20Product: Slack CPO Noah Weiss on How to Master Product-Led-Growth, The Biggest Mistakes Founders Make When Scaling Into Enterprise & What Needs to Change with your Product, Team and Processes when Scaling From PLG to Enterprise

23:04So we can use Slack Connect between companies working in a project together, between vendors. We have Slack Connect channels with every one of our customers to do customer success and support, the stripes head of sales famously said, you know, once we're the Slack Connect channel with a customer, I know the deal's gonna get done. The thing that I think we were, you know, maybe overly cautious on is, we were really, really slow in delivering that product to market because we're really worried that people's mental model of Slack was very much that it was this walled garden for my organization. You know, there was no external notion Slack.

23:35It was whatever was in Slack was just fully internal. We were really anxious, frankly, about breaking the walls of that garden with this idea of Slack Connect channels that could connect you to other organizations. And then, to point about simplicity, does people's mental model what Slack is get more blurry? And I think we probably had it in beta for about two years. It was a really long time to bring to market. Frankly, especially given the competitive backdrop there, I think if we had expedited into market back before there were more products that people were starting to use or get for free as defaults.

24:08And back when I think the ubiquity of Slack was something that felt like maybe inevitable. This could have created enough gravitational pull or existing customers who love it. Just forced the rest of the world to come use it with them. And I don't really miss that moment, but I do think that moment was delayed enough that maybe we missed some of the more like exponential return to having brought it to marketer. You mentioned speed that I'm asking it I used to be so nice on the show when I was younger. I'm asking the tough ones. If we're honest, I'm sure you hear what I hear. People say the speed of innovation at Slack is slower today.

24:44What are the biggest bottlenecks to the speed of innovation in Slack? Where it was most true was 2018 to 2020. Back then, but that's when we really made this kind of hard rotation focusing on the enterprise buyer, the enterprise organization. We did prioritize for a while kind of scalability and solving those really complex. Fortune 500 use cases and compliance and security needs. And I think we did take the eye off a little bit, that core pace of product innovation, of pushing the boundary of what category could be forward. COVID was a real wake -up call for us because suddenly even our existing customers were coming to us and saying, oh my God, I'm living all day in Slack, but also now having all these other needs and can Slack fill these needs or do I need to look at other places for them?

25:29It's right at the end of 2020 through now. I would say, and this is not a rebuttal, but my perspective of these is that I think that the pace of innovation has kind of increased pretty dramatically. You know, you have huddles, you have clips, cameras, which was just launched, you have work flip. And that is because you have clarity of understanding who you're building for, be it the enterprise button. I think what it actually is is that we got to the place where we realized there was diminishing returns for focusing the majority of our efforts on the enterprise buyer. or once you get through a lot of the blockers that are just, hey, the CIO is gonna say no, unless you have DLP and EKM and IDR, I'm not gonna go through all the three letter acronyms that will be blockers.

26:10But once you do all those, then you start realizing what we felt all along, which is you wanna keep pushing the capabilities of the product for the end users, for the teams we're trying to work on a more productive, the like, full way. And those teams need new things. And it felt like, honestly, and Stuart said this publicly too, the pandemic and the shift to this hybrid world, I think it kind of gave us almost a new level of meaning and urgency that we were doing because the level that people were depending on Slack, the expectations they had for what Slack could do had just grown incredibly basically overnight.

26:45No, you mentioned there's three latter acronyms. Most people have no idea what they mean because generally most people don't have to scale into enterprise but many startups do and many startups actually I think respectfully don't understand quite what it takes. What do you think of the biggest mistakes that start -ups who start in SMB make when they scale into enterprise. It's hard because honestly a lot of the work is really kind of removing blockers and I think there what I would really recommend honestly is like that's where you want to hire people who have domain expertise you don't want a bunch of folks who worked our early stage startup and never worked enterprise before to be like let me try and figure out from from first principles what like a little traumatic key management is and why the Chief Security Officer of a Fortune 100 company cares about it.

27:29This is not a place where you should read the wheel. You should not take a novel approach. But the biggest mistake I think people make, and it's a little bit kind of reflecting for ourselves, is over -rotating on the enterprise buyer where you think that they're hardly more conservative. They don't want features to be shipping every single day at 10 users because they're and Farron was trying to centrally run an organization where they have enablement and education and so forth. And I think you can introduce to your point about speed. It can introduce a level of cultural conservatism because the enterprise buyer will say, hey, I have these blockers, a block then, and please stop shipping things so quickly.

28:07And then the small, immune -sized business will say, I don't even know what those acronyms are on on care, but what else can your product do? And by the way, I'm very value -conscious. So I'd love your product to do more for the same price. And I think that becomes attention and I think if you over rotate you can lose some of that speed That product innovation DNA and I think that's the thing to watch out for the most is not losing the core of the fiber That got you to build a product that people the enterprise along in the first place How do you know when's the right time to move into enterprise?

28:36I think there's two paths and there are some Product categories where you need to start in the enterprise because there isn't an SMD buyer things in the like security compliance infrastructure space. Those buyers for good or for bad are gonna be the CIO or the CSOE at an organization to start with enterprise is often the answer and don't sweat that you don't have a bottoms up motion or PLG motion. I think if you start with SMBs, I think the thing to look out for is, are you seeing pockets of teams or subsets of an organization that are starting to use your product kind of independent of each other?

29:11And if you start seeing that, so for example, I can imagine, I've heard interviews too, it talked about Figma, they started seeing different pockets of a large organization start adopting Figma. This is a very similar to Slack story. And then once you see that, you're like, okay, maybe we don't have all the control and administration that a large company needs, but we have that organic demand that obviously people large companies are getting value. And so that's where you start saying, well, let's go talk to the CIO at Uber. You already have 300 people using it. They paid for it with their corporate card.

29:41What if you went and enterprise level agreement and then they'll tell you the 17 things that are missing and then that be good your enterprise journey How do you determine where to focus? It's so fucking hard because you've got SMBs wanting speed new products I want this situation that is racing your enterprises who want security often as a product leader Which customers you serve when you have to our answer that if we have to choose who we're serving about else It's actually the end user who's using a product and living in it for 10 hours a week because it really can make something that they love, that they feel like actually makes their working life simpler and more pleasant, more productive.

30:17They're not only gonna tell their co -workers, they're gonna tell their boss, they're gonna tell their friends, and they may even advocate for us with IT. That's SMB. Not so I would say actually independent of SMB or enterprise, because actually that's the magic of how Slack spreads at most large enterprises. So I think we've said this publicly, but over 85 % of our enterprise customers, so you know, customers of over 1 ,000 users started in self -service. They started by signing up on Slack .com, just like an SMB, sharing it with some co -workers, just like an SMB, putting a credit card down, just like an SMB.

30:47But at some point, that grew enough that they then had a discussion with our sales team about becoming an enterprise -level customer. Fundamentally, if we have to choose, we choose the end -user of Google Insilival Day. But I think we do it, balancing what we know are the needs of the organization, the administration, the buyer, who sometimes isn't the end -user, obviously, the larger company. But I think just fundamental to our DNA build a product Cus it was love enough to tell their co -workers and their friends in the rest will take care of itself How do you think about the product decision of short -term product feature improvements and Shipping a little bit of what delivers revenue today in all honesty versus longer -term strategic best generative AI Introductions you name it.

31:31How do you think about that balance? Yeah, I mean, it's good back a little bit to the very beginning of the discussion with the Google 70 -2010 model, which is like one way of thinking about it, because I think there, if you just apply that, you'd say 70 % are the first category and 10 % are the other latter category. What do you think you've done this in the 10 %? In that 10 % bucket, would be the entire Slack platform and kind of workflow automation system that exists on top of it and that ecosystem, which didn't exist when I first started Slack. building network on top of this world garden that existed with slot connect.

32:04I think slot connect is so interesting. Did you disagree internally? We definitely debated the benefits would be outweighed by the complexity that it introduced. And also, you know, email is what we joke about. It's kind of like here at your post. It is the lowest common denominator. Everyone can be reached by email. So what would slot connect be 10x better than email for? And could you actually deliver on that? Because you do have the post mail that everyone can So yeah, we debated a lot. I think the AV stuff was another audio visual with Huddles and Clips and some of the newer co -working capabilities we've been introducing.

32:37I think for a long time we thought Slack was a just primarily tech space product and adding dimensionality to it, moving into a space that has a lot of other competition and components. I think that was a huge bet to take. How long does it take for you to know a new product works? The thing that we do, which I think has become a playbook for us at least, We start off always with an internal prototype of something that's big, but we make it rough, we make it ugly, it's unpollished, and we see internally, before we do all the refining, the polishing, the scaling, the performance work, are people like, wow, this is super interesting.

33:14Like this could change the way that we work internally. Okay, if you do that with a small group, then okay, if we're fine and a bit, scale that to the rest of the company, and then you just are actually looking at data of like what percent of slack is using it every day. What percentage of those people are using it the following week in the week after? What's the depth of usage or those things growing? And it's a big leap that we do long before we launch things is that we have a really just rapid customer base, many of whom want to pilot new features before they're ever out in the wild. And most of the new capabilities that we launch can't be experiments at a user level because there are social features, right?

33:47You can't sit on a huddle by yourself. You have to be able to use it with the rest of your organization. So we have this whole pilot or champion network that we use of companies of every customer segment size and basically every country in the world. And we do these progressive pilots where we'll roll out these new capabilities. We'll measure with surveys by talking to folks and also by looking at kind of adoption metrics as well. We'll find a product and then increments and increase the pilot. And usually by the time that we're watching something that's really big and new to the world were pretty confident because of the diversity of pilot customers who hopefully became totally smitten with this new capability that it's gonna be something that all our customers love.

34:28What do you know, since big and new, that you thought passed all internal checks and then didn't hit with the public and what did you learn? If you go back, I want to say this must have been in 2018 -2019. We bought this company that was kind of a lightweight, wiki tech Ex -settler, maybe almost like an early, no -shiny, kind of probably before Nation existed very early on. We tried to incorporate it as a very basic, wissy way document composer in Slack, and it was called hosts. We were like, well, obviously you in the hosts in Slack, it's like a message about it to richer, more formatted, more visually appealing.

35:04For many reasons, this seemed obvious, and yet when we launched it, it really got very love adoption. It never really grew. And I think what we realized actually, this goes back to one of the things I think Google really, and stills in you, is that the most important feature by far for any product is actually speed above all else. That is like the oxygen for a good product experience. And it turns out to build like a rich documenting experience. If it takes a couple seconds to load, if there's latency on the key presses, if moving objects around takes longer than you think, you're gonna just say, well, I'm just gonna go back to the thing I I use every day in some other browser tab.

35:41I think it took us a long time, and obviously we've launched Canvas recently, or we're rolling it out actually now, and it's a different take on the same space. But I think what we realized was that the bar for just speed and quality, for something that is as ubiquitous as a rich text editor, was much higher than we're able to hit. And our customers, we could see in the data, like, they seem obviously valuable. And at the end of the day, they didn't use it because they had good enough alternatives. and that was humbling but valuable to learn. I'm fascinated you said there about that acquisition on posts from a product leader mindset for a massive voice in our acquisition, especially so product centric acquisitions.

36:19How do you think about that by versus build and respectfully, why buy when often the price is very high? To be honest, and this is maybe colored more by our experience at Slack, we've struggled to buy a product that we can then repurpose and incorporate that was faster at the end of the day than if we decided to build a different scratch. The question was, well, why does that happen? Why do you do it? I think the reason is often very simple, which is you look at your existing organization and then you look at your ambitions. And when your ambitions are upstripping your ability to scale your organization, you sometimes think, okay, this whole area that we're excited about, can we just buy a team here?

36:56I'll say you have the equity or the dollars to do it. And will that be a faster time to market to kind of realize some of the vision that otherwise we just don't have the capacity for? And I think it's just fundamentally very, very hard, especially if you're a hyper -scaling kind of company to be able to do Acquisitions of products, not teams. Teams are very different. Like we've done a lot of talent acquisitions and those of which are amazingly well But when we're trying to actually buy a product, I think you're right I think I think often the thing we've learned is that it doesn't actually Decrease time to market.

37:26You might bring an expertise and that's a good reason to do it But that's at least what we've learned for more small -scale acquisition I think it's different if you're a large company buying like a multi -billion dollar business or Salesforce buying Slack That's a very different propulsion. Do you think you'll get it in scratch? I think we're good at talent integration. I think we struggle at product and technical integration And this is another reason I think if you look at a large company that's very inquisitive like a Salesforce or Google There's a reason why they have an entire M &A division that isn't just about purchasing the company It's about actually integrating the company after and again And I try to think, at least, lack what we were still independent for most of our life, we didn't have the capacity, we were doing acquisitions regularly enough to build that muscle internally to become great at inter -ration.

38:11It was always a one -off, and it's hard to get great at one -off. Now, why are you weakest as a product leader? When you do a self -reflection, and when you whisky at the end of the year, why are you like, I really need to improve here, and what are you gonna do to improve that? I think it's really hard to create a team environment within a product manager organization where people feel really connected to each other, where they feel energized by each other's work, where they're pushing on each other, where they have a lot of shared context. Most product organizations, the PMs, they feel like their primary team is going to be the engineers and designers that they work with.

38:44Those are the people they work with every day that they have the closest connection to. And I'm still trying to figure this out. I'm still trying to crack it. I was like, how do you make a PM organization feel less isolating? How do you create connection between people with the work on very different parts of the product, to learn from each other, to push on each other, to build product with each other. I get to work at a place that has cracked this, and I think that's part of there's a why, maybe there's so much hunger from PMs to kind of learn externally, to learn from podcasts, to learn from newsletters, to learn from other communities, because it is hard to foster that connection internally.

39:17What about a more style metric, and how do you think about effective more style metric setting? Yeah, I keep that works. It's harder to do, I can get enterprise and consumer, because really the metric we care about is are people willing to pay for the product, but most of the things you do in a product don't directly affect that metric. So it's a little bit harder than I think in the consumer world where it's more of a direct one to one. But I think those PMs are wired to really care about impact above all else. So that's the thing that motivates them. Impact to the customer experience to the product experience in the business.

39:48I know it's their metrics help with that. It's kind of like head not heart. When they think about what we obsess about, but different than how you feel connected and energized by your team. What piece of conventional product wisdom do you think is BS? A lot. The biggest, I don't know if I would say the mistake, but there's been like a professionalization of product management over the last five to ten years. And by that I mean coming up with what is a very like a rigid idea of what the role of the PM is and all the frameworks that you could be applying. And I think, no, Naka, I think it's great to have education, inspiration, and get that from many different areas.

40:22But I think a lot of PMs, really on your career, I think you look for all these shortcuts that are like, this is a framework I can use for a product shout out or document, or this is a framework I should use for understanding customer feedback. To me at least, it's much more of a combination of the arts in the science, the head in the heart, knowing things that are like frameworks but not really abying them, powerplunge. I think with the role started, my impression, and 20 years ago or so, is that kind of started by filling in the gaps in a product development organization where who was the single person who felt responsible for defining a why behind the product, the understanding of the customer or strategy that's going to be longer -term than the next release, and from an operational perspective, kind of being the glue, being the multiplier for everybody else.

41:11And I think that's an inherently very fluid definition. What I always kind of see with PMs is I think you're very rigid definition of the role. I do this, the other roles do that, where I apply this framework, this is the only framework work I should use. I think you miss a lot of opportunity to have impact and even just enjoy the job. Take a more expansive view of what product can be. Take a less rigid view of copying, pasting frameworks and advice and figure out what the team needs, figure out the customer needs and focus on that. No, I could talk to you all day but I do want to move into a quick fire out my eye, pepper you with questions again but we just relatively time bound it.

41:47So it's not too dissonant to the last half an hour but I say it's not They've been ready to rock and roll. Let's do it. Okay, so when is the right time to hire a CPO? I would hire for sale, I had a product before CPO, because it's only better to start with fewer titles when you're small. And I think the right time to do it is when the product founders here, presuming that they are a product founder, feels like the teams are now locking on them for high -quality fast decisions of direction. So when the development team starts slowing down because the CEO becomes a bottleneck, you probably need someone who can serve as a de facto head of product to start accelerating no organization.

42:25What other function does the CPO have the most tension or conflict with? I think in a poorly functioned organization, I would say engineering or design, and a well -function organization there should be your best friends. I think at an enterprise offer coming to the answer is always going to be sales because what you promise to customers and when you can deliver to customers can often be at odds. At a consumer organization it might be marketing because that's kind of the same dynamic. Which product lead outside of Slack? Do you most admire and why? Julie Zhao, who is... I think she was actually a designer by training, but was at Facebook for many years.

43:00I think she is the most incredible thinker and writer about product craft, how to design, the nature of working between a product development team, I literally think she does, she's great. Love that one. Is product more art or science? What's the ratio? and if you were to put a number on it, what would it be? On a really mature feature area, it's more science than art, because it's about optimization, and you have so much data and scale. So there I'd say 80, 20 science art. If you're at an early stage company, or at a really early part of the product development by CycleFurne feature or new product capability, I would say it's like 75 % art, 25 % science, and you can be informed by the science and the measurement, but there's so much art in the curation, in the editing, the creative approach, the vision that you have to focus on before you have enough scale to get into optimization mode.

43:52What would be your biggest advice to a PM who wants a promotion today? Deliver impact. That's it. Everything else is an input. If you can change the trajectory of the customer experience or the business, and you can point to what you did, that is the single most silver bullet you can have for a promotion process because everything else is an input to deliver an impact. You can call up a CPO who's starting their role the next day. This is the night before your first day of CPO slack, yeah? And you can give them any advice knowing what you know now. What do you call up that CPO to be in Tellum? The most generic advice I would say is no one's looking to you to make any rash decisions.

44:32In fact, they actually want the opposite. In the beginning, what you should really focus on is understanding the team, the culture, the customers, the vision, the strategy, We focus on the things initially that are guaranteed accelerator to the velocity of product development organization. Those are the lowest hanging fruit. The things that are about process execution so on. Focus on team after that, because I think you have to spend a lot of time to understand the team in the culture where there's holes, where there's gaps. Then I would focus on changing the fundamental strategy or mission the last, because that's the thing where you have to have a lot more context and understanding to be informed enough to have a good perspective.

45:10You can be CPU of any product other than Slack. Which one would you be CPU of? Not that I would do it necessarily, but I think the most interesting company right now that's an independent company that's not like a beefy myth. I would say it's OpenAI. And that's, forget even the technologies out of it, I think strategically for them right now. There's just an incredible exponential set of pathways in front of them. I know there's really interesting questions to try to think through in an industry that is rapidly changing. So let's say OpenAI. For getting all constraints, financial, hierarchical, legislative, if you could change anything about slack, what would you change?

45:47I wish there was a way to have both the bandwidth but also the kind of divergent projects experience where we could build for both kind of like work adjacent and work use cases while at the same time. I think every year in our history we've always had that that wasn't something we could pursue and in that market has become more saturated. But that would be my answer. Penultimate one, navigating and building in the age of generative AI. It's a new space. It's changing really quickly. It reminds me a lot of their early days of mobile back in What it was 2008 to 2009 where you need to keep such a close pulse on how the fundamental technology and platforms are changing that are enabling new types of products to be built and that changes every three months keeping close pulses is one of the I would call a product principle actually from Google back in the day as it relates to kind of ML and insertionally products that I still think is really relevant now, especially now is this idea that I think the prominence and the promise that you put into the product experience needs to match the underlying quality and confidence in the data in the model.

46:47And I think that's actually the thing that is hardest right now, the whole issue is hallucination and everything else, but these products are promising a lot to people. If you trust them blindly, you're going to get burned. And I think figuring out how to have a little bit more of a symbiotic experience where you feel like this is an assistant, but not on that you should trust unconditionally and that it's more transparent with you of, here's what I think, but you should check this or you should modify this or you should give me feedback on this. I think that's gonna be really important for organizations to figure out.

47:16Now, final one, what recent company product strategy? Did you look at and go, that was smart, well done. Been in realizing that this thing that was in research labs, this thing that was in a bunch of academic papers, which was the Flores language models, that the proof of concept, which isn't that much more sophisticated, you know, from a consumer experience. It's just actually making input box and a text output box. There was something magical there that would help people envision a world that was a very different model of interaction between people and machines. Seeing them execute on that, and then obviously I think, you know, Google has been playing catch up.

47:54I think actually now, first, we've come into doing a good job of that. The space didn't evolve very quickly, but I think OpenAI kind of realizing there's something magical here and forgot that the smallest possible product packaging of that To then give the consumer world a glimpse of what the future could look like I think now the question out of the space will ball is you know between the consumer product side Which I think there's not gonna be so many different variations that are gonna win and then you have in the platform and the infrastructure side How do you enable any other company to integrate AI into their products?

48:25I think that's going to be the most interesting thing to play out over the next 12 to 18 months. No, you've been unbelievably patient. I've just gone cow, cow, pow on peppery of questions. I love conversations like this, though, where it is totally natural. I've so enjoyed having you on. Thank you so much for doing it and it really has been awesome. Thanks so much for having me, Harry. Have a great time. I mean, what a fantastic guest have on the show. If you want to see more from us behind the scenes, of course, you can by going to YouTube and searching for 20VC, but before we leave you today, this episode is brought to you by Linia.

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