The NFX Podcast

April Underwood shares the Product Thinking That Built Slack & Twitter

Episode Summary

Twitter and Slack are two of technology’s most talked-about companies. They are both category-defining products marked by hypergrowth, each amassing a large base of deeply loyal users and a valuation of more than $20B. But Founders rarely get access to the product decisions being made behind the scenes, or the strategy and frameworks that guided them. April Underwood was instrumental at both companies, first as Director of Product at Twitter and then as Chief Product Officer at Slack. She is a powerhouse product leader with an unusual depth of experience in growing both B2C and B2B products from 0 to 1 to ubiquity, and building world-class product teams along the way. April joins the NFX podcast to offer inside stories and lessons learned from leading product at Twitter and Slack. Founders and product leaders everywhere will benefit from the 3-part framework she developed at Slack for hiring great PMs, her insights about leveraging early adopters, and how product CEOs can stay close to their product teams without slowing them down. Read the full essay -

Episode Transcription

Pete Flint (00:00:33):

Welcome everyone to The NFX Podcast, great to have you here. So I'm really delighted to have April Underwood joining us today. So April and I first met I think around 2017. So I was just transitioning off the Zillow board and April was joining the board. And so we've stayed in touch pretty much since then kind of on and off. I really enjoy the conversation about product and entrepreneurship and investing. And April has just had one of these amazing careers leading product teams initially at Twitter and then Slack where she was chief product officer. And so seeing firsthand the transformation of an evolution of those businesses, consumerization of the enterprise, and those are obviously category-defining businesses in themselves. So our audience at NFX is, I would just say founders that I think could really benefit from your product leadership and insights.

Pete Flint (00:01:23):

And so I think today we're going to have a fascinating conversation about product and platforms and network, and maybe touch on a few other things at the end. So welcome April, it's so good to have you. So April, you've led product teams at both Twitter and Slack, and both of them are category defining businesses I think worth North of $20 billion or more. On the one hand, there's a lot of similarities. But perhaps in your mind, what are some of the differences being inside those organizations, scaling the product? What are some of the core things you've seen that are different that perhaps you learned through that experience?

April Underwood (00:01:57):

Yeah. It's an interesting question because I think the reality is there are great many differences between the two. There's actually a decent number of folks that worked at both Twitter and Slack. And I think one of the biggest surprises for myself and for others as we transitioned from Twitter over to Slack was just how different they were. They're pretty systemic differences. Slack is an enterprise software company, you build software, you make it as good as you can, and you charge a fair price for it. Twitter is an advertising supported business. And so fundamentally the way you think about the product, the business, your users, your customers, very, very different in that model. And so the business models are different. The types of problems that you're solving are very, very different. The cultures are different.

April Underwood (00:02:56):

When you would walk into the Twitter office in 2010, and it's probably still true in 2020, I always described it as a trading room floor because it was so loud when you walked into the Twitter office, it was kind of like the service. And I think oftentimes cultures and the spaces actually really reflect the product that you're building. And so Twitter, you would see and hear employees talking to each other across the floor. There's a lot of laughter, there were a lot of surprises that would happen every day, things that would happen on the surface that would catch us off guard and be distractions in some way for our work.

April Underwood (00:03:36):

But you walked into Slack in 2015 when I decided to join, and you could have heard a pin drop because it's a product that's built for work, it's a product built for getting things done. And when you walked into the Slack office, not only did that permeate through the culture, this concept of doing your best work and working hard, but also people were literally using the service. We understood the value of having more of that conversation happen in Slack so that other people could benefit from the back and forth and that the next 10 or 100 employees could actually benefit from that historical backlog of those conversations. And so there was less shouting across the floor. So truly quite different even though communication is really at the core of both of those products. But it's amazing how communication is so fundamental that it can go a lot of different directions in terms of business, culture, product experience, and more.

Pete Flint (00:04:32):

Yeah, that's so different that kind of B to C side. Your perception of Twitter is kind of like incredible insights and incredible craziness. And then Slack is obviously a very different platform. One of the remarkable things about Slack is that at least my perception is that enterprise software is typically aggressively sold. You can imagine the enterprise salespeople that were knocking on CIOs' doors and send this product, at least it felt in the early years that Slack was really organically driven and very much a product driven growth approach, which is probably somewhat similar to Twitter. Would you feel the same way? I guess I'm curious, how did Slack kind of engineer that growth or it just happened?

April Underwood (00:05:18):

Yeah. It points to one of my main pieces of advice for product folks is that if you have the opportunity to work on something that sits at the intersection of a technological or even a business innovation, but also a cultural one, then run, don't walk. And I've had the opportunity to do that twice. So when I joined Twitter in 2010, it was still the early days for mobile. But the cultural shift was that, you have to rewind back to 2010, Barack Obama's first term in office. This was a time when people were searching for ways to express themselves more freely in a public forum. And so when it came to Twitter, there was a mobile app and people are using these apps on the go and they were connecting online sometimes even with the people that were in proximity to them in deeper ways.

April Underwood (00:06:18):

A lot of these things were technology driven, but there was a cultural thing that really made it feel like such a unique opportunity. And the place that you work when it comes up in dinner conversation, you know that that will be all you get to talk about for the rest of dinner, because everybody is captivated and wants to hear everything about it. I felt the same when I joined Slack. But with Slack, the shift was it was BYOD, so Bring Your Own Device. So now you've got people who are further using mobile devices or they're using their own laptops. Or even if they're not, they were at a point where the fragmentation of tools for the workplace was so vast that IT departments were giving especially engineers and technical teams more freedom to choose the tools that they wanted to use.

April Underwood (00:07:09):

And that opened the side door for a product like Slack to come in, and it was better than anything like it before. In fact, most of our customers used to say they didn't have anything before Slack, suggests that there was just nothing that filled that space in their mind prior to Slack. But also there was this cultural shift that not only did employees want to have a say in how they did their work, but they also wanted to

show up to work as their full selves. And so the ability for anyone to create a channel inside your Slack team meant that people created spaces to talk about things that were orthogonal or even completely unrelated to the work. And it wasn't people getting distracted, it was actually instead really culture and connection moving from the water cooler into that digital experience inside Slack. And that was a cultural shift.

April Underwood (00:08:07):

So I ultimately see a connection between the drivers for adoption of Slack. I see connections to that all the way back to what I experienced at Google from 2007 to 2009. When I joined there, it was shocking that you could join a mailing list for just about any project in the company. The founders and oftentimes CEO would stand up in front of the entire company on Fridays and answer questions. And you can see that now, those were the breadcrumbs for the expectations of employees that nearly every company in 2020. And Slack has been the tool that's been necessary to enable that communication at scale. So you asked specifically what did we do to stoke that?

April Underwood (00:08:54):

I think to some degree we tied ourselves to the secular trend that was already happening in the workplace. But certainly, the way the product was designed from the very outset, the vision that Stewart laid out from even before I joined was so clear that it allowed us to execute extraordinarily well over my time there in filling in corners of that vision, which was for Slack to be this communication platform but also increase the central nervous system for your entire company and how you worked across a variety of applications.

April Underwood (00:09:30):

So there were a bunch of growth tactics that were used, we redid the new XP a million times. We did a lot of things that every company I think does in the service of growth. But I would say that vision and connecting to that broader cultural shift in market need, those were the things that really lit the fire that drove that adoption early on. And then it spread like wildfire.

Pete Flint (00:09:56):

It's so true. They were just at the tip of the spear or those phenomena. And I'm curious how, as I imagine back to the early days, it was a small group of influential technical people that were driving some of this early adoption. And there's this very special product magic that appears in these platforms where it's early stage, there's perhaps this tightly defined group. And then the latest stage, Slack, it's CEOs as well as the summer intern who were using these platforms. And then the Twitter, it's obviously pretty much everything in the world. How do you think about just tightly defining or not tightly defining the audience and going off for a specific audience? And then how do you think about perhaps evolving the product set so you don't lose the magic that early adopters had but you enable it to scale to this huge almost ubiquitous platforms?

April Underwood (00:10:52):

Absolutely. I have experienced this, I don't know, confidence curve that grows early on and then wanes for a bit and then restores to a happy balance around whoever that initial audience is. So with Twitter, it was influencers, it was journalists, et cetera. Some of the feedback we got at times would have driven us to potentially build features that would be pretty relevant to more technical audiences but maybe not to mainstream folks. And then there's you can tell a lot of the same story with Slack. And at times, I would

find myself or my team lamenting that we needed to make sure not to build things just for that audience.

April Underwood (00:11:45):

And so what I challenged the team to do instead was reframe that and think about why is it fantastic that this is the first audience that we have? And how do we leverage that to play to our strengths? And so with Slack, for example, there was a little bit of the adage for a while we were taking some heat that we were mostly used by engineering teams. And it finally dawned on me that it was like, well, of course we can, of course we are because we are popular among engineering teams for a few structural reasons. The finance department doesn't really question the engineering team when they say they need a tool. Engineers usually have more access on their machines and they're able to decide to use the tools that they want to use more often, they oftentimes have much bigger budgets for tools as I alluded to as well.

April Underwood (00:12:39):

And by the way, they oftentimes are the taste makers for technology selections within the entire organization. So we could have spent time thinking like, "Oh, we've got to really like pour all of our energy into figuring out how to make Slack work for this other portion of the organization." But recognizing that actually getting it right for that audience was the avenue for us to spread wall to wall. I think ultimately helped us make sure not to throw the baby out with the bath water and maybe forget our original users in service of chasing the next set of users. Because oftentimes those early users are the pathway to the other users. So I think that was true for both Twitter and Slack. It's always a challenge, you don't want to box yourself in. But I think it's oftentimes a PR challenge in terms of how you frame it and how you tell your own story more so than it should be taken as some directive that you need to react against in your product roadmap.

Pete Flint (00:13:44):

And just going back to what we said at the beginning that there seems to be this evolution from early adoption to some period of challenge or negativity by some of the early adopters, then a resurgence over time. If that happened by this organization, I guess what was the tension to the organization and how did you overcome that tension to bringing perhaps growth and engagement or other elements of tension that happened during those perhaps formative scaling years?

April Underwood (00:14:10):

Well, I'd say platforms are where this oftentimes shows up because platform developers are oftentimes some of your most vocal, one of your most vocal constituencies. And if you get confused about your developer platform and think, well, I've got to serve my developers and I need to serve my customers, then I would argue that you've already made a misstep because you're seeking to serve your customers and you're seeking to bring developers along with you who have a vested interest in serving those customers as well. And when you make that mental shift, then I think that leads you to ensure that you're building capabilities for your developers that allow them to solve the problems that you're hearing about from your customers.

April Underwood (00:15:02):

I would say with both Twitter and Slack, we befell what I believe is a common misstep for early platforms, which is to think that the API is a product and to expose the API and think, well, now all this good is going to come. And the developers are happy because they have access to APIs. But they're

really unhappy down the road when they realize that some of the things they have spent their time and energy and money doing are not actually in line with your vision for where your platform is going. I'll call out one example with Twitter, we had built the Twitter API. It had been out for a while and a thousand flowers were blooming. But when we built the tweet button, that was this moment where we stepped across the threshold and we instead built features for developers that actually solved consumer problems very directly.

April Underwood (00:15:56):

And we built that consumer experience wrapped around that, and developers could plug it in in their apps or in their websites. It was a tool for them that actually made it much easier for them to offer this capability. But we were opinionated in what that consumer experience was going to be. And by the way, when we did that, we also took a step further to say, well, people are asking for a tweet button, but what do they really want? They want traffic. And there's two ways that they can get traffic. They can get traffic because there are tweets with links to their website, lots of those links get shared on Twitter. But the other way they can do it is they can build an organic following by actually encouraging the people who are most likely to follow their branded account immediately after they've shown that they're likely to, which is when they've tweeted a link to their website.

April Underwood (00:16:43):

And so when we built that feature and we built it with publishers, a specific slice of developers in mind, and we built a customer experience that was relatable, that solved a real customer problem. But we actually even gave those developers even more because we got at their core need. They saw usage, they saw their organic audience build through the use of that feature. It gave them a ton of value. And if we had just published an API and maybe said, "Hey, one thing you could do with it is you could do these 14 things, and here's a spec for how you would do that," it never would have happened consistently. It wouldn't have gotten the usage.

April Underwood (00:17:24):

So these are some of the things that I think that it's imperative for you to think about, which is that at that point in 2011, 2010, we were moving beyond an audience of both consumers and developers that really benefited from maximum control and instead moving into an era where us demonstrating our vision for the platform and setting goals for what we wanted to deliver for our given customers or publishers on the platform and having that reflected through our platform features started to really frankly, in my opinion, give the platform some shape and a purpose that it lacked when it was just an API.

Pete Flint (00:18:04):

It's so interesting. So often we meet companies that they aspire to be a platform, and then they're building the platform from day one, but just forget to build a product, which drives to the platform. And then clearly articulating what is the hierarchy of needs or what's the hierarchy of constituents. Because when you have more constituents, then there's more complexity. And if there's not precision on that hierarchy, all things can fall apart. I'm curious, is this evolution from product to platform? Are there any other things that people get wrong about that evolution to building a platform as opposed to just building a product?

April Underwood (00:18:44):

I believe you have to earn the right to be a platform. Being a platform means that you're doing one thing and you're doing it well enough for a large enough audience of people that you become a trusted avenue by which they may choose to adopt other tools or try other things or take the next step after the native capabilities that you offer. When I think about platforms, I oftentimes draw almost like a Maslow's hierarchy of needs. And to have a really meaningful platform opportunity, you need to start from a place of doing something well that's pretty low on this stack. And so for example communication, exchange of knowledge, I would assert is the most fundamental activity for knowledge workers, period.

April Underwood (00:19:38):

You need a device that is connected to the internet and running an operating system so that it can run your app. But after that, then you've got to talk to each other. And that's why I was drawn to Slack in 2015 to first lead platform before I stepped up to run all of product, because solving that fundamental need ... And by the way, not just enabling back and forth communication, but also aggregating that knowledge set and building search on top of it and creating more value for the customer out of it. Solving those core needs makes Slack a very fruitful place upon which you can start to introduce snippets of experiences from other applications. Really mattered at that moment because there was just this huge proliferation of workplace tools.

April Underwood (00:20:29):

We could have decided, "Well, why don't we just keep everybody in Slack all the time? And let's basically build a browser into Slack and just have you experience all of these different tools inside of Slack." And I think that old school platforms got into this mode where they kind took this territorial point of view. We never needed to take that approach. And the reason was because it's a champagne problem, but people were already spending all of their time in Slack. So we weren't trying to coerce them to spend more time in Slack. And our business model was such that we didn't make more money if you spend eight hours in Slack versus seven hours in Slack. And so there was no driver like you might see on an ad based platform for us to have these incentives that misaligned us with the developers on our platform or with our own customers.

April Underwood (00:21:19):

And so instead it made Slack the right place for notifications to show up from Google Drive or from Figma or from Miro or from all of these other tools because this is where people were spending their time. We built this platform that allowed the information to come into Slack that was urgent, real time and the actions that could be done in a very short amount of time to be done in Slack. And the minute you needed to do something more sophisticated. If you're going to go design some wire frames, for God sakes, go to the place, that's the best place in the world to do that, which is your design tool. We're not trying to embrace that, we instead want to help route you off there. What we do want to enable are those handoffs because those handoffs between people which are ultimately communication, we're best suited to be in the place where people could already be found.

Pete Flint (00:22:13):

So interesting. Maybe just changing tacks a little bit, let's talk a little bit about dog fights. When we first connected, it was this post the Trulia and Zillow dogfight, and then obviously Slack has major competitors with Atlassian and Microsoft. There's this adage around focus on your customers not your competitors. But it's a tight rope walk, you can't be too myopic. I'm curious, as a product leader going through those periods of intense battle, what did you learn? And what were some of the guidance that

you gave the team in managing this hyperintense competition that happens in all technology companies?

April Underwood (00:22:55):

This question is such a good reminder for me that it needs to be stated explicitly that a product is not just the code. I always remind my team that pushing code to production is not a lunch. A launch is the point at which your target audience actually understands what you have to offer and why it matters to them. And this is where I think the role of the product manager or certainly the product leader of the executive team to just continue to hone that strategy to help customers understand your vision, where you're going, what makes you different than that competitor. To lean into principled stances I would say as well. And I do think that customers over the longer arc have an appreciation for teams and companies that are dedicated to solving their problems and in an earnest, honest, pure way.

April Underwood (00:23:54):

And I don't mean to be Pollyanna about it, but I do think that that matters. I'm saying this with Twitter on my mind too because Twitter 10 years later, I'm very, very proud of Twitter and how it's showing up in 2020 with the policy choices that it's making, with the product choices that it's making. But it wasn't always clear, it wasn't always clear where we were going. But I think that it's becoming more clear, and I think that their market valuation would suggest that the world and customers are understanding that better and better every year. I just think when it comes to dog fights, it can be very distracting. And so it puts a big onus on leaders and on product managers to help ensure that customers as well as the employees of that company just really stay completely locked in on the vision and on the things that you're trying to do extraordinarily well and a commitment to do them extraordinarily well.

April Underwood (00:24:59):

I like to believe that the companies that can maintain that focus and that clarity of vision, they do win by some measure. Do they win the most customers or the most revenue? Maybe they don't. But I do think that those can be sustainable businesses with a long life ahead of them. And that's generally what I'm always aiming.

Pete Flint (00:25:22):

Yeah, I couldn't agree more. I think the focus combined often with network effects and, as you say, clear leadership just can really make seemingly subtle differences but important ones over perhaps incumbent. Zoom is front of mind, it was the ... I don't know how many companies came before it, but against these multi-product companies that were doing many things and perhaps couldn't do the one thing that was really valuable extremely well. And obviously social networking and lots of Twitter like companies, but there's only one Twitter, and they just did it better than anyone else.

April Underwood (00:26:02):

Yeah. Both the companies you mentioned especially in 2020, we are all reminded that it's not a strategy, but it is true that sometimes you need to be the right company when everything changes. When I first heard of companies starting to tell employees to go home back in March, and I think Twitter was one of the first to actually, just coincidentally. The thought in my mind was the minute that all of these fortune 500 execs are stuck at home spending all day on video conferences rather than in the boardroom and they discover how bad and finicky their video conferencing software is, then whatever the price tag is, they're going to be switching to Zoom. And it was just so obvious to me that Zoom was the best product

experience, but it did take this exogenous event I would say to really create a shift in the need. But man, talk about being the right company in the right place at the right time. And I think their success as well deserved.

Pete Flint (00:27:10):

And talking about network effects, at least in my experience at scaly marketplaces, network effects was important. But I noticed in 2008, it was like, we just want to grow and we want to survive. And then coming out of that, you realize that, "Oh my God, this network effect thing is just incredibly powerful and incredibly defensible for a business and created something very valuable." And I'm curious how much ... And network effect, we obviously love network effects and effects. How much at Twitter and Slack, do you think about perhaps engineering network effects or is it just that they were strategically intentionally or otherwise baked into the core product at the beginning, and as a function of scale, it created these highly defensible and highly valuable businesses? Is it something that product teams think about day in and day out?

April Underwood (00:28:07):

I think that it is. Whether they're naming it as such, it's the driver to teach people how to use your product so well that they're driven to teach other people to use the product. I'd say some of the first order growth drivers when I think about Twitter, we didn't necessarily talk about them as growth drivers, but certainly that's what they were meant to be. We might've used the word ubiquity back then, it was a decade ago. There might've been other ways that we talked about it. But getting a tweet button on every major news publication and with news pubs creating a lot of the content that might both be shared on and bring people to come to Twitter in the first place was very much a growth strategy.

April Underwood (00:28:56):

The work that Chloe Sladden and the media team did to convince the broadcasters to put hashtags in the bottom right hand corner of the television so that people would have a way to participate in an online conversation about this honor experience that was disconnected from the network far more than it is now, that was a growth strategy as well. With Slack, you think about the fact that some of the developers on our platform started to use login with Slack because they realized that once people, that if teens actually used their Slack logins, not only it was easier for them to get up and running because we took care of auth and profile and some of those onboarding steps for them. But also those people would by default have the Slack app installed, it was an avenue for notifications that would actually make it so that those would turn out to be more engaged teams that would be more likely to be more sticky.

April Underwood (00:30:02):

So I think there are a lot of different tactics that get used in service of growth. But I think they're also table stakes for good product experiences now too. And this gets a little bit to how you start to think about structuring your product organization. I think it's no longer the case you need to have a growth team that does all of this stuff because, like I said, these are table stakes for building an experience that is easy to discover, easy to enter from lots of different avenues, lots of different channels effectively and easy to quickly engage with other people through that service. And all of those things drive growth and network effects.

Pete Flint (00:30:47):

You touched there on just like building product teams. So you've been in some of the greatest product teams in Silicon Valley. If you're giving advice to early stage founders who are looking, may just be a couple of engineers and themselves or something a little bit bigger, what advice would you give from early founders to help as they think about scaling their product teams? In addition to that, what do you think makes a good product manager to help them to be successful?

April Underwood (00:31:18):

So I do get asked often when should I hire my first PM? And my answer to that is actually pretty similar to the answer that I would give to a group product manager or a PM director deciding whether or not she should hire one more PM. Which is not to be overly, I don't know, cerebral about it, but it's like if you are the blocker for your engineering and design team to make forward progress, then you need to hire a PM. I mean, not for one day, maybe not even for one week. Especially as a founder, if you pull your team and you regularly find that people are waiting for answers or waiting for guidance to be able to make for progress, then you really have no choice, your hand is forced.

April Underwood (00:32:04):

And I think that oftentimes founders wait a little bit too late there. And so they lose some amount of productivity for their team because they get to a point where they're just not able, especially once you've actually got customers and you also need to respond to those customers or PR requests or whatever those things are, you find that you're slowing your team down. There's a lot of value in a founder and being very close to the product and close to the team for as long as possible. In any growth company, whether you're in zero to one or later, you always have to be thinking about how you're firing yourself from various aspects of your job. And this is one that I think people get quite emotional about and dare I say territorial or even have some ego tied up in owning this piece. And I think that that can do teams a disservice. So I'd start by asking your team.

Pete Flint (00:32:59):

Sure. Now, we see that all too often. Transitioning from product leader to company leader, it's often a very tough thing for founders to do. And so you must have hired hundreds if not more product leaders over your time. Are there any tells that you have or areas of someone's personality or the way they think that you dig into to help to identify really strong product talent that you think might thrive in that culture?

April Underwood (00:33:32):

Yeah. So I have a pretty structured way that I think about PM hiring, and it's served me well so far, so I'm happy to share it. So when I'm looking to hire a product person, whether this is a PM or whether this is a VP of product, I take a step back and really think about a few different dimensions of product because nobody is born a product manager. People don't even really graduate college product managers with a very, very few exceptions where maybe they have some coursework in the topic. And so it is a learned skill that you learn on the job. And ultimately everybody comes to product from somewhere else. They started as an engineer and moved into it, or maybe they were on the business side and showed enough understanding of the customer that they made the leap over into product.

April Underwood (00:34:27):

They could have been the founder and so they were everything, and then product is the thing that they kept. And so there's a lot of different ways that people become product managers. And so the three

axes that I think about are functional subject matter expertise and growth stage experience. And I developed this really during my time at Slack because I did built out the team. These were things I was thinking about every single day during my three and half years there. Functional, it starts with just what flavor of PM are we talking about here? Because if you go to one company, maybe every PM has a CS degree. And then at another company, the PM is expected and have an MBA and be more of a business leader.

April Underwood (00:35:12):

They can be completely different, so you can't just look at paper and assume all PMs are the same. But very specifically, if you're looking to hire a product leader, because PMs, they have their lineage of what functional background they came from before product, you can oftentimes find somebody who can actually help round out some holes within the team, and that may actually be needed. And so, for example, if you're hiring a product leader but your engineering manager maybe is having some challenges scaling, you might hire a more technical product person, because maybe they can help fill that gap. Maybe you don't have anybody running marketing. And so actually you want a product leader who can just take that on and run with the ball for a little bit until you reach a scale where you hire somebody for it. Whatever the case, you should think about it because you should be looking at PMs from fairly different companies and cultures based on the answer to that question.

April Underwood (00:36:13):

Number two is subject matter expertise. Sometimes it matters, sometimes it doesn't. Especially in more junior roles, you can just hire generalist PMs, they can work on anything and they're hungry to learn new problems and new audiences. But as an example at Slack when I was hiring a product leader for the enterprise organization, I absolutely was looking for somebody to come into the organization who had built and sold enterprise software. And so I hired Ilan Frank, who continues to this day to be the leader for the enterprise product and team at Slack. And he was a fantastic addition to the team because he was somebody, he leveled all of us in the product organization up around what it looked like to be a product leader for large customers and how you needed to just show up for them and pitch to them and face objections from them as well as just deep understanding of the audience and their needs.

April Underwood (00:37:08):

And then third is growth stage experience, which I think oftentimes gets discounted. But there are people that have worked in 20 person companies, there are people that have worked in 2,000 person companies. There's a very small audience of people who have been lucky enough to work at a company that grows along that trajectory from 20 to 2,000. And there will be some roles that will just require somebody who can scale and morph and level up so quickly every six months where actually finding somebody with growth stage experience is more important than the subject matter or even what flavor of PM they are, because they just know how to lead through that change. So this structure for me, all it does is it forces me to pick which one of these three axes is most important. And then I use that to guide my sourcing and look for candidates that match that profile so that I make sure that I don't make compromises on the attribute of this product leader that is most important for this job. So it's always a bespoke process for me to hire a PM.

Pete Flint (00:38:08):

That's super helpful. That's such a great framework for thinking about how to hire product managers and product leaders. You touched on it earlier just around the interaction between product leader and

founder. I imagine both Twitter and Slack, the inventors of the product, the CEOs of the product who had deeply passion about it, rightly so. And I'm curious, how did you navigate that or any tips for product leaders coming into an organization, navigating preexisting founders with deep seated passion for their own products, any advice for people performing that role?

April Underwood (00:38:48):

Yeah, absolutely. My approach with, and really I'd say our approach for me and Stuart at Slack was to have a pretty extended calibration period. And I think that that was really a key to success for us. When I became VP of product about six months in, I did two things. I pulled together the CTO, the VP of engineering, the head of design, and really brought us together to start functioning as a team so that we could break ties amongst that group. We could just ensure that over time we were consistent in the vision that we were sharing with the organization and the guidance we were setting in the role definition between our teams that we were in total lockstep around that. And so we were all, three of us, except for the CTO who is Cal Henderson the amazing engineering co-founder of Slack. The four of us came together, it really just unlocked this rhythm where we could start to get things done.

April Underwood (00:39:51):

We could build our teams, we could hold them accountable. We could review products and establish a road mapping process and just get the engine going. And so that was really fun work. And going off and doing that in a vacuum as a product leader would have been one way to get it done and come out of the cave and be like, "Okay, team, here is the road mapping process." But instead by working as a team, we all felt ownership of it. And we could also back each other up because you can't have every leader in the room all the time. But the other thing that we did is we brought Stuart along for that process.

April Underwood (00:40:27):

And so for at least four quarters, and if I remember correctly, it might've been six, we had Stuart in the room for all of those processes so that that would be an opportunity for the team to hear feedback directly from him. It would be an opportunity for him to observe the team's progress as well as just get a read on how this organization was shaping up and give feedback to me and give feedback to my engineering and design peers as well.

April Underwood (00:40:58):

And so this calibration period, I counted it up a few years ago, it was hundreds of hours of calibration time. But I think it was absolutely critical, and I think that a lot of product leaders come in and they want to get the CEO out of the room as quickly as possible or the CEO founder. And I think that's a failure mode. It's too abrupt for the organization and for the humans involved, and it also means that it's just inevitable that some amount of the vision or the spark or the commitment to quality, just the way of thinking that made the company successful will get lost in the process. It is going to evolve over time, that's natural, it should. Extending that experience, that calibration period a little bit longer than maybe feels necessary is probably the right amount for a leader who is stepping in to run a product organization for a strong product founder CEO for the first time.

Pete Flint (00:42:00):

Yeah. I've also seen the opposite as well where founders of, they perhaps come from a business or engineering background and they hire an amazing head of product. This person's run it at Google or Facebook or ran massive engineering teams or product teams. And they basically transition and

delegate far too quickly and they create this incredible turbulence in an organization because the alignment is not there. In my experience, 100% the same. If you're going to onboard, or as you say calibrate, then it's just like you're in a very strong position if you do it a little bit longer than perhaps feels comfortable as opposed to less comfortable. I'm curious, you've talked about your own evolution and that evolution in the early days of Slack. I'm curious as you think about your own professional development in these organizations, is there any advice that you'd give you former self to things to do or not do or perhaps skills that you would have wished you'd learned earlier or perhaps unlearned?

April Underwood (00:43:04):

I started my career as an engineer back in 2002, working for Travelocity. But I had the opportunity to work with partners and product leaders and marketing, and a bunch of different parts of the organization. And externally right out of the gate, because I was working on what was called Travelocity partner network where we powered the travel tab for places like Yahoo and AOL and American Express. I came to product by way of engineering, but I have throughout my career, I have moved into business development roles at times. I have taken product marketing teams under my wing when they needed a place to go in the organization, even though I myself haven't spent a lot of time officially doing product marketing. What I have found is that having experienced stepping a little bit outside the lines of traditional product management has for me been incredibly valuable.

April Underwood (00:44:07):

It makes me who I am today, which is that I like to think I'm somebody that looks at problems from a lot of different angles and also has an incredible amount of empathy internally about what it's going to take to do something successfully. And what's required to build not just a successful product or a successful business on top of it, but a successful company. One that people want to be a part of for a long time and where they can do their best work and where they walk away with fond memories when they do decide to move on. And so those are things I aspire to. I think my experience sitting not only in the product management organization has been a huge asset for that.

April Underwood (00:44:48):

The challenge that I faced though is that that created a number of different times in my career. And I do think that there's probably a gender element to this as well where I had to defend that I was really a PM. And I think I ended up spending too much energy in my early career having to constantly prove myself. And just to put a specific example on it, when I was a Travelocity, I wanted to transition into PM. And I was doing a lot of the PM work for my project to be clear, but I was told I needed an MBA. So I went and got an MBA and I graduated and I went to Google and I joined in program management, which I was a little frankly confused about. I just didn't totally understand exactly where I fit within the organization until I got there post MBA in 2007.

April Underwood (00:45:41):

And I learned that I could probably never be a product manager at Google because I didn't have a CS undergrad degree. And so these goalposts kept moving around for me. And I think a lot of people have this experience and I definitely think that a lot of people of color and women have these stories of trying to prove that they are PMs. And so the advice I would likely have to myself is to tackle that challenge head on, is to have been more confident and more questioning about those barriers that were put in my way. I think I pushed them a bit, but it's easy for that feedback I think to get into your head and make you think, well, maybe I'm not a PM.

April Underwood (00:46:22):

And fortunately, the story turned out great for me. I've gotten to do product at Twitter and Slack over the last 10 years. I absolutely characterize myself as a product leader today, but that would be my advice to some of the folks out there who are earlier in their PM careers or who are founders where maybe investors are questioning whether they actually have the right chops in the room. The only way to be a PM is to build and ship product. And frankly, that's accessible to anybody

Pete Flint (00:46:53):

That's super helpful. And you mentioned diversity and gender. I've just seen firsthand how differences of opinion and perspective and background lead to just far better outcomes particularly on the product side and across the board. Is there any advice you give early stage teams as they're thinking about this, about things that they should be doing that they may not be doing?

April Underwood (00:47:17):

I think focus on diversity as early as possible. Some of the work that I've done with my angel investing group, hashtag angels is focused on actually putting real measurement around the equality or lack thereof in the industry as it relates to equity compensation. We wrote a blog post in 2017 called the gap table, it was a play on the cap table which of course is just a list of shareholders in a given company. And what we highlighted is that there's a lot of talk in the industry about equality and equity, but it's all focused on salary. None of the stories that you hear about people making it big in Silicon Valley have anything to do with salary. It's all about the equity.

April Underwood (00:48:08):

And of course, oftentimes equity is worth zero. But when it's worth something, it can be quite big and it can go on to position a person to make different choices in their career, to take bigger risks, to start companies, to invest in other companies that may go on to be successful, to back politicians and philanthropic causes that are near and dear to them. And so the stuff really matters. I mentioned that in the context of team building. The people that see outsized equity outcomes are the founders, are the investors, are the executives and are the very early employees, which often skew quite technical in software companies, in technology companies in general. And so all the more reason that at the point at which you start issuing equity, it's imperative that you are already thinking about diversity because that decision that you delay by 6 or 12 or 24 months in the best scenarios can be orders of magnitude in difference for those employees in terms of their outcomes.

April Underwood (00:49:11):

And money is nice, but what it can do and the downstream effect of that in the industry is incredibly important. And so that's the advice that we hashtag angels are always giving to our founders is to start early. There are lots of different organizations out there today, especially that I think we've all become more aware of in the last few weeks on Twitter that help you find amazing black designers, amazing black engineers, founders that you can back, Latinx founders. It's all out there, there's no excuse to not find the talent because it's never been easier than before to find talent that is going to help you have that diversity on your team. And your product is going to benefit from it, your customers will, and certainly those employees will.

Pete Flint (00:49:58):

Yeah, so true, I couldn't agree more. You've been very successful and obviously a huge amount of personal ability and drive and commitment, but also you've been surrounded and I'm sure mentored and had advice from a number of amazing people throughout your [inaudible 00:50:16]. So the people that have had a significant on your own personal growth throughout the years that you want to highlight.

April Underwood (00:50:24):

Yeah, absolutely. I'll call out a couple of folks. One is Dick Costolo who was the CEO at Twitter. We first met when he had sold his company FeedBurner to Google back in 2007, right around the same time I joined. He was really bright, he was also a hoot. And he was working on some business things that were really relevant to some of the more operational work that I was doing as a program manager. So I really wanted to connect the work that I was doing to his business strategy to close the loop with this otherwise cost center type work that I was doing around content acquisition. So I got to know him, had the opportunity to work for him for five years at Twitter. And near the end of those five years even though we had a great relationship, always talked in the hall, I realized that I was a little frustrated with him because I wanted sponsorship. I wanted him to spend time with me and help me be successful, not just to react to me if I came to something with him.

April Underwood (00:51:31):

And so I approached him about it, and he was open to it. And he took the feedback that there was an opportunity for him to do more especially for women in the organization. And I think since that time has very much done that for me but for others from the ex-Twitter network. And it's frankly inspired me to think about the same thing that I can do for people of color in the organizations with whom I've worked. And so I'm just starting to learn my muscles as a sponsor and being on the other side of the table. But it's absolutely something I want to do. And sometimes you need to be called into service and to do it. And when you are, you got to answer that call. And that was what Dick did for me.

April Underwood (00:52:11):

Some of the other people that I've been really grateful to call what I almost called friendtors tours, all of my hashtag angels are women with whom I have worked, with whom I have angel invested, we've backed over 120 companies together. But they're also the people that I call because they have their own areas of expertise and their own board experience or executive experience that they can lend me. And so maintaining that tight network now for five years, five years going on six of having those people that I can call at any time is a really important network for me.

April Underwood (00:52:51):

And then finally I'll say working for Stewart Butterfield for three and a half years, I learned more about product and about care for the craft and just being incredibly thoughtful about every decision you make and how that impacts the people on the other side of the screen using your product. Learned more in the three and a half years that I worked with him than the rest of my career combined on those fronts. And so I've been very, very lucky to get to work with some great folks along the way and to get to develop personal relationships with them that have directly contributed to my success and my growth. And so I'm always trying to pay that forward with the folks that are just coming up behind me.

Pete Flint (00:53:37):

Yeah. It's such an amazing group of people. And I love the word friendtors, it's definitely a ... If you can find mentors or friends and find that balance, just wonderful. And I've certainly seen that myself. So I just want to touch on a moment about how you see the evolution of enterprise software. And enterprise software is the wrong word because you think of this starchy DOS like environment of badly designed experiences. And we've seen this evolution of the consumerization of enterprise. I know you've touched on this supporter movement here. From your vantage point, what do you see is going on on perhaps the business side of software, how that's evolving, and how do you think is perhaps different or very similar to what's going on the consumer side of things?

April Underwood (00:54:26):

Well, I'd say we're just getting started. The work that we did at Slack over my time there, but that the company has been doing for the last five years really addresses a large and growing market. And yet there are still so many different tasks and significant work streams and audiences that still are untouched by this movement. When we were building Slack, it just made sense that of course the app that you have to use to communicate with anybody should be intuitive and should be as easy to use as the consumer messaging experiences you have. In fact, it should probably be better because you are likely to talk to your colleagues in a digital fashion more than you talk to anybody else. It should just sing and it should just be an effortless experience to communicate in defined information in inside Slack.

April Underwood (00:55:27):

And so we were always striving for that, how do we just build the very, very best experience that we possibly can? This is too important to get wrong, like it is rude to not get this right. But I would say that when I think about a completely different vertical, so you get outside of knowledge workers and you think about agriculture. One of the companies that I've backed recently is called [Gunnar's 00:55:50]. And the founder is building and her team are building software for farm workers. A lot of them still use punch cards to punch in and punch out. They need to track their hours, they need to get paid, they need to be trained. They need to know what the latest restrictions are around COVID, they need to know how to use new materials that maybe can make a farming process less detrimental to the environment.

April Underwood (00:56:16):

There's so much opportunity for evolution in agriculture, but it's just such early days in digitizing that industry. And when I found this company and got to know the founder and was just so impressed by what she was doing, it just reminded me that there's still so many cards to turn over with this consumerization. And even I would state, just basic digitization. There are still a lot of people that go to work every day and don't have tools to use for their daily activities that are even on the same playing field as the apps that we have for consumer use. So I think there's a ton of opportunity there. And I think all of that evolution is absolutely inevitable. So those are bets that I like to take as an angel investor.

Pete Flint (00:57:00):

And it's clearly accelerating right now as everything is going digital and more remote. The trends have been going for a while, they've just been ticked up a few years it seems. They were interesting opportunities six months ago, and I think they're way more interesting opportunities today.

April Underwood (00:57:18):

I think that's true. The area that I've been just absolutely captivated by is just watching the local businesses here in my community of San Anselmo, California undergo what is effectively a pivot

overnight. And these are offline businesses that rely on foot traffic, and they have demonstrated creativity and a sense of urgency. All the things that we look for out of Silicon Valley founders to figure out how they can find customers, sell their products, fulfill orders, and do all of that under duress and under a bunch of different constraints because of shelter in place. And they're doing it. And so I've been incredibly focused on that part of the market, a part of the market where there are tools like Shopify and Squarespace. Ultimately, I think there's a lot of untapped opportunity for how these businesses work, how they work together, how they engage in their communities. And so this is something that I just can't stop thinking about and is an area that I expect to see a lot of evolution in the coming years.

Pete Flint (00:58:24):

Yeah, for sure. And you've talked previously about how to make enterprise software more delightful. I'm curious if there are any learns, like properties of user that you can break down, When you say delightful, how do you manifest that in a product organization?

April Underwood (00:58:40):

It's a great question. It almost ends up resolving to, can you teach taste? And I would say I haven't answered that question for myself yet. I think you can try, you can seek to establish principles, product principles that you use. You can use storytelling as product leaders and as executives in the way that you give feedback to teams to help them trace back their steps and potentially find another path forward when they build something that has an absence of delight. But I'll be honest, this is where I think as a product leader you have to get smart about how you put your talent to use. And that talent includes the PMs and the designers that have just demonstrated the greatest ability to take something beyond just meeting a set of needs but actually going further to actually meet unstated needs or even start to stoke the idea that there are things that people want out of the experience that they didn't even originally come there for.

April Underwood (01:00:01):

I don't expect that every single PM or designer within an organization is always going to hit it and find that moment of delight 100% of the time. I think it's both unrealistic as well as I think it's personal to an organization and to a brand. But what you can do is you can make sure to match the right people to the parts of the product where it matters most. And you can also engage, whether it's founders or just almost product culture keepers within the organization to have some amount of editorial review to help bring some consistency. I'd love to figure out some magic trick to be able to make it so that everyone in an organization has an equivalent level of being able to deliver this. But I actually think for product leaders, that's the wrong way to think about it because I think this is a human capital problem. And it's more, how do you structure processes in a way that actually ensure the best outcomes for the team as a whole rather than trying to implant a chip in every single person and get the exact same results every time?

Pete Flint (01:01:07):

April, this was a fascinating conversation. So many terrific insights for our audience. So I want to thank you once again for sharing with us today, and I'm looking forward to hopefully seeing you in person before too long.

April Underwood (01:01:22):
Absolutely. Thank you so much for having me. It was a lot of fun.