Carrie Osman: Exploring the SaaSpocalypse and the Continued Rise of AI

Christine Maslin: Welcome to Shesess Unplugged, the podcast where we dive deep into the world of female leadership in the private equity SaaS industry. I'm your host, Christine Maslin and I'm on a mission to spotlight the incredible female CEOs who uh, are making waves in our industry. Join us as we embark on a journey to explore the triumphs, challenges and pivotal moments in the careers of 12 extraordinary female leaders. Over the course of 12 episodes, you'll hear firsthand from these trailblazers as they share their insights, experiences and the secrets to their success. Today, I'm delighted to be joined by Carrie Osman, founder and CEO of Cruxy. Carrie's built Cruxy into a, ah, growth intelligence specialist. Working with some of the world's most demanding technology firms and private equity investors. Cruxy helps leadership teams interrogate product value, sharpen pricing and packaging and capture the value they create in the market. Carrie is also the creator of Cortex Cruxie's proprietary data engine. And she brings a unique vantage point from inside PE backed SaaS boardrooms where questions of pricing, power, ARR durability and AI driven change are uh, becoming central to value creation. In today's conversation, we'll cover Carrie's founder journey and leadership story and then we'll shift into what she's seeing right now as AI reshapes SaaS economics and pricing models. Carrie, a very warm welcome to Shesas Unplugged. Um, it's so great to have you here.

Carrie Osman: Thank you so much Christine. It's an absolute pleasure to be here today.

Christine Maslin: Great. So let's get started. I'll kick us off with the um, with the first question. How do you describe Cruxy and the work that you do in your own words? Yeah.

Carrie Osman: So I mean, very similar to how you did. I think, you know, we get out of bed to ultimately help very demanding leaders for whom success is non negotiable to get to the crux, to say the cheesy line of the problem around product value and pricing. And I think pricing is often looked at in a silo, um, from what we see in the market and specifically around software and technology, I think people have taken the old school rulebook of pricing for, for other segments and they've applied it to tech. From my perspective, coming from the consumer goods world, I immediately came in through thinking about product value because that's how I was trained and obsessed over, uh, you know, what does the customer actually want? Are you giving the customer what they want? What band do they sit in? What's their affordability and really drilling very deep into, I guess, the psychographics and demographics of the customer to really understand what they value and why. And I think that's, you know, that's ultimately what we're doing. We're going into products to say, what do people value, why do they value it, what will they walk over broken glass for? And what does that mean for how much you should be charging them in a world where it should obviously be a fair exchange of value. And that's something I really stand behind. So that's what we're doing. I think it's the way that we're doing it. Firstly being very niche and extremely specialized, as you mentioned in your introduction. And secondly doing it using a lot of data, using a lot of technology, not seeing the world as, you know, services or software data and AI, seeing that you can get out of bed to answer a question for someone and you can answer that question using a lot of different methods in your toolkit. So, yeah, that's kind of, I guess, how I explain what I do. But I often sometimes say I help people with money make more. It really depends who I'm, you know, how many lovely glasses of champagne or Negronis have I had that day? Um, as to how, how, how kind of high level versus into depth I go. But as you know, because we've met before, you know, I'm not afraid to get into the weeds. So, uh, happy to oscillate in either one of those camps.

Christine Maslin: Great, thank you for sharing that. Yeah, really interesting, um, that your consumer background has given you quite a different lens actually to look at it through. Can we talk about some of your. Or can you share some of your early experiences that have really shaped how you think about business and strategy?

Carrie Osman: Yeah, of course. I think going way, way, way back, I suppose I had, you know, my mom and dad, both of whom worked in business in different guises. They never really owned their own companies. My grandfather actually did, but it was a small woodworking machinery company and my mom ended up disbanding that so he could take some money out of the business. And then running a woodworking machinery business for Italians, you know. So my mom did that, having only ever been a PA and she's quite an, you know, insurmountable character with regards to empathy, drive, um, and the ability to get things done. So learned a lot that way. And then my, my father was in greeting cards and one of the early lessons I had from him was I said I didn't like this greeting card with a Lot of words in it. And he said, this is your first lesson in business. You're not the customer. So I think I definitely grew up around a dinner table of, you know, ultimately you have the deep in depth conversation. We were always challenged to have a point of view. You know, what do you think about that? And I specifically remember my father having American colleagues because he was working for Hallmark. And I think it's probably why I'm American with a British accent, which is one of the jokes I have with a lot of Americans. They're like, you can't be British, you just can't be British. You reply to emails at the weekend. You love business. And I'm like, no, I know this, how weird it is. I am British, but I embrace my, my American kind of get shit done spirit, that's for sure. But yeah, so father had these, you know, Hallmark colleagues coming over and I remember being kind of seven and being invited to a dinner with his, you know, really senior, senior bosses, I guess, in, in the US and we were in St. Andrews and my parents were like, this is really important for dad. You've got to, you know, sit there, be really well behaved, listen, you know, listen really deeply and if they ask you questions, you've got to answer. So I think, you know, people talk about what privilege looks like and I didn't, you know, I went to state school and I didn't, you know, that form of privilege, you know, I think is, is for some people and not for others. But I think the privilege of being taught about curiosity, deep listening, business and having a love, a love of business. I mean, my mom and dad still now, you know, my dad's 79 and we saw them for m. Mother's Day, you know, and they still now are like, you know, that's enough of the small talk. How's the business? Like, how's the company going? And they remember everything about the company. They remember everything about, you know, me and what I've been doing. And I think to have people around you who really do care about you and your progress is obviously, you know, you can't, you can't buy that, right? You can't buy that start in life. So very grateful for that. Through that, I ended up being encouraged to go and do an internship for someone called Peter de Savre, who owned lots of luxury hotels. I moved into the middle of Devon, living in the kind of waiter's quarters and he basically said, you can shadow me, shadow the sales, marketing and all this kind of part of the hotel in the day and then in the evening, you host the bar. So I'd have to get an evening dress, get changed in the office and go in and host the bar. And that was also great learning. He stood me in the front of the bar and said, tell me what you see and go around every table. And it was, you know, what are you noticing about these people who did the falconry today? Did they have a good time? Are they arguing? Did they get on well, what could we put in their room to make their evening? You know, very incisive combination of empathy, care, uh, attention for detail and customer experience. So that was an amazing experience for me. Went off traveling because I kind of decided I wanted to go and do some gritty Africa, South America travel. So I did that. And then I ended up getting onto Mars's fast track management scheme. And that was again, my father saying, you know, I call him Papa. So my papa saying, you know, Mars is training is exceptional. I know that you want to be a CEO or run a company, go get the training, go learn from people who are best in the world. And again, you know, I rocked up having a mom who'd taken me shopping to get the right outfits. And then I was told, get in early, you know, be the first in the office and just stay in the, you know, take on extra. Ask people, can I take on that or just do it? Don't ask, just do it. And do extra things every week. Take on extra. You know, show them that you are keen and that you want to learn and read a book every weekend and, you know, you can achieve anything. It's all on you. And I think that sense of accountability that obviously was drilled into me from a young age, but equally was really double clicked on in Mars because accountability is one of their five principles. And it was rewarded hugely. You know, they absolutely loved people that were, you know, acting like CEOs of their work streams, acting like CEOs of the business. And ultimately I got given a P and L very early in my career. And I would say there is nothing like the sharpening of the mind when you have the accountability for a P and L. And in a consumer goods environment, you are accountable to a lot of people for their jobs. Because if you don't drive volume and it was pedigree cams and the factories in Melton Mowbray, and you go and visit the factory and there's a lot of people's jobs and a lot of families that are all reliant upon that supply unit staying operating. So that's kind of a bit of a whistle stop tour of my background. And then I got to a point in Mars where I thought, you know, this is amazing, what an experience I've had. But the handcuffs were going on with regards to you're moving to this country or then do this job. And it was becoming bigger, bigger roles and much more political. And I would say that I definitely have the DNA of someone that likes to get things done. So I thought, well, I may as well give it a shot at starting my own company. If I don't start it now, I probably never will, which is probably a truth. You know, I think a lot of people you speak to start their own company, there's this moment where they, they're kind of, is it the red pill or is it the blue pill? So that was what it was like for me.

Christine Maslin: Amazing. Um, thank you for sharing some of those lovely stories. I think it's really interesting how, you know, our early experiences, um, you know, really, really shape who, who we become as adults and as leaders. And, you know, it sounds like, um, you learned a lot from, you know, from your parents, and they're very supportive and continue to still be so today. I know your sister joined you recently, didn't she, at your business at Cruxy as well. So it must be really interesting for them now when they see both of you to talk about your business. I know.

Carrie Osman: I don't think there's a topic, you know, it's. We don't really. It's like we talk about the P and L more than we talk about kind of how we're feeling, let's put it that way. It's like I needed a lot of therapy for that. But there was, there was good things and bad things about that upbringing. But I'm going to embrace the good.

Christine Maslin: Absolutely. Yeah. It sounds like they're really supportive and I bet they're so proud, um, of you today. But also some of those, those early moments or those early leadership role models, like Peter, for example, um, you know, just interesting stories. Thank you. And, you know, definitely some common themes I'm seeing with other, you know, great female CEOs that I've interviewed on this podcast in terms of, you know, working hard, going above and be saying yes to opportunities, being curious, taking ownership. You know, it's. It's all. Yeah, it's all great to listen to.

Carrie Osman: Interesting, isn't it? Because they're all things that are so easy to nod along, to correct, like, you know, be curious. It's like, nod, nod, nod. And I remember someone At Mars, saying, what's the last book you read? You know, and I used to say this to people all the time. You want to go on a training course, you know, what's the last book you read? Or what's the. It's not just about listening to a podcast. It's using from that podcast, taking one thing and acting upon it. And I think that it's really easy now, especially with this kind of complete, huge amount of content that we have everywhere around us, be it AI slack all the way through to absolutely awesome, really thoughtful, considered, etc. There's so much the haystack is just enormous that I think it's the people that find the needle and then use the needle to, you know, do a cross stitch. It's like, use it for something. Actually use it to make a difference. And if you don't use it, in my experience, very quickly, you translate something that you've read or learned, um, into action.

Christine Maslin: It.

Carrie Osman: It's almost an empty promise, isn't it? So I think it's, as you say, it's easy. They're all great concepts, but I think it's how do you map that down and pull it into action, which is my obsession, really.

Christine Maslin: Yeah, I couldn't agree more with that. And just, I guess taking us on to the next question. You talked about your experience going through Mars, and that experience sounds really exciting. What lessons would you say from your time in larger organizations like Mars still influence how you lead today?

Carrie Osman: Oh, that's a great question. So I can think of a couple of things. I think one is definitely the power of influence. When I joined Mars, I'm ENTJ as a profile. I thought that if you're competent and you're driven and you work hard, that's what really counts. And I really didn't value how much taking people on the journey, having real empathy for their situation, and actually really influencing how bought in they are. I really underestimated how much of a difference that could make to me, both personally and, um, to the success of the things that I was working on. So I transformed a lot of the, um, dog food business when I was there. And I worked with an amazing guy who now advises me called mj, Mark Johnson, and a lady called Fiona Hughes. They were both absolutely outstanding. I have not rarely worked with business leaders like that. And I think that they helped me because I looked up to them so much and, um, because I thought they were so outstanding, they really helped me to realize that the job is not done because the content is done. Or because you've got to a good answer. The job is done when people's hearts, minds and hands are wrapped around that idea, when they're talking about it, when you're not in the room, when they're supporting it because it's the right thing to do for the business and you've got them there. And I think that power of influence, and it doesn't necessarily look the same for everyone. For one person, influence is the hardcore numbers put into a pack, printed off so that as they get on a flight they can review them for another character. It's caring about, you know, their weekend because they're really into hiking with their family and you really listen deeply to what they're into and then you meet them on that mountain, quite literally or figuratively and you really care about what it's going to take for them to feel heard. And I think it was a great lesson for me in both hopefully becoming a lot more emotionally intelligent. I think have worked really, really hard on my emotional intelligence. I think I'm naturally not very emotionally intelligent. But I was lucky that I had a coach who said to me at Mars, you have low emotional intelligence, but the good news is you can work on it. And I started working on it and now my scores are really, really high. But it's been something I've consistently thought about. You know, for ages I used to stand back and think, what does each person in this room want from this meeting? What does each person in this room want from their life? What does each person's room want from me? You know, how can I make this a win for them? And I think putting on their glasses and being forced to stand not only in their shoes but in their world was something I just underestimated. I never thought that was part of business. I just thought, you know, you come to a great answer. Uh, you factually are correct, you're rationally, you know, on point and you present well and you know, people are all rational and they'll just agree with you. Sounds ridiculous, doesn't it? But really thoughtful. Power of influence is one thing. I think the second thing would be focus. I was lucky enough to work, you know, in Mars, which is obviously huge brand owner. They've got so many different brands and within that, uh, channels to market, within that packaging types, I mean, of course there's complexity that's rife in a business of that scale and size. They were unbelievably good. The people that I was lucky to work with at being very decisive about what we're Choosing to do and what the trade off is of what we're not going to do. So we had like a 3, 2, 1 business strategy, you know, drive, develop, defend for example. That just helped galvanize the whole business in. You get out of bed and you're worried about the three. That is what we are getting out of bed to do as a team. Everything else comes after that. So reflecting not only focus in not making people spread themselves too thinly, being very decisive about what good looks like, but also focus in then what resources you put behind Drive. You know, that's going to be a weekly meeting that's going to be these types of battlefields. We're going to operate in this way. They're going to, we're going to put our best people on those areas and then really orienting a different mode and a, ah, different cadence for drive versus defend and develop. That was something I'd seen focus at a conceptual level, you know, PowerPoint slide. But seeing it really pulled through into where are your best people spending their time, how often are you meeting, how much energy are you putting behind these things? The CEOs coming sitting on the desk of the person that's driving the really key areas of the business and they're not doing that for the others. Doesn't mean they don't care about them, but they're just living the focus through their behavior. So I think they're two of the main things that I took away and try to really, really live and breathe in my life. I suppose not just work because I believe that anything that you learn is helpful in all areas of life.

Christine Maslin: Yeah, very well put. Yeah, um, that really resonates with me. Power of influence and focus. Love it. And you know what you said about low emotional intelligence, I actually can't believe. It's really interesting to hear you say that's something that you've learned over time because having met you, you know, you're one of the most emotionally intelligent people that I know. So that's, you know, that's really encouraging actually to hear that. I mean I'm, I'm also a big fan of um, you know, and I'm naturally very empathetic and I think that helps. But you know, you're right. Many people doing a good job, being competent and working hard just doesn't, doesn't cut it. It's not enough on its own. You need to be able to influence people and to do that you need to have empathy and be emotionally intelligent. So um, yeah, really interesting to hear that. Thank you.

Carrie Osman: And I think the interesting thing is, as you say, Christine, at a senior level, being competent is not the job.

Christine Maslin: Yeah.

Carrie Osman: At a really senior level, there's an expectation you're meeting the waterline on competence. Otherwise, really, I mean, you know, that's obviously deeply worrying. There's other problems then, but I think there's the, uh, you know, the job is influence. The job is buy in. The job is if I can get everyone from a, you know, four out of 10 in terms of belief to a seven, the compound effect of what belief does to not only the human body, but the mind, how much we will be able to achieve as a group of people. Never doubt a small group of committed people can't change the world. It's the only other thing that ever has. As the quote goes, this really, to me, is like shifting the mindset of what the actual job is. And I feel really excited when I meet people, especially women, but also guys, you know, meet different people, and I try to help them navigate what the job is at those different levels of seniority. Because, of course, as I go through, as I, you know, morph into the leader I need to be for Cruxy for the next wave, I similarly am going through the learning myself. So, you know, the day we stop learning is the day we die, as far as I'm concerned. So I think it's being open to the fact that everything is morphing and changing and all you, you know, all you have is the ability to learn, absorb, stay on the front foot, listen deeply. And I think those things set you up, you know, much better for the world of AI, et cetera, than just being a highly competent and skilled operator.

Christine Maslin: Yeah, absolutely. Absolutely agree. What was the spark, Kerry, for founding Cruxie back in 2013?

Carrie Osman: I experienced a leader come into Mars, and it made me think about what I really wanted to do and who I wanted to be. And I think it really made me reflect on, you know, I'm doing well here. This is a, um. It was a moment. It almost shone light on the kind of moment I was in. It's like, you're doing well. You can keep riding this wave. You know, of course you have to keep learning and growing, but I'm pretty sure that that could have been a really exciting and compelling option. And I've seen, you know, friends from back in the day do really well and go on to do great things. So it was a moment where I thought, what is it that you really want to be? And I was on a Center for Creative Leadership course with Mars. And the coach, as part of it, said to me, you know, you must be really proud of where you've got to. And I just said, well, no, if I. If I had any balls, basically, I would have started my own company. And she said, well, why haven't you? And what's stopping you? It's once you've said it out loud, isn't it? I don't know if you've ever experienced this, but it's a bit like if you're with, you know, sorry to make it about that, but if you're in a relationship and you're like. You say to a friend, I think I should just leave. And then you're like, oh, no.

Christine Maslin: Oh, God, I've said it.

Carrie Osman: Next thing you know, the bags are packed. Now it's that. It's that raw moment of truth. And I think I faced it in the. Oh, no, I'm not proud. You know, of course I've. I've done fine. You know, I've done fine. But this is not something I should be proud of. I should be proud of if I started a company, and that's what I'd be proud of. And I should. I have the gumption and I have the capability, and that's what I should do. But it was almost just being confronted by that reality that I was probably fibbing, not fibbing to myself, because I don't think you're really thinking. You're just. You're going through the motions because you're driven and you want to get to a certain level, and you're drinking all that Kool Aid, which tastes delicious at the time, and you don't quite realize that maybe, you know, it's quite addictive, and maybe there's other. There's other options for you, and there's other pathways, and those pathways could be more compelling.

Christine Maslin: Like you say, kind of that moment of saying something out loud, it kind of really start. It forces you to think about something. I mean, I remember when I. When I founded Capital Futures 11 years ago ago now. And one of the things I remember about it is everybody congratulated me. Like, I, you know, like, I've been successful already. And I was thinking to myself, well, I'm, you know, I'm kind of, uh, brave or stupid, I don't know which. But, you know, you haven't started the journey yet.

Carrie Osman: Ah.

Christine Maslin: And you've got that whole journey ahead of you, and it's pretty daunting. But, um, yeah, thankfully, I made it a success.

Carrie Osman: No, I'm sure. And I I agree. I mean, even now, I'm sure you're the same. You know, people say, oh, you've done so well, and you're like, what are you talking about? Like, you know what I've got in my locker? Like, I'm coming at you like, yeah, my teeth are out. Like, let's go. And I'm just like, calm down. It's okay. Don't need to take your rage against the machine out on everyone, Carrie. Like, just go sit in your box and think about what you've done, you know? Um, but I do find it very, like. It's very interesting that. And also, you have this with friends. I'm sure you've had it a lot where lots, uh, of people are like, oh, I might start a company. And you're like, okay, what do you imagine that will be like? And they're like, well, I guess I'll get loads of flexibility. And, um, I kind of say, well, imagine for 13 years, every single time you wake up in the middle of the night, it's about the company. Every time you wake up in the morning, it's about the company. Every before you go to bed, it's about the company. You sit at dinners looking. And my other half's always like, I know you're just thinking about cruxy. And I'm like, obviously, I am just thinking about cruxy, but I've got to lie to you because it's embarrassing that that's all I think about. Like, surely I need to pretend that I'm thinking about, like, you know, geopolitical trends or something and, like, attempt to be a lot more interesting than I am. But the point is, it's an obsession, and that's what makes you push it that extra percent. That's what makes you get up and on a Saturday morning, think, oh, I've got this idea, you know. So in a way, you know, it's funny when people say, oh, you've done so well, or they say they might start a company, and you. You kind of want to take them to one side and be like, are you sure? Like, watch out, because it's not easy.

Christine Maslin: Yeah, yeah, yeah, absolutely. And you add. You need to also add in every holiday that you've ever been on.

Carrie Osman: It's so wild when people. I speak to some friends, and someone the other day was saying, oh, you know, my other half, um, she's woman. Other half's a male, um, guy. And she said, oh, you know, my other half. And we'd gone on this holiday, and, like, he was just on these calls, and I was like, I'm gonna give you another perspective here because it's really tricky, isn't it? It doesn't matter which sex or whatever. It doesn't. Nothing matters other than, you know, you feel this great sense of drive and care and desire for the thing you're doing. And with that, uh, passion comes, you know, of course I'm gonna do a cool one. I'm on holiday. Like, I'm not insane. Of course I'm gonna do that. I want to win. And it's hard to translate to people who are like, I could never imagine that being my life. And they don't need to because it isn't their life, but they need to at least, um, it's like the you do you and I'll do me. M. You know, that's the best phrase ever.

Christine Maslin: Yeah, agree, agree. So, um, just to round off this section of the. Of the podcast, also just want to ask, you know what. What have you found to be the most rewarding part of. Of building Cruxy?

Carrie Osman: I mean, I've got two. I think without doubt, seeing human beings transform is one of the most joyous things that I will ever experience. I was lucky enough to experience it a bit at Mars. I have been lucky enough to see people. I mean, one of the people on my team, she's on maternity at the moment, but Lily Covington, she joined as an internal. You know, to see her go into a room of, you know, a board of a publicly listed company and talk about her, uh, just demonstrate sheer competence and knowledge and depth and, you know, I am unbelievably proud. And that comes through every moment that we've debriefed and every, you know, you've got to go in, shoulders up, head held high. All these little moments that can conjoined to create that is just amazing. Also, other people in the team, you know, Akosh, we've got lots of different people in the team that have been here, you know, a while. And to see their journey is really, really amazingly fulfilling for me. And I think if there's nothing else that I achieve in life, then seeing people go on to do great things and to develop themselves as truly 360 leaders with empathy, but also with drive. Knowing when to make the call, knowing when to upset someone because it's the right thing to do and you've got to. And it's for there. It's for everyone's good and knowing when to hold the line, but also doing it with care and grace. I think that, you know, hopefully that's a legacy that I leave. And, you know, there is nothing like it, you know, sitting on a call and just introing the call and then going quiet and just seeing the team, like, absolutely crush it is just. Yeah, that is joy for me. So I think there's that. And then the other thing, which is a bit more self oriented is proving people wrong. I mean, I met hundreds of people who told me, what a sweet little lifestyle company. I met hundreds of people who said to me, oh, you do? Oh, uh, so you're, like, doing marketing.

Christine Maslin: So do you.

Carrie Osman: Websites. How did you get from me introducing what I'm doing, that I'm doing marketing? I'm not doing marketing at all. I'm doing, you know, commercial strategy and pricing. And, you know, I wasn't as precise about the way I explain it, which is partly why I explain it now in quite a precise way. But people just underestimate you. And they. And they. They don't. I experienced a lot of people, not really, to be honest, being on my side. The people that I've met who are really on my side and have been vanguards of what I'm trying to achieve have, namely been Americans. And to think that we grow, we live in. I'm a British person. I've grown up. My parents are both from, you know, London. My grandparents are from one square mile of London. And to think that of the people I've met in the UK and Europe, the majority have not been on my side. There are a handful who have been absolutely amazing. Ben Chalice. You know, there's some amazing people that have really been epic. Lindsey McMurray at Pollen Street. Mark Horgan. There's some people in my life who have been amazing, but they're more the outliers. I feel like people in Europe and the UK are still looking for a big brand name and they don't understand why I don't go and work at Bain. And I find that crazy because obviously when you're in the us, they're like, wow, you started a company. Entrepreneurship is a godlike role in America. And here it's almost like, oh, you weren't successful enough, so you started a company. So I still find that odd. And obviously I will prove them all wrong. Christine, one small step at a time.

Christine Maslin: Yeah, absolutely. I mean, yeah, it's kind of. Yeah. Interesting to, um, to listen to and. And just the two stark, you know, differences between how generally culturally it's perceived in the US versus the UK and. And Europe. Quite right. I've Never. Never heard it quite put like that, but I agree. Yeah. Probably experience some similar as well. Obviously we've got very different businesses, but can definitely relate to, you know, to some of what you're saying for sure. Now we're going to shift into the second part of the podcast, which you are incredibly well positioned to comment on. Very topical right now. Um, AI consumption, economics and SaaS pricing. In your opinion, why are software valuations still under pressure globally?

Carrie Osman: Yeah, so I think the saaspocalypse, as we've experienced in recent weeks, ultimately says, in my view, we thought that software was the ultimate. We thought that it was highly protected. These long contracts, obviously ARR is something that every investor looks to and they think that services revenue or cyclical revenue that isn't recurring is obviously weighted at a very different multiple to recurring revenue. And they think that that gives a business high protective walls and ultimately makes them slightly untouchable. And I think what's happened is AI has obviously come in and, um, not only has it moved a lot faster than many people thought it would, I believe that it's also demonstrated that some of these software businesses now could be built very quickly using different AI build tools. Some of them obviously are not necessarily as protected as one might think. They don't have proprietary data, they're not highly regulated, they don't have, you know, they are really codifying and building in software a number of repeatable tasks that are a workflow. And ultimately that is something that AI can do very effectively. It can be trained to do it, it can do it very quickly. You can ultimately build those types of tools pretty fast now. So I think we've gone from thinking that software is everything. ARR is, you know, all that matters. And of course, businesses with high walls that are in specialist industries that are regulated are generally seen as good businesses with some proprietary walls around them and knowledge. But I think what's happened is the ground has shifted beneath them because all of a sudden it doesn't take five years and a load of specialist knowledge and data to necessarily build all of those businesses. It still does some, but it can be done a lot faster, it can be tested a lot faster, quicker. We can get to an MVP in extreme pace. And I think what that, uh, ultimately means is that all of a sudden all of these things that we thought were very, you know, untouchable about software all of a sudden get called into question. I actually come from a place where I think that still some, there are things which are hugely, um, not untouchable, but they are, they build huge walls around a software business. As I've mentioned, the regulated nature, the specialist knowledge that's needed to uh, actually complete that workflow, the data that sits running through the software itself and whether you've got access to that data and whether you can conjoin that data to say here's what benchmarks it exposes. I don't think all of software is created equal. I think that the software, which is much more simple, workflow based, ultimately, you know, things like, I'm not choosing, uh, an example, but not for the sake of this business, but you know, expenses processing. I mean there are obviously very quick ways to use AI to scan a receipt. Say where is this? What is this? And can you log it to this Excel sheet or can you log it to Xero? So that is an example of something that for me, you know, not complex expense processing to lots of different PO numbers in a mars, but SMB expense processing is an example of something which we ultimately could, you and I could hackathon that this afternoon and we'd probably come up with a good version. So that's what I think is really at risk.

Christine Maslin: Yeah, yeah, there'd definitely be winners, um, and losers for sure. No, that's really interesting insight. Thank you Carrie. And you know, I know there's been some commentary suggesting that highly leveraged software businesses may find it harder to fund the level of AI driven transformation required in this cycle. From what you're seeing inside software companies that you're working with or otherwise, do you think capital structure is becoming a constraint or is it sharpening discipline around where value is really created?

Carrie Osman: Yeah, it's interesting. I haven't yet seen anyone say that capital is their constraint. I've seen a lot of companies and um, probably because of the area that I work in as well, I've seen a lot of companies where the constraint is the true understanding of the customer and their workflow. And because they don't understand that in enough depth, with enough precision. And I'm Talking about the 10 layers deeper than you know, the workflow mapped on an Excel really what is it that people are doing? What is it that they're feeling? What are they currently using as a workaround? Why would they do that? How might AI disintermediate that step? They mhm, don't understand that with the level of intimacy that I think you need to, to be able to work out where you shine your light with regards to AI. That is what helps you work out what is the AI we should buy because we need to add it very quickly. It's a no brainer. Uh, we don't need to own this proprietorily, it's just we need to add it as a service and we need to kind of disintermediate our own product by making sure that we make this faster and more effective for the customer. What is it that we should be building ourselves and genuinely being quite brutal about whether you really need to build it within your walls or whether there's other people that you can build with. I know the fractional AI people are super busy doing a lot of building with. So what are the things that you really should build and that you should own and that they should sit within your walls? And then of course, really zooming out and looking at the risks and opportunities that AI presents. They're the things that I'm seeing people missing. I'm not seeing many investors who are not willing to invest where there's that level of clarity coming from, for example, the portfolio company. If we sit with a portfolio company that says we've done all this work, here's how we understand our customer. This is the AI we're going to build, this is what we're going to buy, this is what we're not going to do. We're going to actually disintermediate this part of our product. We think it's not needed in two years, no one will need it anyway. We're going to stop investing there. All of that level of clarity. I have not seen a company with that level of precision where the investor isn't willing to put the money where they need. They have capital and they're willing to deploy it. Where they see, you know, the numbers ring true and that there's a good return. I think that's obviously an investor, you know, they've gone to their, you know, their investors and said, we will be great guardians of your capital, we will protect your capital and we'll make sure we use it wisely. They obviously have an accountability to make sure that level of work has been done before. Just saying, open the floodgates and let's give them another X million. So that's kind of how I see the problem at the moment.

Christine Maslin: Yeah, really interesting, um, risks and opportunities and I think there is a lot of scaremongering, isn't there, going on. You know, I think some people are embracing, other people are kind of worried about it and it's being honest about the uncomfortable truth and then getting a clear strategy around, like as you say, what isn't going to exist and what people won't need to use your solution or product for in the future because it will be replaced by AI. And you know, where can AI enhance what you're currently doing? Um, no. Really interesting to get your perspective on that. Thank you. Yeah.

Carrie Osman: And I do expect. My take is that people have to do this work. No, there is no shortcut to rethinking your business and your business model and the role it plays in the problem it solves. That is just hard work. It was, you know, hard for Kodak and they didn't really get it right. You know, it was hard for Blockbuster when Netflix launched and love film. And I remember all those days. It's always been hard. Right. It's a really difficult thing and it's often been done by sector. You could argue the cloud did it slightly, but not really at this scale and not at this speed. And I think that for people who are not standing back and really rethinking their businesses, they will regret not moving faster. And I'm not saying not moving faster in terms of jumping on the next bandwagon, I don't think that's right at all. But doing the precise review of where they stand, getting to that shared level of honesty about the current state and then using that knowledge to make some decisive choices.

Christine Maslin: Yeah, absolutely agree. And we're seeing that a lot with the clients that we work with as well, for sure. What do you think AI is doing to the traditional seat based dialogue ARR model?

Carrie Osman: Yeah, so I think the seat based model where we charge for the number of different users of the software is obviously reliant upon value being in the individual. So the number of people using the technology, really we're arguing, if we go with that model, we're arguing that the number of people using the technology is directly correlated with the value that people are getting. So, you know, we add another 10 people, the business gets more value. That is fundamentally changing with AI. That also has changed with a lot of different software businesses which have stuck with seat based models even though their value really does not correlate with the number of people using software. So I think what we're seeing is that 20 to 40% of software buyers are planning to reduce seat counts in the next three to five years, driven specifically by automation, AI and leaner operating models. Seat based models are, uh, limited with regards to the expansion they achieve across teams and use cases because they create friction and a barrier between someone in a bank saying, yes, actually we've got, why don't you go for your life and give this a try. Obviously that all has to be negotiated because it's another team and it's another use case. So what we're seeing is that buyers are starting to consolidate vendors. There's been a lot of this going on in software for a while, but it's obviously compounded with AI and the net effect is, you know, depending on the numbers you look at, up to a 10% ARR decrease year on year in a mature customer base. So from our perspective, seats are very rarely correlated to the value of software or technology. They were used because they are a smart, simple, easy to comprehend and understand measure. And I think there's something for that. You know, if it's easy for the customer understand, it's a fair metric. It makes sense. You rock up to a business and they know the number of people they've got. They also know, you know, what they're going to need. I think it's, it's very simple and easy to comprehend and I think there's a lot to, to argue for that. The problem is we're going to enter a world where a business that, that has 2,000 users who use a product one hour a week, say 2,000 hours in a week, is very different to a business that has 200 users who live in that product every day. And that means is that the one with 200 users who live in that product every day will be having extreme usage. They will become extra experts. There'll be advanced practitioners of, you know, the use and the capability of the technology and the one with 2000 who are using it for one hour a week. You know, they are just, they are just going to be in the basic category. Like highly likely they'll be in the basic category of usage. Now nothing is ever as simple as it seems, so there will be many shades in between those two extremities. But the point being, seat based really does limit you to the value sitting in the individual rather than the value sitting in the outcome or the value sitting in the way the technology is used or the value sitting in the technology enabling us to achieve X roi. So from my perspective, I think seat based has always been limited, but there have been benefits and advantages to it, uh, both in simplicity and ease of understanding. And I think that this new world really makes you sit up and take note because all of a sudden we are talking about teams that will be completely disbanded because the workflow will be put into AI, it will be automated and those people and resources will be redeployed. And ultimately if you're on a seat based model that would reduce your ARR to negligible, even though the value of your technology could be extremely high.

Christine Maslin: Yeah, really interesting. It's fundamentally changing, isn't it? Um, it's kind of moving more towards that value, um, and consumption piece. And it's just interesting what you talked about around the ARR. Ultimately we'll start reducing because the number of seats will be naturally reduced by AI and efficiencies that have been driven over time. But of course that example that you gave with the kind of 2000 users versus 200 users that are living in the product as opposed to the cost to the software company of the 200 users living in that product will be significantly higher than um, the 2,000 users that are using it for one hour per week. So actually the cost of the software company goes up and perhaps the user count comes down which forces that. Another thing that forces that change. Ultimately, can you explain to us in simple terms what consumption economics means? Yeah, of course.

Carrie Osman: So ultimately what it means is that we would be charging someone on what they use. So think of your electricity or your water. That is a consumption based model. You're not paying upfront, ah, for the amount of water that you use. Or I'm not, you know, Thames water, I'll use the example, you know, you are paying specifically for the usage of that product or service. So if you think of a consumption based model, ah, in its simplest terms, think of back in the day mobile phone contracts where a hybrid model would be, you pay 20 pounds for your phone license and you get 500 minutes and 100 texts. If you remember that world, you would obviously that is a hybrid model because you're paying for an amount of consumption. And then if you remember when you tipped the cap and you went into, you know, the 110 techs that you sent, those 10 techs were charged on top at a premium. So that's what we would think of as a hybrid model. You would pay for a platform fee that would have a number of seats that would have an amount of usage of AI all included in the fee, uh, maybe a service layer. It really depends when you then you pay for that upfront, you pay for that, you know, committed to in a contract, be it three to five years and then on top of that you would pay if you breach that cap. So that's how I think of that. The hybrid I think of as a mobile phone is an easy analogy back in the day, obviously not now. Now mobile phones are just so cheap it's crazy contracts, aren't they? When you think of what they used to cost as a percentage of the wallet. And then pure consumption is obviously, you know, electricity is a good example where if you remember that we have, you know, a lot of challenges around the national grid in the uk. That would be a good example of if national grid is, you know, very tight on electricity available, we will end up paying more for that electricity. Or you decide that you want to go on, um, you know, holiday and you leave it to the last minute to book the flights. And the flights are really expensive because there's only five seats left. That is very consumption driven. It's almost an agile way of thinking about supply and demand and price being truly set through the shifting supply and demand. So if data centers become hard to build and everyone is using a lot of AI and the demand is going up, the supply is limited through the data centers and how fast they can be built and of course the energy it takes to fuel them, obviously that will naturally drive the price point higher and that is we are going to be the victims of that. If you're just on a pure consumption based model.

Christine Maslin: Yeah, really interesting. Thank you. Carrie, what do CEOs most underestimate about AI, uh, driven variable cost structures in your opinion?

Carrie Osman: So I think most CEOs that we're speaking to are not looking at, I suppose either side, but let me explain what I mean. So obviously the downside exposure from OpenAI, uh, or anthropic, for example, changing their pricing, that is a massive risk to a lot of companies. A lot of companies that we work with are obviously building on one of the foundational models, OpenAI or Anthropic. And if you assume that their pricing stays as is and you don't model M out, the differences that could happen, there could be significant margin pressure that comes from those fundamental foundational models. Changing their pricing, that's just a given. So that needs being out, that needs working through. We need to see how does that drop through to the P and L. And of course that's the downside, right? That's the risk that we're, that we're taking. Secondly, obviously a lot of people are using AI within the business. We were talking about that before we started how we embed and use AI within cruxy and within different businesses. That is obviously also often being underestimated in terms of the scale of usage, how many different developers are using Claude code and what does that mean for your Claude code annual license and how is that going to increase? It will Obviously mean that you can do a lot more with fewer people, but how do you hedge that cost and make sure you're predicting it adequately? As we know all assumptions will be wrong, but you still need to at least have those assumptions baked into the P and L. And I think then the other thing, so they're both on the negative, I suppose, their risks and their costs that need to be thought through on the positive is what is the willingness to pay that I can extract from a customer if I bake in these different elements of AI? What is the willingness to pay that I can extract from customers not wanting to leak to their own AI, but wanting to use my software business as the conduit of their AI tooling or their capability? And there can be a lot of headroom there and upside, if you think about that in the right way. So I think their two things are more about margin pressure and protection and downside risk. And then there's one which I think represents quite significant upside risk or sorry, upside opportunity from our perspective.

Christine Maslin: Thanks, Kerry. Really great to get your perspective on that. And I agree it goes back to, uh, CEOs being real about what the risks are and working through the different scenarios as well as of course, embracing the opportunities. You've said customer intimacy becomes the edge in the age of AI. Can you tell us more about what you mean by that?

Carrie Osman: Yeah, of course. I think one of the things that software did which is helpful and um, unhelpful in the same sense, is ultimately it said rather than having a proprietary technology which you go and obviously put on premise and, you know, give the company the hardware and give them all of the services wrapped around that. We went into a world where services were not what anyone wanted to do. People didn't really want to kind of get that close to customer. And obviously you didn't want to build technology for a specific customer. You know, that was seen as a negative. Don't build it for a one off customer. You need to build it so that everyone has got the same solution. And you all have seen this in your work. Uh, you know, this happens across the board. Lots of people have built, you know, these Quasimodo kind of technology solutions because they've done one thing for one customer and then they've added a few features for another customer. And people talk about that, you know, that's the roadmap where you're the victim of what the customer wants and you're then you end up building a software which of course is not clear, doesn't have a decisive problem that it solves because you're almost all things to all people, if you like. That was seen as really negative in the world of SaaS. I agree. It doesn't make sense. You want to build something that everyone wants that's compelling for the majority, and that means that you have that strong win rate. You deploy the technology and you get that great NPS and customer success metrics off the back of having a strong universal product, of course, to the ICP that you're selling to. In the world of AI, obviously you can build almost very quickly a, uh, product that can be really shaped to the needs and requirements of very niche customer segments. So you almost have the ability to serve micro segments with really thoughtful, considered really amazing features that are built for, you know, not quite CEOs called John who have, you know, live in this area of the world and have this many connectivities. But you can make the product ultimately shaped and built almost for the end customer. AI gives us the ability to build something which is really unique to a certain segment of customers and where in software that had to be a broad group, now it can be a smaller group because the cost of code and the cost of development and the time it takes is much faster. And what that means is that to be a 9 out of 10, you can really get a lot more bespoke about what you're building and why. But to do that, you need to know the customer inside out. This isn't generically the ICP, which is a broad group of, you know, 500 to 2,000 employee companies in the US who look like this or in one of these five segments. This is much more bespoke to their technology stack, the specific problems they're solving, why they're solving them. And I think AI gives us the ability to build something very compelling to more niche groups. And what that means is that, uh, that intimacy that you need to have the level of understanding. When we spoke at the beginning of the podcast about Mars, teaching me the power of influence and putting on someone else's glasses and standing in their shoes and entering their universe, that really is now the new edge. If you can do that and think about the way that a user, uh, and an economic buyer are going to experience the software and the technology, the way that AI is going to be embedded, the way it's going to be deployed in the workflow, I think that really is giving you a new edge because it gives you the ability to become a specialist in obsessing over how you solve that problem better and smarter than they can alone.

Christine Maslin: Excellent. Thank you so much, Carrie. I think that kind of brings us to the end almost kind, um, of time wise. I think I could have asked you 100 more questions and we could have carried on talking for, uh, for a lot longer. Do you have time now for a quick, quick, uh, fire round? Of course. Wonderful. What's one small thing that brings you joy day to day?

Carrie Osman: Coffee.

Christine Maslin: Good one. Mine is jasmine green tea first thing in the morning. Um, favorite place you've traveled in the last year?

Carrie Osman: Oh, Botswana. I just absolutely adored it. Went to the Okavango Delta. If anyone is listening and they haven't, they're like, oh, what's the point in safari? Oh, I'm not sure I'm a safari person. Like just lean in and go. Because it is, I mean, obviously it's a massive treat, but it is like the most unbelievable experience and I had the most reflective, amazing, grounded time and it's just Africa is an amazing place and it always makes me feel filled with energy and spirit and good vibes.

Christine Maslin: That sounds amazing. It's definitely on my list. I've got a seven year old son, well, nearly seven, so I think I need to wait few more years before I can bring him, um, bring him along, but probably not too much longer. He's quite adventurous, I think he'd enjoy it. But, uh, no, that sounds lovely. If you weren't doing this, what would you be doing? I don't mean the podcast, I mean being the founder and CEO of Crocsy.

Carrie Osman: I'm quite autistic, so I just love like processes and how things work. And like the other day I was saying to my partner, like, I could just be a plumber or I could do any. I just, I get so much joy. I like waitressing. Anything, like anything. I love work.

Christine Maslin: Well, plumber would be quite a good thing to reskill in right now. Probably.

Carrie Osman: Exactly. But I do think the world of private equity has been really interesting to me. Having never known it working now on the edge of it, seeing a lot of the good, the bad and the ugly and really thinking, God, really is. Do you really think that's what the company want from you? Like, the CEO is really annoyed. You can smell it. You know, you get a nose for it basically. Um, so I think, you know, I have an undoubted like desire to at some point put my, put skin in the game with regards to the financial side. And I think that, you know, I'm doing that obviously with cruxy and it's amazing. And the journey's awesome. But I think, yeah, at some stage, that private equity side, I think would be a really interesting lens to see.

Christine Maslin: Lovely. Who's a woman leader you admire right now?

Carrie Osman: Oh, I'm just obsessed with Brene Brown. I feel like there's nothing she can do that won't bring me joy. And it's funny. Cause I think she's so badass as well as. So thoughtful. And I think that whole radical candor. I love Kim Scott as well, but that whole radical candor, uh, like, it's not kind. I kind of think of it as, like, mean to not tell someone if they've done something that's upset you or whatever. Because I've been in a bitchy environment. And I think that it's much nicer to be direct and caring. You can still wrap your arm around someone and be like, I really respect and think you're amazing, but you're getting in your own way here. And I think that the fact that a lot of people think that's mean and they think that lying to someone's face and then talking about them behind their back is nice just. I just think that is just bizarre to me.

Christine Maslin: I think it's just. It's a very British thing, isn't it? Going back to your point earlier, I think of a kind of American culture versus UK and Europe. But, uh, yeah, I agree. I just think it's uncomfortable for a lot of people in England specifically to be that confrontational with. With other m. People. Yeah.

Carrie Osman: But I think that's even how they see it. They're like, oh, it's a confrontation. And I'm like, it's not. You're helping them. Like, think of it as, oh, my God, what an amazing. You know. Would you like me to tell you that you've got toilet paper on your shoe and your. Your dress is tucked in your pants? Or would you, like, not tell you and, like, let you walk around like that for a day? Just, like, think of it as. I don't know. I think I try.

Christine Maslin: Yeah, I know. I agree. It's not. It's kind. It's just. It's that mindset, isn't it? Of. Of. Yeah. Being direct enough to. Yeah. To tell people and that culture that we are. We kind of find ourselves in. Around what. What you should and shouldn't say to people. But I agree with you. I totally agree with you. Yeah. And absolutely love Renee Brown. What's your go to? Way to reset after an intense week.

Carrie Osman: So what I usually do is on Saturday, I just have. I don't have children. So it's a bit different for different people. But I basically just. I get my nice coffee, go for a walk in the park, like, just give myself the day. And then on Sunday, I just sit down with my notebook and I just process. It's like I process by writing down. This went really well. Obviously, if there's anything I just need to jump onto because it's.

Christine Maslin: It's got.

Carrie Osman: Got to be done, I'll do that. But I think this concept of, like, zooming out and it really is, you know, half an hour, an hour. But I go through every single name of, you know, in the team, mainly the people that are working for me. Where are they at? What's their mode? What do I need to do to kind of. What did I do well last week for them? What can I do better? Uh, I zoom out on the business and the critical goals and think about where I need to push harder, where I need to step back, where my level of intensity and pace is kind of getting in our way. And I find this an amazing thing to do. It's almost like the most valuable time in my week to really just frame and reset and think about what we've achieved, what the gaps are, uh, what's needed, but not in a panicked way, in a very calm. I listen to a lot of Einstein study music to get myself into a very calm place. I'm quite weird. Christine,

Christine Maslin: do you know, I'm gonna use this, though. I really like it. It's, um. I'm.

Carrie Osman: I'm a weirdo. But anyway, I. Inside swimming music and. Yeah, so that's kind of a few of the things that I do. But I find the Sunday, Monday's way too late. By the time you're in Monday, you're just on the back foot. I think Sunday, get your head in the game. You feel ahead of it. You know, write up my notes on what I want to achieve with the team, prepare the one on ones. But it's not loads of things prep. It's more just clarity. I think getting to the mental clarity is something that we often underestimate but can free a lot of. A lot of things up.

Christine Maslin: Yeah, it, uh, allows you that time to actually think through things. And I like the piece around. You know, you think through every single team member and where they're at and you know, how your impact might be affecting certain things. And I think that also just helps with that empathy and emotional intelligence piece, doesn't it?

Carrie Osman: Definitely.

Christine Maslin: Great. Well, that kind of brings us to the end. Um, I think that this topic has been super interesting to listen to and I think it could be a good one for our next event that we'd probably plan in June, our next Shesas kind of panel event. So stay tuned for that. And I think we'll probably be calling upon you, Carrie, to see if you might like to join our panel again for, um, for that one. Because of course you've got a very unique vantage point with, uh, the work that you're doing.

Carrie Osman: No, thank you so much. I'll be delighted to. And it's been an absolute pleasure. And Christine, you obviously have achieved amazing things yourself, so thank you for the honour of speaking. Thanks to anyone for listening and of course really fired up to help support the Shesas community and hopefully bring that raw energy as well as the, uh, as well as the knowledge on the pricing side, which we're all still learning. So, I mean, we can bring different perspectives to the table on that front.

Christine Maslin: Thank you so much, Carrie. It's been a real pleasure to have you on and, uh, look forward to catching up with you again soon.

Carrie Osman: Thank you.

Christine Maslin: Thank you for listening to this episode of Shesass Unplugged. I hope it inspired you in your personal journey. If you enjoyed listening, please subscribe and share this episode with others. You can find out more about Shesas at our website, shesas.org you can also find us on LinkedIn.