SaaS Stories
SaaS Stories is my not-so-secret quest to learn what it truly takes to succeed in the world of SaaS—and I’m inviting you along for the ride! I have the pleasure of sitting down with brilliant minds and industry trailblazers to explore their journeys, uncovering the secrets behind their growth, the gaps they spotted in the market, and what really drives them.
It’s not all smooth sailing—there are challenges, unexpected turns, and moments of reflection where they share what they’d love to change about their journey. Think of it as a candid, insider’s look into the world of SaaS, with just the right amount of curiosity, empathy, and wit.
Join me as I dive deep, selfishly soak up all the insights, and hopefully share a little inspiration with you along the way—one SaaS story at a time.
SaaS Stories
Scaling SaaS without breaking it: A blueprint for sustainable growth
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How do SaaS companies scale without losing focus, burning out teams, or overcomplicating GTM execution? In this episode of SaaS Stories, Dave Boyce shares the real drivers of sustainable growth across product, sales, marketing, and customer success.
We explore why one clear GTM motion beats fragmented expansion, how repeatable founder-independent systems unlock long-term acquisition value, and where AI-powered automation is already streamlining qualification and sales enablement.
Dave also breaks down the importance of segment focus, customer-led demand generation, and aligning execution to the milestones that matter most.
A masterclass in operational discipline, scalable GTM strategy, and building systems that compound revenue and trust.
Defining Aligned Go-to-Market Strategy
Speaker 1How do you define a truly aligned go-to-market strategy ?
Speaker 2for SaaS companies . The alignment that you need is within the motion .
Speaker 1What are the key ingredients for maintaining that kind of momentum in SaaS ?
Speaker 2Well , you actually have to understand what's contributing to that growth .
Speaker 1What are some other big mistakes SaaS companies make when trying to scale To take on too much . Scale to take on too much . Welcome everybody to another episode of SaaS Stories Today . I'm super excited to be joined by Dave Boyce from Winning by Design . Welcome , dave .
Speaker 2Thank you , joanna . We're across time zones today .
Speaker 1Absolutely . I typically am with these podcasts , which makes them that much more exciting . Now you're a bit of a unicorn , because you've got experience across product sales , marketing and customer success , which is just gold . How do you define a truly aligned go-to-market strategy for SaaS companies ?
Speaker 2Another word for unicorn in this case , and that is old , seen a few things and also just curious and old . Like you know , when you're a curious person you roll up your sleeves and you figure stuff out and you throw yourself back in the battle Each time we sold a company . One time I stuck around for a while , but generally I just wanted to get on to the business of building again .
Speaker 1So yeah , you end up seeing a lot .
Speaker 2And one of the things I saw a lot of , yeah , is go-to-market motions . Like you know , a sales-led , an enterprise , two-stage inbound kind of inside sales motion , product-led motion One thing I'm sure we'll talk more about . But you can't do it all and the alignment that you need is within the motion , in my opinion . I'm not trying to align across motions , I'm trying to align within the motion . So am I running the right marketing motion that matches the right qualifying motion , that matches the right monetizing motion , which could be sales or product led , that matches the right onboarding , that matches the right retention ? If I can get all of that aligned within the motion , then I'm good and I'm going to tune that as almost like a production line in a factory and if I go build a different production line it's going to have different set of motions and I'm going to tune it separately . But I can't get confused and managed by averages and I'm going to get all messed up .
Speaker 1Yeah , now it's so interesting that you mentioned alignment , because I'm always going on about sales and marketing alignment and all the teams need to be kind of working with the same energy and goal . Is that what you find works really well ?
Speaker 2Same energy . I like the idea of goal . Like I can't tell you how many times I've , you know , seen a marketing leader give a presentation to a board , you know , declaring up into the right victory , and then they leave the room and then the sales leader stands up and says , well , we didn't quite get there , we'll get . You know , we'll get them next time . That's not alignment . We're working towards an overall . And even that still doesn't even contemplate . What about CS , who is actually renewing a big base of ARR and trying to expand on existing customers ? So if we want to look at growth , it's a system . It's not just a set of silos that sit next to each other and we do have to be playing the same game . I totally agree . Alignment's a great word .
Speaker 1I absolutely agree with that myself . Now you've helped grow multiple companies to 50% plus and more . What are the key ingredients for maintaining that kind of momentum in SaaS ?
Speaker 2I'll tell you what it's not . I mean SaaS . I'll tell you what it's not . Well , actually it was from about 2000 to about 2020 or 2022 , to be precise , it was just throw more money at the problem . You know , money was free . You know we found one thing that was working , we could just throw money at it . Oops , the unit economics are upside down . That's fine , We'll just throw more money at it .
Speaker 2We're running out of market down , that's fine , we'll just throw more money at it . Oops , we're . Um , we're running out of market , that's fine , we'll color outside the lines and we'll just throw more money at it . We'll be able to rate like that did work for a while . Um , but if you really want to be sustainably scalable , you actually have to understand what's contributing to that growth and and that is a that's an arc like a revenue architect mindset , not just to operate the factory mindset , like I have to understand how was the factory built ?
Speaker 2Why is this there ? Why am I running this motion , what you know , why do I qualify these customers out and these customers in ? Oh , it's because downstream I'm going to have a renewal problem . Okay , great , I'm going to think I'm going to architect that as a system and once I kind of have that thing going and I can see my renewals , my expansions and my net new customer sales accruing into a repeatable , scalable motion . That's the key ingredient for 50% plus year over year growth . And , by the way , you're not going to do that forever . You're going to do that for a little while . It's going to work its way down to 40 , 30 , 20 , but , but you can do it for a while .
Speaker 1Yeah , if I read between the lines there , I think he was saying as well , like it's important to find the right customers , not just any customers , and that's kind of helps with the scaling .
Keys to Sustainable SaaS Growth
Speaker 2Is , and that's kind of helps with the scaling . Is that right For sure ? The sugar rush of an amazing like big . And a lot of times this happens when I'm selling big contracts . But it doesn't just have to be big contracts . A lot of times I'll go celebrate my new seven figure customer like hurrah , we just won Horizon , we just won Citigroup .
Speaker 2Question is did you win them based on center of the bullseye , exact match with your fit with your product ? Or did you win them and or did you make some promises beyond your roadmap ? Are there some kind of digestion issues that you're going to have once you pull that seven-figure customer in ? How long is it going to take you to actually get them to success ? Is it going to take over your entire company or half of your company or a third of your company ? So big contracts can be a problem if you're not used to it and contracts for a customer that is an off-label use of the product can be a problem . Like , yeah , it seemed good in the time but now I'm going to fight , fight , fight for the renewal , fight , fight , fight again for the renewal . It has to take up a disproportionate amount of time . So clear , kind of center their bullseye fit customers are the best customers .
Speaker 1Yeah , no , that's really interesting . I've seen this happen before , where you know companies have one giant customer and it's kind of funding most of the business and the staff are mainly working on this one client . They then lose that client and it's just , you know , chaos in that organization . It's terrible worst .
Speaker 2Unfortunately , I have some of those battle scars . It sounds like you do too . It isn't . That's not a scalable business . That's kind of like a custom dev business or a services business yeah , no , absolutely I mean .
Speaker 1With that in mind , what are some other big mistakes as companies make when trying to scale um ?
Speaker 2you know a lot of this . Um , it's all well intentioned , joanna , right , like you're , we're all optimistic , you know we're all . We're all optimists . Like we're techno optimists . Like we're techno optimists , we're probably like generally optimists . That's why we do what we do .
Speaker 2We take , take on hard problems , try to invent things that never existed before . That's great , you know . More power to all the founders out there who , who motivate themselves to do that . But that optimism can also encourage us to take on too much too soon . So like oh , that's a problem I could solve . Oh , that's a problem I could solve . Oh , that's a customer I could serve . Oh , that's a product I could build . Oh , that's like a market segment I could attack . Yes to all of that . But just because you can doesn't mean you should . So the biggest mistake I see is taking on too much too soon . Like , let's get it right for one customer segment with one customer in one mark , kind of in one market with one motion . Let's get that right , let's get that scaling , let's get that repeatable , let's work out the kinks , let's get to $10 million in ARR on , kind of like that , before we go bite off , you know , whatever the next horizon is , you know , an adjacent market , a channel motion enterprise , something a new adjacent product , like we'll get to those things .
Speaker 2But we don't have to do it all at once .
Speaker 1I'm definitely guilty of this , but it also leads to burnout in a way , doesn't it ? Because you're just like running around going , yeah , I can do everything .
Speaker 2you know you , you're motivated , but there is a point where you hit the wall , when you're like , oh okay , step back it's taken huge companies down , like huge billion dollar valuation , north billion dollar valuation companies down , not because the entrepreneur wasn't motivated , not because she wasn't talented , not because the team wasn't talented , not because the entrepreneur wasn't motivated , not because she wasn't talented , not because the team wasn't talented , not because the product wasn't good , just because they started too many fires and they couldn't tend them all at once .
Speaker 1That's really interesting . Now you've sold quite a bit of companies and some major players as well , like Oracle , amazon Maybe for all the founders out there listening with an exit strategy what makes a SaaS business attractive for acquisition ?
Speaker 2It is back to basics time , joanna . We went through that growth at all costs phase and what made a company attractive ? There was literally like growth rate period , end of story . Um , and what I spent for growth didn't matter , and um , you know , because we'd come fix that later . Um , then we went through a period of oh , there's no money anywhere . Like you know , all the all the vcs and pe is kind of shut down for a little over a year and then we had to like , oh , like , we got to figure out how to be efficient .
Speaker 2We do need growth now . Like , it still is true , growth does all the work in evaluation . Correlation , like the rule of 40 , is not equal weight , it's not profitability carries half and growth carries half , growth carries most , growth carries most of the valuation . So we need growth , but the kind of growth we need is sustainable and scalable .
Speaker 2So you know what we've been talking about in terms of like , just go fine-tune that motion so that the repeatable process , the repeatable going after the same type of customer with the same volume . I would rather run the exact same play and only succeed 70% of the time than try to go snowflake every single customer
Common Scaling Mistakes
Speaker 2and go for an 80% or 90% or 100% success rate , because the latter thing's not scalable , and all acquirers know this when they get in there and I've had deals succeed and fail on this test . If it's repeatable and scalable , then they know they can plug it into what they're doing and they can keep running those plays . If it's not , if it's dependent on a super dynamic founder or a snowflake one-at-a-time thing or an amazing engineer who's never been seen before and never will be again , those are not repeatable things that are scalable and so therefore they're not going to add value to the acquirer .
Speaker 1Yeah , got it , and I think a lot of people listening right now are probably wondering how do you even get to 70% growth ? And speaking of growth , maybe you talk a lot about product-led growth . But tell us a little bit about product-led growth and can we also touch on maybe some other tactics , like I've heard , sales-led growth . I've heard you know , customer-led growth . There's so many different ones . Which one do we choose ?
Speaker 2Yeah , that is a critical decision and that decision happens early Because you're going to you're going to decide which of those factory production lines are you going to build from a GTM perspective , and so you're going to lock into one early . But the very first thing you're going to do is is going to be all founder led like , and even if you're starting a new , a new product within an existing company , you got to do a decent amount of found . I'm gonna call it founder led sales . But I'm interacting directly with the customer . I don't actually care if it's scalable , I just need to understand who is the customer , what is the job to be done that she has , how does she make progress against that job and how can I meet her where she is with the product that's gonna really work for her . So I'm gonna be the number one to be the number one sales rep , the number one customer success rep , the number one support rep . While I'm figuring that all out , then I got to make the decision okay , I think I figured out this formula Is this best suited for sales led Meaning ?
Speaker 2It's going to be very hard for a customer to get out of the gates on her own with no assistance , including , you know , matching up the value proposition , building the ROI case , you know , going for budget , running through an initial pilot , and or can I actually automate all of those things , in which case many customers would rather do it on their own , like many of us in our personal lives , like we don't want a salesperson selling us , snapchat or or Dropbox or Canva , or , speaking of Australian companies , canva and and Atlassian , two amazing huge giant PLG success stories Like the , the , the , the two founders of Atlassian .
Speaker 2They just said from the beginning like engineers don't want to be sold to , they want to find the product and get their hands on it . So let's just build it in a way that I can self-serve in . So I will make that decision early and it does depend on the kind of my target customer and the value proposition and then , once I make that decision , I want to live with it for a while until I've either proven to myself that it's wrong or I've been able to scale it to like $10 million .
Speaker 1It sounds like you know easy to use products . Definitely product-led growth , totally understand that . I mean Canva . I got in there and it was so straightforward I definitely didn't need a demo or anything like that . But with more complex B2B products that are in , you know , say like industries that are also quite hard to understand , you think that might be more of a sales led growth model .
Speaker 2Traditionally , that is indeed the case .
Speaker 2Now we are creative , like we entrepreneurs and business leaders are creative , so we are figuring out how to reduce the complexity , how to create more straightforward on-ramps , how to build interactive demos , so self-service interactive demos , so that I can demystify that even if I'm trying to self-serve my way into a purchase .
Speaker 2Even SAP has interactive demos and sandboxes that I can access before I make a purchase , which helps me educate , helps me educate myself , like 70% of the way down the track before I have to start purchasing . So , and the other thing that we have to think about now is well , what's the role of AI ? Because even because even a complex product can be explained by an AI agent . So I might actually be in that kind of purchase process and I may not need a human to help explain to me whether I need the gold , silver , platinum package , whether I need the you know this version or that version , whether it will work for my use case , whether there are any companies like me using it , because all of that could have been loaded into an agent's brain and I could literally be talking to that agent at 1130pm at night and getting all the straightforward answers , not quota driven , without a human , and that also helps me get a ways down the track .
Speaker 1Now that's really interesting and I think you know more and more we're going to start using AI agents for absolutely everything in our lives . Unfortunately , that's the way of the world .
What Makes SaaS Attractive for Acquisition
Speaker 1I've also seen the self-serve model grow substantially , especially since COVID days , you know . Digital transformation kind of sped up more than it should have . Everyone was buying B2B software as a self-serve , even software that was worth , you know , in the millions of dollars . I think that went up by 30% or something like that . What's your take on the self-serve model and where does sales and maybe customer success play a role there ?
Speaker 2where the sales and maybe customer success play a role there . Yeah , I much prefer talking about it as self-serve versus product-led or ai-led or um . Self-serve is indeed , I think , the way the world is going like . I think we all would prefer to um educate ourselves until we wouldn't . So the chief customer officer for Canva , a guy named Rob Giglio . He says , look , I want my customer to succeed on her own for as long as she wants to be on her own and then , when she gets to a place where it would help her to get some help , I want her to be able to raise her hand , get some help . We're going to show up not with a question of , oh , what can I sell you , but we're going to , as a human , we're going to show up with a question of hey , how can I help ? So I've already you know she's already experienced with Canvas . She's already experienced a lot of the stuff you experienced .
Speaker 2But now maybe she wants to standardize across her department , or maybe she wants to do , she wants to do something that would require some like infosec approval or legal approval from the company where she works , and that's something that she's not equipped to go do on her own . Hey , could I get some help , sure . So here comes a salesperson . Salesperson helps her get through those hurdles . Now she continues on her impact journey and that's amazing . But in Rob's view , it's my choice . When I want to talk to a human , I can talk to a human . When I want to talk to a robot , I can talk to a robot . When I want to just get hands on the product and get started , I can do that too , at my choice .
Speaker 1Yeah , yeah , for sure , I think . Yeah , talking to humans might become more and more appealing as AI takes over the world slowly but surely .
Speaker 2Oh my goodness , we were on vacation a couple of weeks ago and I was going back and forth in the car with an AT&T agent and my family was making fun of me . They're like you're getting so upset , but this is what you preach , like you want automated GTM . I'm like I know , but I can't get through this agent right now and I just need to talk to a human .
Speaker 1But it'll get better .
Speaker 2That's the worst it'll ever be . Today's the worst it'll ever be .
Speaker 1That's true . It can only get better from here . Absolutely , and we will talk about AI in more detail in a second , but first tell me a little bit about Winning by Design . What problems are you solving for the SaaS world ? How did you get started in Winning by Design ?
Speaker 2Amazing . So my journey to Winning by Design was through , like you said , building and selling companies and then we sold the company about four years ago and I was trying to figure out what I wanted to do next . And what I wanted to do next was write a book and dive into product-led growth and automated GTM . I called the founder of Winning by Design and said what are you doing about automated GTM ? He said why don't you come over here and figure it out with us ? So that's my journey . But Winning by Design is a growth advisory firm . We generally work with companies between 20 million and 500 million in ARR . We don't work with a lot that are over 500 million . A few Canva is one of them . We don't work with many below 20 million , but it's really those kind of that . I've got the product market fit right . I've scaled to a certain point . I've got to kind of rebuild an architect and make sure that I've got scalability architected right into the company . How do I do that ? We work on an advisory basis with those companies .
Speaker 1Amazing . What's the general advice that you find yourself giving to some of those companies that they absolutely need ?
Speaker 2Well , we've developed and when I say yeah , we've developed six models that really help you think about where you are in your growth journey . And what would really need to be focusing on is making sure I have repeatable motions built in and a data model structure that allows me to kind of run experiments against that go-to-market motion so I can fine-tune that production line . So what to focus on ? When is one thing that we work with customers on which GTM motion makes sense ? You asked it before , like should I be running PLG ? Should I be running a two-stage inbound motion ? Should I be running an enterprise motion ? Well , let's look at it , let's look at the unit economics , let's look at the customers and let's make sure that we've got the finely tuned factory line . And then we've got some other models that help you think about the math and the long-term growth prospects and how you know how ARR compounds . But really , what to focus on ? If I were to say one thing compounds .
Speaker 1But really what to focus on ? If I were to say one thing , it's what to focus on when One thing at a time .
Speaker 2One thing at a time , I can't do it all at once .
Speaker 2So let me go tackle this thing , because it matters now and then I'll tackle that thing because it's going to matter when I get to 20 million , and then I'll go tackle this thing because it's gonna matter when I get to 100 million . And there's a , there's a . We've seen this playbook a lot of times , so , especially for a first-time founder , that can be really clarifying . Like , thank you . Like I've got board members telling me I got to worry about all sorts of things and some of it is relevant now and some of it is relevant but not
Product-Led vs Sales-Led Growth Models
Speaker 2until later , and so just helping them parse that .
Speaker 1Yeah , interesting For all the marketers listening and , selfishly , for me too because I'm in marketing . But , um , what are some marketing campaign strategies ? You know that you have found always work well for sass , for scaling sass um , here is a often missed opportunity .
Speaker 2I think most of us kind of forgot this . Some AI native companies are leveraging it and a lot of PLG companies are leveraging it , but a lot of kind of just B2B , saas , native , kind of run and gun companies forget how valuable our customer base is , and so we have marketers aimed at non-customers and meanwhile we have $20 million worth of ARR locked up in existing customers . Of course they can expand Great but they can also be advocates . Like . Each of those customers probably has between 10 and 50 , maybe even 100 users . Each of those users is a human . Each of those humans has a network and in today's world , a new buyer is going to go to her network before she goes to me to figure out what the best solution is here .
Speaker 2So I would not sleep on the users of my product as campaign vehicles . As a marketer , like I want to create heroes out of my individual users , I want to help them tell their stories . I want to tell it may be the individual users , it may be the managers , but I want them to tell their stories . Like we brought this product into our organization , we went up into the right on this dimension . I would like to help other people do that . We went up and to the right on this dimension . I would like to help other people do that . So building kind of opportunities for user led growth , I think is a slept on opportunity that we , every SaaS company , has .
Speaker 1I love that advice . I think it just makes me remember a quote by Jason Lemkin . He says customer success is where 95 percent of the revenue is . Lemkin , he says customer success is where 95% of the revenue is , and it's so true . It's so much easier to get more growth from existing customers but also get them to refer you as well , because there's definitely people within their networks Also . They're moving around from position to position , so there's kind of new companies that you can get to know . Now . You've served on multiple boards um , you're a busy guy but one in particular is Forrester . I've done multiple courses with Forrester , from demand gen to account based marketing . Absolutely love their work . Can you tell us a little bit about your time at Forrester , what you've learned ?
Speaker 2yeah , I mean , I think a big thing at Forrester there will be no big secret if you're reading the , you know the annual reports and the 10Ks and listening to the analyst calls the Wall Street analyst calls . A big thing at Forrester is how do we disrupt ourselves in the age of AI ? So you know , there was a day when the source of all truth in an emerging market and this was true for Forrester and the dot-com boom , you know , which is ancient history for most people listening to this the source of all truth was the Forrester analyst who you know was right at ground zero , figuring out a dot-com strategy , an e-commerce strategy , all the players , all the platforms , all the service providers . That day is not today .
Speaker 2A lot of that information exists out there and I can get access to it just on a generalized AI model like Cloud or ChatGPT . So Forrester has to figure out a how to automate and we're doing this how to automate a lot of the work that we do in terms of research and publication and access to information . But then also , how do we add and this is something force has always been good at on top of that , how do we add an analyst ? Take that , it will be useful that will allow you know you , joanna , or me , dave to get a takeaway out of all that information rather than just swimming around in the data .
Speaker 1It's interesting , and so what can you give SaaS founders needing to talk to the board tips on like ? How should they be speaking to the board tips on like ?
Speaker 2how should they be speaking to the board ?
Speaker 2oh , that's a big question , joanne I can tell you , I'll give you some mistakes that I've made when I've been , when I've had my own board , and the main mistake that I've made is not having enough courage of my own convictions . So , like , especially in the founding mode , when you're looking for product market fit , when you're looking for go-to-market fit , the person in the room who knows the very most about your business is you . It is not the board members , but often , because they cut a check you know they cut me a check for $10 million or $30 million . I think I need to listen to them . Yeah , there's some stuff that they know , but mostly I know more about my market than they do .
Speaker 2So trust your humanity , trust your instincts and and be courageous , Like when you see something . Be courageous . You don't want to be belligerent . We've all seen the entrepreneur who thinks you know , she knows everything and she's the only one who knows anything and and dismisses and everything from the board got it . That's no good , but I want to trust , you know . I want to trust what I see and I want to speak straight to the board . The other thing I want to do is be vulnerable , Like if something's not working . I remember I went to an advisor named Clayton Christensen one time . I've been working on this company for like a year and a half and he could just tell from my just the way I was . I was trying to sell through it with all sorts of positivity and optimism and he's like , Dave , I can tell that it feels like you're pushing a rock up a hill and I'm like , yeah , it does .
Speaker 1And he's like okay that happens .
Speaker 2The answer is not push harder , like . The answer is not pretend everything is fine . You got to go find water flowing downhill and you'll know it when you find it . So I had to . He had to drag it out of me . He had to drag vulnerability out of me . But these board members have seen a lot . Even though they maybe have not built a company in your market , they've either built other companies or they've been on boards of other companies and there's nothing you can tell them that they haven't heard before , nothing . So just be upfront . Don't pretend that everything's great . Be vulnerable and ask them for advice . See what they've got and then filter it through your lens and then go work on it in a way that makes sense to you .
Speaker 1I love that advice . Be vulnerable , and you know like people are scared to do that because they think they'll get judged
Self-Serve and Customer Choice
Speaker 1or they'll get , you know , thought of as less than . But really , the board's there to help . They want to help . So by giving them that vulnerability , yeah , you're opening yourself up to a lot of opportunities , right ? Yeah ?
Speaker 2And and the truth is , depending on who you've raised from , like I've raised from angels , who I didn't get money back to . I've raised from angels who I did get money back to and institutionals , but angels is really that's what looks like , really personal . It's like friends and family , like someone you have a personal relationship with . They write you a check for $100,000 , $200,000 . Whoa , like you know , that's a lot of money . Like , oh my goodness , like I better take care of that . And then you can't get it back to them . It feels horrible .
Speaker 2But when I went , but when I've and honestly I've avoided conversations with those people while things were going bad because I just didn't want , I just didn't want the discomfort and in this case that I'm thinking of specifically I then circle back to them after all , the smoke had cleared , after the smoking crater was completely evident . We're going to walk away from this thing with our lives and not much more . And they didn't get any money back and apologize to them . And they're like Dave I , I didn't give you any money that I couldn't lose and if you had made money for me , I wasn't going to share it with you . If you lose money , I'm not , you know , I'm not going to blame you for it .
Speaker 2Like that's the game , so they understand the game , so just be vulnerable with them while you're trying to figure things out . Don't wait for the apology later , because nothing can be done at that point .
Speaker 1Yeah yeah , that's great advice . I did promise we were going to come back to AI , so now's the time to chat about AI . What's some of the most exciting ways you've been using AI and AI agents to ? To help you automate you know , day-to-day tasks at winning by design or , um , even just life in general ? I mean , I know I use it for personal use as well . It plans all my holidays for me yeah , I love that .
Speaker 2Actually we had a plan , a plan a holiday recently . It's so interesting you got to go verify that things that it's suggesting actually exist . But mostly it was pretty dang good At Winning by Design . We have a couple of agents running right now . One is an inbound SDR .
Speaker 2So if you go to the winningbydesigncom site you can meet an AI agent named Jack . You can have a conversation with him about the types of things we're talking about . He's read the revenue architecture textbook . He's read all the winning by design frameworks . He's read all of our advisory materials and then he's been trained to qualify you as a potential customer . So he's literally running our methodology , which is called Spiced . He's looking for situation , pain , impact , critical event , decision . So situation is who are you ? Pain is kind of what are you experiencing right now ? Impact is how could I help ? Critical event is are you working against any calendar event or anything in the future that you know that would drive urgency into this ? And then decision is how we make it .
Speaker 2So if you go talk with Jack , he's running that . He's trying to figure out like , is this a place where I can help ? And if so , he'll hand you off to an AE and he'll surface a calendar and just book a time and if not , then he'll steer you to like a self-service course or a book or something . So that's one agent . We've got a couple of agents doing stuff like that , joanna , but it's the critical thing is that those agents are all working inside of a system .
Speaker 2We talked before about things as an aligned system . You don't want just this agent off doing what her own thing and that agent off doing his own thing . That would be more like growth hacking and great , you'll get empty calories kind of sugar rush out of a little bit of you know , like SEO optimization over here or a little bit of you know . But what you want is all working inside into the against the same kind of integrated view of your GTM , which , which you know , we codify in what we call a bow tie data model , and so we can run these experiments , we can see where we're improving on onboarding or on retention or on expansion or on acquisition or on awareness generation , and we can feed that all into it and we can employ one agent over here , a human over here , an agent over there , and they're all working on the same system .
Speaker 1That sounds really fascinating . I might have Jack on the podcast next .
Speaker 2Nice . We've never done that . That would be very interesting .
Speaker 1I wonder what they'll say . Oh , absolutely , I mean , that's kind of scary thinking about it , you know , because I think I recently played with an AI where you fed it a white paper and you turn it into an interview between two people and it actually sounded so real . I was like well , there's your podcast .
Speaker 2Oh good , yes , I think you're probably talking about Notebook LM , it's really good , yeah , that's the one . Really good , yeah , fantastic , absolutely .
Speaker 1You also teach at BYU , amongst many other things that you do in the world . I mean , how do you find the time ? First of all , and second , what do you believe today's
Winning by Design's Approach
Speaker 1SaaS founders need to understand ? That wasn't so obvious maybe 10 years ago .
Speaker 2Yeah , it's really fun to teach Joanna . It keeps you sharp , forces you to kind of be on top of your game . It's one of the ways I forced myself to kind of be on top of your game . It's . It's the way that I . It's one of the ways I forced myself to kind of write the book that I , you know , I told you I aspired to write after we sold this last company . It's , I'm proud to say , it's now written and , uh , will be released in August .
Speaker 2Um , but , um , you know , forcing yourself to teach something is a really really good way to learn it , and I was able to get guests into the classroom and really crack open case studies and really understand , kind of the underlying principles of AI and product-led growth . But what I would tell a founder right now and you're right , I work with several of them is the playbooks that got us to here . So you're looking out at all the people that are running successful SaaS companies , the playbooks that got us to here . So you're looking out at all the people that are running successful SaaS companies . The playbooks that got them to where they are will not get them to where they need to go , because the entire world has changed .
Speaker 2I've spent the last week on the road with CEOs and CROs that work in private equity portfolio companies and they all know , even though they're sitting on top of a 50 or 80 or 100 or $150 million AR company , they all know that the playbooks that got them to that point are not going to get them forward . Ok , well , which playbooks will get them forward ? Ai native playbooks will get them forward , which actually gives you , the founder , an advantage , because you might actually know more about that than your competition does . So it's about speed . It's about speed , just like have the courage of conviction to go , architect your way forward , and if you can go faster than your competitors in your market , you will have the the advantage yeah , that's interesting .
Speaker 1Tell me a little bit about more about ai natives , like how can can CEOs use that to their advantage ?
Speaker 2Yeah , so that's the conversation we've been having over the last several weeks . We hear these crazy stories right Like Cursor to 100 million and I think this week they announced 500 million in ARR with 30 employees . I bet they have a few more than that , but the last count we saw was 30 employees , 500 million revenue . And then we've got Replit and Lovable and doing similar things . Those are AI native . They're not employing salespeople , they're using , they're not writing their own code . I mean , they're writing 10 , 20 , 30% of their own code , but agents are writing the rest . They're running all their own GTM through their own kind of customer like user-led , customer-led marketing , like we were talking about , like they've just architected that all in , okay , cool .
Speaker 2So let's say I'm a CEO . If I'm a CEO founder , I could probably go copy a decent amount of what those companies are doing . I would be going to school on that and figuring out how much I could replicate . But if I'm a CEO , kind of a SaaS native company , and we got 10 , 20 , 30 million in ARR already and I'm watching them over there do that , I also want to copy some stuff , like I want to see what's working . I can't just rip and replace what I'm already doing . But can I get an AI agent running my demos for me ? Yes , I can . Can I get an AI agent building SEO pages in the hundreds ? Yes , I can . Can I get an AI agent qualifying inbound demand ? Yes , I can . Can I get an AI agent listening to all my conversations and figuring out which customers are happy and which ones aren't ?
Speaker 1Yes .
Speaker 2I can . So there's a lot of stuff that I can start automating that will speed up , that will not only help my humans perform better , but also offload some of the tasks , and that is what we need to be doing right now , because if we don't do it , someone else will do it and they'll just run right past us while we weren't paying attention 100% .
Speaker 1Yeah , I think there's going to be a massive gap between those that use AI well and those that don't . But speaking of all these tasks that AI agents can do , I mean , with that in mind , what skills are you looking for when you're hiring a human ?
Speaker 2So , yeah , the real kind of , one of the real sources of angst right now is the is the novice gap . Like you know , I've got kids in college , graduating college . I have six kids , joanna , some already graduated , but they're right , in that age , right , they're just launching careers . And so , are there any careers left for a novice , or is AI doing all
Working with Boards Effectively
Speaker 2the easy to do stuff ? Careers left for a novice or is AI doing all the easy to do stuff ? And now I have no on ramp into a you know a big person career anymore . Because , because there's no kind of entry-level jobs left . Well , I get it , but for the AI literate person , I think there are . Like I have a 17 year old that's our youngest kid whose summer job is training AI agents . That's his summer job . He's not working the drive-through .
Speaker 1He's not working .
Speaker 2He's training AI agents . What does he know about AI agents ? Nothing , but he has courage and he's smart and he's creative , and so we need people like that , and even when I'm hiring at higher levels , I want to hire AI literate people . I do not want to hire the person who's trying to keep AI out . I want to hire the person who's figured out how to pull AI close In any job CS , sales , marketing doesn't matter . They've figured out how to leverage AI , either in a bespoke way , like you're doing for your holiday planning , or in an architected way , like Jack's doing on our website . Anybody with any of that experience is highly , highly interesting to me .
Speaker 1Yeah , no , for sure , I think , someone who embraces technology and ai and has a passion for it , and therefore they'll learn it in record time as well for sure dave , my last question for you a bit of a tradition on the podcast is if you could go back in time and give yourself one bit of advice . What would that be ?
Speaker 2I'm going to put it , I'm going to encapsulate it in a little phrase that hopefully you know , people will remember , and then I'll explain it . But what I would say to myself is that , dave , like this one thing , remember this one thing and you will go far Courage is in short supply , no matter the arena you're in . Courage is in short supply In a corporation , courage is in short supply . In the startup world , courage is actually in better supply . But you can always deploy courage to your advantage , like stepping into the unknown , even in the startup world . Right now , like you said , everything's changing . We're all going to be disrupted by a .
Speaker 2Okay , cool , so the courage . Run to the problem with courage . Figure it out and and and the . In the land of the blind , one eye is king . Great . First to the ball is the one who's going to figure it out . That takes courage . Deploy that courage . Don't . Don't operate from a kind of mindset of play , not to fail . Operate from a mindset of get to the problem sooner than anyone else with courage , and everything else is going to work itself out like it really will , like the sun will come up tomorrow . You will figure out how to pay your bills . You will solve problems as you go and the closer you can get to kind of the coalface of the problem , the better , and that's just a , that's a function , in my opinion , more a function of courage than than anything else I love that .
Speaker 1it made me think of a book that I recently read , called um the obstacle is the way , and it's all about what you just said , like have the courage to go through the obstacle , learn about it like don't run away from it , don't , you know , be afraid to fail . Just keep going that this is the way forward .
Speaker 2I'm going to check that out . The obstacle is the way . That sounds like a good lesson , yeah it was a really good read .
Speaker 1Speaking of good reads , maybe just give us a quick intro into your book . Where can we get it ?
Speaker 2and I think you mentioned august is a release date august is a release date , but you can order it now . It's um I . I went with the traditional publisher and they've done an amazing job . They've got it out on amazon , barnes and noble um target anywhere that you would order books International too , like crazy . Like it's available and will be available in Chinese , it's available in Japanese booksellers , so you can . It's called Freemium , the book's called Freemium . Go to any of those places and just search Freemium , and if you have to search my last name too , once in a while I've found that , but mostly it just comes up under the name premium and it's all about product led and AI led growth .
Speaker 1Amazing , I'll definitely be getting that . Dave , thank you so much for being on this show . I think we've got some really good advice , you know , for all our audience . You've been amazing . Thank you so much .
Speaker 2I love it . Joanna , you're going to have a lovely day , I can tell , in sydney , with the sun streaming in behind you it's so great we're at the end of our day , but , um , I'll have a good weekend day starting tomorrow yeah , no , I think the future looks good here , so I hope you have a lovely day , all right .
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