# Why You Need a Growth Hire Pre Product-Market-Fit? Why Every Company Will Be a Media Company and How To Do It Communities; What Really Are They? How To Build Them? What Makes The Best? Why Do Many Not Work? · Kieran Flanagan, SVP Marketing @ 20Growth · Aug 10, 2022 · 55 min · 12,491 words Speakers: Harry Stebbings, Kieran Flanagan Source: https://www.996.fm/episodes/20vc--ep-b6730901/ ## Cold open **Harry Stebbings** [0:00]: Welcome to 20 growth with me, Stebbings. Now 20 growth is a monthly episode where we interview world leading experts from the world of growth, and today's discussion is a total mind meld between two content creators who really love their craft. Totally off script and totally unplanned, it is a fantastic discussion. And so with that, I'm so excited to welcome Kieran Flanagan, SVP of marketing at HubSpot, where he's helped the business grow internationally, move to a product led business, quadrupled its marketing demand, and built out its media team, including the acquisition of The Hustle. He's also an adviser and investor in many incredible early stage companies. And I wanna say huge thank you to HubSpot CMO, Kipp Bodnar, and Dharmesh Shah. Some amazing questions, suggestions today really did make such a difference. But before we dive into the show today, ## Sponsor read **Harry Stebbings** [0:42]: do you really think you should be spending your time on building and maintaining your data infrastructure? Absolutely not. Your time is better spent on data analysis, and Mozart data helps you achieve this with that out of the box modern data stack for startups. Set up your data stack in under an hour with no engineering. 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Just clean data on day one when it matters most. If you're ready to onboard millions of rows of data, head over to flatfile.com to do it in minutes. But that is enough from me. So now I'm so excited to hand over to the one and only Kieran Flanagan, SVP of Marketing at HubSpot. Three, two, one, zero. You have now arrived at your destination. ## Conversation **Harry Stebbings** [4:13]: Kieran, this is such a joy to do. I so appreciate you taking the time. I heard great, great things and great stories, by the way, from your colleague, Kipp. So thank you so much for joining me today. **Kieran Flanagan** [4:22]: Yeah. Thanks for having me on, Harry. I'm a fan. I'm excited to be on and excited to speak to a fellow European. I mean, is rather lovely to have another **Harry Stebbings** [4:29]: European on the show, but I do wanna start. You run and work in some of the most impressive growth orgs now obviously at HubSpot. How did you make your way into the world of growth? And what was that entry for you? **Kieran Flanagan** [4:41]: Yeah, I think that I'm a computer engineer by background, went into marketing, have done a lot of different things in marketing. At some point was asked to build a product led motion for HubSpot. I was very fortunate that pre me, there was a guy called Brian Balfour who set up a lot of the templates and the ways that HubSpot could do this and had the opportunity to do something quite unique at HubSpot when we were an established company to build a PLG motion and build out the marketing and growth and kind of learned on the job because I was a marketer going in to learn about growth and do growth. I've kind of just always tried to do the thing that I think is the next thing that's important. That's what I actually get excited by, like the new thing. **Harry Stebbings** [5:19]: You mentioned obviously kind of PLG, but this is PLG before PLG was such a term and so popular. How do you think PLG has changed as a go to market in the short time that it has been so popularized and used? **Kieran Flanagan** [5:33]: Yeah, I think there's three stages companies go through and then I'll talk about how that's changing in the market. The companies generally, even back then, they go through the phase where they're like, hey, we should do growth without really knowing what growth is, but they want to move a metric in a meaningful way. So they try to do that. They do it in a way where design and all of that is an afterthought. So it creates chaos, but at the chaos, there is something good. They're like, wow, growth actually works. Let's get serious. And they try to create then we go from chaos to centralized. Like we create a centralized team. We build a growth function, we decide where that lives within the org, the founder sponsors that, and that starts to work really, really well. I think the next iteration of that would to me is we have central growth teams and they do growth principles and they work with a product team to instill those principles in how you create product, how you do onboarding. I think at some point you can see growth being much more decentralized into just how PMs create the product itself. We build in mechanisms to promote the product through virality or these other things. We build onboarding flows, we build upgrade flows to get people to buy our product. And so I think you go chaos centralized and decentralized. In the market, growth has become much more well defined. You have brands like Reforged, which I think has for the most part been a trailblazer and set the standard, helping the market themselves realize what growth is, how I should think about growth, how I should structure that team, how it should work within companies. I think it's becoming more defined. Like I've seen that from founders that I've talked with two years ago today. It's a much more understood concept. The roots to it **Harry Stebbings** [6:57]: are still **Kieran Flanagan** [6:58]: confused **Harry Stebbings** [6:59]: though in a couple of different ways. Actually, fuck it. Before we start about the roots to it, just so we actually understand on a definition, what is growth Kieran? It's thrown around. What does growth mean to you and how do you define it? **Kieran Flanagan** [7:11]: I define growth in the PLG way where it actually helps to power your go to market. Growth to me is how do I acquire, onboard and upgrade people and then retain them. Growth means something different dependent upon the go to market motion you have. Right? Let's talk about two different go to market motions. If you're in a marketing or sales led business, you do have growth teams, but they predominantly look after performance marketing channels like paid advertising, affiliate. They don't touch the product because it's a marketing sales led business. And then on a PLG motion, which I think growth is much more prevalent, you have a growth team that owns the performance market and part of it, like how do I get users in here? Then the onboard and touchless and retention. Growth is a way that you can build models, iteration and experiments to actually power your go to market. **Harry Stebbings** [7:49]: In terms of the roots that we said that are still confused though, I think a couple that are most striking for me is when we realise that we want to have a growth function within the organisation. As a founder and you're advising me as my hypothetical advisor, do I hire a growth leader who builds the team? Or do I start with growth engineers, growth designers, whatever role that is, but more junior? How do you advise start with leader or start with junior? **Kieran Flanagan** [8:15]: That is a great question. I've talked to great companies who have started growth with a single engineer. If you really define a core metric that you want that engineer to move. And so I talked to some founders who were trying to move retention and they had a single engineer obsess over how do I get people to retain better within my product. I think when you need a leader is when you need the bandwidth, because for the most part, when you have engineers or you have these kind of dotted group people, they're reporting up to the founder or maybe they're reporting up to someone else. Then over time, that team grows and you actually need a core leader to start to manage that function. And when you have a meaningful amount of work for them to do. And so we can actually discuss what that means because I think growth could be applicable pre product market fit, right? When you actually are trying to figure out how do I instill these mechanisms within my product to better acquire people, to better onboard people, to better retain people. It's built into your product roadmap. That kind of comes back to centralized decentralized. If it's decentralized, it's just how the PMs work. If it's centralized, there's a single engineer who obsesses over that. I wanted to ask, I've **Harry Stebbings** [9:15]: done now seven growth shows and every single person has said about growth post product market fit. There has not been one discussion about growth in any form pre product market fit, almost that it doesn't exist. How would you think about actually, is there a role for growth pre product market fit? And what does that look like in terms of tasks and activities? **Kieran Flanagan** [9:34]: Yeah. So I think this is an interesting place. I'm not surprised. When I was actually thinking about this, had like, oh, like proper growth function is Series A and beyond. Right? And that's typically the advice you would give. Like series A and beyond, you have things that you want to start to actually grow. Why would you want to do that pre product market fit? Well, actually, growth can be instilled in your product roadmap. Rather than being an afterthought, I can build my product in such a way where I can think about how does this product going to require users. One of my favorite examples is genius.com, right? It used to be rapgenius back in the day when there were large lyric sites. Now, when you were building another lyric site, there was already well established lyric sites. Like how do you differentiate in that? But they built and built this really creative feature that allowed you to annotate the rap lyrics. Why was that so ingenious? Well, now it made their pages much more rich in content. And so they just outranked everyone else. Everyone else had lyrics. They had lyrics plus annotations. That's an example of a feature that you can build pre product market fit to say, hey, we're going to build in this feature because we believe that's how we're going to outcompete all these other brands. So I think that's an interesting way to think about growth and why there's something there in the pre product market fit stage. But again, it could just be built into the way engineers and PMs think about building their tools. **Harry Stebbings** [10:41]: I think one thing that's important is to know what metric we're looking to move, whether it's pre or post product market fit. How do you advise founders on knowing the right metric to choose as the North Star metric to focus on? **Kieran Flanagan** [10:53]: I think pre product market fit is retention. You're looking for cohort of users that use your product in a meaningful way and post product market fit, it's revenue. I think revenue is the combination of all those different things. How do I acquire users? How do I get more of them to upgrade? How do I get more of them to retain and actually pay me money? So pre product market fit, even though like I'm giving you examples of how you acquire users, ultimately what you're trying to do is find retention and you could find that I'm acquiring wrong users and doing the wrong stuff. But I do think growth, the mentality of growth for me, I just think it's going to be instilled in the way we create products. I've talked to founders who are pre product market fit and just want to shoot the breeze. What they really want to understand is like, how should I start to build in this stuff in my product now? I don't want to wait until I start to acquire users and do these things. I want to actually start to think about how I build these mechanisms into my product from day one. I think that's actually a really smart thing to do. To start to build traction, spin the flywheel much, much sooner. **Harry Stebbings** [11:46]: What are the biggest mistakes that you see those founders doing when you're having those conversations? **Kieran Flanagan** [11:51]: When they're actually bringing growth into pre product market fit? **Harry Stebbings** [11:53]: Yeah, when they're bringing growth into pre product market fit, when they're trying to think early about creating that flywheel, when they're having that chat with you, they're commonalities where you're like, oh, not again. **Kieran Flanagan** [12:03]: I think a lot of the times, the things that they're thinking about don't matter. A lot of the times, they're trying to think about how do I acquire users at scale? How do I do all of these things at scale? One of the things I talk to founders is you should try to grow into the problems you have. Don't try to take on other people's problems. So their problem is like, how do I build a great product obsessed over customer feedback and find a use case that actually fits within a group of customers who will use me on an ongoing basis? Now there's sometimes where to do that, there's some growth mechanisms you can build that will be really interesting for you to build at an early stage. But a lot of the times I've talked to founders and pre product market fit, they're obsessed over things that just are not that important right now. They don't need to worry about how do I build great onboarding flows. They don't need to worry about how do I build virality loops, which everyone wants to do. And so you have to grow into the problems you want. I think most of them, even though I've said there's reasons to do growth pre product market fit, but nearly sometimes a waste of energy and a waste of resources. Okay. **Harry Stebbings** [12:55]: Do I have growth in this isolated unit in the corner in the growth team that hailed Facebook that fell from heaven? Or do we have them integrated into product, into engineering and as part of the core org? How do you advise founders on that decentralized versus centralized or kind of collect? **Kieran Flanagan** [13:12]: If I think about our biggest learnings, then the PLG wrote and one of my biggest learnings, I learned a lot about myself, I learned also that we really underestimated the change in team structure going from a traditional SaaS B2B company to a PLG company. Because we went from a company where sales and marketing were in the go to market team, and now we had sales, marketing, customer success, engineering and product. How do all these teams actually work together? Let's kind of go through that question in terms of different go to market type companies. If you're an Airbnb, a Fiverr, a Thumbtack, your product is basically your entire go to market. The product is the way that you acquire, onboard, upgrade people. The perfect split there is you have a central growth team that lives in product. They own all the go to market metrics. And then those kind of companies marketing is really how do I build a great brand? How do I build great product positioning? Then you have product led companies Calendly, Miro, Figma. And what they do is they have a marketing team that help acquire the demand and then a product team that sits within the product team that's centralized that deals the onboarding monetization and retention. It's very rare. I think you will find a company that has that kind of model that also has like the SEO and the paid search in growth that usually belongs in marketing. I think that's actually the right structure. What you need to do is build great relationships between marketing and product. And then again, in the marketing and sales led business where you have a demo trial, the growth teams you find in those business sit on marketing and they just run performance marketing. So in the heyday, they were called performance marketing, but growth sounds like cooler. So they've just changed their name to the growth, but it's like the same. It's the same stuff. **Harry Stebbings** [14:38]: So we now have discovered those two big questions and we want to hire. We wanna hire for our growth team within this hypothetical startup that I'm running. How do I structure the hiring for growth talent? What does the interview process look like? If you could break it down for me, I've never done it before. I'm starting from zero. **Kieran Flanagan** [14:55]: I think all great hiring process is have three sections. It depends how big you are, how these like if you're Google, maybe they last a year. If you're a smaller company, want to get them done within a day. But when I think about great interview processes, one of the things I love to do is just like reach out and say, we catch up and just talk normally? Get to know each other. What are the things you enjoy doing? What are the things you're passionate about? What are the things you want to do in the future? And start to see, I think there's something here that this person is going to find really interesting. I think that's the first part. Then there's the formal part where you actually have your team the people you think are really important to dig in their experience and to dig into the way they think and solve problems to give you perspective on like, oh, actually, we do think that this person is a great company fit, great problem fit. Like they're a fit for the problems we're trying to solve and a great team fit. And then I think it's debatable if you want do the case study or not. I think case studies in growth hires, you can build a great case study because you can give someone a theoretical growth model. You can ask them to tell you what metric they would prioritize, how they would run a great experimentation process, give you three different examples of experiments and how they would think about running those and why they would pick one over the other. And so to me, it's the informal, formal and case study. That to me is the pretty good process to run if you're trying to hire a growth manager leader for your team. **Harry Stebbings** [16:06]: Who do you bring into the process and at what stage? How do you think about bringing the team with you with the hire? **Kieran Flanagan** [16:12]: I would do an initial conversation, again, that informal conversation. I try to do an informal conversation and make sure that there is a good match. And what you're trying to match is the people who do best in roles will enjoy the thing they're doing. Getting the informal chat, you can just get a sense of like, is the problem you're trying to solve something they're going to find interesting? And the controversial part about that is what most people try to do is find someone who solved the exact problem before. And I think that's a great thing to do it. But there's a great quote. He's the kind of like godfather of mindfulness. And he has a great quote, in the beginner's mind, is endless possibilities. In the expert mind, there are very few. And so when you bring in someone who has experience but also has something new to learn, something is new, actually all your senses become much, much more aware. So I think in the informal conversation, you're making sure that it's something that they have the experience to do, but also something that will stretch them as you bring them towards that beginner's mindset. I think if that goes well, then we bring them into a scenario where we have the team and some other people who we think would be able to dig in on certain aspects of their experience of the way they think to give us like a three sixty view of the candidate. And then in the case study, we have a small group of people who will like look at the case study, quiz the person on that case study and make sure that we've got the full perspective of all of the things that we need that person to be good at to excel in that role. **Harry Stebbings** [17:27]: So the formal and the informal, I can do. The case study, I haven't done this before. What do I actually do? Do I just give them access to our Google Analytics? What do I give them? And then also, what should I be asking and what should I be looking for in the case study? **Kieran Flanagan** [17:42]: Yeah, think on the case study, one of the case studies that I would like to do is a theoretical model. And within the theoretical model, there's a theoretical goal for the company. Hey, we want growth to help us grow to 10 customers per month. Here is the model today across my entire go to market, like all the different metrics that matter across that go to market. Based on that model, ask them to tell us what are the most important metric to focus on. Because one of the things, if you're a pre seed seed series a founder, you are going to need someone who focuses on the most important things in a given point of time because you don't have the resources to do every single metric and every single experiment. So I would say, here's my theoretical growth model. Here's my theoretical thing that I'm trying to get to over the next six to twelve months. Here's what I think is really important. Please come back to me and tell me metric, how you would build a team to actually be successful in that metric. Give me some examples of experiments. Tell me why you think those experiments are right. Within the question, what I would do is I would actually counter and say, I think one of these experiments is much, much better. These are the reasons to see if they actually have a strong point of view, to see if they're not scared to actually say, Hey, I actually disagree with you for these kinds of reasons. You want someone with a strong point of view, not just someone who's going to be swayed because you told them you think that they're wrong. **Harry Stebbings** [18:53]: Do I, the founder, need to have the growth model already in place when I'm hiring them? You said that the first question is like, here's the growth model. Do I have the growth model already? Or can I say, hey, it's yours to construct? **Kieran Flanagan** [19:04]: I think that's actually pretty interesting. I think you could do one of three ways. You could actually already have growth within the company and actually have a model you can give them. You can build a theoretical model and give them that just as a case study. It doesn't need to be anything that complex. Or you could actually have them build a hypothetical growth model for your business. The only thing with that is the reason I like to give them the data beforehand and the reason I tell founders that it's cool to give them the model beforehand because if they were just doing the model themselves, then they can't really challenge themselves, like being on the treadmill. You could basically decide to get off it whenever you want to get off it. And so if you give them a growth model with some complexity in it that you want them to see if they can isolate it and spot it, it just makes that, I think, a little bit better. **Harry Stebbings** [19:43]: Can I ask specifically, what are the biggest mistakes that you see founders make in the hiring and recruitment process for growth teams? **Kieran Flanagan** [19:50]: I don't know if I see commonalities mistake more so founders are unsure even when they're hiring for growth and when they're hiring growth people. I don't think they're still sure what they want the growth team to do. They know that they want a team to come in and iterate and work on their go to market metrics. I don't think they've really defined what they want that growth team to excel at in the next twelve months. And the other thing that I think is really pivotal when you bring in a growth team is the founder has to be the sponsor of that team, and particularly for the first year, because the team can cause some friction, especially if it's not in the product team and it needs to touch product or if it's touching these other things that are owned traditionally by other teams. You have to have a CEO and a founder sponsor the growth team and say, hey, we're structuring this team for this specific mission. And what we need is great collaboration from other teams and support from other teams to make sure they're a success. **Harry Stebbings** [20:37]: We're going talk about cross functional communication because this was a core strength of yours. Couple of things from Kipp before we dive in to post hire. First is like, Kipp told me about your insane ability to scale with company and transition from playbook to playbook, which I think is a sign of a true unicorn person. What are the signs that someone, a candidate, can move with playbook and scale from phase to phase very efficiently? **Kieran Flanagan** [21:02]: So yes, everything can be distilled down into a simplistic framework. And that framework has like a couple of inputs that matter. Because when you actually ask someone like, oh, how is this team working? How does it be successful? It's like long winded presentation. They're doing all these things. Like like, what are the couple of things that truly matter? And if you can always obsess about the couple of things that truly matter and try to continue to build systems around to scale those inputs until there's just nothing left, that's how you actually build true scalable playbooks. The other thing of a great leader who can scale with company is the job of any leader is to make themselves redundant. They actually want to have a team that is good enough to take away their work. Because if they don't take away their work, as the company grows, you get more work, but you actually haven't relieved yourself of the work you already have. And so now you're in a real pinch, right? You actually just have too much stuff, you're spread too thin, and you can't actually think about the big things you need to pick. Every great leader to me actually figures out how do I make myself redundant so I can actually build green space and build available time to take on new things. **Harry Stebbings** [21:56]: What are you trying to make yourself redundant for now? **Kieran Flanagan** [21:59]: Oh, wow. That's a good question. I will tell you that there's a couple of areas I built at the media org within HubSpot. It's about 80 people now. We acquired The Hustle. And so I put all of that together and I hired someone recently who is incredible. And so I think that's one of the areas. Then I have an incredible person who's actually helping to make me much more redundant on the customer demand generation model that I built on HubSpot. So you want to have people that you think are going to be much better and brighter at you in those spots. And I think that's what I've constantly tried to do. And if you look my career in HubSpot as every two to two and a half years, I get new missions. And I can do that because the stuff I used to do, have people who are better at me at doing that anyway. This one was from Kipp too. He asked, what were your biggest hiring fuck ups? Did he tell you to say that? **Harry Stebbings** [22:45]: Yeah. **Kieran Flanagan** [22:45]: I'll give you a great one. I'm not going to mention names. I'll tell you a great one that actually is prevalent within marketing is hiring people based upon how good their personal brand is. Their personal brand is always much better than their skill set. Some of the truly great people are doing work. Right? And so, like, if it's not your full time job to be a content creator, it's really hard to do both those things to be in a company doing great work and also be a chronic creator. I know lots of people who can do that. I know a lot of people who do have great personal brands and they truly are great. But I think every mistake I've made is because I do gravitate towards people who can create truly great personal brands as well because they create a lot of thought leadership content. It's easy to see how they think. There's been some times where that work they do is much better than actually what the true extent of the work is. Now there's counterpoints that, but a lot of times founders especially get really swayed by people who have like really big personal brands. **Harry Stebbings** [23:33]: I think the other thing, talking about mistakes in hiring growth thing, one thing that I consistently see is people who mistake company brand where the person works. They're in Google's growth team. They're in Facebook's growth team. And the truth is you're kind of on a gravy train anyway if you're at the right time in the right team, and actually moving to a 10 person startup is very, very different. And I think that's the biggest mistake of the fuck up I see founders make. I'm totally with you on personal brand also not being an indicator for success. **Kieran Flanagan** [24:00]: Yeah. I've said before, and I got really negative comments for saying this, but I've said before, like, an average marketer at a great company makes more money than a great marketer at an average company. Right? Because they can ride the gravy train to success. And so you have to try to figure out what that person's done versus what the collective we have done. And I think that's an important thing for founders to try to figure out. And a great personal brand will make more than both **Harry Stebbings** [24:20]: combined. **Kieran Flanagan** [24:22]: Yes. Man, the creator life is a good life. Again, that part of the hustle, we got some really great creators, and I've never been more appreciative of how hard it is to be a great creator and how amazingly talented great creators are. Do you know what? I'm **Harry Stebbings** [24:33]: totally going off tangent here, but fuck it. I have to and I'm very passionate about this. I think so much product marketing and messaging is just shit. It's bland. It doesn't speak to anyone. It's neutral. And I think actually, I said tweeted the other day, if you want someone who gets product messaging, hire people who specialize in memes and gifs because they know what resonates. How do you feel about what I just said? **Kieran Flanagan** [24:57]: Brands don't want to have points of view. They want to sit in the middle with everyone else because it's safe, it's comfortable. I think we are increasingly moving to a world where everything is pop culture. If you actually look at fintech, ten years ago, someone said, hey, you know what's going to be one of the best content spaces online? Financial. Like you're like what? Like that's boring. No, like fintech is like moved totally pop culture. You're seeing it in business. We're moving much more pop culture. Like you're a great creator. You're creating content on places like TikTok that gets thousands of views. We're going to continue to see that brands who don't get with that and don't know how to plug into the culture of today and sit in the middle, say, born things and being born in terms of their product position and brand. I think they're going to struggle. And I think there are people with points of views, Meme creators, gift creators, creators themselves that are going to be much more important for companies to enable to create environments. They will want to work with those companies and help them actually plug into the culture. I always **Harry Stebbings** [25:52]: say the best brands make armies. You are either full or you are end, but the worst thing is sitting in the middle. 100%. Do you think that is HubSpot today if we're being analytical? **Kieran Flanagan** [26:03]: So I think that's a great question. I think we build our tribe around inbound marketing. What's interesting to me is a transformational company will always move towards at some point just a message that is not transformational anymore. If you're a transformational company and you have a transformational message, so like ours was inbound marketing, hey, like either in the inbound camp or you were doing all of this outbound stuff that people hate, like people hate those kind of marketers. At some point, if you win that conversation, then that just becomes the ad hoc way of the way that people think about marketing. Like inbound is not new now. We kind of won that war. People agree that that is the best form of marketing. And so your transformation just becomes best practice. And so it's hard to keep that passionate for or against when you've actually won the conversation and people agree and implement that and it becomes best practice. And so that's something I think a lot about is like you build your tribe at the start, but eventually I think your tribe becomes a much bigger cohort of people. **Harry Stebbings** [26:57]: How do you push brand to the edge at scale when you're a public company, when you have corporate brand as well as investor brand and many different types of brands that you need to hit? Can you really be as edgy and adventurous as you would like to be? It's challenging with scale. **Kieran Flanagan** [27:14]: Yeah, I think it's really challenging. For me, even though I said like companies shouldn't sit in the middle, I don't disagree with why it happens because you have a large market that you were trying to market to and you don't want to alienate them with such point of views that are like half of my audience agree and disagree with that. But I think you can do it in a way where it's not alienating to your audience, but it is engaging to your audience. For me, every tech brand in the future becomes a media brand because we have something to say. If you think about content in most companies, we've traditionally leveraged education to build an audience for our product services. And why have we done that? Well, when the internet became popular in 2006 and continue to grow, educational needs become more niche. Brands were able to fill those educational needs by serving a smaller subset of the market. That service actually helped to onboard those people to their products or services. I think in the future, brands are going to have to think much more about inspiration. Like how do I create inspirational content to say something to my audience? How do I create educational content to get them to engage with me each day, every week? To me, that's the whole kind of discussion around why are you seeing all of these tech companies moving much more into media? It's because we want to be ever present within our consumers' life. **Harry Stebbings** [28:22]: It's astonishing. I ask pretty much every founder that I meet obviously on the investing side. You have a billboard in Times Square. What do you put on it? It's about 10 words or less. What do you want your audience to see? I'd say 5% can articulate what their company does in 10 words or less and tell a story with it. I think that's astounding. **Kieran Flanagan** [28:39]: Elon Musk, for all the things he's done, he's also probably one of the better examples of a brand who is willing to do edgy things in a way that does not alienate his tribe, actually makes his tribe want to embrace him even more. They're fanatical fans of everything he does. For or against you **Harry Stebbings** [28:57]: have a feeling on Elon Musk and actually, you know what? He is the best when it comes to understanding what does and what does not resonate with consumers. But he is the ultimate AB testing machine. **Kieran Flanagan** [29:07]: Yeah. If you look at his reach compared to any traditional media org's reach, like he has much more reach. He does that because he plugs into the culture. He knows how to instill emotions, whether they are positive or negative on mass scale. And I think that's what brands are trying to do is trying to create some sort of emotional connection to their audience. You want it to be positive for the people you're trying to reach and not care too much, but not get swayed by the negative. Sometimes the negative is not something to actually not stop doing things. **Harry Stebbings** [29:36]: We will get back onto the schedule. The very difficult thing though is for actually, I think for companies hiring this day, and I don't mean this badly, the people who are genuinely brilliant at content, news of the world either are too expensive or do their own thing. **Kieran Flanagan** [29:48]: Yeah. Yeah. **Harry Stebbings** [29:48]: You you can never hire other amazing people. Your Andrew Chen's is Andreessen. He's made millions by Andreessen. Like, you're never gonna get him to join a content team. Do you know what I **Kieran Flanagan** [29:57]: But I think that is a great point. That is a great point because we under invest in content. Like, mentioned this before is that we'll spend a million dollars on Facebook campaigns and then outsource our articles for $10 and expect, like, why is this content not working and the the Facebook thing is working really well? Well, you're spending $10 an article. So it's first of all, we think in how we think about media, building an environment where creators actually want to work. There's interesting ways that you can build environments that you want creators to work. One of those is like pay well, freedom. I think long term, you can talk about things where you have upside on the things that they create. I mean, that's hard to do, but I think that's something you can do. The other thing you can do, which is something we launched recently as a creative program. So you're right. All of these people will not want to work within a company because they want to do their own thing. Cool. Well, how do we create a creator program so we can actually have them be part of our network, but they actually get paid on the content they create. They get total editorial freedom, and you start to make yourself an interest in place for both internal people to work because you get to work with these creators or external people to work because you have a program that supports their growth, but also incentivizes them to grow because you are paying them on the upside. **Harry Stebbings** [31:04]: Do you know what I find amazing though? How many companies and funds and startups produce content? They spend hours and hours. Even if they do what you say there, which is spend more money on the creation side, they spend more money on it and they produce great content and they click publish. Forget about it. Why is no one coming? No distribution is thought to it. People don't understand distribution today. I think this is why you've been successful. But I think we both get distribution and it astounds me how people create for so long and distribute not at all. **Kieran Flanagan** [31:34]: Right. I think great distribution starts with great ideas. The thing that I have learned from the people who I have been immensely impressed with in The Hustle is they have great ideas. They are able to find things that are interesting that is not widely covered, and then they are able to have their own spin on things. And so they have their own kind of brand in terms of how they create content around those things. And so they're not just stuck in the middle doing the same thing as everyone else. But then to your point, they also know how to get distribution on their content. Like they think, how do I actually get people to see this? So much great content goes to waste because to your point, we just publish and then we think, hey, like my job is done. Someone will find it and good things will happen. **Harry Stebbings** [32:11]: Does it have to tie back to revenue? Do we have to see x piece of content led to x amount of leads that led to x amount of converted dollars? Or can we be a little bit more elastic in terms of how we think about it? **Kieran Flanagan** [32:23]: I think data has been the best and worst thing to happen to marketing. Why best? Well, marketers used to stop doing crap stuff because no one wanted to give them anything good to do because they couldn't figure out if it actually created any real revenue. Like marketing wanted a seat at the revenue table be taken seriously. But hey, how do we actually show the value of the things I do? Over time we got better data, but then we become so focused on that that we just try to iterate away to marginal gains. Oh, I have to show every single piece of content. Every single thing I do has to actually result in some sort of revenue for the business. And so now everyone is coming into the middle because if we do that, we all end up doing the same stuff. I think creativity and brand is how you build a big company in the future. Founders who can truly see that they want to invest in something that will make me differentiated, will make me stand out, that will create a larger audience around my brand. And I know that that thing is not going to be unmeasurable. I know that thing is going to be really hard to quantify. We did the hustle deal. We did not do the hustle deal based upon metrics. We did not pitch the board and say, oh, these are all the kind of cool metrics. It's a bet on how we want to be seen within the future, how we want to build our audience in the future. So I think there is, but I think that is a real struggle for most brands. I think most brands are baked in. How does every single action you take get me some amount of pennies, dollars and customers? One word that's thrown around **Harry Stebbings** [33:39]: so much in the brand, content, new gen marketing that we talk about now is community. We both hear it the whole time. And I kind of laugh to myself because I'm like, what the fuck does that mean? Yes. What does it mean? What does it mean to you? And in this excitement of like, oh, I see so many community startups. **Kieran Flanagan** [33:58]: I'm like, oh, what do they do? I think so product led growth used to be the thing that I think was really hard to define when you went to certain companies. I think it's actually much more defined now. Community led growth, even just speaking to companies or advising companies, even just having commonalities of what's included in community does not exist. To me, when I think about community, for the most part, think about, oh, go create an account, connect with other people, I discuss things with them. Then you go to another company, like, well, it's anyone who's in our email list, anyone who's on our Twitter following. And you're like, okay, so it's just everything. And I think community is your tribe. It is like the group of people who believe in the things that you do, and then they are engaged with you in some meaningful way. We're going to have to define that over time because at the moment to me that is like, well, I've created an account and I'm starting to interact with people, but they believe in the things that you believe in and they are starting to engage with you in a meaningful way. But that definition does not, I don't think clearly exist. Does **Harry Stebbings** [34:49]: it **Kieran Flanagan** [34:49]: and does it **Harry Stebbings** [34:49]: scale? With scale, you have community denigration. **Kieran Flanagan** [34:53]: It's a great conversation. I'm so glad **Harry Stebbings** [34:54]: we wanted to have this conversation. How do you think communities can scale? If you are going to build an IPO able massive company, having community led at the beginning is capped, No? **Kieran Flanagan** [35:05]: So first of all, I think it's how you define community. So we're defining community by like, if we include our media mediums in that, it depends what you include in community. If I just include my Slack channel, can I grow my Slack channel to like a million users? That could be a meaningful way of how I grow my business. And that's pretty hard to do. But if it includes like your events and your media and then all of the people who are in Slack and Discord and stuff. So I think first of all, it depends how you define it. But I do think you said something important, right? So community to me is like, how do I master breadth and depth? And so depth is how do I get a small group of people who want to interact with each other and achieve something and become better in something together, right? The best communities to me are the smaller communities who truly have for something, who are truly trying to learn something and they can connect with each other and learn from each other and do those things. And so community led growth, is like, oh, a community is going to be the way we grow our business in the future. So we'll grow our community and then we'll have people from our community go and use our products and services. Intrinsically, the opposite of how you would want to grow a community because it actually you need to care about breadth. I need to get thousands or hundreds of thousands of people into my community to be able to actually grow my business in a meaningful way. And so how do I create depth if I have breadth? I think in the future, we're going get better tooling to really help us figure out how we can segment our community into different cohorts of depth. The tooling is not good. And then we will be able to build breadth with better incentives. And I think the cliche is the incentives are coming from the Web three industry, and it's really about ownership. And today, community gets you maybe better knowledge. It gets you information around the product. It gets you people who are shared interests and hobbies. In the future, it should get you ownership and a stake in that company. And to me, that's how you can start to really build the breadth and it can be a meaningful part of your go to market. But I think the number of winners in community led growth is small, but they get exponential returns because how many communities can someone be part of? Two, three. So a small amount of winners, but they get exponential returns. What will cause the winners to be winners, do you think? I think it's understanding the value you can deliver and you have to understand the value you can deliver at scale. And so first of all, you have something intrinsic. Your brand is associated with something that person wants to learn. So the best example I can give you is if you think about the three pillars of community, for the most part, communities are built around personal growth. Like I myself want to get better by joining this community. Then they are around the connections you create. I actually can connect with peers and they make me a better version of myself. And then the third part, actually is an untalked about where you can build the moat around your company is the reputation. Like by doing those things, I actually can achieve something, but I can show people that in a visible way and get some sort of payback from that. I think the companies who win in the future excel at those three things, which is breadth, personal knowledge, like how do I create a mass amount of people who can learn things from me, be a better version of themselves, depth, which is the connections, like how do I get them into smaller groups and make sure that they are connected with people they can learn from and engage with. And then the big thing is how do I take all of the things that they have built in that community and give them something back through reputation. But I think in web three, that's through ownership and web two is reputation and web three, that's ownership, I'm actually creating value in the community, but now I have ownership in this company. So I'm actually getting something back. **Harry Stebbings** [38:16]: I have to touch on the breadth and depth. I think this is the biggest challenge with product messaging and product marketing that I see today. When you look at horizontal tools in many ways, like say a Notion is a brilliant example. It could be used by dentists and it can be used by software developers. When we go back to that breadth and depth, it's very similar. How do you market and message such a horizontal product without alienating the depth, without alienating the verticals? But then also not just stick in the middle. How do you describe Notion? Collaborative work docs. Well, that doesn't speak to anyone actually. **Kieran Flanagan** [38:51]: Yeah. I think most of the horizontal tools, they stay horizontal to get mass distribution and they've verticalized to monetize. You have a Calendly, which is applicable to anyone, right? What a great tool, a great company. They monetize through sales teams or they monetize through different verticals. And so you're getting at their messaging. Like, when I go to their website, how do I know this tool is for me? I don't know if that's how those tools grow. They grow, like, through virality, word-of-mouth. Right? You have a small group of people who use that and they start spreading it to other people. I don't know how much their position in I'm sure it matters, but I don't know how much it truly matters that I go there and I see that this product is for me because I probably onboarded to the product through a referral, through someone sharing a notion with me, through someone doing word-of-mouth because it has such broad sets of use cases. But the way they monetize when you actually need to go vertical and monetize and you do need to start to figure out like what are the teams that would truly want to use this, whether that's, hey, this is truly great for engineering teams. I think that's when it becomes really important. Can I take it back **Harry Stebbings** [39:49]: to community on something I did forget? Do you think HubSpot's done community well? With the benefit of what you know now, is there anything you'd do differently looking back? **Kieran Flanagan** [39:58]: This is a great question. So again, how you define community? I would tell you, most people would say HubSpot has built a really large, vibrant community through our content. But I'll give you like an honest answer. I think we build a tremendous community, but we have a lot more to build. If you think about community as like our community at hotspot.com, like the connections part, where do I go to get connected to others? We've primarily focused on building a community of products. Like, how do we build a community around our customers, the people using our tool? I think the thing that we could do better is we have all of these people, millions of people consuming our educational content. We've never tried to build a community of practice, which is how do we build a community around knowledge and connect those people to each other and connect those people to cohort learning and live work workshops and live classes. We're doing that much more. So we haven't blended the community, like the connections part with the personal achievement part as well as we could have. So I think that's where we can improve that community of practice around education and connections. **Harry Stebbings** [40:54]: It's really tough though, because you could be very proactive and allocate a lot of dollars to really being proactive in making those connections and finding those synergies. That said, for a business leader looking at budgets, there is really no payback period. There is no correlation to revenue. And it's very difficult. I feel sorry for people who own the budget lines. They're looking at these very intangible things going, there's a big spend for a very questionable return and I'm a public company. **Kieran Flanagan** [41:23]: This comes back to how do you build a portfolio across the things that are short term that I can measure and the things that are long term that I can't measure? Because predominantly, like, that's what we're kind of discussing in the long term unmeasurable bucket. To do something like that, you have to have very deep conviction. I talked to a founder recently. I won't give the company the name. They are building something for three to five years. They don't accept to measure in terms of, like, how much revenue this is generating for the business. They just have truly deep conviction that if they pull this off, they will actually win within their market. Some of the things that we've talked about, like community media, all of these kind of things. And so you have to have a founder that has deep conviction in terms of how they see the future and not try to kill something because it doesn't immediately show direct attribution to revenue. Because again, if we tie everything to revenue, then we're all going to do the same stuff. It's not gonna differentiate that much and it's hard to build something differentiated when we're all measuring ourselves in the same way. I've also **Harry Stebbings** [42:16]: absolutely fucking loved this discussion. Cool. You know when you have a schedule and you're like, yeah, fuck it, whatever. I do want to dive into a couple of elements though before we move into a quick fight. These were just elements specifically that I was told I had to ask you about. One is cross functional communications with growth. How do you think about making sure growth and other areas of the org are synergistic and aligned? How do you nail cross functional comms? **Kieran Flanagan** [42:44]: I'll give you a couple of my learnings. So if you ask someone, oh, like, what's Kieran like? One of the things they'll tell you is, well, like, he was very black and white. This is the right thing. This is the wrong thing. This is how things are. This is how they shouldn't be. And, actually, in cross team comms, it's not black or white. It's really black and white. Right? You actually have to be able to understand both sides of the story. And, actually, there's most of the things live in between in the gray. Most of the things live in the fog. And so I never used to dive into the fog. I used to say, wow, you're doing this thing. It's dumb. And then you didn't know all of the reasons that those things existed. That happens across teams. And because you speak different languages, if you're all black and white, then everyone seems like they're doing kind of dumb stuff. The first thing is like you have to live in the gray. You have to have the context for why things are the way they are. The second thing is marketing and product speak somewhat different languages. The job of great PMs crystallize problems and then present them to their engineers. Their engineers are like, Oh yeah, we believe in this problem. Here's how we think about this problem. And we will go and figure out how we build that solution. Marketers are very solution orientated. Marketers could do a lot better if we ground ourselves in the problem and some do some don't. But I think we're much more solution model. Here's the solution. Here's the solution. Here's the solution. And so when you go and start working with growth teams who sit in product or product and engineering teams, marketing are like, here's the five things I need you to do. Oh, well, I've just told the PM, I need you to do these five things. PM has to go to the engineering team, do these five things. That's not how engineering teams want to work. You have to start to figure out how do we all speak the same language? How should we work together? How do we make sure that we are aligned around the problems? **Harry Stebbings** [44:11]: How do you actually do that? I'm the CEO. Do I say, right, product team, right, growth team, come in and we are going to sit down and discuss the dictionary of how we speak. How do I actually do that? **Kieran Flanagan** [44:21]: You know, I'm gonna be honest with you. Like, the way we got there is, like, through lots of friction and fighting and falling out with each other and getting back on side with each other. I would be lying if I said, oh, well, we had this really amazing playbook. That was the hardest part, I think, of the PLG motion for us is we just miss really underestimated how hard it would be for all these teams to start working together. I think we got there through grinding it out. It's the way I think about how you get to be a great presenter. You just have to grind it out. I think that's how we got there. We got there as like we trusted each other. We're okay with falling out with each other. Over time, we got to a place where things work much, much better. **Harry Stebbings** [44:59]: Can I ask final one before the quickfire? I think onboarding is just universally done terribly badly. When you think about onboarding for the new growth and marketing hires, what does good look like to you? And what standard do you hold yourself accountable to as this is what we need to do to make them successful? **Kieran Flanagan** [45:15]: I think one of the things we do that is really good, it's our people ops team, it's not me, is we build one hundred day plans for people. Because when you come into a new role, you're like, oh, wow, what do I do? And especially in remote, actually remote onboarding is a whole other topic, like remote work onboarding. So we do a hundred day plan. We're like, here's all the different people you should meet, and we make sure that we get them into your calendar. Here's what we would love for you to do on month one. Here's what we would love you to do in month two. Every two weeks, we check-in and ask how you're doing across that one hundred day plan, ask how the meetings went, ask is there other questions you have so we compare you with other people. And that one hundred day plan isn't actually about at the end of this, we need you to have achieved A, B and C. It's at the end of this, we hope that you understand your role, understand your team and understand the kind of path to success. So it's just making sure that you feel set up for success versus like you have to have achieved these things within a hundred days. Like there are things that we want you to do along the way, It's much more set up for you to be successful and make sure that we are setting you up to be successful within your role. **Harry Stebbings** [46:14]: As a leader today, I listen to you and it just seems very natural. It seems like you have your shit all in place. When you think about your own weaknesses as a leader today, where do you think your weakest? **Kieran Flanagan** [46:25]: Operations. When I mean operations, mean like building the project management tool and all of that kind of stuff. I don't enjoy doing it. I don't enjoy doing operations. I don't enjoy doing all of the admin work that comes with managing lots of people. It's part and parcel of the role, that's not where I'm like, oh, how do I build a great operating model for my team today? I have to force myself to do it. Final one, I promise before the **Harry Stebbings** [46:44]: quick fire. You angel invest as well today. How has angel investing impacted your mindset to growth in company building? **Kieran Flanagan** [46:51]: Yeah. Growing a company is really fucking hard. Founders are amazing people. It really has just home how hard it is to build a company because like when you've been in HubSpot and I joined when we were 300 people, like we're thousands and thousands of people now, you're kind of like, oh, well, like this is what it's like in a startup. Like they just grow and they become like really successful. Angel Investo has really grounded me in that. Wow, it's just really hard to build a company. Like it's really hard to build something that's truly successful. And the founders that do it are inspiring. Like, they actually will put all things on the line to actually try to make this company a success. Mostly grounded me in our artists, like grounded me in the things you the all of the decisions you have to get right and all of the things that have to go your way. **Harry Stebbings** [47:29]: Yeah. I was always thinking it's about kind of speed and velocity of decision making. I think speed of execution is just everything and I really see that the more I invest. I do wanna do a quick fire though, Kieran, because I could talk to you all day. Tell me, we're gonna be focused around growth. What growth tactics have not changed over the last five years? **Kieran Flanagan** [47:46]: I think like email automation, I think they have remained constant, still important, but have not changed that much. What tactics have died of death on the other hand? Yeah, don't know if anything dies, right? I think it just kind of becomes less effective. You look at paid advertising, I think that's going to become less effective over time because of privacy, because of Verizon CPMs. So you look at search, one of my favorite channels, but how that holds up over time with Google decreasing the amount of traffic you can actually get from them. I think if anything died in the last couple of years that came to mind for me, it was like anyone who was trying to market on Clubhouse. But I think for most tactics, plateau versus die. What would you say is **Harry Stebbings** [48:18]: the biggest **Kieran Flanagan** [48:19]: mistake **Harry Stebbings** [48:19]: founders make when hiring growth teams? **Kieran Flanagan** [48:22]: I think it's how you set them up for success. Right? What their structure is, how you make sure you align them with the business and other teams, and how you can be a sponsor of their success. What one piece of advice would you give to a growth leader starting a new role today? Customers, data, and team. Like, if you're close to all three things, you're gonna be successful. Know your customers better than anyone else, know your data than anyone else, and be an advocate for your team better than anyone else. **Harry Stebbings** [48:45]: How is onboarding different in a remote versus an in person world? **Kieran Flanagan** [48:49]: The meetings matter, making sure that the person being proactive about getting that person set up to talk to other people. Everything in remote work is on scheduled time. We all have to schedule time and put the Zoom link in and actually interact with each other through these kind of video chats. Whereas when you're doing it organically within an office, it's much easier to have these organic conversations with people. So you really have to be proactive about making sure that that person gets time with people and gets to spend time and start to meet people. **Harry Stebbings** [49:14]: What would you most like to change about the world of growth? **Kieran Flanagan** [49:16]: I think the more defined it comes, the easier it is for founders to figure out how to leverage it and when to leverage it. So I think what the team is, the structure of the team, goals of the team, and how it should be aligned with other teams, I think that is the best thing that could happen for it. **Harry Stebbings** [49:29]: How many domains have you bought? And which one have you been closest to pursuing? **Kieran Flanagan** [49:34]: I have bought, let's say, a 100. I had a bit of a issue with buying domains at some point. You know, the one I nearly was like, oh, this could be a good idea was I bought a remote cal.com. I think it's dropped, I so don't think I have it anymore. And what I was gonna create was remote workers because, like, if you think about it, your community has moved online to some respects, so you don't get the same kind of ability to network with people who are in your industry. So remote workers could have a calendar. They could put in times that they actually want to get matched with people, put in interests, and they will get matched every month with other people who have the same schedule as them. Because one of the hard things is scheduling, but I never did it. I think it's worth a billion dollars. Yeah. **Harry Stebbings** [50:11]: You want to invest? No. I I would have happily if you would like to do it. I would love to, but it it actually exists in The US. In The US, it's called lunchbox. Oh, lunchbox that in. Yeah. Andreessen backed it, I think. Okay. I think it's worth about 1,000,000,000 now. It was a very good idea. You go. I should have done it. Fuck. Just kept the domain name and tried to sell it them. That is brilliant. Final one. What one company growth strategy have you most been impressed by recently? **Kieran Flanagan** [50:35]: Yeah, think Web two point Canva, Web three point Stepan, they're my Why on those? One of the things when I talk to founders in B2B, every founder now tells me who are doing product led growth, oh, the thing we really want to do is replicate the Canva template model. So what Canva did was they templatized their entire like, everything you could possibly do with a product to create a template for. Then they actually created a marketplace, so now people can actually create their own templates. And you can buy them, which extends the amount of traffic that they can acquire from search. Like, they just execute really, really well in terms of how they built an amazing distribution engine. And then I think Stebbings, which is a kind of play the move app. I think their game mechanics are really interested in terms of how they've grown. **Harry Stebbings** [51:13]: Kieran, as you can tell, it was such a natural conversation. I've loved this. Thank you so much, and this has been such a joy. **Kieran Flanagan** [51:19]: Yeah. Thanks for having me on. I'm a huge fan of the podcast, and I appreciate you asking me. **Harry Stebbings** [51:25]: That was so much fun to do with Kieran. As you could tell, we had a schedule. We completely left the schedule in the theme of loving content creation and distribution, both as creators ourselves. Wanna say a huge thank you to Kieran for being so accommodating and flexible with the schedule there. Absolutely loved it. 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