Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916

1. 0:00 – 1:40

   Kieran's backstory

   1. HSHarry Stebbings0:00

      (beeping) Three, two, one, zero. You have now arrived at your destination. 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, your colleague, Kipp. So thank you so much for joining me today.

   2. KFKieran Flanagan0:19

      Yeah. Thanks for having me on, Harry. I'm a fan. Um, I'm excited to be on and excited to speak to a fellow European, not that far away.

   3. HSHarry Stebbings0:25

      I mean, it is rather lovely to have-

   4. KFKieran Flanagan0:27

      (laughs)

   5. HSHarry Stebbings0:27

      ... another European, uh, on the show. But I do wanna start, you know, uh, y- you run and work in some of the most impressive growth orgs, uh, now obviously at HubSpot. How did you make your way into the world of growth and what was that entry for you?

   6. KFKieran Flanagan0:42

      Uh, yeah, I think that... I, I'm a computer engineer by background. Uh, went into marketing. Have done a lot of different things in marketing and at some point kind of was asked to build up a product-led motion for HubSpot. Um, 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 Brian is, uh, someone I look up to in that industry. And, uh, had the opportunity to do something quite unique at HubSpot when we were an established company to build a PLG motion, a product-led motion, and built out the marketing and growth and kinda learnt on the job, because I was a marketer going in to learn ab- about growth and do growth. And so my career 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.

   7. HSHarry Stebbings1:32

      I, I, I have so many questions. We don't... (laughs) Like, you can tell, like, no wonder, you know, no one can do a 20-minute meeting with me. Um, my first question to you is,

2. 1:40 – 3:48

   How product-led growth has changed

   1. HSHarry Stebbings1:40

      you managed to 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?

   2. KFKieran Flanagan1:54

      Yeah, I think there's three... So there's three stages companies go through, and then I'll talk about how that's changing in the market. So the companies generally, back... even back then, and maybe today, like I spend a lot of time with founders, they go through the phase where they're like, "Hey, we should do growth," without really knowing what growth is, but they wanna move a metric in a meaningful way, and so they try to do that. They do it in a way where team design and all of that is an afterthought, so it kind of creates chaos, but out of the chaos, there is something good. And 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, we sponsor that, uh, the founder sponsors that, and that starts to work really, really well. I think the next iteration of that would... to me is like truly, uh, curious is, we have central growth teams and they do growth principles and they work with the product team to instill those principles in how you create product, how you do onboarding. I think at some point you can see growth be much more decentralized into just how PMs create the product itself. We build in, uh, 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. I think in the market, growth is becoming much more well-defined. Like, you have brands like Reforge, which I think has, for the most part, been a trailblazer and set the standard, and I think they are 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. So I think it's becoming more defined. Uh, and particularly, uh, like, I've seen that from founders that I've talked with. You know, two years ago to to- today, it's a much more understood concept.

   3. HSHarry Stebbings3:33

      I, I, I... Listen, I totally agree, it's a much more understood concept. I think the roots to it are still confused though, in a couple of different ways. Number one way is... Actually, fuck it, before we start about the roots to it, just so we actually (laughs) understand on a definition,

3. 3:48 – 5:02

   What is Growth?

   1. HSHarry Stebbings3:48

      what is growth, Kieran? It's thrown around. What does growth mean to you and how do you define it?

   2. KFKieran Flanagan3:56

      I define growth in the PLG way where it actually, um, helps to power your go-to market, right? Growth to me is, how do I acquire, onboard, and upgrade people and then retain them? I think 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 pretrom... predominantly look after performance marketing channels like search, uh, paid, paid advertising, affiliate. Like, they don't touch the product because it's a marketing and sales-led business. And then in a PLG motion, which I think growth is much more prevalent, you have a growth team that owns the performance marketing part of it, like, "How do I get users in here?" Then they own the onboard and touchless and retention. And so to me, growth is a way that you can build models, iteration, and experiments to actually power your, um, your kind of go-to market. Uh, but I think it definitely means different things within different companies.

   3. HSHarry Stebbings4:46

      I totally agree with you, but I like the breakdown there on the go-to-market perspective and how it changes that. In terms of the roots that we said that are still confused though, I think that a couple that are most striking for me is, when we realize that we want to have a growth function within the organization, as

4. 5:02 – 6:47

   Who to hire first in Growth? Senior or Junior?

   1. HSHarry Stebbings5:02

      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, grow... whatever role that is, but more junior? How do you advise? Start with leader or start with junior?

   2. KFKieran Flanagan5:19

      Uh, that is a great question. Um, I think you can start with engi... Like, I, 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 growth people, they're reporting up to the founder or maybe they're reporting up to someone else, and 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 mo- roadmap. That kind of, that kind of comes back to centralized/decentralized, right? When it's- 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 wanna let you get in there, 'cause I saw a...

   3. HSHarry Stebbings6:29

      Well, I, I wanted to ask, 'cause you know, Blenny, I've 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. Can you help me understand, how would you think about actually,

5. 6:47 – 8:26

   Is there a role for Growth pre product-market fit?

   1. HSHarry Stebbings6:47

      is there a role for growth pre-product market fit, and what does that look like in terms of tasks and activities?

   2. KFKieran Flanagan6:53

      Yeah, it's really... So, I think this is an interesting place. I'm not surprised. I, when I was actually thinking about this, I had like, oh, like proper growth function is series A and beyond, right? And that's like typically the advice you would give, like series A belo- beyond, you have users, you, you have things that you want to start to actually grow. (laughs) Uh, why would you want to do that pre-product market fit? Well, actually, growth can be instilled in your product roadmap, right?It... R- 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 acquire users?" Like, is it... I'll give you a really great example. One of my favorite examples is, uh, genius.com, right? Used to be Rap Genius back in the day when there were large lyric sites. Now, when you are building another lyric site, you, there was already well-established lyric sites. Like, how do you differentiate in that? Well, they beat, they built, in-built this really creative feature that allowed you to annotate the rap lyrics. Like, I'm into hip hop. I love to know what, you know, the different lyrics meant. So, you could actually annotate them and say, "Oh, well, they meant this, this, this." Why was that so ingenious? Well, now it made their pages much more rich in content, and so they just outranked everyone else, right? 'Cause 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 gonna build in this feature 'cause we believe that's how we're going to out-compete all these other brands." So, I think that's an interesting way to think about growth and why there's like some, you know, there's something there in the pre-product mark fit- pre-product market fit stage. But again, it could just be built into the way engineers and PMs think about building their tools.

   3. HSHarry Stebbings8:18

      Totally get you. Can I ask, 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.

6. 8:26 – 9:30

   How to choose your North Star Metric

   1. HSHarry Stebbings8:27

      How do you advise founders on knowing the right metric to choose as the north star metric to focus on?

   2. KFKieran Flanagan8:33

      I think pre-product market fit is retention. You're looking for a cohort of users that, you know, will use your product in a meaningful way, and post-product market fit, it's revenue. And I think revenue is the combination of all those different things, like, "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, you're, what you're trying to do is find retention, and you could find that, "I'm acquiring the young- wrong users, I'm doing the wrong stuff." But I do think growth, the mentality of growth, for me, again, coming back to the fact that I just think it's gonna be instilled in the way we create products. I've talked to founders who are pre-product market fit and just wanna shoot the breeze. And what they really wanna understand is like, "How should I start to build in this stuff in my product now? Like, I don't wanna wait until I start to acquire users and do these things. I wanna 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, because it starts to build traction, spin the flywheel, uh, much, much

7. 9:30 – 11:10

   Biggest mistakes founders commonly make

   1. KFKieran Flanagan9:30

      sooner.

   2. HSHarry Stebbings9:30

      What are the biggest mistakes that you see those founders doing when you're having those conversations? Are there commonalities?

   3. KFKieran Flanagan9:37

      Um, when they're actually bringing growth into pre-product market fit?

   4. HSHarry Stebbings9:42

      Yeah. When they're bringing growth into pre-product market fit-

   5. KFKieran Flanagan9:44

      Yeah.

   6. HSHarry Stebbings9:44

      ... when they're trying to think early about creating that flywheel, when they're having that chat with you. Are there commonalities where you're like, "Oh, not again."

   7. KFKieran Flanagan9:51

      Yeah. I think a lot of the times what they... I, I think a lot of the times, the things that they're thinking about don't matter, right? I think 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?" Like for me, one of the things I talk to founders, and I'm not a founders, I have a lot of respect for founders, but just in terms of going through the growth we went through in HubSpot is, you should try to grow into the problems you have, right? Don't try to take on other people's problems. So, their problem is like, "How do I build a great product, obsess over customer feedback, and find a use case that actually fits within my customers, uh, fits within a group of customers who will use me on an ongoing basis?" Now, there's some times where to do that, there's some growth mechanisms you can build that will be really interesting for you to build at an earlier stage, whether that's like, "How do I acquire these people? Uh, how do I retain these people?" But a lot of the times I've talked to founders in pre-product market fit, they're obsessing 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 (laughs) very few people can actually build them. Um, and so you have to grow into the problems you want. I think most of them, even though I've said there's- there's reasons to do growth pre-product market fit, but nearly all of the time, it is, um, sometimes a waste of energy and a waste of resources.

   8. HSHarry Stebbings11:09

      So then

8. 11:10 – 13:40

   Growth teams: Decentralized vs. Centralized

   1. HSHarry Stebbings11:10

      the next question is, okay, do I have growth in this isolated unit in the corner in the growth team that hailed Facebook, you know, that fell from heaven? Um, or do we have them integrate into product, into engineering-

   2. KFKieran Flanagan11:24

      Right.

   3. HSHarry Stebbings11:24

      ... and as part of the core org? How do you advise founders on that decentralized versus centralized or kind of collective?

   4. KFKieran Flanagan11:31

      Yeah, this is actually the... If I think about our biggest learnings when we went down the PLG road-

   5. HSHarry Stebbings11:37

      Mm-hmm.

   6. KFKieran Flanagan11:37

      ... and just my big- one of my biggest learnings, I learned a lot about myself, but I learned also that, um, the- we really underestimated the change in team structure going from a traditional SaaS B2B company to like 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, and like, how do all these teams actually work together? If you kind of a- and let's, let's kind of go through that question in terms of different go-to-market type companies.So, if you're like an Air- if you're an Airbnb, a Fiverr, or Thumbtack where you're a large- you have- your product is basically your entire go to market, right? The product is the ad- the way that you acquire, onboard, uh, upgrade people. For me, the gr- the perfect split there is you have a central growth team that lives in product. They own all the go-to-market metrics and for the- and in 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 like Calendly, Mural 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 does the onboard and 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, and I think that's actually the right structure, and I think what you need to do is build great relationships between marketing and product. I- I know we're gonna- we're gonna talk about that. And then, again, in a marketing and sales-led business where you have a demo trial, you really have w- uh, the growth teams you find in those businesses sit on marketing and they just run performance marketing, so when... The heyday, they were called performance marketing, but growth sounds, like, cooler (laughs) so they just changed their name to the growth. But it's, like, the same, it's the same stuff. It's- I guess you could say, well, hopefully they've instilled growth principles, so it's much more, uh, iteration, much more experimentation, much more framework and model-based, but it's still like performance marketing, really.

   7. HSHarry Stebbings13:26

      I mean, growth is so much cooler as a label though-

   8. KFKieran Flanagan13:28

      Yes.

   9. HSHarry Stebbings13:29

      ... imagine I'm on a LinkedIn, I mean, growth?

   10. KFKieran Flanagan13:31

       Yeah, yeah. (laughs) Hey.

   11. HSHarry Stebbings13:31

       Ooh baby, that is exciting. Um, okay. So, we now have discovered those two big questions, and we wanna hire, we wanna hire for our growth team within this

9. 13:40 – 17:05

   How to structure the hiring process for Growth

   1. HSHarry Stebbings13:40

      hypothetical startup that I'm running. Uh, 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.

   2. KFKieran Flanagan13:53

      Uh, I think all great h- hiring processes have three sections, right? And I think it depends how big you are, how these- like if you're Google, maybe they last a year. If you're a (laughs) smaller company, you wanna get them done within a day. But, like, I think the- n- when I think about great interview processes, there's the informal... Like, one of the things I love to do is just, like, reach out and say, "Can we catch up and just talk?" Like, talk normally, not try to, like, me quiz you on things. Like, 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, is there, like, "Ah, I think there's something here that this person is gonna find really interesting," right? I think that's the first part. Then there's the formal part where you actually have your team and the people you think are really important to dig into their experience and to dig into the way they think and solve problems to give you perspective on, like, "Ah, actually, we do think that this person is a great company fit, g- great problem fit." Like, they're a fit for the problems we're trying to solve, uh, and a great, um, and a great team fit. And then I think you can- it's debatable if you want to do the case study or not. I think case studies in growth hires, like I've done a lot of growth hires- or not just growth hires, marketing hires, lots of different types of hires. I think in growth, 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, uh, 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. Uh, I think that to me is the- you know, a pretty good process to run if you're trying to hire a- a growth manager leader for your team.

   3. HSHarry Stebbings15:25

      Tell me, who do you bring into the process and at what stage? How do you think about bringing the team with you with the hire?

   4. KFKieran Flanagan15:32

      Um, so I- 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, right? And I- and what you're trying to match is the people who do best in roles will enjoy the thing they're doing, and I think in an informal chat you can just get a sense of like, is the problem you're trying to solve something they're gonna find interesting?

   5. HSHarry Stebbings15:52

      Yeah.

   6. KFKieran Flanagan15:52

      And- and the controversial part about that is what most people try to do is find someone who's solved the exact problem before, and I think that's a great thing to do it. But there's a great quote from, uh, a, um... I can't recall his name, but he's the- he's the kind of like godfather of mindfulness, and his- his great quote around like the- in the beginner's mind, um, in the beginner's mind, there is endless possibilities. In the expert mind, there are very few, right? And so when you bring in someone who ha- who has experience but also has something new to learn, when 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 new, bring them, uh, 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 o- o- of their experience, of the way they think, to give us like a 360 view of- of the candidate. And then in the case study, kind of similar, 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, um, perspective of all of the things that we need that person to be good at to- to excel in that role.

   7. HSHarry Stebbings17:03

      So the formal and the informal

10. 17:05 – 19:05

    How to do a case-study for a potential Growth hire

    1. HSHarry Stebbings17:05

       I can do. The case study, again, I haven't done this before. What do I actually do? Do I just give them access to our Google Analytics? Like, what do I give them? And then also, what questions should I be asking? Again, I don't know what I'm looking for, so it's very hard hire for me. What should I be asking and what should I be looking for in the case study?

    2. KFKieran Flanagan17:27

       Yeah, I think on the case study, I- one of the, uh, case studies that I would like to do is give someone a theoretical... Again, it's different per role, so I've done a lot of these in terms of like media growth, different per role. But if we're thinking about growth, a theoretical model, and within the theoretical model, there's a theoretical goal for the company. Hey, we want to grow to, uh, 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. And a- ask them to, 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, uh-... uh, founder, you are gonna 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 is ex- my theoretical thing that I'm trying to get to over the next six to 12 months. Here's what I think is really important. Please come back to me and tell me how you would prioritize a metric, how you would build a, a team to actually help you, uh, be successful in that metric. Give me some examples of experiments. Tell me why you think those experiments are right." Within the question then, what I would do is I would actually counter and say, "I think one of these experiments is much, much better, and 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, no, I actually disagree with you for these kind of reasons," right? You want someone with a strong point of view, not just someone who's gonna be swayed because you told them you think that they're wrong. Um, and so that- that's, um, there, that's the kind of case study that I would run

11. 19:05 – 20:10

    Does the founder need a growth model in place before hiring a Growth leader?

    1. KFKieran Flanagan19:05

       for, for a growth person.

    2. HSHarry Stebbings19:06

       Do I, the founder, need to have the growth model already in place when I'm hiring them? You said there, 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"?

    3. KFKieran Flanagan19:18

       You could buil- Uh, I think that's actually pretty interesting. I think you could do one of two ways, or 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. I think it's pretty easy to 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. Um, the only thing with that is, the reason I like to give them the data beforehand, and the reason I d- tell founders that it's cool to give them the model beforehand, because if they were just picking, doing the model themselves, then they can't really challenge themselves. It's kind of like being on the treadmill. Like, you can only, you could basically decide to get off it (laughs) whenever you wanna get off it. And so if you give them a growth model with real, uh, you know, with some complexity in it that you want them to see if they can, uh, s- isolate it and spot it, it just makes that, I think, a little bit better.

12. 20:10 – 21:32

    Biggest mistakes founders make in hiring for Growth

    1. KFKieran Flanagan20:10

    2. HSHarry Stebbings20:10

       Can I ask specifically, what are the biggest mistakes that you see founders make in the hiring and recruitment process for growth teams?

    3. KFKieran Flanagan20:19

       Uh, that is a really great question. Um, I, I don't know if I see commonalities mistake more so founders are unsure, even when they're hiring, uh, 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.

    4. HSHarry Stebbings20:36

       Huh.

    5. KFKieran Flanagan20:36

       Like, they, they, they, they know that they want a team to come in and iterate and work on their go-to-market metrics. But I don't think they've, like, really defined what they want that growth team to excel at in the next 12 months. And the other thing that I think is really pivotal when you bring in a growth team and, and it's the first time you're doing this, is the founder has to be the sponsor of that team, in particular 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, 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."

    6. HSHarry Stebbings21:18

       Mm-hmm. We're gonna talk about cross-functional communication, 'cause this was a core strength of yours. Um, I, I do wanna touch on, uh, a couple of things that actually from, uh, Kipp before we dive in, uh, to kind of post-hire. Uh,

13. 21:32 – 24:07

    The signs that an individual can scale with the company

    1. HSHarry Stebbings21:32

       first is like, Kipp told me about your insane ability to scale with company and transition from playbook to playbook, which I, 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?

    2. KFKieran Flanagan21:52

       I think ... So, everything is a, everything is a framework, right? Like, e- 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, h- how do you, how does this team work and how does it be successful?" It's just like long-winded presentation. They're doing all these things like, ugh. Like what, what are the, what are the couple of things that truly matter? And if you can always obsess about the tru- 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 sca- true scalable playbooks. The other thing of a great leader, sign of a great leader who can scale with company is, the job of any leader is to make themself redundant, right? 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, you're, 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. So, every great leader to me actually figures out, "How do I make myself redundant so I can actually build, uh, green space and build, um, enough time an- time, available time to take on, take on new things?" Um ...

    3. HSHarry Stebbings23:00

       What are you, what are you trying to make yourself redundant for now?

    4. KFKieran Flanagan23:05

       Oh, wow, that's a good question. Um, I will tell you that there's a couple of areas. And so, um, I built up the kind of like media org within HubSpot. It's about 80 people now. We acquired The Hustle. And so I kind of put all of that together and I hired someone recently who is incredible, Jordan, who was, uh, used to be the chief growth officer at Motley Fool, which is one of our- my favorite publications. And so I think he's gonna be better at me in that role. He has better, um, knowledge around media, and I think over time he can make me almost redundant in that, in that role. And so I think that's one of the areas, and then I have an incredible person who's actually helping to make me much more redundant on the customer d- demand gen-eration model that I built in HubSpot. So, you know, you wanna have people that you think are gonna be much better and brighter as you in those spots, and I think that's what I've constantly tried to do. And if you look, my career in HubSpot is every two to two and a half years I get new missions. And I can do that because the stuff I used to do, I have people who are better than me at doing that anyway.

14. 24:07 – 26:50

    Kieran's biggest hiring mistakes

    1. KFKieran Flanagan24:07

    2. HSHarry Stebbings24:07

       Tell me, uh, and this one was from Kipp too. Uh, he asked, "What were your biggest hiring fuck-ups?" (laughs)

    3. KFKieran Flanagan24:13

       (laughs) Did he, did he tell you to say that?

    4. HSHarry Stebbings24:15

       Yeah. (laughs)

    5. KFKieran Flanagan24:16

       Uh, oh, that ... You know what? I'll give you a great one. I'm not gonna tell, I, I'm not gonna mention names, but I'll tell you a great one that actually is prevalent within marketing, is hiring people based upon-... how good their personal brand is.

    6. HSHarry Stebbings24:29

       Huh.

    7. KFKieran Flanagan24:30

       And their personal brand is always much better than their skill set, because some of the truly great people are doing work (laughs) , right? And so, like, if you're, 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 content 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, uh, 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. Um, and I think there's been some times where that, that has been, that work they do is much better than, than, um, than actually what the true, true extent of the work is. Now, there's counterpoints that I think you talked to Matt. Matt is, like, one of the c- you know, opposite of that. His, he has a really big personal brand, but he's also one of the smartest people I've ever worked with. And so, I think it works sometimes, but a lot of the times, uh, founders, especially, get really swayed by people who have, like, really big personal brands.

    8. HSHarry Stebbings25:31

       I totally agree with you. I think the other thing, you know, we were talking about mistakes in hiring growth. I think one thing that I consistently see is people who mistake company brand where the person works.

    9. KFKieran Flanagan25:41

       (laughs) Yeah.

    10. HSHarry Stebbings25:41

        They're in Google's growth team. They're in Facebook's growth team.

    11. KFKieran Flanagan25:44

        Yeah.

    12. HSHarry Stebbings25:44

        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 and fuck-up I see founders make. I'm totally with you on personal brand also not being an indicator for success, so-

    13. KFKieran Flanagan26:01

        Yeah, I've said, 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 (laughs) . And I think that's an important thing for founders to try to, to try to figure out.

    14. HSHarry Stebbings26:21

        And a great personal brand will make more than both combined (laughs) .

    15. KFKieran Flanagan26:24

        Yes. I, I, yes. Man, the creator life is a good life, and I've actually, uh, w- again, that hustle, uh, part of the hustle, we got some really great creators, and, um, I've never been more appreciative of how hard it is to be a great creator, and how amazing those pe- how amazingly talented great creators are.

    16. HSHarry Stebbings26:42

        Ugh.

    17. KFKieran Flanagan26:42

        Like, it's just a, it's a real skill to be able to get, create things that people care about.

    18. HSHarry Stebbings26:46

        Do you know, I'm, I'm totally going off tangent here, but fuck it, I have to,

15. 26:50 – 29:50

    The Future of Content Marketing

    1. HSHarry Stebbings26:50

       and I'm very passionate about this. I, I, 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, 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, 'cause they know what resonates. E- how, how do you-

    2. KFKieran Flanagan27:12

       Yeah.

    3. HSHarry Stebbings27:12

       ... feel about what I just said?

    4. KFKieran Flanagan27:14

       Brands don't want to have points of view, right? They wanna sit in the middle and with everyone else 'cause it's safe. It's comfortable. I don't have to worry about getting tweets and my employees seeing the tweets and saying, "Oh, you're, this is, like, we don't agree with this." I think you h- I, we are increasingly moving to a world where everything is pop culture, right? If you actually look at FinTech, 10 years ago, if someone said, "Hey, you know what's gonna be one of the best content spaces online? Financial." (laughs)

    5. HSHarry Stebbings27:41

       (laughs)

    6. KFKieran Flanagan27:41

       Like, you would be like, "What? Fi- like, that's boring." No, like, FinTech has, like, moved totally pop culture. You're seeing it in business. Like, we're moving much more pop culture. Like, you're a great creator. You're creating content on places like TikTok that starts to get thousands of views. But we're s- we're gonna s- continue to see that, w- where brands who don't get with that and don't know how to plug into the culture of today, and sit in the middle, saying boring things and being boring, uh, in terms of their product position and their brand, I, I think they will, ch- they're, they're gonna struggle. And I think there are people with points of view, mem creators, GIF creators, creators themselves, that are gonna be much more important for companies to enable to, for, uh, to create environments that will, they will wanna work with those companies and help them actually plug into the, into the culture.

    7. HSHarry Stebbings28:25

       I, I, and I, I totally agree with you. I always say, the best brands make armies. You are either for or you are-

    8. KFKieran Flanagan28:31

       Yeah.

    9. HSHarry Stebbings28:31

       ... against, but the worst thing is sitting in the middle.

    10. KFKieran Flanagan28:33

        In the middle, yeah, 100%.

    11. HSHarry Stebbings28:34

        Do you think, h- do you think that is HubSpot today, if we're being analytical?

    12. KFKieran Flanagan28:38

        I, I think that's, so I think that's a great question. I think we, we built, we built our tribe around inbound marketing.

    13. HSHarry Stebbings28:44

        Yup.

    14. KFKieran Flanagan28:44

        Right? We built, we built that tribe. And so what happens, actually, like, I think we can discuss this. What's interesting to me is, a transformational company will always move towards an, at some point, just a, you know, a m- a, a message that is on-, is not transformational anymore. So, let, let me give you what I mean, 'cause I don't think I explained that right. If you're a transformational company, and you have a transformational message, so like ours was inbound marketing. Hey, like, you were either in the inbound camp, or you were doing all 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 w- ad hoc way of the way that people think about marketing. Like, inbound is not new now, right?

    15. HSHarry Stebbings29:21

        Yeah.

    16. KFKieran Flanagan29:21

        We kind of won that war. People agree that that is the best form of marketing. And so your transformational messaging just becomes best practice. And so, it's hard to keep that kind of for-, that passionate for or against when you've actually won the conversation, and people agree and implement that and it becomes best practice. Um, and so, that's something I think a lot about, is like, how you build your tribe at the start, but eventually, I think your tribe becomes a much bigger

16. 29:50 – 32:00

    How to make edgy marketing when your company is at scale

    1. KFKieran Flanagan29:50

       cohort of people. Um...

    2. HSHarry Stebbings29:52

       And how do you push it to the, 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.

    3. KFKieran Flanagan30:12

       I think, yeah, I think it's really challenging. I, I, for me, even though I said, like, companies shouldn't s- sit in the middle, I don't disagree with why it happens, because you are trying to be... You have, like, a large market that you are trying to market to. And you don't wanna alienate them with such point of views that are like, "Oh, well, 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, right? And I think that is, to me, the whole 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 products or ser- services, right? And why have we done that? Well, when the internet became popular, 2006, and c- and continued to grow, educational needs become more niche and brands were able to fill those educational needs by serving a smaller subset of the market, but that service actually helped those people, or helped to onboard those people to their products or services. And so, we always thought of content, I think, in terms of, how do we create educational content for the people we want to use our products? I think in the future, brands are gonna have to much, 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? And to me, that's the wh- that's the whole kind of discussion around why are you, 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 consumer's life.

    4. HSHarry Stebbings31:43

       Yeah, and it, 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

17. 32:00 – 33:30

    Elon Musk: The Ultimate A/B Testing Machine

    1. HSHarry Stebbings32:00

       and tell a story with it. I think that's astounding.

    2. KFKieran Flanagan32:03

       Yeah.

    3. HSHarry Stebbings32:03

       Like, that worries me.

    4. KFKieran Flanagan32:04

       Like, Elon Musk is probably one of the, like, for all of 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 alien- does not alienate his tribe, actually makes his tribe want to embrace him even more, right? Like, they're f- they're fanatical fans of everything he does.

    5. HSHarry Stebbings32:26

       For or against, you have a feeling on Elon Musk.

    6. KFKieran Flanagan32:29

       Right.

    7. HSHarry Stebbings32:29

       And actually, you know what? He is the best when it comes to understanding what does and what does not resonate with consumers.

    8. KFKieran Flanagan32:36

       Right.

    9. HSHarry Stebbings32:36

       He is the ultimate AB testing machine.

    10. KFKieran Flanagan32:39

        Yeah. Yeah, if you look at, um, his reach, if you, compared to, like, any traditional media org's reach, like, he, he has much more reach. Um, and he does that because he plugs into the culture. He knows how to instill emotions, whether they are positive or negative, on, on, 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. And for the m- you want it to be positive for the people you're trying to reach, and not care too much, not not care too much, but not get swayed by the negative. Like, then sometimes the negative is not something to actually stop you, make you stop, uh, not stop doing things.

    11. HSHarry Stebbings33:19

        We, we will get back onto the schedule. The, 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, I don't mean this rudely, but the, I think, you know, Mies

18. 33:30 – 35:10

    Companies underinvest in content

    1. HSHarry Stebbings33:30

       and Yous of the world, like, either are too expensive or do their own thing. (laughs)

    2. KFKieran Flanagan33:35

       Yeah.

    3. HSHarry Stebbings33:35

       Like, you know, you could never hire, I would never do a content role, um, there are o- other amazing people, you know, your Andrew Chens of Andreessen. He's made millions by Andreessen. Like, you're never gonna get him to join a content team. Do you know what I mean?

    4. KFKieran Flanagan33:49

       Yeah, but I think there's, I think, I think that is a great point, right? That is a great point, because we underinvest in content. Like, I mentioned this before, is that we'll spend, you know, a million dollars on Facebook campaigns and then outsource our articles for $10 and expect, like, "Why is this content not working and the, (laughs) the Facebook thing is working really well?" Well, you were spending $10 an article. So, it's first of all rethinking how we think about media. Media should be, uh, a place, uh, rethinking how we think about media, building an environment where creators actually want to work, and so there's interesting ways that you can build environments that you want creators to work.

    5. HSHarry Stebbings34:22

       How?

    6. KFKieran Flanagan34:22

       One of those is, like, paid 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, is a creator program. So you're right, like, all of these people will not want to work within a company because they wanna 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, within reason, and we can talk about that. And you start to make yourself a interest in place for both internal people to work, because they get to work with these creators, or external people to work, 'cause you have a program that supports their growth, but also actually, um, kind of incentivizes them to grow because you are paying them on the upside.

19. 35:10 – 36:40

    Content Distribution

    1. KFKieran Flanagan35:11

    2. HSHarry Stebbings35:11

       Do you know what I find amazing though, which is, like, how many companies and firms 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 then they click publish, and then they go, "Why is-"

    3. KFKieran Flanagan35:27

       Forget about it. (laughs)

    4. HSHarry Stebbings35:28

       "... why is no one coming? Why is no one coming?" No distribution is thought to it. People don't understand distribution today. I think this is why, you know, we've been successful, you've been successful, but I think we both get distribution and it astounds me how people cr- create for so long and distribute not at all.

    5. KFKieran Flanagan35:46

       Right. I think great distribution starts with great ideas. That is the one th- the thing that I have learned from the people who I have been immensely impressed with in The Hustle is, they have, they are able to, they have great ideas, they are able to find things that are interesting that is not widely covered, like they just find these nuggets of, of data, they find these nuggets of, uh, of information, and then they are able to have their own spin on things. Like, they have an angle, right? There's a, there's a specific angle that they take 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, again, stuck in the middle, doing the same thing as everyone else. And so, uh, 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?" And, um, so much content goes to waste. So much great content goes to waste, because to your point, we just publish and then we think, "Hey, like,

20. 36:40 – 38:21

    Attribution of content marketing to revenue generation

    1. KFKieran Flanagan36:40

       my job is done. Someone will find it and good things will happen."

    2. HSHarry Stebbings36:43

       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?

    3. KFKieran Flanagan36:55

       I think data has been the best and worst thing to happen to marketing, right?

    4. HSHarry Stebbings37:01

       (laughs)

    5. KFKieran Flanagan37:01

       Be- wh- why best? Well, marketers used to just be stuck doing crap stuff because no one wanted to give them anything good to do because they couldn't, 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. We could actually say, "Oh, well, we can do these things, and we can generate this amount of revenue." But then we've become so focused on that, that we just try to iterate, 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, I'm... Everyone is like i- stuck in the, 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. Like, I think founders who can truly see that they want to invest in something that will make me differentiated, that will make me stand out, that will m- create a, a larger audience ar- around my brand, and I know that that thing is not gonna be unmeasurable. I know that thing is gonna be really hard to quantify. We did the Hustle deal. We did not do the Hustle deal based upon metrics, right? We did not pitch to the board and say, "Oh, these are all the kind of cool metrics." It's a bet on how we want to be, um, seen within the future, how we wanna 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, like, how does every single action you take get me some amount of

21. 38:21 – 39:50

    What is "Community"?

    1. KFKieran Flanagan38:21

       pennies, dollars, um, and customers?

    2. HSHarry Stebbings38:24

       One word that's thrown around so much in the brand, content, new gen marketing that we talk about now is community.

    3. KFKieran Flanagan38:32

       Mm-hmm.

    4. HSHarry Stebbings38:32

       We both hear it the whole time. And I kind of laugh to myself because I'm like, "What the fuck does that mean?" Like... (laughs) Uh, can you tell-

    5. KFKieran Flanagan38:39

       Yes, what does it mean? No-

    6. HSHarry Stebbings38:41

       Wha- what does, what does it mean to you?

    7. KFKieran Flanagan38:42

       I... Yes.

    8. HSHarry Stebbings38:42

       And then there's excitement about, "Oh, commu... I see so many community startups." I'm like, "Oh, what do they, what do they do?" (laughs)

    9. KFKieran Flanagan38:49

       I think comm- community is... 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, like I, uh, e- even just speaking to companies or advising companies, even just having cl- even just having commonalities of what's included in community-

    10. HSHarry Stebbings39:07

        Yeah.

    11. KFKieran Flanagan39:07

        ... does not exist. Doesn't... To me, when I think about community, for the most part, I think about, oh, like I go create an account. I connect with other people, and I discuss things with them. Then you go to another company, and it's like, well, that's anyone who's in our email list, anyone who's on our Twitter following. And, and you're like, okay, so it's just everything. It's like literally everything. And I think community is your tribe, right? 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, right? They are engaged with you in some meaningful way. And I think as... We are gonna 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.

22. 39:50 – 44:35

    Does Community scale?

    1. KFKieran Flanagan39:50

       But that definition does not, I don't think, clearly exist. Um-

    2. HSHarry Stebbings39:52

       Does it, and does it scale? With scale, you have community denigration. We see this with Y Combinator, for example. And I'm... I'm really picking fights now, but fuck it. (laughs)

    3. KFKieran Flanagan40:01

       (laughs)

    4. HSHarry Stebbings40:01

       It's Thursday afternoon. Um, yeah, you know, it doesn't scale well. With an increase in size, you have a reduction in quality.

    5. KFKieran Flanagan40:07

       Oh, yeah. This is a great conversation. I'm so glad you, we wanted to have this conversation.

    6. HSHarry Stebbings40:11

       Yeah.

    7. KFKieran Flanagan40:11

       Uh, yeah.

    8. HSHarry Stebbings40:12

       That is like, that is really, really hard. How do you think communities can scale? If you are gonna build an IPO-able massive company, having community led at the beginning is capped, no?

    9. KFKieran Flanagan40:24

       So, I, first of all, I think, I think it's how you define community. So, we're defining community by like... If we incl- if we include our media, a- mediums in that, and like if you start... 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? And that could be a meaningful way of how I grow my business. Then, that's pretty hard to, 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, how you define it. But I do, but I do think you said something important, right? The best commu... 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 wanna interact with themselves- 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 a passion for something, who are truly trying to learn something. And they can connect with each other and learn from each other and, and do those things. And so, community-led growth, which is like, oh, well, community is gonna 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. Is it tr- 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? And so, I think in the future, first of all, again, it really does matter how we define community, because if I just say it's Twitter followers and Instagram followers, then yeah, okay, well, it's like pretty easy to grow that many. But I don't, I don't think that's what it is. I think in the future we're gonna get better tooling to really help us figure out how we can segment our community into different cohorts of depth. Like, the, the tooling is not good. And then we will be able to build breadth with better incentives. And I think, you know, the cliché is, uh, but it's true, the incentives are coming from the Web3, um-

    10. HSHarry Stebbings42:19

        Mm-hmm.

    11. KFKieran Flanagan42:19

        ... industry, and it's really about ownership, right? In, in the f- in today, community gets you maybe better knowledge. It gets you information about a product. It gets you people who have shared interests and hobbies. In the future, it should get you ownership, like actually 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, of your go-to-market. But I think, I think the, the number of winners in community-led growth is small, but they get exponential returns because how many community- communities can someone be part of? Two, three? So, a small amount of winners, but they get exponential returns.

    12. HSHarry Stebbings42:54

        What will cause the winners to be winners, do you think?

    13. KFKieran Flanagan42:58

        I think it's how you... I think it's understanding the value you can deliver. And you have to understand the value you can deliver at scale. Um, and so first of all, you have something intrinsic... You, your brand is associated with something that person wants to learn. Like, they, there's, there's some sort of achievement. 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, right?

    14. HSHarry Stebbings43:23

        Yeah.

    15. KFKieran Flanagan43:23

        Like, I myself want to get better by joining this community. Then they are around the connections you create, right? I actually can connect with peers, and they make me a better version of myself. And then the third part, which actually is an untalked about way you could build a moat around your company, is the reputation. Like, by doing those things, I actually en- I actually can achieve something, but I can show people that in a visible way and get some sort of payback from that. So, jobs is, like, the best example of that. I get credentialed, I get some sort of, um, qualifications, and I get matched with jobs who want people like me. Now, there's other ways you can do that, if we go into, to Web3.0. I think the companies who win in the future excel at those three things, which is breadth, personal e- acknowledge, like, "How do I create, uh, mass amounts of people who can learn things from me and 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 c- 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 the reputation?" But I think in Web3.0, that's through ownership. In Web2.0, it's reputation, in Web3.0, that's ownership, right? I'm actually creating value in the community, but now I have ownership in this company, so I'm actually getting something back.

23. 44:35 – 46:36

    How to market a horizontal product without alienating the verticals?

    1. KFKieran Flanagan44:35

    2. HSHarry Stebbings44:35

       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...

    3. KFKieran Flanagan44:44

       Mm-hmm.

    4. HSHarry Stebbings44:44

       ... uh, uh, let's say a Notion is a brilliant example as a tool. It could be used by dentists and it can be used by software developers. How... And when we go back to that breadth and depth, it's very similar, but like, how do you market and message such a horizontal product without alienating the depth? Without e- alienating the verticals?

    5. KFKieran Flanagan45:08

       Yeah.

    6. HSHarry Stebbings45:08

       But then also, not just stick in the middle. You know, how do you describe Notion? Collaborative work docs. Well, that doesn't speak to anyone actually. But you... Do, do you see what I mean?

    7. KFKieran Flanagan45:18

       Yeah, I think most of the horizontal tools, they ho- they stay horizontal to get mass distribution, and they verticalize to mono- they verticalize to monetize. And so, like, you have a Calendly, which is applicable to a- anyone, right? What a great tool, what a great company. Tobi's built a f- a- an amazing company. But, um, they, they monetize through sales teams or they monetize through, um, you know, different verticals. And so, I think in terms... You're getting at their messaging. Like, when I go to their website, how do I know this tool is for me?

    8. HSHarry Stebbings45:48

       Yeah.

    9. KFKieran Flanagan45:48

       I don't know if they... if that's how those tools grow. They grow, like, through virality, word of mouth, right? You have a small group of y- people who use that, and they start spreading it to other people. I don't know how much their positioning... I'm sure it matters, but I don't know how it 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, 'cause 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. This is truly great for teams who want to build CRMs, lightweight CRMs." Like, whatever those things are, I think that's when it becomes really important.

    10. HSHarry Stebbings46:32

        Can I, can I... Uh, because sorry, take you back into community on something that

24. 46:36 – 50:27

    What should HubSpot have done differently with regard to Community?

    1. HSHarry Stebbings46:36

       I did forget.

    2. KFKieran Flanagan46:37

       Yeah.

    3. HSHarry Stebbings46:37

       Do you think HubSpot's done community well? And with the benefit of what you know now, is there anything you'd do differently looking back?

    4. KFKieran Flanagan46:45

       Yeah. Um... This is a great question. So, I think we... It dep- again, how you define community. I would tell you, most people would say HubSpot has built a really large vibrant community through our content, right? That's how they think of it. Like, our academy, if you actually go to G2 Crowd, you'll see that our, our academy is probably the best rated online education platform, and we're not an online education company, right? That is part of our community. But I'll give you, I'll give you, like, an honest answer. So, I think we've built a tremendous community, but we have a lot more to build. If you think about community as, like, our community at hubso- .com, like the connections part, "Where do I go c- where do I go to get connected to others?" We've primarily focused on building a community of product. 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 have hundreds of thousands of people who are all credentialed, uh, through our academy and taking our software courses. 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, like, through 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 for communities of practice, which is people who want to get better at, at, uh, educational content and educational topics. So I think that's where we can improve, like, that community of practice around education and connections.

    5. HSHarry Stebbings48:18

       It's, it's, it's really tough though, because, like, 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, I feel sorry for, you know, people who own the budget lines, 'cause 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." (laughs)

    6. KFKieran Flanagan48:50

       On... Yeah, I... Well this is, um... This comes back to, like, how do you, how do you build a portfolio across the things that are short-term that I can measure, the things that are long-term that I can measure, and the things that are long-term that I can't measure? 'Cause predominately, like, that's what you, what you're, what we're kind of discussing in the long-term unmeasurable bucket. And I think to, to do something like that a-... you have to have very deep conviction. I talked to a founder recently, I won't give the company or the name, and they are building something for three to five years that they, they don't expect to measure, they don't expect 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. Like, and it's, you know, i- i- it's a- it's around, um, 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, uh, you know, direct attribution to revenue. Uh, because again, if we tie everything to revenue, then we're all gonna do the same stuff. Like, we really are gonna do the same stuff, for the most part. 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.

    7. HSHarry Stebbings50:06

       I, listen, I, I totally agree. Um, I've also absolutely fucking loved this discussion. (laughs)

    8. KFKieran Flanagan50:13

       Cool. (laughs)

    9. HSHarry Stebbings50:14

       Y- you know when you have a schedule and you're like, "Yeah, fuck it. Whatever." Um, so I, I totally agree with you. Uh, I do wanna, uh, dive, dive into a couple of elements, though, before we move into a quick fire.

    10. KFKieran Flanagan50:24

        Yeah. Yeah.

    11. HSHarry Stebbings50:25

        And these are just elements specifically

25. 50:27 – 53:50

    Cross-functional communication with Growth

    1. HSHarry Stebbings50:27

       that I was told I had to ask you about. One is cross-functional communications with growth. It's a very challenging topic. How do you think about making sure growth and other f- areas of the org are synergistic and aligned? How do you nail cross-functional comms?

    2. KFKieran Flanagan50:45

       I'll l- I'll give you a couple of my learnings, um, and things that I w- was bad at and had to get better at. So, (clears throat) I think s- if, if you ask someone, you know, "Oh, like, what, what's Kieran like?" One of the things they'll tell you is, "Oh, well, like, he was, like, very black and white, like, '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, uh, or white, it's really black and white, right? You actually have to be able to understand both, uh, sides of the story, and actually, there's most of the things live in between, in the gray, right? Most of the things live in the fog.

    3. HSHarry Stebbings51:19

       Mm-hmm.

    4. KFKieran Flanagan51:20

       And so I never used to dive into the fog. I used to say, "Wow, you're doing this thing? It's dumb." Right? "It's just kinda dumb." And then you didn't know all of the reasons that those things existed. And so I think when that happens across teams, and because you speak different languages, then everything kind of seems, if you're all black and white, then everyone seems like they're doing kinda dumb stuff. Uh, and so the first thing is, like, you have to live in the gray. You have to l- 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. Like, the, the job of a PM, great PMs crystallize problems and then present them to their engineers, and 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," right? Uh, marketers are very solution-orientated, right? Actually, I think we all could, marketers could do a lot better if we kind of ground ourselves in the problem, and some, some do, some don't. But I think we're much more solution-oriented. "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.'" And that PM has to go to the engineering team, "Do these five things." That's not how engineering teams wanna work, right? And so, so that- that is a, that is a thing that just does not work, uh, until you kind of speak, you have to start to figure out, how do we all speak the same language? Like, how should we work together? How do we speak the same language? How do we make sure that we are, are aligned, are aligned around the problems?

    5. HSHarry Stebbings52:42

       How do you actually do that? I'm the CEO. Do I say, "Right, product team, right, growth team, right, marketing team, come in, and we are gonna sit down and discuss the dictionary of how we speak"? How do I actually do that?

    6. KFKieran Flanagan52:54

       You know, I'm gonna be honest with you. The, 'cause I don't have a great, like, the way we got there is, like, through lots of friction and fighting and, and, and falling out with each other and getting back on side with each other. We did not, I- I would be lying if I said, "Oh, well, we had this, like, really amazing playbook that we kind of rolled out and we all started..." We went through, that was the hardest part, I think, of the PLG motion for us is, we, you know, we just missed, really, uh, underestimated how hard it would be for all these teams to start working together.

    7. HSHarry Stebbings53:26

       Mm-hmm.

    8. KFKieran Flanagan53:26

       And I think we got there through grinding it out, (laughs) is the way I think about how you get to be a great presenter. You just have to grind it out. And I think that's how we got there. Maybe there is people who, like, have way better playbooks and frameworks for that. But for me, I would be lying if I said that we had one. Whereas I think what we got there is, like, we trusted each other, we were okay with falling out with each other, and over time, we got to a, a place where

26. 53:50 – 55:15

    How to onboard for Growth

    1. KFKieran Flanagan53:50

       things worked much, much better.

    2. HSHarry Stebbings53:51

       Can I ask a final one for, uh, before the quickfire? I think onboarding is just universally done terribly badly.

    3. KFKieran Flanagan53:58

       (laughs)

    4. HSHarry Stebbings53:58

       When you think about, like, onboarding for the new growth and marketing hires, what does good look like to you, and what are you, what standard do you hold yourself accountable to as, "This is what we need to do to make them successful?"

    5. KFKieran Flanagan54:10

       Yeah. Yeah, well, I think one of the things we do that, uh, is really good, um, and I'll, it's our people op team, it's not me, is, uh, we build 100-day plans for people.

    6. HSHarry Stebbings54:18

       Oh.

    7. KFKieran Flanagan54:18

       'Cause when you come into a new role, you're like, "Oh, wow, how do I, like, what do I do," right? Um, and especially in remote, actually remote onboarding is a whole other topic, like remote work onboarding. So, we do a 100-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 for you to do month two." Every two weeks, we check in and ask how you're doing across that 100-day plan, ask how the meetings went, ask, "Is there other questions you have so we can pair you with other people?" And that 100-day plan isn't actually about, "At the end of this, we need you h- to have achieved A, B, and C." It's, "At the end of this, we hope that you, um, 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 100 days. Like, there are things, like, we want you to do along the way, but 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.

27. 55:15 – 56:00

    Kieran's biggest weakness as a leader

    1. HSHarry Stebbings55:16

       Can I ask you, um, as a leader today, I listen to you and i- it just seems very natural. It seems very structured and 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 you're weakest?

    2. KFKieran Flanagan55:31

       Operations. I'm not ... Like, processes, you know, when I mean operations, I mean like building the project management tool and all of that kind of stuff. Uh, it's just, 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. Um, it, it's part and parcel of the role, but that's not where, that's not where I'm like, "Oh, well how do I build a great operator model for my team today?" It's like-

    3. HSHarry Stebbings55:56

       I-

    4. KFKieran Flanagan55:56

       ... I have to force myself to do it.

    5. HSHarry Stebbings55:58

       I'm with you. I, I, I delegate

28. 56:00 – 57:10

    How has angel investing impacted your mindset?

    1. HSHarry Stebbings56:00

       it. (laughs) Uh, final one, final one, I promise, before the quick fire. You angel invest as well today. How has angel investing impacted your mindset to growth and company building?

    2. KFKieran Flanagan56:09

       Yeah. Uh, growing a company is really fucking hard. Founders are amazing people. (laughs) Like, it really has just brought home how hard it is to bring, 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 kinda like, oh, well like this is how, this is what it's like in a startup. Like, they just grow and they become like really successful. And angel investing has really grounded me in that, wow, it 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, uh, you know, ki- I, I, uh, kind of inspiring. Like, they actually will put all things on the line to actually try to make t- to make this company a success. Um, yeah. I, I think, I think mostly grounded me in how hard it is, 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.

    3. HSHarry Stebbings56:58

       Yeah. No, I, I totally agree with you. I also think it's about kind of speed and velocity of decision-making. I think speed of execution is just everything-

    4. KFKieran Flanagan57:05

       Yeah.

    5. HSHarry Stebbings57:05

       ... and I really see that the more I invest. Um, I do wanna do a quick fire though, Kieran, 'cause I could talk to you

29. 57:10 – 57:34

    Growth Tactics that have/haven't changed over the last 5 years

    1. HSHarry Stebbings57:10

       all day. Tell me, we're gonna, and it's focused around growth. What growth tactics have not changed over the last five years?

    2. KFKieran Flanagan57:18

       Um, I think like email automation. I don't ... I think they have remained constant. Still important, but have not changed that much.

    3. HSHarry Stebbings57:25

       Okay. Totally agree. What tactics have died a death on the other hand?

    4. KFKieran Flanagan57:30

       Yeah, I don't know if anything dies, right? I think it just kinda becomes less effective. You look at paid

30. 57:34 – 58:09

    Biggest mistake founders make when hiring for Growth

    1. KFKieran Flanagan57:34

       advertising. I think that's gonna become less effective over time because of privacy, because of the rise in CPMs. You look at search as my, 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. Uh, but I think for most tactics, plateau versus die. (laughs)

    2. HSHarry Stebbings57:56

       Um, tell me, what would you say is the biggest mistake-

    3. KFKieran Flanagan57:58

       (laughs)

    4. HSHarry Stebbings57:58

       ... founders make when hiring growth teams?

    5. KFKieran Flanagan58:00

       Uh, I think it's de- defining h- the ... 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,

31. 58:09 – 58:27

    Advice for Growth Leaders Starting Today

    1. KFKieran Flanagan58:09

       and how you can be a sponsor of their success.

    2. HSHarry Stebbings58:12

       What one piece of advice would you give to a growth leader starting a new role today?

    3. KFKieran Flanagan58:17

       Uh, customer's 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 b- than anyone else. And be

32. 58:27 – 59:02

    How onboarding differs for remote workers

    1. KFKieran Flanagan58:27

       an advocate for your team, um, better than anyone else.

    2. HSHarry Stebbings58:30

       How is onboarding different in a remote versus an in-person world?

    3. KFKieran Flanagan58:35

       The, the meetings matter. The making sure that the person ... You take and the ... Be- being proactive ab- about getting that person set up to talk to other people. Everything in remote work, work is on scheduled time, right? 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 a bus- when, when in an office, it's much easier to or- have these organic conversations with people. So you really have to be proactive about

33. 59:02 – 59:28

    What would you most like to change about Growth?

    1. KFKieran Flanagan59:02

       making sure that that person gets time with people and gets to spend time and start to meet people.

    2. HSHarry Stebbings59:06

       What would you most like to change about the world of growth?

    3. KFKieran Flanagan59:11

       Uh, I think, I think it needs to become ... I think the more defined it comes, the easier it is for defi- uh, 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. Um, I think that that, uh, that is the

34. 59:28 – 1:00:40

    How many domains have you bought?

    1. KFKieran Flanagan59:28

       best thing that could happen for it.

    2. HSHarry Stebbings59:29

       How many domains have you bought?

    3. KFKieran Flanagan59:31

       (laughs)

    4. HSHarry Stebbings59:31

       And how clo- and which one have you been closest to pursuing?

    5. KFKieran Flanagan59:35

       Uh, I have bought let's say a hundred. Uh, I had a bit of a issue with buying domains at some point. (laughs)

    6. HSHarry Stebbings59:42

       (laughs)

    7. KFKieran Flanagan59:42

       The o- the one, you know the one I nearly was like, "Ah, this could be a good idea," was I bought, uh, remot- remotecal.com. I think it's back. I think it dropped, so I don't think I have it anymore. And what I was gonna create was, um, 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 wanna get matched with people, put in interests, and, uh, and they will get matched every month with other people who have the same schedule as them, 'cause one of the hard things is scheduling. But I never did it.

    8. HSHarry Stebbings1:00:16

       Uh, I think it's worth a billion dollars, is-

    9. KFKieran Flanagan1:00:19

       Yeah. Yeah. Do I-

    10. HSHarry Stebbings1:00:20

        ... our

    11. NANarrator1:00:20

        We'll put-

    12. KFKieran Flanagan1:00:20

        You wanna invest? (laughs)

    13. HSHarry Stebbings1:00:21

        No, I d- I, I, I would have happily if you would like to do it. Um, I would love to, but it actually exists in the US.

    14. KFKieran Flanagan1:00:27

        Oh, it exists? Ah.

    15. HSHarry Stebbings1:00:28

        In the US. It's called Lunchbox, I think.

    16. KFKieran Flanagan1:00:31

        Oh. Lunchbox.io. Okay.

    17. HSHarry Stebbings1:00:32

        And R- Yeah. Andreessen backed it, I think. Um-

    18. KFKieran Flanagan1:00:34

        Okay.

    19. HSHarry Stebbings1:00:35

        And, uh, it ... I think it's worth about a billion now. It was a very good idea.

    20. KFKieran Flanagan1:00:39

        There you go. I shoulda

35. 1:00:40 – 1:01:53

    What company's growth strategy have you been most impressed by?

    1. KFKieran Flanagan1:00:40

       done it. I shoulda done it.

    2. HSHarry Stebbings1:00:41

       (laughs) Fuck. (laughs)

    3. KFKieran Flanagan1:00:42

       Damn it. I give the domain ... I should've kept the domain name and tried to sell it to him.

    4. HSHarry Stebbings1:00:45

       (laughs) That is brilliant. Uh, final one. What one company growth strategy have you most been impressed by recently?

    5. KFKieran Flanagan1:00:52

       Yeah. I think Web2, Canva. Uh, Web3, Step- Stepn. They're my-

    6. HSHarry Stebbings1:00:56

       Why, why, why on those?

    7. KFKieran Flanagan1:00:58

       I think Canva are one of the best ... Like, one of the things when I talk to founders in B2B, like it's so, it's kinda funny. Every founder now tells me, who are doing product-led growth, "Oh, the thing we really wanna 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, they created a template for. Then they actually created a marketplace so that people can actually create their own templates. Uh, and you can buy them, which extends the amount of traffic that they can acquire from search. Like they, they're ac- they just execute really, really well in terms of how they've built a, an amazing distribution engine. And so, um, I think they're really cool. And then I think Stepn, which is a kind of move, play, uh, play the, play the move app. Um, I think their game mechanics are really interesting in terms of how they've grown.

    8. HSHarry Stebbings1:01:41

       Listen, this has been ... 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.

    9. KFKieran Flanagan1:01:48

       Yeah. Thanks for having me on. I'm a huge fan of the podcast, and I, I appreciate you asking me.

Episode duration: 1:01:53