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For some underrepresented people in tech, life is getting better. For others, this is the ‘dark timeline.’

Even though Slack’s April Underwood feels like less of an “underdog” recently, she says that’s not true across the board.

Slack Chief Product Officer April Underwood

The year 2018 would have been nearly impossible to predict back in 2012, Slack’s Chief Product Officer April Underwood says.

“During that period, we’re getting ACA, gay marriage is being legalized, people are getting maternity leave benefits,” she said on the latest episode of Recode Decode. “There were a number of amazing things that were happening ... Where we are now is the dark timeline. So it would have been a .0001 chance that we would’ve ended up exactly where we are today.”

But for Underwood, who describes her current role as “the best job that I’ve ever had in my career,” life as a female tech employee has gotten better over time. But she told Recode’s Kara Swisher that she has had to come to terms with the fact that there are still a lot of people for whom this is only a dark timeline and “the ways in which it’s improving are [not] evenly distributed.”

“Being a woman in tech for so long, I felt like an underdog,” Underwood said. “I felt like everybody else was having a conversation or new way of doing things, etc. And I didn’t. It’s funny, I feel like I in many ways assimilated to the best I could, tried to be one of the guys, whatever it was.”

“The fact that even I have the awareness that it’s not quite right to think of myself as an underdog anymore, not only because I’m the chief product officer at Slack but actually because maybe things have improved for the group that I’m in, much more than they have for other groups ... I think that you can get into that underdog mindset, and it can be a little bit hard to flip the switch,” she added.

You can listen to Recode Decode wherever you get your podcasts, including Apple Podcasts, Spotify, Google Podcasts, Pocket Casts and Overcast. Below, we’ve shared a lightly edited transcript of Kara’s full conversation with April.


Kara Swisher: Today in the red chair is someone I’ve wanted to talk to for a while, April Underwood, the chief product office at Slack. She’s been at Slack for three years now, but before that, spent nearly five years as the director of product at Twitter. Lots to talk about there. We’re taping this episode in late August, but releasing it just before the Slack Frontiers Conference in San Francisco. April, welcome to Recode Decode.

April Underwood: Thanks so much for having me.

There’s so much to talk about. You guys just raised a whole bunch of money. Slack has done a lot of stuff in the past couple of years.

That’s right.

Let’s just get your background. I’d love to understand how you got to where you got. Obviously, it goes without saying, you’re one of the few really high-ranking female leaders in tech. There’s not as many as there should be, and you’ve worked at a lot of these places that are obviously creating a lot of news. I’d love to get your thoughts on that, but first, give people a background of how you got to where you got, because I think it’s very important to understand people’s origins.

How we got here, yeah. I mean, you wouldn’t have necessarily been able to predict that I’d end up here, I would say. I’m from Texas. I grew up in Amarillo, Texas, which is in the Panhandle, if you’ve ever driven down I-40 and seen the big signs for the restaurant that offers a 72-ounce steak for free if you eat it in an hour.

No.

That’s where I’m from. For our listeners who have driven across the country on I-40, there you go. I grew up in Amarillo. I was lucky to go to Montessori School. My parents were very focused on education, but growing up in that place, the helium plant was one of the biggest employers there. There was not a lot of technology, and so I really didn’t grow up knowing that this technology industry existed, but I did have a real interest in computers. I don’t think I realized it.

I think to some degree, I just was a little bored, but we got a computer when I was a kid, and I’d play games, but I’d also do kind of weird things, like I had a baseball card collection, and so I typed all the metadata from my baseball cards into a spreadsheet so that I could sort it, so that I could easily find out whether or not I had whatever that Texas Rangers baseball card was, or what have you. In a different environment, maybe now, it would have been clear that actually I was really unnaturally interested in technology and computers, but I didn’t pick up on it. I don’t think anybody really did. I went off to college at University of Texas in Austin, and I chose chemical engineering.

UT.

Yeah, that’s right. Hook ’em Horns.

Hook ’em Horns. I should have worn my T-shirt today. I have one.

I bet. That would have been an honor. I went to UT and because I’d done well in chemistry in high school, I thought, “Well, then I should be a chemical engineer.” The first time we were going to visit a company to learn a little bit about the roles, we had to get a hard hat and steel-toed boots, and that was the first sign that I had that I actually knew nothing about chemical engineering, and learned that it was a lot of oil and gas.

Yes, it’s big in Texas.

It wasn’t that interesting to me. I went to University of Texas at Austin in part because I had a good number of scholarships there, and financially, that was really important for me to be able to do college, and I gave them all up because I realized that it wasn’t the right thing for me, and so I got to work doing what I’d pretty much done my whole life, which was, I went and got a job. I went in the Texas paper, the campus paper, there was a job that paid $10 an hour, which sounded better than the waitressing and barista jobs I’d had before, and it was doing tech support for internet service providers.

This is while you were at college.

This is while I was in college, my second semester, freshman year. I started working on the side, and I was helping people reinstall their modem drivers so that they could get on the internet.

I recall that.

The trick was, I had to teach them how to do this complicated technical thing, and then they would have to hang up the phone and it’s sort of like, “Good luck,” because they mostly had one phone line. I think that was the first point at which I started to think more about software. I taught myself to code so I could get off the phone and start creating the training modules for the other employees, and I started just realizing the extent to which these products were really powerful, but also were really, really hard to use for a lot of people. They did it anyway because they were so useful, people wanted to be online, but the experience needed a lot of work. That was the point at which I decided to go into software and became an engineer. I worked at Intel. I worked at Travelocity. I transitioned into product management.

You moved to California.

Yeah, well, I graduated in December of 2001, so on the morning of 9/11, for example, we actually had a speaker in one of my classes from Southwest Airlines, and none of us even knew what to say. We had no idea what had just happened, and so the economy was really, really falling out.

Yeah, it was.

I had the opportunity to interview with Intel, and I’d always, always wanted to live in the Bay Area. We didn’t take a lot of vacations when I was a kid, but we’d come to the Bay Area once, and I just was obsessed with it. I wanted to come out here and I had an interview with Intel in Santa Clara. It was the same day as my graduation, so I decided not to do the interview, and I said, “Well, just send me to the next closest place.” I assumed Oregon was just the next exit off of the freeway from San Francisco, and so I ended up in Oregon working for Intel, assuming I would spend a lot of time here, and then once I actually looked at a map, discovered that that was a little impractical.

I worked there for a while. I transitioned to Travelocity back in Texas to spend more time with my family, and I was an engineer and became a product manager ultimately because I started asking a lot of questions. I was being asked to code things, specifically Travelocity-powered, the travel tab for Yahoo Travel at that point, and I started asking business questions about why we would pay so much rev-share to Yahoo for these bookings and so forth, and in doing so, kind of found my path towards product management. That kind of brought me to how I landed there.

People don’t quite understand what product management is, I think, what it really does, because it’s a combination of technical and business, essentially.

Yeah, absolutely, and it’s also a role that has changed a lot. I think it roughly changes every five years. So product managers are ultimately responsible for picking the right things to build and then bringing definition to them. In doing that, what I mean by that is, understanding the customers, understanding the market, and then taking a principled but also rational point of view as to, “Well, we should do this first and then once we do this, then we can do this, and it’s going to unlock these business opportunities.”

You really do have to be able to have the technical aptitude to have some sense for what’s feasible. You need to have the business orientation as to what matters, but then you also need to understand users, and so when I got into product management in the early 2000s, there were a lot of women in it. It was more of a business function. It was considered more of a marketing or a GM kind of function, and we can get into it, but it’s been really interesting to see how I think Google had a phenomenal impact that actually brought it much more technical, and then I think with the rise of mobile, design became more important.

Absolutely.

It’s a really interesting role in that you’re sort of always having to evolve yourself.

Evolve yourself, absolutely. You worked at Travelocity, and then how did you get to Twitter?

I worked at Travelocity for a few years, and at that point, actually, I made the transition into product management, but before I did, I was told I needed an MBA to be a product manager, so I thought, “Okay, well, that sounds straightforward,” so I applied to business school. I got into product anyway, but I also got into business school, so I went to business school at Haas, which is UC Berkeley’s business school. I was a little disenchanted with tech at that point. This was 2005.

Why? That’s early. You weren’t in it for very long.

Yeah, but sometimes ...

Was it the dude thing? Were there so many that ...

... people around the age 25 have questions about ...

Quarter-life, they call it. You’re at your quarter life.

... have questions about what they want to do. What was interesting is that when I went to business school, then YouTube came out and got acquired by Google. The iPhone came out literally while I was in school, so I was in school from 2005 to 2007, when basically the whole new era emerged.

Everything. Facebook.

Then I fell in love again.

Facebook, yeah. Facebook.

Exactly. It came out in my second year of business school.

The iPhone.

... which I only knew about because my sister was in junior high or high school or whatever, so I’d heard about it. I went to Google after business school. I interviewed with them. I was in a role where I was focused on all of the work that we needed to do to ingest the content that couldn’t crawl on the web, so content was a really critical thing, because of Google’s mission to organize the world’s information. You know, the data that powered local search on maps, the data that powered books search, etc., for all of these different properties.

I had this really interesting but in some ways very narrowly scoped role, and what I realized only afterwards is that I got to work with all of the initial teams that built all of those Google properties, and so many amazing people that I’m lucky to know and be friends with and get to work with today were there during that era. I showed up to the Google party a little late.

That’s not too late.

Well, I showed up in 2007, and it felt late.

That’s a little late, yeah.

It felt like showing up at a party after the crush of people has left, and maybe they’re running low on certain supplies. The rosé is out.

You missed the billionaire period.

I did. I did.

The hundred millionaire period, yeah.

I also left Google a few years later thinking that Google had sort of done what it was going to do. I looked at all of the things they were working on and I was like, “This is done,” and I was obviously completely wrong, but for me, that opened up the opportunity that then, I made the leap to a small startup, and then I was there for a few months, and then I had the opportunity to join Twitter, and I made the leap and joined at 150.

What compelled you to Twitter?

I loved the product. Twitter, for me, I started using it in 2007, but really in 2008. I was living in Noe Valley at the time, and I started getting connected with people who lived in my neighborhood because of Twitter. Twitter was small then, and this is still when mobile and mobile apps were new, but this idea that this website or mobile app could actually help me connect with the people that actually were in local proximity to me in a place that I’m not from and where I didn’t know my neighbors and that sort of stuff, that was just absolutely amazing to me.

I really loved the medium. I loved the fact that people were smart and witty and interesting on there. I loved the pace at which it moved, and so I just loved the product. When I got the call from a friend who had joined … And I had gotten to know Dick Costolo when he was at Google during his post FeedBurner stage, and he was over there, and then I got the call from a friend. I belabored the decision a little bit because I was working for a great startup, but I followed my heart, ultimately. I didn’t go there because I thought, “Oh, this is going to be this company that’s going to go public,” and all that sort of stuff. I truly went there because I loved the product.

A lot of hopes at the beginning. I remember. Do remember?

Yeah, it was a different time.

Yeah, I remember when they were Odeo, and before that, which was really interesting, and then they kept switching CEO. Then you could see the problems. I have to tell you. We’ll go into that later, because I want to talk about tech responsibility and things like that. You guys are less pulled into the debates going on right now, but still have to be thinking about them. So, you were there, and through the period of its mega-growth, really, right?

Yeah.

You worked on what?

I joined when we were about 150 people, and by the time I left, we were at 4,000, over the roughly five years. I joined to be a PM on platform, worked on things like the Tweet button, the Follow button, all of these tools to make it easier, ultimately, for publishers to be able to get their content shared easily by users into the network. Worked on that for a while, but I also wore a lot of different hats there.

When you’re at a company through that kind of growth stage, sometimes the fact that you’ve been there a while becomes such a unique asset, and that institutional knowledge is so important that you actually get the opportunity to try out different roles. I started doing product, but we had relationships with Google and Microsoft and Yahoo, the search deals, and we didn’t have anybody really responsible for them.

And you had done that a little bit at Travelocity.

Yeah, and I also had been at Google.

I remember those days.

I ended up building out a good portion of the business development team, and then getting back to my major, which was product on the ads and data side of my last three years there, and built ads, API, and program around it, and so forth. Through my course there, I led product teams, I led business development teams. I also led product marketing for ads for a while too, just out of the need.

The reason I wanted you to talk about this is because I wanted people to understand that switching is really, like, shifting, and shifting, and especially when you’re a woman, you can do that to try to grab for what you want, kind of thing.

Absolutely. Yeah, you know, I hold on pretty loosely to the idea of which function I do, and I think that’s served me well. There have been times in my career where people didn’t believe I was a product manager. When I was at Google, I wasn’t a product manager, because I don’t have a Computer Science degree, and I was there during an era where there was a pretty narrow view as to what was required. The most important thing was to gain credibility with engineers, and so you had to have that stamp of approval. I’d been, literally, an engineer, but because I hadn’t, it was a real blocker for me.

What I’ve found is that rather than exiting the industry, instead, finding those adjacent opportunities, and also, frankly, getting to build teams from scratch, or getting to learn new skill sets like I did during my five years at Twitter, it’s so important to me in what I do now, because as CPO, I’m not just responsible for the actual organizations that roll up to me, I need to have a really broad purview, and the fact that I’ve done a bit of marketing, the fact that I’ve done deals, it makes me a better partner to the other execs around the table.

Yeah, it makes you smarter with the people when they come to you. I remember dealing with someone, I think it was Terry Semel when he was running Yahoo, and he was like, “You know, the Yahoo Search team tells me we’re better than Google.” I’m like, “Of course they tell you that, because they couldn’t get hired at Google.” It was really interesting, because I was like, “You don’t know what you don’t know,” which I think is a problem with a lot of executives, I have to say. They don’t understand everything. If you know how the sausage was made, you do understand when people are taking shortcuts, or they’re not telling you the right thing. You know what to look for, I think, is critical.

You were at Twitter during a crazy period, and Slack, what happens? Because I had met Stewart when he did the photo thing at Yahoo.

Sure. He’s been around.

And he did that disastrous game thing that turned into Slack. That’s the story of what happened here. I’d gone up to Canada, to Vancouver, to visit him when he was doing the game thing. What attracted you to Slack?

What attracted me to Slack actually started back in 2007 when I joined Google. I joined Google out of business school, and at that point, one of the big hiring pitches was transparency, you know, this idea that every Friday afternoon, you’re going to come to TGIF, and you’re going to hear directly from Larry and Sergey, which was amazing, and then also, this idea that you can know anything that’s going on within the company.

It was already a sizable company, and so you would join, and you would start hearing about different projects, and you could just join the mailing lists for almost anything that was going on within the company. This whole idea of transparency, then, you know, during those years, a lot of companies in the world were like, “Hey, what’s Silicon Valley doing? How can we be more like them? How can we shift to more transparency? It seems like it’s driving a lot of innovation. Ideas are coming from anywhere within the organization.”

Ultimately, the tools were not the right ones for them. In my two-and-a-half years at Google and then five years at Twitter, it was this culture of transparency, but the tools were just completely wrong for it, because in an email world, you don’t decide … ultimately, you don’t really decide what comes into your view. Other people decide that for you. Every single time you want to share something with somebody, you have to decide who the right people are to receive it. You have to give it a subject. It’s all this pomp and circumstance to be able to communicate anything, and so it’s very high-friction.

And near the end of Twitter, I was actually thinking about these ideas of like, “Why did Twitter work?” Twitter worked because you could tune into the things you cared about, and there was no cost to unsubscribe, but we didn’t have that for person-to-person communication in work tools.

As I was leaving, I was thinking about these concepts a bit, from my own experience of having just been in an email culture that’s just crushing, where you wake up every morning and you have so many emails that you don’t get out of bed until 30 minutes after you wake up, because you’re just trying to figure out, “Is there anything in here that’s important?” Which is also a problem that, of course, Slack helps solve, with notifications and the ability for you to configure your view of Slack to focus in on the things that are most important. I was thinking about these problems. I left Twitter. I took the first break in my entire life, since I was 15 and a half, or whatever the legal age was to start being a hostess at the Black-Eyed Pea in Texas.

That’s some good eatin’.

Yeah, it’s ... Yeah. Talk about quality control. I mean, I think a lot about quality control now. With Slack, we care a lot about what we launch, but my first quality control job was making sure that the chicken-fried steak would extend over three sides of the plate, because otherwise, it was not ...

You can’t have that!

It was a “Texas-sized” chicken-fried steak, and that’s the only criteria.

It’s got to be big. Oh, man.

Yeah, so attention to detail, important. With that in mind, I took some time off. I launched #Angels with five of my colleagues from Twitter, which is an angel investing group that maybe we’ll talk about later, and I forced myself to take some time off. During that time, I met Stewart, and long story short, he was looking for a head of platform. I’ve worked on platforms pretty much my entire career. We hit it off. I was what he needed. The role was really enticing and exciting, and the company was in an interesting phase, and they were working on a problem I actually cared about, so it made it really straightforward.

Right, and then you thought, “This is the way it goes.” It was really fascinating to me that no one had ever thought of this before, because there were versions of it. I forget all the names of it. I saw so many versions of Slack, and I’m blanking on all their names. I remember one guy had a good tan, and I forget the guy who ran that company.

Man, I missed the tan guy.

Microsoft bought it, I think. Whatever. There was a lot of that idea, and Facebook had even thought about doing Facebook for Work. AOL, a hundred years ago ... You aren’t going to remember this, you’re much younger than I am, but AOL did AOL at Work, and the day they launched it was the day they had their famous 19-hour outage. The guy, Mark Walsh, who ran it, had sold it to all these businesses as the communications tool for a company, the not-email-based communications tool, and it was over in seconds, but it still was a great idea.

It is, and I suspect you’ll probably mention the fact that we’ve recently had an outage ...

Yes, I will.

... so I’ll preempt you there, because I listened to your discussion with Aaron Levie from Box, and I know that that was right after that had happened, so first of all, apologies. I would have brought you socks if I didn’t if I didn’t believe you already had four pair.

I do.

But I don’t want to make light of that at all. It’s bad enough when really important consumer communication tools go down. We don’t like it when our consumer social networks and so forth go down because they are our lifeline in some way to connect to the people we care about and the things we do, but when we’re talking about work, it’s absolutely critical. The bar for us is incredibly high.

I think it’s important to realize — absolutely not as an excuse but just so you know where our mindset is — that frankly if Office 365 or even Google Apps goes down, it’s super frustrating. You’re in the middle of doing something, you can’t do it. But when Slack goes down, you can’t even communicate with other people to know whether or not Slack went down.

It goes down, right.

So we are that bottom stack for ...

Yes, that’s exactly what I think of it.

There’s nothing you can get done at work without communicating, and one thing I remind my team sometimes is we’re not personally saving lives but there are literally people doing work on our platform that are aiming to and trying to report the news and trying to do all these things that are very real-time in nature.

With that in mind, I think that we need to be like the phone company. We need to be at a utility grade or carrier grade to some degree. We’re invested very deeply there. In fact, this year we have forgone shipping some things we’re really excited about because we are shifting the majority of … as many people as we can.

Right, which I think is difficult, I think you’re in a real dicey situation there. It underscores the idea of being this utility grade and being something ... You guys just raised how much money?

We just raised $427 [million], give or take. At a $7.1 billion valuation.

So it’s been creeping upwards and obviously I had interviewed lots of like Peggy Johnson before Microsoft, others, had tried to buy you for years, but you guys are gonna ... You’ve been going it alone, doing this. You’re also in the sweet spot of so many companies who have tried to do this workplace productivity stuff. Microsoft has bought a number of companies to compete with you, Google’s in there, Microsoft bought LinkedIn, there’s all kinds of things they’re trying to do to get into this area. You have huge competitors, and one of the things that is critically important besides working all the time and not going down is also security and some other issues.

Talk a little bit about the reasons why you guys keep moving forward as an independent company, when you’re thinking about that. ’Cause there’s been ... People have tried to buy you, I’ve written about it quite a lot of times, but you guys have stuck with this idea that you can do this independently.

I mean, if we thought we were 80 percent done with what we planned to do, then you think about things differently, but we’re just, in so many ways, just getting started. We’ve got eight million daily active users right now across 500,000 organizations, three million daily paid users. We’ve got Capital One and then we’ve also got the Jackson Hole Wildlife Refuge. We have this really amazing breadth of customers.

Last year, last January, when we launched Enterprise Grid was the first time we even had a product in market that could really address the needs of a company over a couple thousand employees. Since that time, we’ve brought tons of customers to that product, and again, we’re 18 months into that, international, the product was only in English until a year ago, so we’ve just started to bring it in a meaningful way to other markets.

A lot of that is about how many teams in the world can actually use Slack, and we’re ...

How many different kinds of teams.

Exactly, and so we’re still in this hugely expansive phase of building the capabilities that we need so that more types of teams at work can use Slack.

The other thing that’s happening in parallel is we talk about the fact that we’re a platform, and a lot of companies talk about being a platform.

Yes, they do.

But what you want to have in order to be a platform is you need this really stable foundation, you need to provide some service that is so broadly useful that it’s actually ... It makes sense for users, for customers, to be able to make use of more capabilities on top of it. As I described earlier, communication’s like the last thing before the operating system on your device itself. It is just so foundational to everything that people do.

Which is at the heart of Slack, which is the heart. Whenever I try to explain it, it’s like you’re talking ... I just was talking to someone who’s a very well-known reporter, and he’s like, “Should I use this Slack thing?” I’m like, “You’re an idiot. What do you ... Yes.” “For my team?” I’m like, “Yeah, we run our company on it.”

Thank you, you should write some of our marketing copy.

No, but I just ... You do run your company on it. It’s an interesting thing, and it’s the best, so far, that I’ve seen. I, of course, would switch in a second if I had to. We were on something else before you. What were we on? Who was your other competitor?

HipChat has been popular. We’ve recently done a deal with them.

There was another one. We moved on to Slack from whatever it was. It was good, it was good, but you were better.

Great, well, thank you.

Okay, but I’m saying, you’ve got to figure out foundationally what you’re providing people, which is communications and organization.

Absolutely, and so communication in Slack is organized around channels. You’re totally right that other people have sort of poked at this concept before, but in Slack, channels really sit at the center. Channels have all of these great properties to them which are that you can join and leave them at will, you can set notifications on them, so that if you need a push notification every time somebody posts in a channel that is related to what’s about to go to press, that you can get a push notification on any of your devices. They are searchable so that the next person who joins a team can actually benefit from the conversation/discussions that have happened in the past, and it is a fundamentally different way to work. It’s moving ... It’s fundamentally different than inboxes were.

Slack’s platform, which is what I joined to work on and now my responsibilities are much broader, but we have an amazing team working on that. Slack’s platform is just absolutely core to what we’re doing, which is that we launched something a few months ago that made it so that an app on our platform — like Zendesk, for example — could add an action to the gear menu inside Slack, and it seems relatively straightforward.

But if you think about that, imagine a scenario where a customer support team is talking to a customer and they’ve, at some point ... And they’re doing their work in Zendesk, and that is where they live. They also communicate in Slack, but when they’re getting work done and communicating with customers, they live in Zendesk. They need to actually share that ticket with the engineering team within an organization because they believe that it’s likely a bug.

Well, engineers don’t live in Zendesk, they live in Jira. The ability for us to have this platform that allows information to flow and bite-sized workloads like this to actually be executed by teams across applications, there’s ... It’s a huge gap.

Absolutely. Because you’re switching from one to the other and they’re not even communicating with each other.

Right, exactly. Slack becomes that bus or that common denominator. The ticket can be shared into the channel from Zendesk. From an employee directly in Zendesk, somebody can see, “Yep, that looks like a bug,” they can use this new feature to be able to create a ticket in Gira, and we actually are able to facilitate that workflow. Each of those companies had one integration, they built on top of the Slack platform, they don’t have to build with the N-squared or whatever number of customer service and engineering bug tracking tools. They’re able to build into this platform.

What we’re doing with the platform is actually making it possible for customers to get more value out of every single dollar they’re spending on software, which is a lot, and we’re creating a place where not only can they get that work done, but we’re building the search capabilities on top of it that it can be utilized and harnessed in a way that you never could before.

You had talked about this several years ago, this developers part of it, and in Twitter that was a big thing until it wasn’t, right, where they started to create their own things, they sort of killed all the developers that were working on the platform. How do you guys look at developers? ’Cause it’s often a push me-pull you. Facebook, they had the same issue that killed most of them, or many of them. They use them to grow but then ...

Yeah.

I can’t imagine it’s not integral to you all, though. You can’t do that.

Well absolutely, but it’s structurally just so completely different.

Yeah.

We got a number of folks that work at Slack on platform that have worked on other platforms, and in consumer platforms and in consumer products in general, you already have a challenge which is a product and a strategy challenge, which is that you want to offer the best experience around the organic content. And then you also need to get ads in front of people. That’s already a challenge, even if there were no third party involved.

We don’t have that dynamic with Slack. We sell our software to teams to use at work, so our job is to build the best software for them and then offer the best service that we possibly can for them, and we share that goal with the developers in our ecosystem. Their job is to make it easier to run a restaurant, make it easier to ...

And get their software used.

Exactly. We have roughly the same business model as the majority of the developers in our platform, in that a lot of SaaS applications. We have a shared interest, which is helping our customers and be more productive and really address the needs of how work has changed. In doing that, our interests are completely aligned, and so it’s not just ... These aren’t just words, I just have to say that having worked on a number of consumer platforms, there are all these hard problems and you’re like, “How do we balance this?” We basically have none of those at Slack, and it’s really refreshing.

It must be exhausting.

God bless enterprise software. Yeah.

So when you think about the issues, the most pressing issues you have on the platform, I would assume security would be your biggest. It’s interesting that the consumer platforms are the ones being dinged for it this year about the Russians ... Actually, the Russians just used the platforms exactly as they were built, from what I can tell. It wasn’t hacking or anything like that, but in your case, you’re protecting a lot of corporate information, there’s a lot of ... So is that your biggest concern, or is ... I would assume either that, or continually being innovative to keep up with competitors, larger and more deep-pocketed competitors? How do you think about the issues around the platform?

I’d say the thing I think about the most is a little bit different, so I’ll come back to that. I think that security’s absolutely ... It’s table stakes for what we’re doing, and so both the way in which we work as well as the expectations we have for developers that build apps that go into our app directly are very high. We take an approach which is that we review those applications, we do a variety of testing around them, we make sure that our customers understand what information is or isn’t being shared with them. That’s the approach that we take, which is quite hands-on and it is also exactly what you would expect given the job that we’re doing.

In terms of innovation, I don’t really worry about that that much. We have so much further that we want to go with the product. There’s so many opportunities for us to help teams be able to work together more effectively. In a world in which there’s software that makes so many of the tasks that used to take up a lot of people’s time so much faster, from expense reporting software to design tools to operations tools for supply chain, there’s software for everything now, and what that means is that people have a lot more ... really spend much more of their time coordinating and collaborating and communicating with other people. That’s where ... That’s both the bottleneck, but it’s also just literally where the work is.

We need to keep helping people get the full value out of what they can do with Slack, and I’d say that actually points more to ... It’s less about, do we have ideas, like do we have innovative ideas for how we can do that? We’ve got loads of them. The trick is that our audience has expanded really quickly and we are so far beyond the companies that look like us now.

We’ve got Target and like I mentioned Capital One, and we’ve got these large organizations that are quite different than tech companies in Silicon Valley. Within those companies, there are tons of employees that need to understand more about how to make use of a product like Slack. It’s not even so much about Slack, it’s about how do I transition to this new way of working? It’s cultural, it’s about transparency, it’s tactical about just literally how do I make use of this tool?

That’s a lot of what we’re focused on is just, we’ve been really really lucky that Slack has been this movement where people fight to bring it in their organizations. They start using it within their organizations and then over time, the IT team can see the value because it’s so obvious to them, so then it becomes an official supported tool. I want to enable more people to be able to make that case. Not every single person is prepared to make the case for why the company should work differently and use this new tool, and I think there’s more we could do to help them.

What’s the biggest obstacle you face from your perspective, in getting them to do ... Is it just using it? Or getting them on the platform? ’Cause you are dealing with very small groups and very large groups, but I would assume the focus just like at Box or anywhere else are on the big customers.

Actually I think it’s a little bit different than Box. I mean, I can’t speak to where Box’s focus is, but we have a really wide breadth of customers.

Where’s the most? I don’t even know what that is.

I mean, the most customers are smaller, just by the ...

Yeah, small- and medium-sized businesses.

But 65 percent of the Fortune 100 are paid customers of Slack.

But there could be small uses within large corporations, right?

Absolutely.

’Cause certain groups within groups within groups.

It often starts there, but then it starts spreading, and we launched shared channels last year. Do you know what shared channels are?

Yes.

So shared channels are a way for you to be able to have a channel that is shared with another company, and that’s increasingly important in a world in which companies don’t work as islands, they work with vendors and partners and they may do joint work with customers even at times, and so Slack can facilitate that work and bring the same benefits to your internal communication that you get there.

The biggest challenge there is I think a little bit around ... This has all happened really fast for us. As a company, the product’s been in market for about four years. You have to build the product, but you also have to build the business. We’ve been fortunate, the freemium model that we approached has been working, and now we’ve added to it our sales-driven model for the larger companies, but then you also need to build a healthy company, and you need to build the leadership and you need to establish how we do things. And doing all three ... You have to do all three things at the same time. They’re dependent on each other.

I would say the opportunities for how we help more companies understand how to get the most out of Slack ... They’re very, very clear, we just need to go do them and have the right people in place.

What of those innovations do you think are critical that people want ... Everyone bothered you for a while for a response, all kinds of things, I think I tweeted a bunch. “I’d like this, please.” I do it to all the companies. I’m still waiting for the edit function on Twitter, it would be really nice.

Yeah. One area that I’m thinking a lot about right now is just how do we make it possible for people to express themselves inside Slack in a way that reflects the effort and hard work that they put in to whatever it is that they’re saying. In email culture, there’s this world where you actually start the email in a doc or something and you spend all this time editing it, and you get other people to review it before you hit send, and it’s this ...

Gosh, you do that? I don’t, but go ahead.

People do that.

Okay.

People do that in larger companies.

I just think things and push. Yeah, no, they do, I know that.

I think there’s that culture which is that if you’re doing this really important work, that the way you communicate it needs to reflect ...

Absolutely. Well, Slack has actually taken that away. People are a little too loose on Slack, they think of it as Facebook. They think of it as ... It’s really interesting.

Well, and there can be some real benefits.

It’s not your fault.

Yeah, there’s cultural benefits to that and there’s actually efficiency to that as well, but one of the things you asked, what are people asking for? One of the things people want is they want the tools to be able to very easily express themselves in a way that reflects their intelligence and the amount of effort that they put into whatever it is that they’re doing.

We added, for example, you can do Control-B or Control ... you can actually start to add a little bit more of that formatting without understanding markup. That’s a good example where here in our world, it can make a lot of sense to edit, to format your message using markup, but as we get to eight million daily active users, 10, 12, 20, we don’t want to teach the entire world markup. We’d instead like to give them tools that are super intuitive.

Mm-hmm. What about when those veer into people who are on your platform, the developers too? ’Cause some of it, you’re gonna have to own yourselves. What are the critical things you need to own yourselves?

The critical thing that we need to own is the core communication layer.

And channel layer.

That’s right, the channels, the ability to communicate, the ability to set notifications on top of it. Those are many of just the core elements. All of our platform developers get to plug into that, and they get to play along with that.

For example, we added a status so you can say, “I’m at the doctor,” or whatever. You pick an emoji and you can say where you are. We expose that via the API because if you are an enterprise tool that helps people manage their vacation, then there’s the opportunity to programmatically pre-populate that, for example.

Generally, we don’t have as many hard questions like that. I think we have our own calling features, for example, but we also have ... All of the major calling providers have apps on top of the Slack app directory and we’ve made it possible for teams to select one of those as the default.

We are a platform through and through, and so when we build those new capabilities beyond the most foundational things that frankly it would be really hard for somebody else to do on top of our platform, we expose those ...

So people can work on them. What is the one thing you would like to see on the platform? What are the one thing people are asking for from how people work on the platform?

Yeah, that’s a great question because it’s really ... We have such a diverse audience that I wouldn’t say there’s necessarily one thing, but I would say that simple things go a long way. Concur, which is owned by SAP...

Yeah, we use that.

Them building, along with other tools like WorkDay, where 80, 90, 95 percent of the employees interact with that software in a fairly narrow way. As it should be. There’s a small percentage of the company that make use of all of the vast majority of the features — the configuration, the provisioning, all of these business roles, etc. But most people interact with it in that they get a notification and they need to take action upon it. Bringing those simple things into Slack have been some of the things that people have been most excited about to date, including things like ...

I think it was just last week, very recently, we have launched the next stage of our integration with Google Drive. If you live in Slack and then you check your email and you realize somebody had a comment to you in a Google Doc four hours earlier, that’s not a great experience and it’s not a great experience from how you feel about Google Apps or how you feel about Slack. We’ve worked with Google in a really great partnership we have, and so now you can receive those comments inside Slack and you can actually reply to them from within Slack. So that’s an example where Google has obviously done the math. They don’t see more value if you spend more time looking at the Google Doc. We are trying to help companies be productive and efficient.

Right.

So there’s not this eyeballs and time on site, that sort of stuff, at all. So those simple things go a long way because they’re useful by a really wide audience of people, and they allow you to get through some of those distractions and help you focus on deeper work.

Right. What’s interesting is the whole focus on text on Slack, more than anything else. Even though you add the emojis, you add the photos, stuff like that, it really is a text-based system, still. It’s email if you took it to the nth level. I don’t know how to describe it. Do you know what I mean? Because you really deal in text quite a bit.

You do, but ...

And also spreadsheets and stuff, things that are attached to it.

Sure, but there are use cases out there, like I mentioned earlier, the Jackson Hole Wildlife Refuge, they go out in the field and they take photos, whatever photos they need to take, then they post them to channels. Actually, there are lots of design organizations as well, where there’s a lot of sharing of photos or even video. So like anything, it depends on the use case, which is why we need to be as flexible as possible.

I do want to talk about, you did the #Angels thing. It was with all the Twitter people, it was a lot of women, correct?

It’s all women.

All women. Explain what that is.

So #Angels is a group of six former executives at Twitter.

Chloe Slatton’s in there, yeah.

And we worked together at Twitter over the course of those five years, and as some of us were thinking about what we were going to do next, we all had an interest in angel investing.

So we have this thesis that if we came together as a group, we would have more to offer the companies that we backed, because we would do that for one another anyway. But I think frankly, angel investing, it’s a little bit of a not-well-understood job, as it were, and practice. So we just wanted to make that explicit, which is that if Katie Stanton or Chloe Sladden called me and said, “Hey, I’m gonna back this company, would you be interested in investing with me? Will you check them out and tell me what you think?” I would have done that anyway, but the six of us decided to come together.

It was also a little bit of thesis that if you write a Medium post and say that you’re an angel investor, then you’re angel investors. And I would say that thesis proved true, which is really amazing. So right after we announced, we started seeing deal flow not just from founders, but from sometimes the firms, seed-stage and later, looking to see if we would want to join them on deals. And then we also heard from another audience, which was a lot of women. Mostly operators, but also some of the female investors as well, who were like, just glad that we were there, and, “How can we get involved? How can we help?”

Especially amongst operators, I would like to do this and I have no idea how to do it. I’ve seen the men that I’ve worked with doing it, but I don’t know how to get involved. So we started bringing people together. So we’ve created some community around it, we called a bunch of events. Instantly the venture firms had been very happy to partner with us on many of those events. So we’ve done all that, I looked in the spreadsheet last night, we’ve backed 70 or 80 companies between the six of us. Writing our own checks, we didn’t raise a fund, so we’re making those decisions on our own.

But the other thing that we’ve started doing is talking a little bit about what we call “the gap table,” and just trying to bring more education to the industry. We’re focused on women, but generally to the way that the cap table works and the way that distributes wealth in the industry. And why one might want to do something like angel investing but also potentially just have a better understanding of their day job, and that role.

This is an obvious question, why do you do it with all women? Because you’re obviously making a statement about that issue.

Yeah.

Again, you’re one of the few top executives. I try very hard on this podcast, but ultimately you run out of people. You know what I mean? And it’s hard. How do you think you handle that at work? Does that become something you have to focus on over Stewart or anybody else there? Stewart Butterfield is the CEO.

Yeah. Why we started #Angels with all women is oddly enough that I think the other five women I started with are really damn smart, and really good.

Yeah. There’s no Adam Bain in there.

He’s smart too. But there is a camaraderie and a kinship that comes with being perhaps the only woman in the room in your own room, and knowing those other women who are having that experience. Absolutely.

At every company I’ve worked at, I’ve come away with a number of connections that are quite deep with other women there. There’s no doubt it’s due to shared experience. I feel really fortunate today to get to be a leader at a company that has focused on diversity and inclusion since early on. Founders and just people in the world ask me, what should we do about D&I [diversity and inclusion]?

And of course, the truth is I don’t consider myself an expert in it, but because I’m a woman I do get asked about that. And the main thing that #Angels would tell our founders is to start early. Start focusing in on it early. It was a factor in joining Slack, that Slack is a company that has done that. They’d already done the first report and offered transparency into the employee base when I joined. And we’ve quadrupled since then, and we continue to do it.

What kind of grade would you give yourself?

Slack?

Mm-hmm.

We’re tough graders on ourselves. I’m not gonna necessarily peg to a single number, but what I will say is, we’ve always focused on it, and there’s always more work to do. Not only do we want to have an employee base that’s as representative as we possibly can of our customer base, of the populations of places where we have offices, all of that stuff...

But also, we definitely want to avoid Slack being a place where people would decide to exit from the industry. And that’s the piece I think a lot of companies are thinking about now, which is even if you manage to do the work to get the right people in place, how can you make sure that they can be successful and grow?

They stay. That’s the absolute problem. I think people get the issue of recruiting people. I think getting people to stay, or providing management structure around them to be able to succeed.

Sure. And look at my career. I have made changes over time. I wouldn’t say that was directly a factor, that there was some environment along the way that was really bad. But there have been times at which it just felt like the growth opportunities for me sat outside of the company.

Has that changed in Silicon Valley? Not just for women, but people of color, from your perspective? You can’t lump everybody into one group, but you can and can’t. It’s a similar outsider experience.

I think that’s one of the biggest things that I’ve come to a deeper realization about over the last years, is actually you can’t, really. I think being a woman in tech for so long, I felt like an underdog. I felt like everybody else was having a conversation or new way of doing things, etc. And I didn’t. It’s funny, I feel like I in many ways assimilated to the best I could, tried to be one of the guys, whatever it was.

But I do think that, for reasons that are definitely coming from a dark timeline in our country and in the world, Time’s Up, #MeToo, I do think a lot of this is being brought to light right now. But I’m not convinced that the impact or the ways in which it’s improving are evenly distributed.

So I think that’s a big open question for us, and I think there’s a lot of people that are speaking up and bringing this to attention. And I think the fact that even I have the awareness that it’s not quite right to think of myself as an underdog anymore, not only because I’m the chief product officer at Slack but actually because maybe things have improved for the group that I’m in, much more than they have for other groups. I think that you can get into that underdog mindset, and it can be a little bit hard to flip the switch.

It’s also having that responsibility to actually be able to do something at a company, and I think it gets heavily put on women at the top to do something, versus everybody to do something, which is interesting. And being aware of those conversations that people aren’t being part of. It’s a really interesting question.

One of the reasons I became a boss is I wanted to run the conversation. So I’ll just run it, and then you can’t have other conversations except the ones I decide on. Which I think matter, I think it does just matter.

So when you think about that, I want to get to the bigger issue right now, because Slack’s not as dragged into this, but the image of tech has gotten terrible now. All the stuff that’s going around Facebook and Google and other places has really dragged down the concept. How do you look at how tech is looked at? Because you’ve worked in all these various different areas.

I have to take a step back, and I can’t help but think a little bit that, could this have been predicted?

Yes. Sorry, I’m gonna answer this for you, but go ahead.

Well, and that’s great. And I wish … maybe you did.

I think I did.

I do think that just where we were in the world in 2012, you think about all the amazing things that were happening, getting ACA — the exact years may be off. But during that period, we’re getting ACA, gay marriage is being legalized, people are getting maternity leave benefits. There were a number of amazing things that were happening.

Yes. 100 percent.

And even if people had run tabletop scenarios of, “Here are all the things that could possibly happen,” this would have been ... where we are now is the dark timeline. So it would have been a .0001 chance that we would’ve ended up exactly where we are today.

No, you’re right. There was a paragraph in the New York Times today I never thought I’d read in the New York Times. It was like, “Mr. Trump, who worked on ‘The Apprentice,’ and Stormy Daniels, who made this movie,” and they watched “Shark Tank” before they had sex. You’re like, this is in the New York Times. Are you kidding me?

Yeah. How did we get here?

Well, I think that’s what all of us are asking.

That’s what all of us are asking. So I ask that. As it relates to Slack, I’m not trying to dodge it for us, because I think every company in tech should be thinking about this, but it really hasn’t. Because we’re building tools for teams that work.

Yeah. I’m sure Russians use your service, but they really can’t impact elections doing it. Who knows?

We’re not building a platform that enables that. But the thing I do want to say about all of this is, maybe I still bleed a little bit blue from my five years at Twitter...

When you’re really, really close to these things and you’re having to make hard decisions about what to do in a specific scenario, and that’s what you do every day, you have a lot more information than the rest of us. And you know about some hard decision we made in some different country somewhere else in the world that none of us in America even care about right now. So I think that is part of the practice of having to make some of these hard decisions, is that you are very, very close to it.

Now I am further away, because I’ve been gone from Twitter for three years. But I think in general, I think all of these companies, I do think they have very smart people who actually care very deeply about this issue. And I wish that the punchline could be, “And I figured out what they need to do and it’s A, B and C.” That’s the one thing that gives me comfort. I think we’re gonna get there, I think we will find the right way to tackle these problems, but I think it’s gonna take some time, and I think it’s gonna be painful.

It’s the damage that has been done in the process of their learning experiences. Do you know what I mean? And it’s an irresponsibility. You don’t want to be their scold, but on some levels it’s that they took the money, they took the fame, they took everything else and they didn’t fix this one thing that is causing all kinds of pain. You know what I mean?

And then when you point it out to them, they’re like, “Don’t be mean to me,” or, “I tried my best.” “I tried my best,” is not an answer I particularly like. I get it, but you’re not children, and you don’t get an A for effort.

Yeah. These are tough times.

So what would you do if you were running Twitter?

I consider myself to be fairly self-effacing. I think it’d be completely insane to think I have some answer that smart people that have been thinking about it don’t have. I think we’re in a really interesting point as a country and in the world, which is that the tools may to some extent be ahead of where we are in terms of regulation, and in terms of ...

The psyche, really.

Definitely the psyche. I think also, one of the biggest things that is most jarring about all this is to find out this was always here. This hate was always there.

Yes, we’ve just been given amplified tools.

Yeah, exactly. But the thing is, those tools also created an opportunity for this amazing slew of candidates that are running for election to be able to reach people. And all I mean by that is that there were a lot of really great things that had come out of these tools. And then we were in this period where we were through the hard part of human history, we were really punching through, in a number of ways.

And now we end up here, and actually, it turns out, the “bad guys” are able to use the tools just as well or better than the good guys. And that’s ... I don’t have an answer for you.

No. It’s complicated.

How depressing.

It is. It’s interesting, I just did an interesting podcast with Jaron Lanier and he was talking about, never before has all of humanity been able to talk to each other, and maybe we’re not ready for it. And I was like, “I think you really got it.” It’s an unprecedented experiment on humanity to be doing this.

Absolutely.

But let’s finish up talking about Slack, let’s get back into Slack.

Sure.

So when you do that, you also are trying to free corporations. So I’d love to get your thoughts just briefly in the last few minutes we have, of where businesses are going and how work is changing and how what you guys do to contribute to that. Because there’s definitely, in this use-case scenario, it’s pretty much all good. It makes a better corporation, people talk more, it greases the wheels and things like that.

I can’t think of a huge amount of downside for Slack, except people use it a lot and spend a lot of time on it. It’s a little slightly addictive. But not that bad. It’s not as bad as other things. Talk about where you think work is going and how you think of that, because that’s got to be at the heart, theories around that.

Yeah, absolutely. Messaging is the default mode of communication. It is for us, but also roughly half the workforce will be millennials by 2020, and definitely as that audience evolves.

So you’ve got that piece of it, you’ve got the cultural aspects I already alluded to, which I’ve literally lived myself, which is that companies have realized that more transparency, matching their tools to the implicit organizational structure, rather than hard-coding them to the explicit organizational structure ...

And hiding away information.

Exactly. Leads to better outcomes. So there’s the macro trends around what users expect, and that they expect to use software at work that they can figure out how to use without taking a training module. That’s a pretty clear bar that most enterprise software has not met.

I haven’t done my expenses in four years because of it.

Yeah, exactly.

I haven’t. It’s like two years.

So expectations from users are higher. Companies believe that there’s something to this idea of giving their employees access to the contacts they need to be able to do their best work. You layer on top of that the fact that the number of software tools is just exploding, this proliferation of enterprise software, what it means is that people have the best tools they’ve ever had, but they don’t all work with each other. And they have more access to information than they’ve ever had before, so they need ways to control that and to figure out how to harness it.

So that’s where I think things are going. I think that people are going to be expecting to use a suite of tools at work that are easy to use, that work with each other. I think a number of other companies, I would include Atlassian with what they do for developer tools, but I would also include Zoom. We are Zoom customers at Slack, and they built a really great product there. Certainly everything that’s being done at Box and Dropbox, so far. So this whole suite of tools, run by a bunch of independent companies, but they need a place to work together.

To integrate.

So I think the future is one in which people will have access to the information that they need to do their work in an unprecedented way, they’re going to have control over how that work interrupts them and how that information is presented to them that allows them to do their best work, and to stay focused and really do the work that only humans can do, the creative work, the collaborative and communicative work. And they’re going to do it across just an ever-growing number of tools. That’s what we see.

From independent companies.

Yeah. And that’s what we see, and when people start working in this way, they see results. 90 percent of our paid customers report that communication is easier because they use Slack. Two-thirds of them report that they’re more productive. I’d like those numbers to be 110 percent. But I think that we’re off to a good start. So it is a fundamental change in the way that people are working, and it’s gonna take some time, but we’re gonna be driving it.

Where you gonna be working next? Not Microsoft, I don’t think.

No plans. I think I’ve got plenty of work cut out for me. I have the best job that I’ve ever had in my career, and I think I also have the best product job in the industry, so I’m good.

All right, all right. Well, thank you so much, April, this has been a really fascinating discussion, and it was great talking to you. Thank you for coming on the show.

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