure that we're effectively engaging with the customers and delivering that full customer experience. And that's really where Freshworks, I think, and the role that I have particularly is, look, if I sell a deal, I've got the BD team who helps with marketing to create that opportunity. I've got a great pre-sales team and value engineering team who know how to talk about the value and what we're talking about. Very strong AEs and account managers. Customer success focus on adoption, but also technical support who have to focus if something isn't working or people need help on how to do something. So the reason that's important as we put it all together is because I've got to do good deals, right? I've got to do a deal that's not just good for the sales team for 12 months because it makes them, you know, great, we hit the target, but I've also got to make sure I look after everybody else in my organization so that we're not putting extra workload or burden on the post-sales team in the customer success side or in the tech support side as well. So it's very important for me for that entire customer experience because customers don't care about my org structure. They care about dealing with Freshworks and is Freshworks going to look after them? And it's very easy for us to become very insular about, well, that's somebody else's reason, you know, somebody else's team, you need to go there. And for me, ultimately it all comes back to me, right? Outside of the product development and the engineering side, that touchpoint is very much on my watch. And I like the fact that that drives the behavior within my organization where everybody's pulling together.

Yeah. We talked about this a lot at Shopify, like not shipping the org chart and not making the customer feel the organizational decisions that you've made. And we went through, I went through a bunch of versions of the revenue org there. Reorged a few different times and you could definitely tell when you're shipping the org chart. It's, oh, I can't talk to you about that product. I'll bring somebody in and then you pass it on and that's another call. It can be a broken experience. What were the symptoms that you noticed that told you you needed to rationalize and what are the symptoms that people should watch for generally that indicate to them that they may be shipping the org chart or there may be some organizational rationalization that's needed?

Yeah, it's a great question. And there's a couple of elements to that. The first one is, and everybody talks about this a lot, but it's super essential. Just talk and listen to the customer. You actually listen to the customer because the customer will tell you, right? We're very proud of our customer base and they're very passionate and they're very clear with Freshworks and what they like about us, but they'll also give us great feedback in our client advisory boards and making sure that we have those interactions. But it's also spending time with them and listening to them because they'll tell you about the complexity of dealing with you as an organization as well. Especially if they generally have that relationship, which is a, look, we've got to make sure this is together. They'll give you the areas that they need help. So the customers will tell you. The question is, are you listening to the signals? And then are you doing something about the signals? And are you putting somebody to be account for those signals? And I think one of the areas that we really focus on at FreshBooks is like who are the team who wake up caring about this? Who is the individual who's responsible for this? And how do we drive that together? The second one is you can see it in the frictions you just work your way through the systems, or if you start to look at the efficiencies within your own teams as well. So if you start to have a look at, um, internal clashes, maybe on TAM or ICP, but that's not just impacting us, that's impacting the customer as well, because we may be the ones who are trying to fix it for ourselves. It's my account or it's your account. But ultimately, the customer is the one who's waiting for the response or the engagement from us as an organization. They shouldn't have to wait for those areas. The final one would be like our partner ecosystem, super important. And we have to make it easy for the partners to deal with us as well. Many times you create this environment where you're, you're very insular about what's good for us. And ironically, this is where we'll talk about AI later. I'm very passionate about this as well. It's like, it's great for us to become more efficient with our systems. It's great that we're using AI to help and drive that. But what about our ecosystem? Is it helping them? Is it them who are a big part of our additional distribution and our support team? Is it working for everybody in the same way? So there's many signals that you can get, and then you can look at the metrics. If you look at just general sales cycles, deal reviews, you can see where we've got the friction internally as well. And the goal is not to just hear it, but to listen and then do something about it.

And so on the partner ecosystem, is that again, just like talking and listening to the partners?

It's talking and listening, but it's also about they need programmatic ways to engage with you as well. So one of the areas that we're pushing very hard, because we're not perfect at this, by the way, at all. And I don't think any organization has really completely cracked the single entity, which is like a partner and a vendor together. But one of the areas we're focused on very hard is how do we make sure that they're enabled? How do we make sure that they've got the latest information? Look, it's a really competitive world out there. And as a vendor, it's great because you tend to get all the information you require about the competitive market space and how we can talk about what we do and the value that we bring. But you've got to make sure that your partner ecosystem have that side as well. And when we look at our partners, you know, one of the things that we're very proud of is A, they can do really great pre-sales, post-sales on their own. They can do the implementations. So they help our distribution, but they also bring that subject matter expertise that I don't yet have. So for example, I don't have a verticalized team at this point outside of North America. We've got a couple of, um, sled manufacturing. Why? Well, we don't have verticalized products. Now, that doesn't mean to say though that we don't have verticalized messaging and we understand the use case, we understand the persona, we understand the language that we need to talk to people to. But some of these areas, we have partners who specify specifically in that., and it brings that extra credibility and trust to a prospective client or an existing client that we have that ecosystem where we can say, hey, why don't you go and talk to these guys? Because they specialize in ESM for finance teams, for example.

And so maybe just zoom out, like what were the exact changes you made at Freshworks? Like what orgs, what was the org design before and what does it look like now? And how's that all played out?

Yeah, so we basically had this sub 500 employees that was run centrally out of our Chennai, Bangalore, and Hyderabad offices. And then we had 500 and above that was more of a field-orientated organization. And within there as well, we have different segments of different customer bands as well. So we could, we could address the market. Within there, we also had a tech support department as well that was sitting inside one of the sales organizations, but not the other. It was a, it was a, it's dynamic. And then customer success that sort of straddled both, but we didn't really have the clarity of the reporting line that we wanted. So we wanted to make sure that we put the client success team together, which we did. Tech support serving both organizations from a central location. And I've got a great, great team running the tech support side. And then from a sales organization, we actually put the two orgs together so that we could focus on the consistent message that we wanted across any revenue band, because again, that's my segmentation. Like the customer shouldn't have to impact about my segmentation. It shouldn't have anything to do with how they engage with us at all. So we then looked at how do we rebuild the sales organization across both those organizations in the teams and then built out the go-to-market model so we can make it as effective as we could be from a pre-sales environment, business development, and then through the sales and account management as well. And we're sort of, we're on the journey. I think there's, there's other things that we can continue to look at to optimize it, make sure we can support everybody as well as we can do. But the goal was really to take that duplication out, find the shadow walls, put them into a central reporting zone so we could all benefit from like, there's these pockets of brilliance all over the business that we were, if only we could get that and we could put that across all the organization, all of the go-to-market team, that would be phenomenal as well. So without going into names, that's how we put the team together, to be honest with you.

So when you say you brought the sales team together, that means there's now one leader for sub-500 and above 500, or the distinction between those two reps has now gone away. And like, what is, what does the design of the team look like?

Yeah. So if we go down another layer, so what we've actually just been through at the moment is we looked at, um, our core EX business, our employee experience, and our customer experience business. Customer experience business was the traditional market space that we started. And we've actually created two separate sales organizations within there as well. So we have a CX-orientated organization and we have an employee experience, which is our ITSM, asset management, incident management solution. And the reason for that was, was a couple. One was that they're unique in the sense they bring everybody together because basically you're trying to serve somebody who's got a question or needs support or needs help, but they're very different entities in the sense of one could be a business-to-business, one could be business-to-consumer. And what we wanted to do was really focus not only the product execution and the growth, but also the marketing that we put out there also from a go-to-market and the focus we could put in. How do we actually drive not only building those individual businesses, but making sure we were talking the way that the customer required us to talk to. And that's worked out incredibly well for us. It's a relatively new change for us, but I've got two teams focused on that. And I've got in the CX business as a single leader who's running that across the entire ecosystem. And then in my employee experience side, I've got two leaders, one for North America and LATAM and one running international. And then And then I've got customer success rolls into actually my revenue leaders. And then I have technical support that's run by—

The revenue leaders for EX and CX.

Yes, that's right.

Yeah.

Yeah. Because I want, I want the leaders to care about the customer deals that they're doing as well. Right now they do and they're good and they're passionate, but it also makes sense for me to make sure that I've got the right, the right lens on when I'm doing the forecast call, for example, the person I'm doing the forecast call with, they care about retention numbers, retention. They care about the expansion. They care about the new business because I ultimately care about one bottom right-hand corner number, which is, okay, what's the net new ARR? And to have a team that's focused on that as a mindset means that I'm very confident that my teams are working all in unison to what the corporate goals are, which is let's make sure we grow the fundamental revenue base of the company.

And so now you'll have like a CX org that has both the in-market sales teams and the Chennai, like sort of India-based teams all like underneath that one roof? Is that the case?

Yes. Yes. We predominantly have the, the EX team by legacy. We have more field-oriented, uh, people and the CX team, we predominantly have more based out of our headquarters in, in Chennai. But yes, there's definitely, we need to be where the customer is and we need to have those ecosystems and partners to help with that execution as well.

And so what was the, what was the like deliberation process to figure out what the right org chart is? Did you have committees and analysts working on it? Is it just sort of like, was it, was it obvious to you and you just sort of had to sketch it out with a few people? I'd love to understand the process you went through to deliberate what the right shape of the org was and then maybe how you got it sold internally. 'Cause you know, these redesigns. Require a lot of organizational energy and mindshare. So you got to get people aligned. I'd love to hear some of that story. Yeah.

Well, to be honest with you, first of all, I'd love to take credit and say, do you know, I woke up one morning and I had this epiphany and I had re-orged it in my head. And then I went to Dennis, the CEO, and said, hey, this looks like a cool idea. Could we do it? Not quite how that plays out, although I may say that in the future, that it was one of my greatest moments. But the reality was, Dennis is a great CEO who spends a lot of time understanding what we're doing, where we're going, but also some of the challenges that we face as a business and the opportunities. And as we were going through the design for fiscal year '26, which is the year that we're in this moment, we were looking at all the standard things you'd expect us to, right? Well, what's our cost basis? What are we doing really well? Where do we really want to lean into? What are the areas that we think we could be a bit more efficient in? And where do we think we could build out the organization that enable us to execute in lines with the growth priorities that we have and the cost model that we have. We're like most major organizations, most organizations, you can have great ideas, but you've got to be able to do it in an efficient way. My cost envelope is still my cost envelope. So I had to work to that. So you got that as the basis, right? Which is, I work with my CFO and the CFO has a very clear view on what we can spend and how we can spend it. And then we work as a management team and we do, we brainstorm and we talk about it and we challenge each other and we test the models. And then, you know, we get some sanity checking carried out on that as well. And then as you go through that process, it doesn't feel like it's a massively large decision because everybody's aligned on why and the value and the reasons for it. The complex, challenging opportunity part is then pushing that and making that work through the process to make sure the math works for us. And then working with the teams and making sure that everybody understands what we're achieving, why we're achieving it. Because as you know, one of the hardest things for organizations, no matter what size you are, is change, right? Field organizations, you know, typically change is not, is not great because it defocuses from the core goals that we've got them on. But it's about really one of the core principles that I have, which is clarity, strategy, and vision, and explaining to the organization where we're going, why we're going, and why we would like them to come on this journey with us. And I think if we take that time and talk to them the way that the company does, which is, here's where we are, here's where we think we've got a great opportunity, people will very quickly come on board and help you be part of that process as well. So the hard part, frankly, is for the ops guys, as you probably know, like the lift on the ops team. Territories, quotas, complans, TAM, ICP, that, yeah, that's a really heavy lift. But we got a great group of people who fundamentally, you know, very, very strong at that. So, so my life was made a lot easier by the fact that we had this team of people supporting artists behind us who really, really helped drive that across.

Yeah, their time to shine.

This is, uh, do you know what, we talk about unsung heroes, right? And there's many across all sorts of business, but particularly if you look at, um, If you tie it into, into some of the things we're doing with AI, like AI is phenomenal as long as you've got the systems in place, you've got the knowledge and you've got the management to be able to optimize with AI. If your systems aren't talking to each other, if they're not connected, then what you tend to find is AI is actually doing like a shadow RevOps org. And you can find that that's an issue because then you lose control over the clarity of what you're trying to do, but also reporting and information. But the team we've got are phenomenal, so they really made that journey easier for us.

How long did this whole thing take? Like, you know, once you, you're in planning, you realize, you know, we need to rationalize to make the, make our vision with work within the cost envelope. How long was that process of this like org redesign and figuring out who goes where and, and, and before you were ready to like give it to ops to implement?

Yes, it's a really interesting question. I guess we would probably design process 8 to 12 weeks because we needed to go through it and, you know, make sure we check the math. Then you do the sanity checking, which is really just going through, you know, um, look, here's the upside, but what, what, what could we break as well? Because you have to be realistic. You have to be very open that you can't just be rose-tinted glasses. You have to look at, well, what potentially could be the downsides. Again, a finance team maps that very, very quickly. So strong advocates there from my side. And then the execution—

And you're mapping like, what if this affects win rates or what if this distracts from pipe gen?

Okay. Yeah. Yeah. So for example, if you think about, you move, say, just to pick a number, 30% of accounts, that's 30% of reps who need to change. And that's quotas, comp plans in territories, but also we have to make sure that we have the backend And so we've got that supported as well. So depending on how, if it's like 80%, that's a phenomenal amount of work. If it's 10%, it's not a great deal, but still you need to do the math to check to make sure that you're not creating problems for yourself further down the line as well.

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Because as everybody knows, customer attrition is very difficult to recover from and we don't want it and we want the customer to have a great experience, but also internal attrition as well, right? You know, I was watching a couple of your previous episodes and we were talking about how hard recruitment is. Like recruitment is hard, right? Recruitment is hard, especially if you're a growing company, if you're a transforming company. If you're, if you're a big multinational vendor, like recruitment to find the particular skill set that you're interested in is hard. So the worst thing we could do is make changes and the team go, hey, guess what? Tapping out, not for me, not interested, because the loss of productivity is phenomenal. So we have to just make sure we do all those checks to make sure we're fine. So I guess in total, I reckon we're probably 5 to 6 month project, but, but actually the actual deployment of the project is relatively quick because we've done all of the homework in the background that we need to do. To be able to execute. So I'll check a couple of weeks of noise maybe.

Uh, I want to go back, uh, a topic. And so you've now nested, uh, CS and tech support under those revenue leaders.

No tech support sits as a standalone business still. Customer success rolls into the revenue leaders. Okay.

And so the, the counterargument is always, well, like revenue leaders won't pay enough attention to CS. They're always gonna be more focused on the new business number. It's easier to move. It's like, it's typically, you know, where those individuals come from. So it's, it's more familiar. Is your general stance that the revenue leader should own CS and the retention number? Is it particular to a type of business or environment or a type of leader? And then I'd love to unpack the, the leadership parts, but like, should this be the default stance?

Uh, no, is the answer to that. And I think it's all about several things. One is about stage commensurate, like what's appropriate for where you are, like what, and then it's about the product and the solution that you're offering. Does it, does it require ongoing customer success? And, and, and, you know, we can talk about the role of customer success. The other part I'd have a look at is if you have a, um, an organization such as, such as ours, where I generally am passionate about that net retained, that's my remit, that's what I have to deliver, then it's no good me just doing a whole load of new business that churns out, that has no benefit to me as an organization whatsoever. It has no benefit to the customer either. Like nobody wants to go through an evaluation to then be a vendor for 12 months. It's painful. It's not just the purchase, but the cost to implement and cost of change. So expansion is also a very big part of our business. Like we generally like to believe we offer value to customers and they want to expand their commitment to us and we work with them. So I have to have an ongoing relationship anyway, because there's something that I really, we hold dear to our hearts. We need to look after these customers. So if I'm having to work on the new business and the expansion, then by default, it's all about the retention as well. So the question that we could ask though was, well, what's the future of account management, plan success, CSAM, right? Which is the combination of the two. And we don't have an answer for that at the moment. I'm very happy with my account management and customer success team. We are trialing in a few of the long tails about a CSAM, like, could we be more effective with it? Can we use technology to understand it? But ultimately, when I go into a forecast call, I have the 3 leaders who forecast the core part of the business for me, and they care about the same thing as me. And that is about our customers. And as, as, as part of caring about the customers, I have the new business, the expansion and the retention part that we focus on with that as well. Now, if I was in a smaller product and maybe, um, not necessarily a great product, but where there wasn't the change in environment. Like if you look at what AI is doing to customer experience and employee experience is constantly changing. So there's a lot of, hey, how do I do this? Could I do that? There's also a lot where our customer success team were going to say, hey, Kyle, we were at a customer yesterday. They were talking about something that's really interesting. I think you'd be interested in this as well. And share that knowledge about where the market's going. And I like that sitting under the same umbrella. If the product was, I give you an example like Zoom, and I'm not, I don't really know the Zoom business. So apologies for anybody who's from Zoom, but my Zoom, my Zoom kind of like boots up and it works. And the most I do is work out if I'm, you know, putting the blur on, I'm not putting the blur on. So, so there's a lot of work there where I want my customer success from Zoom to be somebody who's talking to me about, you know, my strategic direction and how we can integrate it and how it could be more effective and those things. But there's not a lot of product stuff. That takes place. Now, when we're looking at something like IT asset management, where there's all new devices coming on board, there's all new developments coming very quickly, customers sometimes require help and guidance on, well, look, we're looking to move into this area. Have you got experience in that? And I like that environment where we can be that, that not thought leader for them, but a good partner in talking about where we are and what we're doing. And that should flow for me across any touchpoint with my customers, which is we're not the salesperson or an account manager or a customer success. We're there about how do we, how do we have our mutual journey together?

And so if I'm like trying to back out the heuristics here, so one, one key input would be, is there a lot of expansion revenue? Like, does the growth of the company require meaningful NRR growth? And you mentioned stage, like what's appropriate for the stage. You feel like later stage is better unified or early stage is better unified?

No, I think it's a combination of, uh, there's a combination of multiple factors. So for where we are and what we're doing at the moment, the org structure is designed to be able to execute on net retained revenue growth, right? Which is what we have to do as a business. That's what we report to the market., and we have to do that in a cash-efficient way. So, so they're, they're the, the things that we have to do. The goal then is to work out how do we do that in the most effective way. So for us, this was the, the route that I decided to take because it gives me that touchpoint to the customer and the ownership from the revenue leader. In previous organizations, customer success has sat outside of the revenue leadership. It might be because, um, it, I've got multiple products that I'm trying to serve across multiple areas. Um, in previous companies, I've had a single product where actually it made sense for me to run the customer success journey outside of that because it's much more of a new business motion as well, rather than the new business and expansion. So with, with the previous organizations, it's looking at what am I specifically trying to achieve? What are the goals I want to achieve? What does the customer want from us as well? Because that's super important. And for us, it's just, this is where we, we are for this moment in time.

Okay. And so if you were talking to another CRO from, from a similar stage business, are there like 3 questions you would tell them to ask whether or not CS and sales and other functions should be under like one central leader in sort of business units or built-in service lines in a more matrixed fashion? Like what would those key questions be for other people that are like trying to think through this themselves?

I think for me, there'd be, let's think about it. So the first thing would be. The question first is about when I'm interviewing, are you passionate about revenue as opposed to sales? Because it gives me the early indicator straight on, right? If, for example, I was interviewing last year for a senior leader role that we had, and immediately the leader was talking about how they care about revenue and how they care about the journey. That's, for me, that's phenomenal because it means that I've got somebody who's already all-encompassing. Understanding the life journey of somebody sitting inside the organization. From a, from a CRO perspective, the question would be CRO definition to clarify, right? I need to understand, is it actually you're a sales leader or are you a revenue leader? Because titles aren't always clear about what we're doing there and what we're executing across. So my first question to them would be about, talk me through your understanding of revenue, talk me through billing, talk me through ARR, right? Talk me through ACV, just understand the core metrics that we're looking at. From a structural perspective, I'd be very interested in, depending on their career stages, what have they built out before? What have they transformed? Did they look at transformation or did they continue to drive the business? Did they have any goals or aspirations to run a client success team? So for me, it'd be looking at those key elements. The questions you would ask about that would be, Talk me through your goals on revenue. Talk me through the way you see the lifecycle. Talk me through what happens if you do a deal and the customer's not happy. Yeah. If it's, if the answer is, well, I give it to customer success and they go and look after it. Well, that's not what I personally want to hear for where we are at the moment. It doesn't mean to say it's wrong. It just means to say for where we are and what we're doing, it's a different organization set up for us.

I want to shift gears a touch. So Um, revenue leaders tend to come from sales. And so what are the structures you put in place to get them to pay enough attention to the retention and the CS orgs when, you know, the board, the CEO, you as a CRO, probably all like do what we all do, which is like gravitate to that sales number as the one that like, like really, really drives, drives the business. And so, so what do you put in in place in terms of your leadership approach or systems to make sure that the post-sales orgs get enough focus and attention and resources?

Yeah, for sure. I think the resourcing is a big element to it, but governance, to be honest with you. So I like to inspect what I expect, right? I mean, I have a set of core principles that we look at with regards to forecasting. How do we do forecasting? So we don't just forecast new business, we forecast the whole revenue. I work very closely with FP&A, like FP&A are one of my biggest, biggest business partners because they're the ones who are fundamentally, you know, looking at the revenue for the organization, how it's pacing and how it's trending. So when I'm looking at sales leaders, one of the things that I think I've been pretty good at recruiting is probably somebody who's more a traditional go-to-market in a sense, more of a VP of EMEA or a VP of white portfolio. So yes, I've got some sales directors who are brilliant and they crush it and I'm very pleased with them. But to, to, to move to where I'd like you to be a leader of a region, I do want you to have a bit of a broadened portfolio and you've got a couple of roles under your belt where you can show that it's not just about the core sales number. Now that doesn't mean to say that sales managers can't get there because you just have to show an interest and understand the lifecycle of the customer. But as we bring people in, we talk consistently as a business about revenue, right? It is about making sure that very clear about what we're talking about, very clear about what we're achieving and the expectations of people. So when you do a forecast call, for example, I care about the net ARR. I care about the net ARR for month 1, for month 2, and month 3. And that adds up to the quarter, right? It's super important. And if you drive that, that cadence through all of your teams, then everybody by default has to care about it because they understand how it contributes. I think a big part here, Karl, would be first line managers, right? If you can, if you can crack first line managers, um, who, who may have just an expansion number or a new business, but they, they understand the ecosystem of the retention side as well, then you create that behavior in, in, in the teams and reps and everybody who's coming up as well. So that, that GM model, I guess, is probably where I'm, I'm not being as articulate as I could be. If you've, you've got that GM mindset, general manager. So that's the thing that really excites me about the leaders that we've got.

And I actually think that's a lot more common in Europe. Like those, those roles, I mean, that's typically the first role for an American company that's going over there. So you have so many of these people that have had to be the GM because you don't want to have a sales leader, a CS leader, a marketing leader day one, you know, with big, big, like senior salaries. And so I find there are a lot more folks that come outta Europe that are GM-oriented that fit this model. And in the US and North America tends to be like a lot more predefined. And you could go through a 10, 15, 20-year career as a sales leader and then get planted into a senior revenue role where you now have CS and you're like figuring it out from scratch. That I think is like, more common than like a GM type person going into it. So the markets, I think, play into this too.

I think you're very observant on it. And I totally agree because having worked for predominantly US organizations and, you know, ranging from doing, you know, very small startups and building them up or doing transformation or looking at, you know, how do we do a turnaround of something that GM role gives me that flexibility. I mean, in previous careers, I've actually had FP&A and marketing reporting to me as well and facilities. Yeah, which would make my FP&A and marketing team laugh to even hear that I was trusted with that. But the point is it gives me that rounded view. Now, if you look at the US market though, and the traditional, it doesn't mean to say that you can't have the interest because there's, this kind of comes back to my time at Oracle. Oracle was really interesting because before when you're a GM, you can sort of make a decision and you can decide, obviously you've got to get it approved and things like that. But I could, I could look at what I wanted to do and go, actually, I'm going to do this, or I would like to do that. And irrespective of the team, I could, I could work with them to do that. When you join Oracle, you realize there's an ecosystem of people like you who all want similar things, maybe all at the same clients as well. So what you have to learn then is about this, this multi-matrix management. Because these people are all great. And I, like I said, I really enjoy my time at Oracle, but they have their goals and their objectives. They might not even be in the same business unit. One could be in hardware, one could be in middleware, one could be in software, like apps. So then what you realize is reporting lines can become a distraction, but also if you can talk about, well, how do I influence other people with inside the organization and how do I understand what their goals and their objectives are? Then all of a sudden the reporting line becomes less of an issue. So my, I guess if I got some advice, my advice would be, it doesn't matter what your direct reporting line is, just care about it. Like, just care about it. Just learn about it. Just understand it. Now go talk to tech support and understand what problems are coming through on, on, on the systems. What are the latest trends we're seeing in customer success? If they report to you or not, you know, that's, that's about internal organizational design, like workforce management. But there's nothing stopping anybody across any role just being intrigued and curious about what other people are doing. And it's that curiosity, which is the bit I would look for, is that have you, have you been curious about how other organizations inside your team are working? And I think you'll find increasingly more and more people are. So I do agree it's discrete models, but again, I guess the comment there is Reporting lines are something that are there to be looked at, but also not to stop you expanding your own knowledge and your own mindset as well.

And so as you've gone through this process, you reference, you know, you were at Oracle, you were at Adobe, both companies very matrix, tons of acquisitions. People would say about Oracle, you have to do more selling internally than externally to like encapsulate what that environment's like. I'm wondering, as you looked at this process and you're trying to avoid the monstrous complexity of some of those orgs, and we'll transition into this complexity idea, how did you try to build simplicity into this process from the start?

Yeah, it's one of those areas where if I look at my time at Preece's organizations, complexity can come in many forms. It could come in, um, I was looking at this the other day about span of control and reporting layers. Like how many, how many reporting layers is there between an individual contributor, like an IC1, so somebody's brand new into the business, and Dennis, who's the CEO. Um, because that's really important because it's how long does it take Dennis to get his message down through the organization and where he needs it to be? How big's the span of control? Like how many people does an individual manager have reporting to them? Because If it's over a certain amount, it's very hard to make sure that everybody has the consistent message as well. So when we're doing our workforce management, we were very clear and our HR partners were going amazing at this, was giving us all of the data and information that we required to look at, okay, well, what is, what is our spanner control? What are the levels that we have? And where do we have the outliers where maybe we could look at how we can build a more efficient team? Where have we got groups of individuals whose managers in a different location where we're creating complexity for ourselves? Is there a way that we could have like these IC1s and IC2s who are keen, eager, and want to learn, how do we make sure that they've got a team around them to drive that? So what, what force management is number one on it. The second one would be really being very clear on, on the level of reporting that you require and not making it too onerous so that you're ending up reporting on reporting. And I'm sure we've all been there, right? Where, where you're doing a pre-meeting about a pre-meeting for a pre-read for a meeting, right? And, and you, you're like, hold on, we've just spent so long on this. So how do you reduce noise? So how do we make sure that we make the most efficient time that we have together and drive that traction through the business as well? But for me, the big one in the simplicity will be it just complicates everything. And I'll give you an example. I won't name the company. Working for a company, uh, got acquired. We were one of the very early SaaS companies and we would get an order. It would go through our systems and it'd be provisioned within about 7 or 8 minutes of us, you know, checking the order and making sure everything's okay. Got acquired by one of, one of the companies and that became a 3-week process. And the process was, well, you know, we, hey, we got to be, we got to make sure that everything's okay. We've got to make sure that everything's ticked and it goes through like 4 or 5 different layers of people. Now, my point was, we, we were doing that as the startup company. We were doing all the due diligence that we needed to do. We weren't doing bad deals, but it's a case of where you then go into an environment where that's the way that it's designed and that's the way that it looks at. And one of the things that's great about Freshworks is we, we have some of those legacy processes just through the organic growth that we had, but we are literally going through and saying, right, okay, how do we become more efficient? How do we make this system talk to that system? Why doesn't this system talk to that system? And you'll find a lot of it will be systems just not talking to each other as well as people think, or there'll be a lot of manual work to get the systems to look like they're talking. And when you've got the systems look like they're talking, then you tend to have discrepancies, right? Because you don't, you don't get the single source. So we're working very hard on that system side as well. It's a hard lift though. Like it's a hard lift. I was listening to your, your call with Jason, right? About the AI agents and how you're building those out. And, and, you know, one of the things you spoke about, which is how do you manage all these AI agents that you're creating? Like, how do you go and recruit someone to manage these AI agents? But you imagine how if every department created its own AI agent to fix a problem that they've got without fixing the core systems, that's a lot. And then where is the governance, the discipline, and the control?

One last question before we tie up this like, uh, unified org topic. What was the biggest learning? So, so you've gone through this process probably a bunch of times in your career, seen reorgs go well and, and not as well. What were some of the biggest takeaways from this process that maybe like surprised you or you're taking to the next one?

I can't, I can't be involved in everything. Like number one, I think it's probably the thing I've struggled with most in my career is that I like to know what's going on and I like to have a say and my team are great at pandering to those needs that I have now and then, and, and like then, then going to get the stuff done. But that was number one, which is I spent, I spent a time getting the leadership in place that I required, and I fully trust them to, to make the decisions. And I think that, that people talk about empowerment, talking about empowerment, but actually empowering people are two completely separate things, right? Because, because you have to have that impact. So, so the first would be like just just allowing people to do what they, what they need to do. The second one would be that the clarity of the vision is super important. This, this market's in an intriguing place at this point in time. And, you know, you and I have been through maybe a few cycles, a few ups and downs in the industry as times go by. But there's a lot of people inside many organizations where it's their, it's their first journey on it. And Uh, for all the benefit we can talk about, AI is scaring people as well, right? There's a lot of people who are worried about the future and what it entails for them. So I think being clear with people about the all design and the journey that we're on and that, um, continuing to deliver why we'll do that change, because that's ultimately the business that I'm in is like, I have to deliver my forecast, but being consistent is the core thing for my job. Right. Number one skill set of a CRO is being consistent. You've got it. You've got to do what you say you're going to do and you've got to do it consistently. So that journey vision, I think is really important for me on that side as well. The other thing is just be excited by it, right? I mean, I was talking to Dennis and I was saying on my CV, I think somewhere I put that I like big problems and I like big challenges and I like waking up trying to work out how to fix something. And I do, I generally thrive on that part. I enjoy looking at the complexity. And if you can look at change as something that's for the good and something that enables us to be more effective, and you can take people on the journey with that as well, you suddenly have a group of individuals who are in the trenches with you and we're working our way through it. And we should never underestimate how much overcommunication can be our friend in these times where we're moving segments and teams and things like that.

Okay. I want to get into this topic around simplicity is operating discipline and sort of the setup for this is your philosophy in our intake form is that like organizations tend to become more complex over time and it's sort of our job to simplify. Maybe just lay out your belief there first and then I would love to talk about how you actually do it.

If we talk about simplicity, it's really How do we enable the team to be as efficient as they can be and remove the complexity? Makes sense, right? I think part of what I look at that is, you mentioned it earlier on about sometimes in the large organizations, how it can be difficult to actually get stuff done, right? And you talk about sales prevention officers and things like that, which is so hard to get things booked. If I talk to my teams and I listen to them, The frustration that they would have with us and in other roles, it's not unique to us, right? Which is, how can you make it easier for me to do my job? Right? How can you remove some of the barriers that are slowing me down? And that could be about territory allocation. It could be service orders come through. How do you get it booked through the systems? It could be, I'm trying to work out who to target as my next account. What tools and opportunities do I use? Because it's really important for me that people feel that we're providing them all the capabilities that they require to be able to just go do their job. If you have to take your rep out for an hour a day to go and do admin work or to do some form of checking, it's just not a productive use of the time. But if you forget the productivity, it's just not enjoyable. They don't, they don't want to go through that burden. So for me, if you look at just the core sales role, it's like, well, how do we make sure that they can be as efficient as they can be with the time that that they've got. If you look at the back office, it really is about, if we go back to that matrix management, I have a great set of business partners who I can explain some of the challenges that I have in systems or process or anything like that. And they'll work with me to try and resolve those challenges as well. So if you think about, again, workforce planning. So you think about workforce planning, you've typically got NetSuite, Adaptive Workday, and a recruiting tool., right? So, so we just spoke about recruiting, how difficult is recruiting. I need to make sure that all those are synced up so that my, my recruiters aren't spending time working out what's in headcount, what isn't in headcount. I need to make sure that I've got the latest headcount of joiners, leavers. I need to make sure that I know the open heads that I've got, and I know that needs to know about the capacity planning. Now, if that's going to take me a long time to go and find, or my managers need to go and look at 4 or 5 different spreadsheets and correlate them together. That's just not effective use. That's where the complexity starts to come in. But that's stuff that we can fix. And we're very good at this. But they're the areas where you can look at how can I become more efficient as well. The other part, and I think we, we aren't quite there yet for this, is our org design. Like the org design, as of having these two separate orgs, it was difficult to work out, was that your account? Is it my account? Are we upselling? Are you upselling? So bringing that together gave us that more simplistic view of This is where we are focused on, um, from the different team segmentation. And then the final bit behind the scenes would just be about how do you build that link with marketing and build that relationship so that we can see a clean flow of, um, the universe of interest all the way through to did we win it? If we didn't win it, why didn't we win it? And if we can learn from that process as well. And again, that's the case of how do you make that so it's not a group of meetings every single week about the same subject where nobody makes any changes to what we're trying to achieve.

Why do you think this naturally happens as companies grow? Like, it just seems to be the end state that you get slow. Like, what's the driving root cause that people should be trying to fix?

So, in my experience, when I joined one of the larger organizations, it took me a really long time to work out the difference between somebody's job spec and their job role and what they actually did. Because you sort of like have 3 people who are focused on RevOps sales enablement and they're in 3 different teams. You're like, okay, well, which one is actually the person who's going to be responsible for the work that I need to do? So I think it's the clarity over job role, job specification that is super, super important for us so that we know who is that individual who's responsible for this particular task and that particular action. And that's probably more of an issue or challenge when you get into the larger organizations, when you do have overlain. If you think about in a small organization, you typically have a circle of people who want to do the job, right? Everybody's just a startup. They're great. We're leaning in and we're doing stuff. And then, and then maybe get another product or you get a different arm that you want to look at and you get two circles, right? So you've got these two circles that are now slightly, slightly similar and joined, but different. Then you get the Venn diagram, which is the gray at the middle, which is where you start to lose the accountability of, well, I, I color, I thought that was on on your unit. It's like, no, no, that's not in, that's for you to do. They're the areas where if you think about a multinational org, when you've got 3 circles, 5 circles, 10 circles, 15, 20, 30, 50, you can see where the gray can start to become a big part of the confusion about responsibility and accountability. So accountability is the thing that's really important is who is the person who's responsible for doing this job? And also, can I hold them to account for it? Now to hold them to account for it, I need to make sure that there's nothing in the way stopping them from doing their job and I've given them all the tools that they need. And that's, that's for two reasons. If I, if I make sure they've got all the tools they need and they are trained up and they, they are able to execute, then first of all, then they can be deliverable. They can go and do what they need to do. Secondly, I can hold them to account for it. So my, my job in many ways, Karl, is saying to my organization, tell me what's stopping you from running faster. Like, what's the bits that's slowing you down? How can I help you become more effective? And again, you get plenty of feedback and areas of opportunity to go and move forward with that.

I've got sort of two ideas that I'm curious to get your feedback on. Like, it feels like the duplication and some of this stuff comes from, you know, everybody has their own objectives and we rely on another team to do a thing. We're not getting what we need from there. And then we build some version of that within our own org because we don't feel like we are going to be able to get to our number. And like, I've seen this play out. I've done this myself. I'm like, okay, like I know this team is supposed to do this thing, but like they're not really doing it very well and I need it to happen now. I can't wait for them. I don't, I don't have confidence in the, in the competence of this other team or person.

Yeah.

So I'm gonna build like a, shadow version of that to get that job done for myself. I feel like that there's like there, that's one thing. And then the root cause problem there is not everybody holding the same performance standard or like having the right clarity of conversation of like, I need to do this. You're responsible for these things. I'm not getting it. Like, like go, go fix it. That, so that feels like maybe one. Root cause. And as you, as like the organization grows and there's more business units, more regions, the proliferation happens. And the other thing comes from Elon where, you know, in bureaucrat— in a bureaucracy, in a government, much like in a company, we have all these mechanisms to add things, to add budget, to add headcount, to approve new things. But there's no business process to say, all right, every 90 days we're going to sit down and delete some stuff, delete business process, delete roles, delete tools and systems. And so you just get this like bloat because we have adding tools and no subtracting tools. What's your reaction to that?

Yeah, because it's not, it's not ill intent either, right? It's just, it's all like very normal and sometimes locally maximizing decisions. Yeah. Yeah. It's usually people with best intent who have a timeline that need to execute something and haven't been able to do that. And I think, uh, where it becomes a little bit more formal is when you do get the shadow org that gets created, you know, you find somebody, all of a sudden somebody's got 5 people who's doing a, uh, you know, a sales program and it's not inside the revenue enablement org or something like that. And I think again, when you find that there's a couple of areas that we have a look at. So we do every month, we review our core systems, right? We sit down and we go through the core systems and we look at, okay, who's talking together from a team perspective. And who's talking together from a system perspective. And that open, honest, courteous, and respectful conversation doesn't mean to say it can't be lively, right? About where we are, what we're doing. But because I think we've got such a clear vision about the opportunity in front of us at Freshworks, and we see how we can become more efficient, but also how we can help drive the customer to be more effective as well. We have that common goal. Where it gets challenging is when you probably get this as well, right? Where you get the email and you say, right, who do I talk to about this? I'll speak to the CRM team. Well, who's that? Like, I don't know who's called CRM. Like, who's the individual in the CRM team that I can talk to, to actually understand where we are and what we're going? And I think the key for that, Karl, is about building an environment where people don't become defensive because they know you're not attacking, right? Because if you, if you think about it, a lot of times, if my role is to find all the ways that's stopping you from being effective as you can be, usually that means something's not quite working the way we need it to work. Usually it means something's got to change. So, so, you know, one of the things that, you know, we could kind of talk about that, that I think I'm pretty good at is, is building relationships and partners with everybody who's important to me and the business so that I can explain, hey, look, this one's really important. It sounds like a small issue, but it's really impacting the way that the team are going to market. Or, or this one's actually, it's pretty big, but I can, I can live with it for the time being because it's not something. And building that trust and relationships with your business partners. And I would say again, this is where I would say thanks to Oracle where understanding about influence as opposed to reporting line is so key critical. And, you know, a big part of my job is making sure I understand the other parts of the business, what their priorities are and what they're going. So when I've got my issue and I'm throwing my toys out the pram and you know, ah, you know, it's not working, we've got to fix it. I've got the context of what everybody else is doing as well. So I can automatically prioritize it into, actually, I know Tyler's got this thing that he's got to get done. So I, yeah, but as soon as that's done, can we crack on with this one and building that relationship? Not everything can be a fire. And I think if everything's a fire, then what happens is you get this, this mass of priorities that is really difficult to then prioritize. Because everything's important, right? If you've got a fire, it's like everything's important. Whereas as an organization, we try very, very hard to just make sure we've got the focus on the key things that we need to do, because then that drives execution. When it drives execution, you get into the next one and you can start going again.

So tell me about this monthly meeting. You have a monthly ritual to evaluate things and delete, like, what does that look like? How's it structured?

Yeah, no, it's no more than the leadership team getting together and say we've got 8 projects on the go and the 8 projects we report back once a month about where we are. We give the status update and these are the big, bigger projects. We obviously every week we have our standard meetings, but these are the ones which are probably the longer term changes that we need to do inside the business or the systems. And we have a DACI model and we know who's the driver, you know, who's the person who's responsible for it. And We go through the normal process. You get the pre-read 24, 48 hours before, and you're expected to go into the meeting, not watching the presentation, but talking about, well, what do we need to do as the next steps? And it's a strong governance and discipline that we run to that. And it works incredibly well, right? Because everybody then knows where we are. So it gives me clarity about where the rest of the business is and some of the areas that we need to work. But also some of this, some of this is, is interesting in the sense of if you think about motivation for the teams, a lot of times teams want to know that somebody's heard what their issue is and that somebody's fixing it. Right. People on the whole tend to want, but did you hear me? Yeah, I've got it. Right.

Okay.

And what are you doing about it? And we're doing this. Okay, great. As long as you got it, that's fine. And then as long as you deliver within the sensible timeframe, that ownership and that responsibility and that accountability It's super, which is why we have the DAISY model. Like we have individuals who are responsible for the different changes we need to make or the different areas that we're looking at.

Really helpful. How else are you thinking about creating simplicity for the organization? One of the other things you mentioned is like clarity and vision. How do you operationalize it? And like, what else are you doing to create simplicity for your organization?

So from the clarity and vision side, I love an all hands. Like I've got, I've got, um, uh, a monthly cadence and I do, uh, one month I do the, the entire organization and, um, inside my team. And then the next one I do managers. The, the managers wants to be a little bit more direct, right? Where it's a little bit, hey team, look, this is, this is the areas that I'm focused on. I could be a little bit more open with regards to, uh, some of the areas that I've been asked to look at as well. And some of the areas that maybe we, we need to lean into. And give them the opportunity to ask questions. I am happy for anybody to ask me any question. I hold the right to not answer, or I can't answer, or I have to go away and find something out. But I find that those sessions where I'm as transparent as I can be as a public company and the work that we're doing, right, there's certain things I can say and certain things I can't say. But on the whole, I'm very clear about where we are, what we're doing, and for that particular month or for that quarter, what I like people to focus on. So it might be, for example, um, you know, we made an acquisition of a company called Fire Hydrant, brilliant product, like it's integrated into the Freshservice solution now, incident management, does some amazing stuff. One of the priorities are everybody in the org needs to be trained. Everybody has to be enabled. Everybody has to make sure that they've got the subject matter expertise, they can talk coherently about it. With the best will in the world, that's not the easiest thing to get a group of people to do in the timeline that I may like it, but I can set that as a priority and I can set that as objective. And I can talk about where we are on the different elements of the core metrics that we focus, which would be the different products, the different, um, uh, offerings that we have, and the particular, um, goals that we're trying to achieve with each of those— be it awareness or moving into upsell or new business. Okay.

Um, so clarity, like, you know, sharing transparently, you generating focus through this all-hands cadence. Anything else that you've like built into the organization that you find helps like simplify and—

So we're just going through our next round of employee survey. And I read every single piece of feedback that I get in the employee survey. I look at the marks and the marks are interesting for me. And I can get a good lens pretty quickly as to where we are and what we're doing. But the employee survey is a great opportunity for us to see, you know, where people are that maybe I don't get to talk to day in, day out. And you've probably seen this with your own org as you've grown. Like, you know, the first 5 reps intimately, you know, the first 20 reps intimately. Then I think you said, you know, you're getting up towards 100 reps. That's really hard. It's really hard, right? Because there's stuff that you need to do as well. So that feedback mechanism is super important. The other thing is we do spend time with our leadership team as well. We go outside with the leadership team and we talk about the things that work, the things that didn't, and what we're going to do about it and what I need to do to help organizations be more effective and efficient in what they do as well. So a lot of it is going through that process. The other part is making sure that we just continue to deliver on our promises. Like if people, if we say we're going to do something, we really, really want to do it because that means that we can say to people, we've got it, we understand it, and we're working on it and we'll get it resolved for you as well. The final bit I would say is we should never underestimate that spanner control and reporting layers. Like that, that, that really is as you grow, it's, it's easy to create, uh, say for example, you've got, um, sales director and you've got a VP and then all of a sudden you're like, well, now I need a regional sales director and then I need a regional VP and then, and you can put layers in. Because, because it might be for career progression. It may be because you've got the headcount to warrant it and to justify it. But every layer you put in, you have to think about it as, uh, is it Makusha Russian dolls? You know, those Russian dolls where you've got like a big whiny doll?

The nesting dolls.

Yeah, exactly. So here's my view on information dissemination. If you think about it, Denis is the biggest doll. Apologies, Denis. Didn't mean to come out quite that way. Like he's got, he's got the most corporate responsibility, but he's got the clarity of vision that he wants to do. As you work your way down the leadership team, by default, you're, you're, you're slightly diluting the message all the way down as you take the smaller dollop, the smaller dollop, the smaller dollop. You've got to be very conscious about if you have 15 of those, that's a really diluted message by the time you get down to the individual contributor. And it's very hard to influence as well. Which if you can minimize that so that you're reducing the amount of layers you need to go down to get your information down, you've got a much higher propensity of getting the content and the view and the strategies of the people that you want to have.

Yeah, that does make a lot of sense. I want to ask one more question before we go to the quickfire. So oftentimes you see, again, going back to like best intentions, people wanting to add more layers of process and reporting and basically bureaucracy because it feels like rigor. It feels rigorous to have another meeting to review the metrics and another meeting to drive accountability and another document written to do a thing. But oftentimes that just accumulates and it's a massive drag and then you spend more time talking about the business than actually like building the business. How do you find the line between rigor and and bureaucracy and like, what does that look like for you?

Yeah. And I think, I think that one actually layer onto that as well. What you tend to find is you end up arguing about the data, right? Because somebody's report is going to be different from somebody else's report. That single source of truth is, is hard when you've got people exporting it and doing different things with it and having a look at it. And then you tend to find in the meeting is either the person with the loudest voice or the most seniority tends to be the person who has the most impact on the meeting. Whereas the reality is it should be the data. So, so data accuracy is super important. And that's why we talk about putting all these systems together. So, so from my perspective, um, there's certain metrics that I truly care about that I will look at. I would say, I think the world has changed with things like Gemini and Claude, where you can get so much more proactive nature coming to you. So for example, I have a Claude cowork that every day tells me, you know, the state of my pipeline. And it tells me, basically, is it within the tolerance that I'm happy with for the amount of business that we need to close? If Claude goes, hey, guess what? We're on track. I don't need to go and have a look at it.

Yeah.

So I think increasingly where we'll find our roles is actually more around how do you find a way to do exception-based reporting as opposed to the dataset reporting. Like, tell me when something's not where I want it to be. I don't need to sit in a, I love my marketers to bits. And they love me, I hope. But we don't need to sit there and talk about, hey, great, pipeline's moving in the right direction. Okay, great, fantastic. Unless we're looking at how do we optimize, what do we need to change, or we tried something, it didn't work, great, let's learn from that, what do we need to do? So I think you will see more and more exception-based reporting will become the way forward because you'll, you'll get soundbites of information so much during the day from all of the tools and the solutions that you've got, by the time you come to make a decision, you'll actually feel pretty good because you've taken all these drip feeds of context. And you may think I'm making an instinctive decision, but the reality is you've probably actually consumed quite a lot of the content throughout, you know, the week or whatever it happens to be to actually be able to decide and execute across that. The worst thing is if we sit here and say, hey, yeah, pipeline's down. So last month we didn't create the opportunities that we needed. It's like, what do you mean last month? That I, it's too late to change last month. I can't afford 4 weeks of not generating what I needed to generate. So how about if it trends down after 48 hours or 72 hours or whatever? Can we get it on there quicker? And I think this is one of the great opportunities with combined tools, single source, but also with the AI opportunity in front of us. It can give me so much more insight without me having to run the report the way that I traditionally used to have to do it.

So single source of truth. Proactive and self-led exception-based reporting. Anything else that prevents the accumulation of bureaucracy, the accumulation of machine, of meetings and check-ins that you found most productive?

Yeah. Role protection, right? You know, we know that there's, especially in organizations as you get larger, people are there to do a particular job.. And the question is, is that the most effective use of their time? And reporting tends to be a pretty time-intensive environment. If you look at the people who generate the reports, they're really smart cookies. Like, they know what's going on. So it's a case of, well, if we could automate the reporting and I can put your mind to maybe a program I want to run or do some analysis on our ICP or the TAM or something like that. And that's where I think we can see that it's back to The tools and technologies are enabling us to become more efficient, without a doubt. If you're doing something with that efficiency, otherwise you're not doing anything, right? So, so one of the things that I really look at is, um, in this environment is it's great that, that we are becoming more efficient as an organization, not just with AI, just with tools across the board, but what are you doing with that efficiency to make value out of it? I won't say it's like a net-net, it washes out at the back end. We're just being quicker, but we're not necessarily being more efficient or effective. So how do we use tools and processes not to just make my job easier or quicker, but enables me to then go and do something else where I could be even more efficient or even more effective for the organization as well?

Let's move to quickfire so I can get you out of here on time.

Yes, let's go.

In your mind, what separates a good CRO from a truly great one?

I, uh, sustainable consistency. Hmm.

What do you mean by that?

My role is to be able to provide to the organization I'm working for a consistent execution so that the rest of the business can plan around what we're doing and what we're trying to execute across. But also so that I do what I say I'm going to do. And we would all love to say it's great, you know, we're going to be over quota, everything's going to be fantastic. Sometimes it's not right. Sometimes it's not. And that clarity of it's not, and then seeking the help and guidance when you need that. But on the whole, it's about just consistently delivering what you say you're going to deliver so that you don't hockey stick or you don't have this kind of like up and down curve of what you did last quarter, but what happened this quarter? Why is that so important? A, because businesses care about it. But if you look at the market at the moment, consistency is critical, right? And as we go through this changing market, we keep delivering and we keep delivering and we're confident that the market will recognize everything that we're doing. And we're happy to do that, but there's no point me hitting and missing, hitting and missing. That doesn't get us anywhere.

What's the most common advice you give to new leaders? Like first-time CROs, first-time senior revenue leaders? What advice do you give them?

Prioritize and learn to say no. Prioritize is interesting because sometimes you have to prioritize, but you got to do a few different pieces of the puzzle before you can hit the priority, if that makes sense. So especially when you're building out all design. There's some stuff I wanted to do here and I knew I needed to do probably 6, 9 months work of something else before I could do what I wanted to do. It still was the priority, but I had some subtasks that I needed to do. So priority doesn't mean, so you're jumping on it today. It means in your head, you're clear about what you want to do. The other part is, you know, people aren't shy of ideas. There's lots of ideas and you have to listen, you have to consume, you have to understand, you have to learn from them, but also you have to be very clear as what you will do and what you won't do. And sometimes what you won't do is even more important than stuff that you will do.

Very good advice. What's the hardest lesson you've had to learn in your career?

Oh, it'll be not being involved in everything. That'll be, yeah, I think I'm still working on that one. I'm just naturally curious and interested and excited, right? And that's what I tell my team. But it, and it's true. I just genuinely enjoy what I do. I really, I love the building part, but it means that I have to learn how to step away sometimes as well.

You and me both. What's the best thing you've read like recently, last 12 months or something that's on your mind?

So I don't wanna lose the audience here. I don't really read that much, to be honest with you. It's almost a legacy of like my upbringing and school time and things like that. I'm incredibly observant. So I, for one, love podcasts. I love YouTube. Like, if there's something to watch, like I could watch you and Jason, for example, I can re-listen to it. I can replay it. And I tend to find if I'm listening, my mind doesn't wander. And if I'm reading, my mind wanders and I could probably train myself. I'm sure people here might have some guidance for me about how to do that. But I find that even, even I'm kind of like more of a social native and I'm younger than I really look and I just enjoy consuming audio and video, but I definitely, um, pick up the personality more and I really enjoy that. Reading a book is not, not really my, my ideal environment, to be honest with you. Yeah.

And it's much easier to fit in an audiobook or a podcast, uh, on the go when you had a million things happening. Yeah. Yeah.

Yeah. Especially on a plane, right? A lot of time on planes. So I tend to find with a plane, I can I can lock into a video or an audio more than I can reading.

It's, yeah. Well, uh, Ian, this was awesome. I'm so glad we got to go deep on these topics and we can make this happen. So, uh, really appreciate the time. I learned a ton and, uh, yeah, I think the audience is going to really like this one. Love you.

I appreciate the opportunity and look forward to talking again soon.

Thank you for listening to the Revenue Leaders Podcast. Leadership Podcast. If you enjoyed it, don't forget to subscribe, and you can find a link in the show notes. And be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.