Slack

“Slack just blew away through enterprise because they built for users, not for enterprise buyers. And buyers were cornered to make that decision. As opposed to choosing Slack for the organization, not a single enterprise buyer I know has ever chosen the Slack f…”

“Something else that we do to protect each other's time is we like time, not timestamp, but we put like a little code in all of our messages. That's like either like, you don't have to listen to this before the end of day, or it's timely, or it's no rush so tha…”

“What I think is I look at What could have moved the needle more and what could have made me a more sex successful leader at that company, it would have been partnering more closely with marketing, for instance, to figure out how we could be working on things t…”

“We were responsible for the self-service business at Slack, all the way from first sign out, first team creation, through to the first invites, activation, expansion. Monetization, and even connecting the dots with our SMB sales team to help nurture some of th…”

“Basically if you're a paid subscriber to my newsletter, you get access to the Slack and there's about 10,000 people in there, mostly PMs and founders and growth leaders.”

“When I joined, revenue was around fifty million. When I left roughly four years ago, it was 10 extra.”

“The other skill that I'll also call out, which nobody talks about for some reason is interview skills, you know, because so much Of what gives you a chance to become better as a PM is working at a great company. And how do you get that job beyond networking is…”

“For me specifically, I realized whenever people ask me questions, if I didn't know the answer, I would have like all this negative self-talk. And I'd basically would, you'd ask me a question and question could be something like, why are we doing it this way? R…”

“Within six months, I was able to ship changes in the news experience, especially on mobile, that moved the needle by a lot, like double digit percentages within just six months. And we're talking about top line metrics, like activation.”

“One of the best benefits of working in large companies, they have access to real life strategy documents, vision documents, things like that.”

“So Chris, RCTL, and I kind of, like, intervened. We created this new channel, private channel called Concerning Tweets. And it's just, you know, for this small group of us that Dylan can kind of, like, drop those. And then these are tweets that aren't going vi…”

“Basically all these feeds information land in our data warehouse, which is BigQuery. And from there, they're pushed out via a reverse CTL tool we use called Census to Slack and Notion.”

“What this created was this culture where all engineers and designers could consume that raw feed of direct points of customer with no gatekeeper, no process to access it, no pre-aggregation.”

“We just hired someone named Peter Vidani. When I was 20 building consumer social software, he was like the coolest, most impressive person. He was the first designer at Tumblr, ran the design team at Tumblr for seven years. and the most recently was SVP of de…”

“And when we got to starting the Stripe Billing product, we realized that there were a number of our existing users. These were companies like Figma and Slack. We were already using Stripe for payments, but had these subscriptions business models. And we figure…”

“There's a saying we also have, which is more clicks can often be okay. You know, you often have in, you know, optimization, you know, experimentation circles, like, oh, every click, remove it. But I actually think in a lot of software when it's not transaction…”

“And I think when we have those teams, I think it's important to just give them space to run, to give them kind of a gel free card for maybe the normal process of, you know, okay, our planning quarterly reviews and make it feel something that is like the pace o…”

“Certainly the majority of PMs, designers, and engineers who joined Slack had never worked at an enterprise software company before. It's not like most people had worked at Oracle or SAP. It's most people had worked at consumer companies or game companies, and …”

“We wound up kind of doubling the rate of our new paid customer growth in the year and a couple of years after that and kind of reaccelerating the self service business.”

“We have a kind of central machine learning and search team, but there's a lot of people have expertise in this field to build infrastructure that everybody can use. And what we've done is Because the space is evolving so quickly, like literally every month, li…”

“When the original pitch deck came to the investors, they said, Slack is for companies of five to 50 people. At the time, the biggest company imagined using Slack was 50 people, because I don't know how this is going to work beyond that. You know, it'll become …”

“I think, you know, the origin of Teams really was a defensive move for them to protect Office, because Office is an incredible, very profitable kind of monopoly in the productivity space. And so I think when they built Teams, it was more of a kind of covering …”

“And then by the time we then scaled our enterprise sales team, I mean, truly the exercise initially was just take customer domain, sort by number of active users and call them in the order of that, which is, you know, Hey, by the way, you have a couple thousan…”

“If you work on Figma or you work on Slack, you also live in Slack and you live in Figma all day. So you can become more of a power user than anyone else on earth. And what we were realizing, especially for people trying to build Slack for the next million cust…”

“Whenever a team, I think either gets stuck or feels like they reached like a dead end in a direction is Doing complaint stores about the product area that they're in or using adjacent products just to get inspiration. And then I think it kind of unlocks a lot …”

“By far the biggest thing, which is more of a cultural shift is that we stopped spending so many cycles on design explorations of like static mocks or walkthroughs and said, how quickly can we get into prototyping the path in real software? Even if it's messy a…”

“Often, actually, that kind of owner's delusion that someone else will care as much about the software that you built as you do prevents you from actually making something that's simple, comprehensible, understandable”

“I think as Teams has evolved over time, it's become much more of a video conferencing product that competes with like Zoom and Google Meet, the people who use Teams use it completely different than Slack where you live and breathe and channels and work and kin…”

“What we found was that if you could get five people using Slack the majority of the work week to just communicate at all, that would be a successful team. They're going to be 400% more likely to upgrade over the next six months.”

“I can safely say we have a lot of prototypes internally where we are playing with this.”

“Product market fit is almost like you keep stacking these S curves where you get product market fit in a small group, and then you suddenly reach like exponential growth because you can crack that whole group, that type of audience. But then you start declinin…”

“I don't think that's gonna quite be possible anytime soon, but I think like Spotify heading towards that north star, you end up developing, I hope a lot of really compelling projects for instance along the way.”

“Structurally the way that we've approached it is that we've over time created kind of new teams from scratch that incubate in a new area before the areas mature. So we did that with a lot of these kind of native audiovisual products like huddles and clips earl…”

“Turn off notifications. Quit Slack. When you're doing deep work, check your emails once a day and just like literally go through them in like five minutes. They're off the times. Most of them are useless. Check Slack only at the top of the hour.”

“If I say unfair or secret, I usually mean, like, not something that you probably read on, like, a medium, but like, what did you learn? How did you learn it? And how does it work? And how do you apply it? You also just get amazing, interesting, like, bits of i…”

“I once coached someone who kept giving feedback over Slack and I finally just quit coaching him. I was like, I, if you keep making this mistake, I'm not, I can't be your coach.”

“At Character, at our VC fund, we Had a conversation and decided we're going to try to have our main communication happen in notion so that if we're talking about something, it's in a form, it becomes a document, and the expectation of how you react and respond…”

“Slack started all self-serve. And by the time they went public, the majority of their revenue was enterprise sales.”

“GitLab is very anti-email in a lot of ways. Obviously we use it for external communication, but internally it's on an issue. It's in Slack or it goes into the handbook, right?”

“We basically have, we store it in Asana, basically. We create, like, we have this integration which many companies might have, which is, like, a Slack integration where you can, like, react with an Asana emoji, and then, like, any piece of feedback that comes …”

“I was fired from Slack three different times, which I feel like has to be some kind of startup record.”

“I worked on HipChat and Stride. HipChat was one known, Stride less so we were trying to win the enterprise communications market before Slack and Microsoft Teams came about.”

“Atlassian was going after the users in tech teams. Slack was going after the users in business teams. And in both cases, what happened was a bottom up adoption.”

“At that point, Microsoft launched Teams, and I don't know if you remember this moment where Slack put an ad in the, I think it was the New York Times, copying the Apple versus Microsoft thing from ages before, going, you know, welcome to the game, welcome to t…”

“Your competitor, like if you think of what they do as an iceberg, like the top side, what comes out of the water is what they've shipped in terms of features, but it's based on all this stuff that they've built in terms of research. An understanding of their c…”

“I block off my morning from meetings. You know, a lot of people give that tip. I go even further and I don't open Slack before noon. I've been doing this for eight years. I don't open Slack at all”

“So in 2014, he wrote a master plan for Slack, which was build a product people love. Build a network that Slack connect, build a platform that makes all of your other SaaS products more valuable, the Slack platform, and then do some magic AI stuff.”

“I think he is the best product thinker in the valley, or he's not working in product right now. He's taking time off, but he's got this combination of long-term thinking in, in the details.”

“No email, unless you're dealing with somebody external and now it's mostly Slack Connect anyway.”

“The number of people using your product today is usually, unless you're a Google, far smaller than the number of people are going to be using your product tomorrow. So design it for the people, the bigger number of people who are going to be using it tomorrow.”

“What we did was we moved all announcement information. So like anytime you're sending a status update or large group announcement, we moved all of that to like Facebook meta workplace, like Facebook for work, basically which is now being deprecated. So we'll h…”

“Things like slack which are wonderful tools also chop up your day into little fragments and sort of make you like cognitively diabetic. Cause there's like a lot of empty carbs. In our collaboration and our collaboration tools.”

“Many in SAS SaaS productivity have this sort of sophomore slump where you have a super successful first product, but then it's challenging to build like the next, you know, the next platinum album. Right. So, you know, Dropbox has fallen into that category. Yo…”

“I did a survey of my readers and asked them what tools to use every day in your work and most use. And ChatGPT was Number one above Gmail, above Slack, above anything else. 90% of people said they use ChatGPT regularly.”

“We're actually creating a you know, like a bolt, like Slack bot that's whose job is to Basically act like a developer on your team. And so you can be like, in a thread, you can be like, Hey, I think we should add a homepage. It's like, yeah, okay. Like at bolt…”

“I think the blast radius of a poorly written memo is way bigger than most people think. So if you're just shooting off a message in a Slack channel with 15 other people, and it's confusing, and you didn't include information you should have included, there's g…”

“So I think that, you know, what the IDE is will totally change over time. And kind of our approach to, you know, having our own editor with premise non, it's gonna have to evolve over time. And I think that that will both include, you can spin off things from …”

“I like to say internally, like Claude has no chill. Like if you put Claude in a Slack channel, it will chime in either way too much or too little.”

“Slack and Pinterest, I think are examples of companies products that became companies, but neither one of those places really knew what to do next because they didn't have a bigger vision of the change they were trying to see in the world.”

“And so he built this system where it's essentially just watching everything he does all the time. And he'll be talking to a colleague on Slack or an email, and they'll be discussing some feature that they think is useful to implement. And then a few hours late…”

“Cal Henderson, who's the CTO of Slack, and who also, we worked together on Flickr, so have worked together now for 23 years, have been talking about what we want to do next if there is something.”

“And if we, if people could get over the idea of reducing friction as a number of goal or reducing the number of clicks or taps, do something, and instead focus on how can I make this simple? How, how do I prevent people from having to think in order to use my …”

“If you can't see almost limitless opportunities to improve, then you shouldn't be designing the product, or you shouldn't be in charge of the company”

“It wouldn't have grown the way it did without those little conveniences which caused people to form an emotional connection because a lot of our growth came from, you know, startup A uses Slack, and then someone leaves startup A for startup B, and startup B do…”

“Someone else invented, I want to be clear that I had seen that idea somewhere else, like someone else, a blog post about it or something like that, but we were the first ones. To my knowledge, that, that really kind of, like, scaled that and made it a standard…”

“The overwhelming majority of people you hire want to hire more people who report to them. And it's not because they're evil and it's not because they're stupid. In fact, they're smart because everyone knows that the number of people who report to you correlate…”

“We still had like nine million dollars left and everyone still liked the game and we were all happy working on it. But I think by that point I had exhausted every non-ridiculous long shot idea to make it commercially successful. And so Decided to abandon it.”

“If your thing is different in any significant way from the alternatives you're not just creating the product, you're creating the market. They're really kind of one and the same.”

“Data scientists often here are using Codex a ton to just, like, answer questions, like, why do you think this metric moved? What happened? So questions, you know, you get the answer right back in Slack.”

“And so we implemented something called the customer love sprint. We said, okay, engineering, stop what you're doing as an entire team. We're going to spend two weeks. Just painting the inside of the cabinets. The only rule was engineers got to pick what they w…”

“I can count on one hand when I was chief of staff, how many people asked me for advice before going into a product review with our CPO or other executive team to say, what do you think is most important to them right now?”

“We used to have this rule After a design review with Stuart, we'd go through the design review and he'd say, no, do it exactly like this. I want, you know, the button here and the interaction to be this. And frankly, he always had better ideas than we did, but…”

“We implemented something at Slack with Stuart because we realized we were coming to him with, like, done designs, and he was like, what the fuck is this? This is completely different than how I had this in my mind. So Allie Rail, early Slack employee, implemen…”

“So what they did is they built their own simulation of Slack and Jira and Okta and all of this software they were integrating with. And the way they did that is they basically took the API documentation for the public APIs for Slack and the client libraries, t…”

“Everyone has these notebook channels where you kind of have like your own like Twitter feed in a way where you're just, Talking about your thoughts about things, and so you can go and, like, join the Slack channel, the notebook channels of people on research a…”

“I think there's this little thing in people's heads where they really like to keep their personal and work agents separate. And I think there's a whole territory. Our COO Brandon Gell calls this computer errands. There's like this whole territory of using pers…”

“Slack was a great example because I think Slack might've just been proven and better and no new. And that's even better.”

“The other shift that I've recently done is I actually have a quad code remote session that I enlist in all of our repos. And so this way I have full visibility into the work that everybody's doing. And this instance, he also has access to all our Slack channel…”

“I think proactivity is a big untapped kind of part of the experience that we're really excited to think about. You know, we're starting to see this with ChatGPD work now where it actually has pretty good suggestions based on, you know, your calendar or your Sl…”

“The first task I gave it was go through my Slack, go through my email and suggest like five things that you can take off of my plate and what it would take for you to do that. And I suggested five and like two of them were actually really helpful. And I just i…”