Scaling Heidi in the US: Lessons in product, people and persistence.

What we're trying to do is so significant. We're trying to beat the Microsofts of the world, these competitors that have raised $500 million. It's this guy Gantuan TAS that if you would have really like looking at Sess over the steps that you have to get there, you just give up, you take everything too seriously. When you lose a deal, it's like, damn it, we need everything to go right and something didn't go right. So let's just throw it all away. And so I think a really fundamental skill is just like laugh at the shit that actually really hurts. Like, because it's going to hurt anyway. And whether you dwell on it or whether you let it impede, what happens next or it might as well be funny as well. Welcome back to Wild Hearts. I'm Mason Yates from the investment team at Bike Bread Ventures. Today's guest is Jesse Criven. A force of nature inside one of Australia's most exciting health AI startups, Heidi. The doctors are the ones running around like headless chicken saying, we love Heidi. This is the best thing since last bread. Literally, I think we had doctors like talk about it in their wedding vows, things like that. Jesse brings such a refreshing and unique perspective. Part operator, part growth hacker, part systems think our part seller. He joined Heidi and its early days. And now he's leading the charge into one of the most complex and competitive health care markets in the world. The United States. Fight succeeds in the US. Jesse will be a big reason why. In this episode, you'll learn how to approach international expansion with precision, how to build trust with fairly customers in a high stakes industry, and what it really takes the scale and ambitious product into a new market. This episode is a masterclass in going global. Let's get into it with Jesse Criven. If we begin with the end in mind, one of the things that I'd love to get from this episode are the lessons from being one of the first, if not the first, with Tom in the US. And the building out of the team and navigating through that journey. And so perhaps a good starting point is getting off the plane. I assume you arrived in New York. Yeah. How did you even choose location to build the American HQ from? So there's no story of diligence and planning and strategy. So maybe flashback three years ago, I did a semester abroad in the States in Penn State. Like a real big party school. It was not, don't get a competitive new pen. It was Penn State. Like it was serious, serious party. And as part of that, we'd go to New York all the time because Pennsylvania is pretty close to New York. And not to do like the romanticized story, but you hop off the bus and you're like, wow, this is fucking cool. Like this is really, really sick. So I got a taste for New York and it was always in the back of my mind. I had worked at Heidi pretty much since Heidi became a thing. Heidi was Oscar before, which was when Blackbird first invested and then once it became Heidi, that's kind of when I joined. And so in the back of my mind, the whole time was like, New York would be pretty cool, right? Then you get evangelized on Heidi and I loved it. And I was just deep in the weeds of that for two years. And then I want to give you the full story of the company and how we got to the point. But we basically got to a point where I was like, okay, the problem we're solving is real. We feel like we've got product market fit locally. And we feel like the problem we're solving is ubiquitous across countries. So let's go and extrapolate and go find out if product market fit is also real in the US, the UK, someone. So I convinced, we'll eat and Tom and Christy, who sort of runs opposite Heidi. Like let's do a four week trip. Let's just go. We had a few users there because it was like, we were just doing paid ads at the time. And so we had a few US users and we said, let's go, go to like New York, Boston, LA, Chicago, like hit all the big cities and host little dinners, right? Just to get a feel for the market and see if we can just get a feel for it. Yeah, when they were in like a carry on, the four of us got there. We hosted this set of dinners. It was like a huge failure to be honest, the dinners. They were, they're a few that were good, but like you book out a restaurant for 20 people and get all these registrations. And then there was literally a dinner in New York actually, the one we did in New York where two doctors showed up. You're doing table and there's like four Heidi people and like two doctors and they're a bit like, no, what are we doing here? I stayed for a bit longer in New York. Yeah, because at the same time, the kind of product led part of the product was actually taking off still in in different countries. We were deploying a bit of spend to different regions to get a like feedback loop. Like what are the cash looking like? Is it significantly more difficult? And we felt like no, it wasn't. And so originally I just said, okay, you guys are going back. Just give me like another month or two to work out of here. Maybe I'll be more thoughtful on some events we can run. I'll get a bit of feel for like the market. I can localize it and things like that. At the time, my role was also very generalist. So I didn't know if maybe I was going to take over, take on like a field market, a style role or like a, this should like a conference quarter. Like we have no idea, right? It was just Jesse go over there and figured out and also we kind of know that you're just like doing a glamorous holiday to New York because you really like it there. And so two months go pass and this is the story of basically like us going from pure product led to then realizing that oh, there's like a sales component to what we need to do in the U.S. as well. We can go deeper into that, but effectively the TLDR from that was we need human beings to speak to our bigger clinics that are starting to get hooked because their individual doctors like this thing as well. So about two months in, I basically committed to like just saying that. So I had flown over another carry on and I still haven't been back to this day. Wow. That was that was about a year and two months ago, maybe a little bit longer. And so we started hiring our first people and that was kind of the story of how we realized that we needed to be here because we realized that there was going to be a real sales customer component to what we did. We couldn't just run like a hundred million dollars business out of Australia to the degree. I know Campbell obviously operates heaps of places, but product led sort of design is much easier to do mostly out of Australia than hand-to-hand combat with health systems in the U.S. So that was how I got there and then yeah my mom still goes me every day and says when are you coming back? I said just you left half your clothes here. My former mate shout out to Sam who also works at Heidi now. I told him like look can you guys just find like attempt to fill my spot in the house for a little bit and they're like yeah, all good. Left all my furniture all my cutlery all my clothes all like furniture everything and it's still sitting there to this day and I think Sam's going to have to move it out for me so thanks Sam. Be winding back you mentioned that you'd spent a bit of money on on marketing trying to just get like a bit of a groundswell of early evidence, traction from doctors. Can you go a step deeper into like what that exercise looks like? Yeah the backdrop of all the experience we did was it's like very novel to do product led in health care really at all. There's a few spotted examples but not really any huge ones like this doximity and a couple others but not like huge successes that are well known and so we needed feedback in a way that wasn't going to cost us like 12-month sales cycles talking to like executives. We also previously in building the product prior to the scribe which is what we sell now. We built a more bulky product it was like more of a practice management system basically like a CRM for health care. It's what all the health data goes into. It's was not fun it was not inspiring and also the feedback loop was so slow that by the time you sold the private equity owners of 300 clinics it got to the doctors and they're like this sucks why did you build this? That's like okay now we get it. So we went through that pain and that in combination with I think everyone in the company is like very much a product person like we idolize the notions the linear the canvass like we idolize great product and so we just wanted to build something that was like a fun and then be solved like a doctor problem for Tom and Mo and other doctors in the team and so in doing that the only way we could get quick feedback is early on it was just throwing money at like ads for instance it's almost like those you know Twitter grifters that do all the like e-commerce build a website we had a great product and it was working with existing people in Australia but it was really like does this work in the US oh well how great is this we're a product like company we just like throw a bit of like paid spend at it and figure out if it works and so there is depth to what we were looking at like we were looking at do the just indicators that there is any meaningful different buying decision or like product behavior so things like with a cax any different and that I guess told us a little bit about the noisiness of the market the cax work quite high in the US in the UK actually lower so like all these different regions are different giving us different signals but the US the cax are a bit higher when you're okay this is noisy not only within the segment but just more generally like doctors are getting marketed to by all these healthcare products or as in Australia that has really happened so there's that we're looking at like you know first week retention in the US they tend to give it one try and if they don't like them that one try they're so busy in their all the different parts of like our data analytics and you have the cax managing all the different of how did people in the world know how to do it? engage in buying behavior, how do people go through the onboarding funnel, all of those things, they gave us little bits and pieces of how do they like to buy, what is their nature, kind of user behavior information. But the only thing that actually mattered, the only thing that was important was we knew that it proved we had product market fit there with the product we were selling. And so that was enough to pretty much ship us out here. It's interesting that doctors had like a 30 second attention span to make a decision. It's like almost consumer app on the iPhone level of like rootlessness. How did you need to then evolve the product overall to, I guess, meet that bar? Yeah, so I think it's actually a big thing that taught us. So right now we're a real hardcore product like it's freemium model, which not only is product led rare and different in the states and in healthcare more generally, but like a freemium model is just doesn't exist, right? The concept is so foreign. Those behaviors taught us that if you give them a free product, you don't make them feel like they've got to put a credit card down. It rewires the psychiatry, like the thinking behind it as to, okay, I'm going in, this thing's free. I'm going to try it. We optimize the onboarding like do you show them the screen of the product first? Do you show them this screen? That's right. Like there was growth e stuff happening. I think the most important thing that we ever did to address that short attention span was make the thing free because now there is absolutely zero barrier to me trying the thing. You know, when you put a credit card down, it's like, oh crap, I better use it, right? Whereas when it's free, it's, oh, okay, I'm going to try a little bit now, but I know that if I can't get to that part of the product, I can come back when I'm free next versus my 14 day trial. If I don't do everything now, I'm just never going to use it ever again, right? So the freemium model was meant early on, the debate's internally about whether or not we should do that. A shout out Tom, because he was quiet for thing about it, like he knew, I guess that's the doctor kind of brain that he knew what that would feel and think. But like it sounded crazy that these AI models are pretty expensive a year and a half to years ago. The idea of having, you know, 60, 70 at that point, like 80, 90% of your users on a free tier and like it was a bit wild, but it was the most important, the most useful thing that we ever did. And it still reverberates to this day. There's so many benefits of having that beyond even just like solving that 30 second attention span problem. I think that the key point there is that also the team was had that additional, I guess, cuck. People are using the product and then you're just giving that money to whoever the foundational model is being used at the time. And so like theoretically it makes sense. You get to use a free, great, like the more friction, but there are many counter examples where like a eucalyptus, one of the like onboarding insights that totally accelerated their paybacks was actually to bring the payment flow earlier on in the decision. So you actually did have more buy in. So what is it about like doctors where the like that freemium is preferred? Yeah, I think it's the nature of actually having marketer structure and who you're like actual end and end by a money bag holder is. You probably can't make a great like unicorn business selling directly to doctors, making like you know, 60 bucks a month. Like yeah, maybe you could figure it out, but the difference, the nuance and you've got a solvux. It wouldn't be fun. Yeah, it wouldn't be great. You've got a solvux of a psychiatrist, then dentist and urologist and everything in between. Yeah. I think the reason it makes sense for us is that the doctors are like almost an entry point into the organizations that they exist in. Pretty much, and this is very US centric. It's a little bit different across like Australia, the UK, actually in the UK a little bit as well, but basically the doctors are your entry point into the health systems or into the private equity owned clinic groups or even just into their 10 person clinic. You don't actually really want to monetize off the doctor that much. You want them to be an advocate to get you in front of the decision maker who then throws down not only licenses for 10 people, but they also get the package that gives them the team settings and the team features and things like that. Right? And so I think the reason it works so well for us is because our competitors are all like headless B2B sales chickens like running after all the CMIOs, like steak dinner here, steak dinner there. I knew we went to the same frat. Heidi doesn't do dinner as well. So I'm not really clear. That's the one table. So we suck at steak dinners. Whereas like our like you think of the cost associated with that, like the enterprise sales, like just the table stakes things you have to do. You have to go to all the five glitzy conferences every year. You have to do this. There's a table stakes cost. You have to lay down. Our model, the free is the cost, like the cost of computers, almost that cost where the doctors are the ones running around like headless chickens saying, we love Heidi. This is the best thing since sliced bread. And the practice managers and the owners pick up on that. The really the really difficult thing about US healthcare is that in these big systems, you can only exert influence through the decision makers because nothing is allowed to be used on its own. So I as a doctor at a mount sign high, which is right next door, right? I can't use anything unless my decision maker is white listed the domain we've gone through security privacy. So that makes it difficult to penetrate an organization like that. Unless you go after the decision makers, the reason our free model works is twofold. One, the doctors are having such an important problem solved and it's free. So they actually don't care and they'll go against the will of their compliance and regulatory teams. Two, in the US, it's a kind of unique phenomena where most doctors in hospitals are salaried. And so they go and do like one or two days as a private physician out of their own practice or they're a part of a different group where they can use Heidi. And so that free version is like soaking up influence with all the doctors at the unit level. And then they're taking it back to hospitals and saying, holy crap guys, like I know we're piloting this product and I know that the CMIO went to school with this guy and we're probably going to use that product. But I'm actually using this outside and this is 10 times better. There have been a couple of those where we've one explicitly that way where they were trying something else. The free product was enough to get someone to just start trying it. And then if you amortize the revenue benefit of that account over that one like free users lifetime, if you pay back the cost of them using free for a couple of months like a million times over, right? Like literally. So that's how we think about it. The value of crews or the value is driven out of the bag holders which are the health systems, not necessarily the individual users. The individual users, like this sounds bad, but they're almost like our cacks mend. Like yeah, yeah, that makes sense. Yeah, so yeah, I think that's my worst in our case. It makes perfect sense. I mean, it's just the function of like adoring fans, the ground swell of like the people have spoken. Yeah, yeah, there's like so much unattributable benefit from having more people use your product. It's like one, you get more like hits at base. So you're getting feedback like this versus back to my point about like enterprise sales cycle. You get feedback once every 12 months or you get feedback from the C suite or you get feedback from like a couple of the doctors that are not having a good time. Resware just like constant fire feedback. The other thing is that you win like ace-metrical pockets of the market where your competitors don't go after. So the Microsoft I'm going to use is the you know, the goose here to make fun of, but they don't get to win over the like lactation consultant out of Idaho that's got a following of 50,000 doctors in their private Facebook channel. You know what I mean? Like you don't get that opportunity. There's all these like very asymmetric people and sort of networks and influence that they have. It's just like impossible to win them if you just focus on the C suite. And so not only is they're like the directly attributable, you know, revenue benefit, but there's also just the influence you get on the market, the company you build the product culture. I think problem like would have alluded to it, but it's just a totally different set of skills. And I think it gives us like a pretty unique advantage. Definitely. You mentioned that the role when you first landed was undefined. And to an extent almost feels still undefined. Yeah. It sounded like there was an interesting dance between how the product would be structured and then by extension how the team would be built. And so one of the things that you mentioned was like, okay, we're going to have almost this sort of like inside sales account expansion team. But that really only works when like you have the triggers in place to be aware that oh, like we now have a groundswell in X, Idaho. Let's go. Perhaps you can talk to that dance between building the team and building the product. Yeah, it's also something I think we got wrong initially. We had this very idealistic view of I mean, because we were seeing at work, like the product individual doctors were signing up, trying the free, doing the trial, converting to paid. It was like the canonical product led the fabled story, right? We thought that that would then extend to like the 10 person clinics, where the 10 person clinics would then set up their administrator and they'd go on and they'd put in their credit card for everyone. And then we'd figure out that and then we'd go and build the self-service for the bigger teams. Like we thought we'd just start to choke off bits of the market with product led solution. To this day, that's not the case, right? Once you get above one degree of separation between the user and the decision maker, it's got to be a sales call. The history of healthcare technology is really expensive stuff that costs tens of thousands of dollars per doctor, where you can afford to put a human in the loop for every single conversation. You can afford to fly a human out to a Idaho, you know, rural site with three people because they close that deal. It's a 30,000 dollar deal, right? We thought that would be a little bit different with cheaper product led type of product. It hasn't proven to be the case. I don't know if that's something that changes over time. I think yes, but for now, and when we first came, that's not the case, we realized very quickly that to bring on five, ten people, you needed someone to talk about compliance. You needed someone to talk about how they'd use it. You needed someone to show them how to set up a microphone, right? The things that you take granted in these SaaS product led industries, you can't take the granted here. We needed to hire people that did a really good job of playing the role of the product and pulling people through to success. Our salespeople were really just kind of success people. I think you alluded to it, right? They weren't salespeople. They weren't ring fencing things behind trial finishes. The products free, they can use it if they want. They want to convert to pro, they need a laundry list of things to tick off. So, early on, we optimized for people that could deeply understand, explain the product and deeply empathize with the user and bring them on that journey. We've started to build the things in the product that ease the work or the burden to move someone through a buying process. For instance, shipping six months ago and administrator seat where they can add people on their own or they can edit team templates or whatever it might be. That probably cut 20, 30% of the work that our humans were doing. Right? So, I think it's a process that evolves where very early on, the human was part of the product. But even when we were selling the most expensive tier, part of it is you get a human assigned to you. So, I think over time, the case mix of product and human urge towards product, but I still think you have to orient the company around solution, solving, customer success. All of our salespeople in any other company would be customer success people. They're friendly, they're jovial, they're enjoyable to work with. They aren't sitting there going like, well, I've got a quarter to meet. So, if I've got to do, you know, it's all like, I just want you to have a good time on the product and you probably need me in order for that to happen. So, here I am. So, that's kind of a mix of product, human, but we're still tuning that very deeply every day. We had a small stint in New York while you're probably partying during your semester off. But like two things. One is often the best hires find these like undiscovered pockets of talent. Two is that actually you've never lived in New York. You're an Aussie in New York. Like oftentimes founders will be like, do I hire someone who's a New Yorker or like, or else they're from and like, who should head up the office? How the heck are you hiring such an epic team? Yeah. Well, when we first got here, it was kind of intuition. And now I think we've pulled like the factors out of the intuition that we can somewhat scale a little bit better now. I think when we first came, it was what I said. It was, we needed people that our customers loved talking to. Honestly, that was like the kernel. That was the thing that mattered because that was the whole brand we were building. So our first set of interviewing and hiring people was, okay, we need someone to, like I just described, bring them on a buying journey from, they want the product for their team, they want to buy it sort of holy. We went through hardcore American sales people. We went through people back in the Aussie team. We thought about it all and we actually got pretty lucky with our first hire. I'll shout him out, Yashan. Yashan out of the shan. Yeah, vetted American salesperson that had run like sales consulting teams and done sales first hand. But then he did like four years in Australia working in like Australian settings. And so he was on his way back from Australia to New York. He said, you know, I want to be close to my parents. Like I'm coming back to New York. It was just totally serendipitous that he kind of had the Aussie experience. And I do think back to what I mentioned very early on, the Aussie vibe for lack of a better word actually was really important early on because you default to making the customer happy and being very relaxed and cordial. And so we brought him on and we're just like instance success through his body at problems. Like he would fantastic. Like to this day, like what total legend. I won't pick him up too much because then he'll he'll make fun of me in the office. But you know, do respect this juice. Well, yeah, I'll make up. Then we brought on kind of like our next two people, which for us it was almost like internal process. There were just all these things that we needed to do like setting up our hub spot, setting up this because it was a bit different. Like the company was growing at the same stage in all regions. It wasn't like we figured it out in Australia then came to the US. It was we're figuring it out everywhere. So the archetype we started to bring on were what's the word like they were total generalist that had not been formed or molded by any particular industry in any one way. We weren't looking for sales people because the sales playbooks didn't work. We weren't looking for ops people because to hire someone from Uber who did ops like there's a very specific way of doing it. We weren't hiring a customer success people that worked at Gong or whatever because we didn't know what the methodology was going to be. And so very early on it was like generalist A, B, do we like you as a person? Like you're going to be in the office 12 hours a day like building a startup that might go under and I might have to go back to Australia. So hopefully you enjoy time together. And then three just incredible people to put in front of a customer. Those are like the kind of the three things. Now what we've extracted I think from that initial intuition it was not clear for when we were doing it in the moment but now that those have kind of become the core tenants of what we look for because pretty much everything we do here in some way shape or form is talking to a customer. Otherwise you won't have the great empathy for all the things that they do. And so those are the principles that still guide us now I think. And we're actually at an interesting point now with the size of the team. It's like 15 20 people where the generalist part of it we've almost sat. All that can be sacked out of generalists where we actually are starting to hire our first like specialist like you are a field. Yeah, I actually think it's like the perfect course because you bring in the people that aren't good at anything but are kind of good at everything. And then you get to a point where they built it up to you know 80% and the last 20% is the hardest but that's the thing that you you win out against competitors around. So like field marketing for instance, customer support, having actually now like dedicated people for certain parts of enterprise sales processes like if you asked me six months ago I'd say like get that out of my face. I don't need that. But now it's we need it because we're limited in how far we can go to the next phase without that extra 20%. So also I'll plug that we're hiring like 10 10 rolls. So if you want to come and and and roll around in the office it'll it'll be a good fun. Yeah, that's kind of an all thesis I think. I don't want to draw the wrong analogy. I remember speaking to someone who used to work in the military. A late SIS. And I was like what's the difference between like the Aussie SIS and like the siltane. And the way that he was describing it was like if it was a general one V one Aussie's would win. But if it was a specialist like sniper off or any equivalent of that the US would win. Do you think that's true of like some talent in Australia versus US like maybe even just like the younger they are is there this sort of laser focus or am I picking it straws here? No, it's really interesting. I think it's like 100% true. I'm trying to like as you're talking about trying to think about why it might be because it's 100%. Like it's what we've experienced fully. A the it's not necessarily just an Aussie thing. It's like it's an it's an approach to things. I do think maybe there's a very American way about going things where from from the cradle you kind of know what you're what you're shooting for. Right. Resin Australia it does feel like. people pick up things differently or I don't know if it's a product of like the really excellent people at a very specific thing. If they come out of Australia they tend to move to the US whereas the people that are in Australia are just the generalists like the people that if they weren't, if they were so specifically good at something they would go to somewhere else in the US where that's like highly in demand because there's a hundred times the companies and so you're more likely to find the I don't know legal procurement pricing sales, AE role somewhere in the US than you are in Australia. So I do think it's true. I can't I can't think of like a good reason as to why but the other thing that's been a big success for us which is on a similar vein is hiring young for the exact same set of reasons. So you haven't been jaded by an industry, you haven't learnt the wrong set of skills that worked really well for company A but now don't work here and you've got to spend half the time unwinding it. You're kind of just like a fresh set of eyes to throw at a problem and again if you just hire people that are smart that you like and throw them at a problem they can kind of first principles their way out of it. And so yeah that Aussie and young I guess kind of exhibit those same traits and so it tends to make up the shape of the team but we found people from the US that exhibit that exact same behavior it's it's the thing that we look for like it's what's most important to us. And how do you think about compensation from day dot? Yeah such a good question. This is this is right now the the thing that I think about the most. That's pretty you're a wizard. No, it's not. Yeah it's really really really hard for a multitude of reasons. One is like the stage of the company we're at. I wish we were in a place where I could project this much quota, this much revenue we're expecting this is the year on you grows so you know we work backwards from a revenue target. We're unlike the steepest part of a gradient and for me to like look at an A in the eyes and say hey you've got to deliver this much quota this this quarter is it's just like totally unfair and I wouldn't even believe it myself and so our sales reps right now and I call them sales reps but they're like I said they're more customers except like just the people that are closing deals. Right now we have a great group of people that were part of that early team that are so viscerally part of the mission we're on where if they close a million dollar deal that's maybe an extreme example they close a hundred thousand dollar deal they're not thinking oh well if I was on a 10% quota I would have got 10 grand of that they're thinking holy crap we've just made like a serious movement on our revenue number for this month and they're thinking about my equity and they're thinking about the glory of startup winning and so there's a part of compensation which I think is early on you can rally people around the right incentives just by way of them wanting the right thing out of the company this will change soon I'm sure of it as you get people in the team gets bigger the deals get bigger you know the million million dollar example probably if someone closed a million dollar deal they're gonna want a bit of it right and that's totally for a lot of it and so it's really hard right like I I constantly go back and forth there's people in the team that would probably be more receptive to it people that probably wouldn't be but then you've got different people in the sales team on different comp structures and if they find out it gets ugly and it's it's quite quite a complex problem and then the other thing that makes it more complex is across functions like I said pretty much everyone is facing a customer and is in some way shape or form driving revenue through the door how do you then compensate the like Allegra is a great example of this she's out head of kind of implementation customer success we're bringing on like one of our larger clients at the moment and just I'm never seen someone go harder at a problem and do better at solving like implementation when when that deal like renews or when they come in for the first time they were just as important at closing that deal as you know the person that got it through the door and then the compliance team then's three months going back and forth with the legal people like everyone kind of it's it's together and so this is something I think about a lot which is in the early stage how do you incentivize the right things in the right way to drive the behaviors you want I've found and I'm not going to say I've got a perfect at all I've found that the biggest motivator is getting people to corral around a shared mission and like really buying in on what the upside of this opportunity could be like paint the picture of if all of us do what we're meant to do in 12 months we'll be here and holy shit doesn't that look incredible right what does that do for equity what does that do for our personal brand like all those things I am totally conscious that at some point you need to just give the sales rep 10 percent of the check that comes in I don't know when that is and I'm honestly not looking forward to it and we've tried experimented with other different methods that like I won't go into for different reasons but really the only thing that works is like either end of the spectrum they're either like compensated fully by by or incentivized fully by compensation and that sort of thing or they're incentivized fully away from compensation and also as a like a young guy looking after the 10 it's also always like uncomfortable and that's just maybe me as a person like I can acknowledge that but I hate like telling being the arbiter of like if it's if it's not on like a very objective scale like performance bonus we've experimented with before like you get a three out of four this quarter you get a four out of four yes we can write down on the board like what the goals are next quarter but what if the priority shift which they do at our stage right and so it's it's just something that's very difficult and I found the most reliable thing is just getting people in on the mission it's equity it's buying the the goal that we're trying to achieve I think over time like that becomes a more sophisticated equation I think if anyone got up at a bed and we're excited about performance managing around compensation I probably have some question marks on their character what kind of weirdo are you exactly that is a complex problem and I think you've sort of like glued at it but incentive alignment between what what our dependent teams is the beauty of equity and hopefully compensation structure is down the track exactly that's that's the one nice little gold nugget we can dangle in front of people that they always like no matter what their role is yeah totally right when you were launching in the US you've spoken about the archetype one of the other big questions is how do I infuse the culture of what's made high-eat special in Australia into our new office I know a site mate partly literally was overseas for many months at a time founder and CEO of site mate blackboard portfolio company and just went over to their own self like plug plug plug well I was just like in awe of like so Tom hasn't taken that approach which is probably healthier for Tom than it was hardly so I'm just curious like what the what the approach was with the team yeah that's back to my point about like being a node like the good thing is that I was there from zero at Heidi so like I had context on the decisions enough to where I could like explain most things right why are we here why do we choose this why is this that whatever to give Tom his fair credit like he is up here quite a bit to be honest he he does his round trips and then gets yelled out when he goes home for leaving and then it's like jet lag and I should go to the UK this last trip that we did was just a total nightmare but in the periods where he's not here and especially early on when it was kind of just me trying to bring people on and crowd them was if you can get someone to like a good enough understanding of why things exist in the way that they do rather than just being very dogmatic about no this is the CRM we use no this is our approach to customer success no this is our approach to sales I think if you can give people a the context on it but be the freedom to go and rewire those like fundamental systems that gives them enough insight on like the underlying decisions in a way that that marries them around the the shared kind of style and vibe of the company I also think being and I say this about Rags as well Raga who runs our UK team in a similar way who also kind of shipped off to the UK in a similar way having been there from the start you're also kind of a little bit of the reason why the company is the way it is for better or for worse right like you are the reason they're about habits you are the reason that there are these good things as well and so just by nature of having been a formative part of the team you just by exhibiting the same like tendencies and idiosyncrasies can kind of create a similar environment here now in having said that like they're very common threads with the New York office and the Australian Office, the UK Office, the Australian Office. But the New York office is quite different to the Australian Office. The ways of working, the ways of communicating, like the styles, all the things that make a company a company are like slightly tuned differently. And so I do think while there's a common thread that unifies it all, they do tend to take on different shapes and forms. And I haven't been back to the Aussie Office yet, but there have been people in the team that I came over from the Australian team and then have gone back a little bit. And they go back and they're like, whoa, like I forgot it was like this. So there is a duty to bring people on the shared mission, but there is also a duty to not be afraid to build it from the ground up where it makes sense and contextualize for this market. Because different markets, different requirements. And I think that's been really important for us. To what extent does capital allocation play a part in your role? Yeah, I think the good thing, or maybe the bad thing, is that the founders trust me a lot. We'll lead our CFO. He wakes up in cold sweats in the middle of the night and text me about, you know, certain spandle things like that. But I think on the whole, trust me enough to where it's not as much of a push and pull where I've got to create a robust plan of, okay, here are the targets we've got ahead in order for me to get this funding to put towards this thing. It honestly is more like the intuition that's got us here has done us well. So like, let's continue until something breaks. And that's not to say that we're spraying and praying in any means of the word. But I think there is a lot of freedom to trust that the people at the front of each of the markets, like again, rags in the UK, myself here, kind of have a good enough intuition to where like, here's a $60,000 conference. It's a lot of money. That's the most money we've ever spent on the conference before by an order of magnitude. But you think it's worth it, right? Let's do it. And then we'll look retrospectively and say, okay, was that a good bet? Yes, no. Why was that a failing on my intuition? Was it a failing on some other assumption? And then that just kind of, again, like, builds the intuition and the trust over time to where now outside of like major decisions, a lot of it does just kind of like come down to regionally what we think is best. And the investments across the different markets are so so different. Like the UK is investing a lot of money in things that are very different to what we're investing in here, which are very different to what we're investing in Australia. And I think it's really hard to do that successfully. If you have like some centralized arbiter of what those things should be. And I think that's testament to Tom and Willeid, the founders and you as well, the technical founder, like we've found a great sort of relationship there where we can it's at a moment's notice, like the time to make a decision goes at the speed of making the decision, not anything else that would hamper it. Hmm, I love that. On the topic of bets, what are two big bets that have gone well? Okay, two big bets that have gone well. I think there was a fundamental thinking at the start. And I think we've like, we briefly alluded to it, but the product led motion would lead to enterprise success. That is a big bet. And when we were doing our like series A, that was the thing that turned most of the people that said no way. It was, look guys, you've got great metrics, product led. It's the best thing I've ever seen. It's growing like crazy, but to win in the US in healthcare is to win all the enterprises. And we don't we don't see the connection. We can't make the jump of faith that that you're going to get to enterprise. We were seeing from conversations with doctors, from the ways we were winning like SMB deals and mid market deals that no, no, this is happening for real. The reason being is that this category of software, this AI scribe, is I think the first piece of technology in healthcare, maybe in like a long period of time, where it's actually designed for the individual doctor to get joy and benefit out of it. You think of things like electronic health records or booking portals or all these things that gets population health tools. They're getting sold to healthcare for some other user. Not to say it's not useful, but it's not for the doctor. Typically actually the doctor sold because of it. You talk to a doctor, they hate EHRs, even though they're probably like a net positive on tracking and data enablement and things like that. The AI scribe means that the doctor has two hours more time per day to do what they want with. So that's the assumption one that you have to make. The next assumption you have to make is okay, what are the decision makers, what are like the axes with which the decision makers are evaluating products by? The net benefit to the company, in the case of like an EHR, the revenue uplift, in the case of population management, the health of the users. In the case of an AI scribe, they're looking at which one is the doctor going to use the most. If we're going to go for 4k out millions of dollars on this tool for 10,000 doctors, which one are they going to use the most? Which one is going to see the most adoption? So the second assumption is that the decision makers are going to look to their clinicians to ask them which ones do you guys like, want and which ones should we buy? Which again is very different to anything historical. A CMIO doesn't ask the doctor what EHR they want, or at least if they do, it's very rare. So if you take those two things, that A, the product is built for the doctor, which it is, and that B, the decision makers are looking to their doctor, it's pretty, it was really obvious to us why making the best product for the doctor and going product led would lead to enterprise success, because you infiltrate all these organizations, you win over the clinician love, and they rally together until their decision makers, which one they want. That came true in a lot of cases, just in smaller doses, and also in more so overseas than in the US. And US investors, most of them, for some reason discount like anything that happens overseas to zero. If it happens overseas, it's not real, right? So the biggest bet we made was staying true to that, and it started to pay off. Like we're starting to win now these multi-million dollar deals, these health systems, like the Beth Israeli, he helps of the world, the Franciscan health of the world, things like that, just because we won the individual doctors over. So I think that's the biggest bet that's paid off. I think kind of a subset of that big bet, and one that we probably talked about quite a bit before was the free version, huge bet, right? Like you're staking a lot of things on that, you know, poor the lead, you know, early on like CFO had on, we're not making this thing free, don't even think about it. That bet is a hard one to make and have conviction in, but again, like that, that is the accelerant that powers the rocket that is product led him to enterprise. Those are I think the two that were the most impactful and that have paid off the best so far. And well, I'll bring it to more specifically to you, what's been a bet that you've made in the last 12 months where you look back and you go, yeah, I'm quite proud of that. I think hiring, like the types of hires that we made, I think it's really easy to get wood over an interview with someone that's closed a million dollars at GONG, and I keep using GONG as the example because they're a great company. They are to me, they've pitted me of like sales. So like these really seasoned veterans in a very specific thing, I think it's really like easy to get led astray by that because they paint your picture of what a sales organization looks like and you go, wow, you could just build it for us. You can do it. Whereas I think it takes a bit more like cajonas to bet on someone as a person and from their personality and what they believe in and the things that inspire them to bet on those kind of people and see them win and do better than the specialists in all the other worlds. I think that's been the most rewarding bet that we made that I think like I early on tried to really champion for. It would have been a very easy and a understandable decision to say we need to fill a sales role, let's find a season bet with five years and like entrust them with the process. It's a bigger risk to take on to bring someone on that's come out of this industry that is totally orthogonal that has never done healthcare, never done sales, never done product where I'd never worked at a startup because you believe in them and see them flourish. So I think that's something that's most rewarding for me. Yes, you know, you close this huge deal and yes, you do this and the company is growing and it's fantastic, but for me, the thing I get the most like the thing that I feel is most rewarding is when the people grow into what you think they can be and that to me has been like the biggest bet that we made. I love that. At Blackbird, we call it the the Hungary not the proven, but it sounds like that's that's been an instinctive decision that is paying off in real time. I think it's like the bet Tom and Waleed made with not only myself but like other people early on as well. It's like who are these kids? They don't have any software experience, they don't know SaaS. Heidi was like literally my first job out of university and so like it just feels right. That's kind of the culture that exists. So yeah. What are two perhaps company bets that were made and one personal bet that was made that did not work out? Okay. So I think that like the other side, like the two sides of the same coin. One is we thought that product led was going to lead us to the stars. I think alluded to it a little bit before, but we thought we'd have this lean machine, marketing machine, the again, inspired by Canva, inspired by Notion, inspired by Slack, we thought we were going to product led our way through healthcare, especially in the US. no shot, like bad luck back to the drawing board. I think we state a lot of energy, time, product, build, everything on that. And I think it took us quite a while to unwind that thinking we had to reorganize the types of people we hired, we had to reorganize in the types of like go to market motions we were deploying in different places. That was a bad bet, I would say, like I'd be honest, to be honest. It was a great story. And like we could sell ourselves on it. But look, we just need to make it this much easier. And then we'll cross the valley of like getting a team to self-service. And then we'll cross the valley of getting this to self-service. And at the same time, we're like, you know, thinking about our Slack experience. There's 100 of us on the Slack channel. And we've never talked to a Slack account executive or customer successors. And it's like, we could do the same thing. And just like, no way, just didn't work. That was a company bet that I think we learned pretty quick and acted on it quick enough. A bad company that we made. I'm gonna go, I'm gonna throw it back, to be honest. Like before Heidi was even in the US. This comes back to the hiring part of it. And it's part of the reason we have such like a strong visceral feeling on what type of people we want to hire. It's because there was honestly like a period where we hired in the wrong way. And I have to do this like cautiously to not be mean. But basically the more degrees of separation between like the founders, the head of the snake and the operators, the young guns that are going and doing the thing. The more pain a company feels, I think, at an early stage. We made the mistake early on of hiring too much in that middle band where like beyond anything else, it was kind of clutter. Like it was processed for process sake. It was people that maybe had like incredible history and like very sharp intelligent people that just couldn't make it work in the startup world. I think that was a really big bet or like approach we took that hurt us, nearly toppled the company to be honest. Like we were in a very downward spiral. Go ask Tolo, like some of those board meetings were pretty brutal. And then I think once we got back to like founder, head of the snake, operators, doers. And the founders themselves are like doers as well. Like they are one and the same, right? Like Tom's doing it spending as much time on Figma and like doing PRDs as like our head of product as is the design team as other individual product contributors, right? Will lead is doing as much like enterprise selling into the NHS as you know, Rags who runs like the kind of the team there as well. So I think that was a bet that we learnt from pretty well. But it was one that like we were close. Like like last couple thousand feet, the airplanes like yelling all the bells out of us. And like, that's a great analogy. Yeah, I think maybe. And then the personal bet, I think it's honestly a bet that I've still like doubled down on. And I know it's not good is just like finding balance. Like there've been periods like over, for instance, the Christmas break in the US. It's like a lot more hardcore shutdown than in Australia or like other places like it's really hardcore. No one's working. I've never like performed better or felt more clear and like better performance than like the couple of weeks or months coming out of that really nice break. I think I'm definitely like hitting the throttle now day to day where it's like red line every day. And probably like net output is not fantastic. Like compared to if I was more diligent with taking time to do other things and stuff like that. And so it's like personal, but I think getting balanced right when you take on a responsibility like this and you move to a new city and you do all the things that anyone in that given that opportunity would do to be able to like find balance that is not balance in the way of like, you know, a clock of a five and you do thing, but like balance in a way that at least like maybe you're in like one gear below red line, right? It's a thing that I still haven't figured out and like betting on the company this hard personally is probably like short my talismas or something a little bit. But I'm but something something I know I have to work on at least. The problem is I tried I went for I went, okay, I need six days in Antigua, right? Okay. I grew up on the beach. So I'm like huge beach kids like the part of my home sickness is most that I feel the most is beach, summer, sun. So I think all right, middle of winter in the US, I'm going to Antigua, I'm getting 30 degree weather every day beach. It could not get more perfect, you know, the team is fantastic like I can throw them things. This is really bad. Like the whole time there, I felt more agitated than I ever felt in my life. I felt like I was, I felt like I was in a free fall like back to the plane analogy. I'm really like reaching with the analogy now, but I felt like I jumped out of the plane like free myself from the notice dive, but like the parachute wasn't pulling and the plane was still going down. And everyone I love was still in the plane. So I like, I kind of like free fell back into the plane and I came back like two days earlier because I just hated it. So there's definitely like deeper set things that need to be figured out about ways of working. If anyone knows the truth to that, that is like withdrawals where it's like the first week is always hectic. Yeah, yeah. And like you're not, you haven't switched off. Yeah. Even though you would, you've attempted to, you know you're in free fall. Yeah. But it's like, oh, like do I need a month off to like really reset or it like minimum two weeks? Like if anyone has any solutions there, just hit us up. Yeah, please, please, I'll do anything for life at last. Because it's also like, I think you can pick your struggles at some point. Like what is the struggle I want now? Like maybe it is a bit more tired, maybe it is a bit more like lethargy, maybe it is, you know, all the things that come with being quite hardcore. I think overall like the sentiment from being here and from what we're doing, especially the team back to, like not to bring it back to what we're talking about before, but it's just being around incredible people. It doesn't really in the moment ever feel like exhausting. It's more like when you really zoom out and it's like Sunday afternoon and it's like, what did I achieve last week? Okay, here's, you know, 100 incredible things our company achieved and what we did. Like did I learn a new instrument or did I, like experiment with a new recipe, right? Things like that where the balance part, the balance equation is just, what are you optimizing for? So it's constantly a work in progress. Do you know what you're going to be optimizing for over the next year? Yeah, more my knees in the bank. (laughing) The Heidi that is, yeah. Yeah, I think company-wise, yeah, there's like a company answer in a personal quote, like answer. I think the company answer is you see now we're like, in each of these different pockets, we're hitting like a point where Tom can't be involved in everything. I can't be involved in everything. Even the people that like roughly look after that area focus can't be involved in everything and we're having to change the ways of working to where like, you kind of just have to relax and accept that you will never be able to control everything in the company to the degree, like to the degree that you want to. If we've done a great job in a year, it's like all of these cylinders are firing autonomously. The layers of reporting where it makes sense, makes sense and the teams are talking to each other cross-functionally, really nicely, but there's no one that's like the actual puppet master that's pulling it all along together. That's where we're at now. It feels like, at least where we've got our key team that are in the weeds of everything and that's why we succeed. But we're hiring like 10, 15 roles at the moment. That doesn't sustain much longer where I want the company to be in a place where in a year, like the cylinders are firing independently, right? That's a completely thing I think is really important. Personally, it's a good one. Personally, Korea, I think it's like Sappy and it's the same version of what I just said for the company as well. But if I can empower all of the people in the team to be profound leaders and very prolific in what they're trying to pull off in their teams and to do it completely autonomously, that for me, like I said, is the most rewarding thing. I just want like a hundred times more that. Like a hundred more leaders that are running their teams as an extension of the fundamental Heidi DNA, a hundred more people that are taking ownership in a way that we think is incredible. 'Cause I think it's like, you then look at the company and it's a thousand little versions of mini versions of like the Heidi that was there in like the shitty six person like Fitzroy Loft, right? - Yeah. - That is so incredibly rewarding beyond anything else we do. To see people like grow into their role is just, it's the best thing ever. And so more of that please, whatever that is, that'll make me a happy man. - One final area and I'll let you go. - Yep. - You'd left Heidi at the end of 2023. - Yep. - You were, I think the head of Alps at Hattori and then you rejoined Heidi again. - Yep. - First of all, for those who don't know, just share like why you'd left and then like going into the abyss and then why you decided to come back. - Yes, so there's nuance to that. So A, the role was like totally made up. There were three of us. So I wanted to be head of ops at the time. Who? I was still actually working at Heidi while working at hatchery. So let me explain what hatchery is. So hatchery was an idea from Moe, who's the head of product at Heidi, around how do you create, I guess what we would now call like an agent, like, but this was a bit before like the kind of the concept of agents. How do you create like the agent of education for an individual user? Like how do you get them to some predefined outcome or goal, whether it's like a learning goal, or test that they want to pass, whatever it is. How do you just like, or put them in like order a pilot to get them to that end goal by like, surfacing them, YouTube videos, surfacing them, question, bank, surfacing them, mini-tests, like basically create the hands off, road to succeeding in a learning goal. At the time, Moe was kind of like, I'm in lighting that on the side as a little side project. It was him and one other founder of hatchery, like a technical founder. I, at the time, was like, BDI, do know kind of the world of startups. I was starting to get the feel of it from Heidi. I kind of knew the lingo. I started listening to all the podcasts that you have to listen to. I was like, oh, this is great. Like I get it. Startup is cool. And then like Moe, Moe's, most fantastic. Like he does a great job of like selling you on the vision of hatchery. And we would just talk about it constantly. Like in the office, we would pass a house hatchery going like, this and the other. It became quite clear, quite quickly, that like I was somewhat more enamored by hatchery and what they had going on, like literally the two of them, compared to what was happening in Heidi. This was around the time that I alluded to before, where we had that kind of like messiness in the company, where in this downward spiral things were, to not sugarcoat it, I was hedging bets. Like completely, that's what I was doing. I wanted to get experience in like an even earlier stage start up. And I wanted to do it with someone that was at work. So basically what would happen is we broke in. Heidi was very like nine to six kind of culture at the time. What wasn't fantastic. Six o'clock would hit. Everyone goes home. Me and Moe were there to like 10, 11 p.m. doing hatchery stuff all night. That was such an incredible experience because it was, I got all the like the learnings from going like real hard for zero to one, like no venture funding, no money, where like $10,000 is all that's in the bank account. We're figuring out where to spend it, like literally down to the decimals. I got all of that experience without necessarily having to take on all of the risk of doing that solely. Again, back to this idea of balance. Like it came at the cost of like any sleep. There were, that's when I had the most like sleep overs at the office in my life. But that told me two things. One, it taught me that you can't do two things exceptionally well in that kind of world that are like that side by side. I spoke to Walid a lot who's our founder and a bit of a mentor, like great manager. And he was very, like he knew what we were doing, like very intimately involved. He was very helpful actually. But it was very clear like at some point Jesse, you have to make a decision by what do you want to do, right? It became clear that that level of risk appetite actually wasn't for me at the time and probably still to this day isn't worth it. I felt like I was learning more in an environment where we'd kind of de-risked it where someone like Tom had already been a founder and had those experiences and now bringing the founder experiences here and having the startup experiences in a slightly more like safe way. That was what I wanted more versus like just hardcore, like if it fails, no one knows your name, no one knows the company, you never raise money, no one cares about you, like bad luck, you're off to go like start off with the next pack of graduates that are looking at MVP gigs or whatever, right? That's not, I think what I wanted and that was kind of the second learning. It was like the risk appetite I had was like pretty far down the curve of like high risk, but it wasn't all the way at the end of like full on zero to one. Now having said that what we have kind of done in America is go zero to one in some way again. And so I think there will probably be a day in which I go, all right, let me solve something that doesn't exist. But at the time, I actually, like this is the advice that I give like friends in startup world or that like have an inkling, like a spark when the right for startup is maybe don't go like all the way in zero to one unless it's something you like cannot stop thinking about. If you want startup go Z series A even like series B, build the tools, learn the lingo, learn the stuff, get first principles experience whatever, but like first principles is like my least favorite phrase. So when I say it, I have to like, I get sick inside. But get, and then go take it somewhere else. That's what I thought and that's what I kind of tell people sometimes. - I love it. Jesse, thank you so much. That was so much fun. - Yeah, yeah, this is a leap. - It's been so good. (upbeat music) - Thank you so much for joining us on this latest episode of Wild Hearts. If you want to learn from other ambitious people that are building, designing and creating the world that we want to live in, then please hit the follow or subscribe button. It would mean the world to us here on the Wild Hearts team. We have an insane producer, Melia Rainer, an incredible editor, Annie Jones from Walkin' to Day One, and our marketing and content support is provided by Jonathan Blakely and we couldn't do it without them. If you're searching for investment, please, my DMs are open, far me on LinkedIn, I'd love to help. And so with that, we'll see you next week, Wild Hearts. (upbeat music)