Twitter and slack are 2 of technology's most popular products, but you rarely hear the product decisions being made behind the scenes. April Underwood was involved in both as director of product at Twitter and chief product officer at slack. What can founders learn about the strategy, frameworks, focus, and leadership that turned unknown apps into global phenomena? April joins NFX partner Flint to share what she learned about world class product development. Welcome everyone to the NFS podcast.
Great to have you here. So I'm really delighted to have April Underwood join us today. So April and I first met I think around 2017. So I was just transitioning off the Zillow board and April was joined the board. And and so we've stayed in touch pretty much since then kinda on and off. You know, I've just had really enjoyed the conversation about product and entrepreneurship and investing.
And, you know, April has just had one of these amazing Currier, leading product teams initially at Twitter and then slack where she was chief product officer. And so it seemed firsthand kind of the transformation of, an evolution of those businesses, consumerization of the enterprise, and, you know, those are obviously category defining businesses in themselves. So our audience at NFX is, Otisage founders that I think could really benefit from your product leadership and insights.
And so know, I think today we're gonna have a fascinating conversation about product and platforms and and network and maybe touch on 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 and both of them are category defining businesses. I think worth north of $20,000,000,000 or Morgan.
So I guess that's sort of, you know, on the one hand, there's a lot of similarities, but perhaps in your mind, like, what are some of the differences being inside those organizations scaling that those product. What are some of the cool things that that you've seen that are different that perhaps you learned through that experience? Yeah. I mean, you know, it's, It's an interesting question because I think, the reality is there, there are great many differences between the 2.
There's actually, a 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 transition from Twitter, over to Slack was just how different they were. And, you know, they're pretty systemic differences. You know, slack's an enterprise software company. You build software, you make it as good as you can, and you charge a fair price for it. You know, Twitter is, you know, is an advertising supported business.
And so fundamentally, the way you think about the product the business, your users, your customer is very, very different, in in that kind of model. And so, you know, the business models are different. The, you know, the types of problems that you're solving are very, very different. You know, the cultures are different. When you would walk into the Twitter office in 2010, and it's probably still true in 2020, I I always described it as a trading room floor.
Because it was so loud when he walked into the Twitter office. It was kinda like the service. And I think oftentimes cultures and the spaces actually really reflect the product that you're building. And so Twitter, you know, you would see and hear employees talking to each other across the floor. You know, there's a lot of laughter.
There was a lot of, you know, there were a lot of surprises that would happen every day, things that would happen on the that would catch us off guard and, you know, kind of be distractions in some way, for our work, but you walked into slack in 20 team when I decided to join, and you could have heard a pin drop. Because it was a 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, was that sort of did that permeate through the culture or this concept of of doing your best work and working hard, but also people were literally using the service. You know, we we understood the value. Of having more of that conversation happen in slack so that other people could benefit from the back and Morgan. And that the next 10 or 100 employees could actually benefit from that sort of, that historical backlog of those conversations.
And so there was less shouting across the floor. And so, so there so it's 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. Yeah. You that that's so different.
The kind of Pete to c side and sort of the that's sort of your perception of a Twitter is kind of like, incredible insights and incredible craziness. And then Slack is obviously a very different platform. One of the sort of remarkable things about Slack is that at least, my perception is that, you know, enterprise software is typically aggressively sold. You know, you can imagine the kind of like, enterprise salespeople that were knocking on CIO's doors and kinda send this product.
At least it it's sort of sent for in the early years that slack was really organically driven and and very much a product driven growth approach, which is probably somewhat similar to to Twitter, would you feel the same thing? Same way. I got some curious. How did that kinda engineer that growth, or was it was it it just happened?
Yeah. Well, I mean, I mean, it kinda points to one of my, you know, main pieces of 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 than, like, run, like, don't walk. And I've had the opportunity to do that twice. I mean, so when I joined Twitter in 2010, You know, it was it was still the early days for mobile.
And but the cultural shift was that, you know, this 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 them more express themselves more freely in a public forum. And so when he came to Twitter, you know, the, you know, there was a mobile app and, you know, people were using these apps on the go and they were you know, connecting online sometimes even with the people that were in proximity to them, in deeper ways.
And, and so, you know, there were, you know, a lot of these things were sort of technology driven, but there cultural thing that really made it, feel like such a unique opportunity. And, you know, the kind of place that you work that 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's sort of captivated and wants to hear everything about it. I I felt the same when I joined Slack.
But with slack, the shift was, it was BYOD to bring your own device. So now you've got people who are further work using mobile devices. Or they're using, you know, they're using their own laptops or even if they're not, they're oftentimes they were at a point where the fragmentation of tools for the actually engineers and technical teams more freedom to choose the tools that they wanted to use. And that opened this side door for a product like slack to come in.
And, you know, it was better than anything like it before. In fact, most most of our customers, you know, used to say they didn't have anything before Slack. Suggests that there was just nothing that sort of 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 in a, like, as their full selves.
And so, you know, the ability to create, you know, 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 people getting extracted. It was actually instead really cultural culture and connection moving from, you know, the water cooler into that digital experience inside slack. And that was a cultural shift.
So I ultimately see a connection between, you know, the drivers for adoption of slack. Oh, you know, I I see a connection to that all the way back to what I experienced at Google from 2007 to 2009. You know, when I joined there, it was shocking that you could join a mailing list for just about any project in the company. That 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 bread crumbs for the expectations of employees at nearly every company in 2020. And slack has has been the tool that's been necessary to enable that communication at scale. So so you asked specifically, you know, what do we do to stoke that? I mean, I think to some degree, we tied ourselves to this secular trend that was already happening in the workplace.
But certainly, the way the product was designed from the very Pete, the vision that Stewart, laid out from even before I joined, was was so clear that it allowed us to execute extraordinarily well, over my time there in in sort of filling in the corners of that vision, which was for Slack to be this communication platform, but also increasingly sort of like the central nervous system for your entire company. And how you worked across a variety of applications.
So there were a bunch of growth tactics that were used. There were, you know, we redid the new XP a million James. We did a lot of things that that every company I think does in the service of growth, but I would say that vision and, you know, connecting to that broader cultural shift in need was, you know, those were those were the things that really lit the fire, that drove that adoption, early on, and then it spread like wildfire. Yeah. And it it's, it's so true.
They were just at the tip of the spear of those those phenomena. And and I'm curious how you know, as I kind of imagined back to the early days, it was a sort of small group of influential technical people that were kind of like driving some of the this early adoption. And there's this sort of, like, very special product magic that kind of appears in these platforms where know, at this early stage, there's perhaps this tightly defined group.
And then kind of the later stage, you know, slack at CEOs as well as the kind of, like, the summer intern who are kinda using these platforms. And then at Twitter, it's, you know, it's obviously pretty much everything in the world. How do you think about just sort of tightly defining or or not tightly defining the kind of audience and and going after a specific audience. And then how do you think about perhaps evolving the product sets.
You don't lose the magic that the kind of early adopters had, but you enable it to scale to this huge, almost ubiquitous platform. Yeah. Absolutely. I mean, I I, I have experienced this sort of, I don't know, confidence curve that sort of grows early on and then wanes for a bit and then restores to, like, a happy balance around, you know, whoever that initial audience is. So You know, with Twitter, it was, it was influencers, it was journalists, etcetera.
You know, some of the feedback we got at times would have driven us to potentially build, you know, features that would be pretty relevant to more technical audiences, but maybe not to Pete stream folks. And then there's, you know, you can kinda tell a lot of the same story, with slack. And, you know, at times, I would find, you know, as myself or my team sort of lamenting, like, that we needed to make sure not to build things just for that audience.
And so what I challenged the team to do instead was reframe that and think about why is it why is it fantastic that this is the first audience that we have? And, like, how do we, like, how do we leverage that to play to our strengths? And so with Slack, for example, you know, there was a little bit of the adage for a while, you know, we were sort of taking some heat that, you know, we were 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 we are popular among engineering teams for a few structural reasons. Nobody really you know, the finance department doesn't really question the engineering team when they say they need a tool. Engineers usually have more you know, access on their machines, and they're able to decide to use, you know, the tools that they want to use more often.
They oftentimes have much bigger budgets for tools as I alluded to as well. And by the way, they oftentimes are sort of like the taste makers for technology selections within the entire organization.
So, you know, we could have spent time thinking like, oh, we've gotta really, like, pour all of our energy into figuring out how to how to you know, 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 to other, you know, to to to spread wall to wall.
I think ultimately, helped us make sure not to sort of, yeah, throw the baby out with the bathwater and maybe sort of forget our original users in service of chasing the next set of users. Because oftentimes as early users are the pathway to the other users. So, I I think that was true for both Twitter and slack And, but it but, you know, it's always a challenge.
You don't wanna box yourself Flint, but I think it's oftentimes a PR challenge, in terms of how you frame it and how you tell your own story. Morgan so than, you know, than than it should be taken as some sort of directive that you need to react against in your product roadmap.
Yeah. And and and and just going back to where we said at the beginning that there seems to be this evolution from early adoption to kind of like some period of kind of you know, challenge or kind of negativity or, like, some of the early adopters, then a resurgence over time.
Like, if that happened in both these Morgan, what, I guess, what was attention in the organization and how did you overcome that tension between perhaps, you know, growth and engagement or kind of other elements of tension that happened during those perhaps formative scaling years? Yeah. Well, I'd say, you know, platforms are where this oftentimes shows up, because platform developers are oftentimes some of your most vocal, you know, you're sort of one of your most vocal constituencies.
And if you get confused about your developer platform and think, well, I've gotta serve my developers and I need to serve my customers. Then, you know, I would argue that you've already made a misstep because you're seeking to serve your customers and you're seeking seeking to bring developers along with you who have a best of interest in serving those customers as well.
And when you make that mental shift, then I think that that leads you to a sure that you're building capabilities for your developers that allow them to solve the problems that you're hearing about from your customers. And, you know, I would say, you know, with both Twitter and Slack, we defaul what I believe is sort of a 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 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 you realize that some of the when when they realize that some of the things they have spent their time and energy and money doing are not not actually in line with your vision for where, you know, your platform is going. And so, you know, I'll I'll call out one example with, you know, Twitter. We had built the Twitter API.
You know, it had been out for a while and, you know, a 1000 flowers are blooming. But when we built the tweet button, that was this moment where we made. We sort of stepped across the threshold, and we instead built, you know, features for developers that actually solved consumer problems very directly. 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, you know, 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 in, you know, lots of those you know, 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 like 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.
And so when we built that feature and we built it publishers, a specific slice of sort of developers in mind, and we we Beller 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, you know, they saw usage. They saw, you know, 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, like, you could do these 14 things. And, like, you know, here's a spec for how you would do that. It never would have happened consistently. It wouldn't have gotten the usage.
And so, you know, So so these are some of the things that I think that, you know, 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, that, that, you know, really benefited from maximum control.
And instead moving into an era, where, you know, us exercising, you know, demonstrating our vision for the platform and, like, setting goals for what we wanted to deliver for our given customers or publishers on the on the platform and having that reflected through our platform features, started to really, you know, frankly, in my opinion, give the platform some shape purpose that it lacked when it was just an API. Alright. Yeah. It's so interesting.
So so often we meet companies that they aspire to be a platform, and then they you know, building the platform from day 1, but just forget to build a product almost which kind of drives drives the platform and then you know, clearly articulating what is the hierarchy of needs or or or what's the hierarchy of constituents? Cause when you have more constituents, then there's more complexity and if there's not precision on that kind of hierarchy, all things can kinda fall apart. I'm curious.
It's like, It's this evolution from product to platform. I guess for that, like, do you are there any other things that people get wrong about that kind of evolution to to building a form as opposed to just building a product? I believe you have to earn the right to be a platform.
I mean, being a plat for means that you're doing one thing and you're doing it well enough for a large enough audience of people that, you've become sort of 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 that you offer. And so, you know, when I, when I think about platforms, I oftentimes sort of draw, like, almost like a Maslow's hierarchy of needs.
And to have a really meaningful platform or opportunity, you need to start from a place of doing something well that's pretty low on the stack. And so, for example, you know, communication, you know, exchange of knowledge, I would assert is the most fundamental activity for knowledge workers period. You know, I mean, 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 gotta talk to each other.
And that's why, you know, that's why I was drawn to Slack in 2015, to first lead platform before I stepped up to brand Olive product. Because solving that fundamental need. And by the way, not just, you know, enabling back and forth communication, but also aggregating that knowledge set and building search on top of it and, like, 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, you know, sort snippets of experiences from other applications. And that mattered at a time, you know, really mattered, you know, at that moment because there was just this huge proliferation of place tools. And so, you know, we could have decided, well, why don't we just keep everybody in slack all the time?
Let's build a, basically, build a browser into Slack and just have you experience all of these different tools inside of slack. And I think that, you know, old school platforms got into this mode where they, you know, kind of took this territorial point of view. And I don't think we needed to we Beller needed to take that approach. And the reason was because, you know, it's I mean, it's a 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, you know, we didn't make more money if you spend 8 hours in slack versus 7 hours in slack. And so, you know, there was no driver like you might see on an ad based platform for us to have these sort of incentives that misaligned us with the developers in our platform or with our own customers.
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. And so we would, you know, we built this platform that allowed the the information, to come into Slack that would be that was, you know, urgent real time and and, you know, 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, like, if you're gonna go design some wire James. For god's sakes, go to the place. It'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.
But we do what we do wanna, you know, enable is are those handoffs because those handoffs between people, which are ultimately communication, you know, Pete best suited to be in the place where people could already be found. Ah, yeah. It's just so interesting. Maybe maybe just changing talks a little bit. May let's talk, talk a little bit about dog fights. You know, when we first kinda connected, it was to sort of post the trulia and Zillow dog fight.
And then you know, obviously slack has major competitors with Atlassian and and Microsoft and, you know, there's this sort of addage around, like, focus on your customers, not your competitors, but it's a tight road walk. You can't be sort of, too kind of myopic.
I'm I'm curious as as a product leader, going through those periods of sort of intense battle, what did you learn and and and what was the some of the guidance that you gave the team and the in managing this this hyperintense competition that happens in all technology companies. This question is such a a good reminder for me that, that it needs to be stated explicitly that a product is not just the code. You know, it's kind of you remind my team that pushing code to production is not a launch.
A a launches the point at which your target audience actually understands what you've what you have to offer and why it matters to them.
And this is where I think, you know, the role of the product manager, certainly the product leader of the executive team to you know, 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, which is, you know, that, like, you know, and I do think that customers over the longer arc, have an appreciation for
teams and companies that are dedicated to solving their problems. In a, like, in an earnest, honest Pete way. And, you know, I don't mean to be pollyanna about it, but I do think that that matters. And I think, you know, I'm saying this with Twitter on my mind too because Twitter is, you know, 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, and I think that, you know, the, you know, their their market valuation would suggest that the world and and customers are understanding that, better and better every year. So, you know, I think, you know, I 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 Beller. And a commitment to do them extraordinarily well. And I, I, you know, 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, but I do think that that, that those can be sustainable businesses, with a long life ahead of them. And that's generally what I'm always for? Yeah. I couldn't agree more. I think the, you know, the the focus, combined often with network effects and sort of as you say, kind of like a clear clear leadership just can really make seemingly subtle differences, but important ones over perhaps incumbent the sort of, you know, Zoom is front of mind.
You know, it was the sort of, you know, I don't know how many companies came before it, but, you know, against these multi product companies that were doing many things and perhaps couldn't do the one thing that was really valuable extremely Beller, you know, and obviously social networking and, you know, lots of Twitter like companies, but there's only one Twitter. And they just did it better than anyone else.
Yeah. And, I mean, both of those companies, you know, both the companies you mentioned, you know, especially in 2020, we are all reminded that it's not a strategy, but it is true that sometimes you need to be you need to be the right company when everything changes. And, you know, when 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, actually, just coincidentally.
The thought on my mind was the minute that all of these Morgan 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, like, Zoom was the best product experience, but it sort of took it did take this exogenous event. I would say, to really create a a shift in the need.
But but, man, we're talking about being the right company in the right place at the right time. And, you know, and I and I think there's success as well to serve. Yeah. Yeah. And talking talking about network effects. So, you know, I at least in my experience at kind of scaling marketplaces, you know, network effects was kind of important, but it was, you know, I I know just like in 2008, it was like, we just wanna grow and we wanna survive.
And then coming out of that, you realize that, oh my god, this network effect thing is just like incredibly powerful and incredibly, defensible for business and and created something very valuable. And I'm curious how much and and network effect is, you know, we we obviously love network effects and effects and How much a sort of Twitter and slack?
Is it do you think about perhaps engineering network effects, or is it just that they were strategically intentionally or otherwise baked into the core core product at the beginning, and there's a function of scale it created these sort of highly defensible and highly valuable businesses. Is it is it something that product teams think about day in and day out I think that it is, you know, whether they they're naming it as such, it's the driver to teach people how to use your product.
So well that that they're driven to teach other people to use the product. Right? I mean, you know, I'd say, you know, some of the sort of 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 have used the word ubiquity back then. It was a decade ago.
You know, there there might have been other ways that we talked about it, but getting a tweet button on every major news publication And with news pubs, you know, creating a lot of the content that might both be shared on and bring people to come to Twitter in the first place, was, like, very much a a a growth strategy.
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 offline conversation in a, I mean, in an online conversation about this on air experience that was, that was disconnected from the network. In, I mean, far more than it is now, that was a growth strategy as well.
You know, I mean, with slack, you know, you think about the fact that, some of our some of the developers on our platform started to use log in with Slack because they realize that once people that if teens actually use their slack logins, not only were they you know, it was easier for them to get up and running because we sort of took care of off and profile and and some of those, you know, sort of onboarding steps for them.
But also, those people would by default have the Slack app installed, which was like a constant, you know, 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. So I think there are a lot of different, tactics, get used in service of growth, but I think there are also table stakes for good product experiences now too.
And so, so I think, you know, And this gets a little bit to how how you sort of think about structuring your product organization. You know, it's not I think it's no longer the case that you sort of need to have a growth team that does all of this stuff because these are just, you know, the, like I said, these are table stakes for building an experience that is, you know, easy to discover easy to enter from lots of different avenues, you know, lots of different channels effectively.
And, you know, easy, to quick engage with other people through that service. And all the all of those things drive growth and and network effects. So you touched there on just like building product teams. So, you know, you've been in some of the sort of greatest product teams in Silicon Valley. Like, you know, if you're giving advice to early stage founders who are looking, you know, it may just be a kind of couple of engineers and and themselves or something a little bit Beller.
Like, what what advice would you would you give from early founders to help as they think about scale in their product teams and and sort of in addition to that, like, what do you think makes a good product manager to help them to be successful? Yeah. So I'll start with so I do get asked often, you know, when should I hire my 1st 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 1 more Pete, which is, you know, not to be overly, I don't know, kind of 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 1 week.
But if, you know, especially as a founder, if you find if you if you, you know, poll your team and you regularly find that people are waiting for answers or waiting for guidance to be able to make forward progress, then you really have no choice. Your hand is Morgan 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 know, you're you're slowing your team down. There's a lot of value in a founder being very close to the product and close to the team, for as long as possible.
But you also you in any growth company, whether you're in 0 to 1 or later, you always have to be thinking about how you're firing firing yourself from various aspects of your job. And this is one that I think people get quite emotional about and, you know, dare you say territorial. And so or or, you know, even have some ego tied up in in owning this Pete. And I think that that can do a James a disservice. So I'd start by asking your team. For sure. No. We see that. We see that all too often.
Yeah. Trying transitioning from kind of product leader to company leader is just a often a very tough thing to for founders of students. And so, you know, you you must have hired 100, if not more kind of product leaders over your time. Like, are there any sort of tells that you have that or areas of someone's sort of personality or the way they think that that you dig into to help to Sort of identify really strong product talent that that, you think might thrive in that culture?
Yeah. So I I have a pretty structured way that I think about PM hiring, and and it 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, you know, a Pete or whether this is a VP of product. I take a step back and really think about a few different dimensions of product because, you know, nobody is born a product manager.
People don't even really graduate college pro product managers with a very, very few exceptions where maybe they have some course work in the topic. And so it is a it is learned skill, that that you learn on the job. And ultimately, everybody comes to product from somewhere else. You know, they 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.
You know, there's a lot of they could have been the founder, and so they were everything. And then product is the thing that they sort of kept. And so there's a lot of different ways that people become, become product managers. And so the 3 James that I think about are functional subject matter expertise and growth stage experience. And I I developed this really during my time at slack because I did, you know, you know, built out the team.
And so, I these were things I was thinking about every single day during my 3 a half years there. And so I, you know, functional is it starts with just what flavor of PM are we talking about Pete? Because if you go to one company, you know, maybe every PM as a CS degree and then at another company, the PM is expected and have an MBA and be more of a business leader. It's 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 sort of have this, you know, they have their their, you know, their their lineage of, you know, what functional background they came to came from for 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, a 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 the Beller, run with the ball for a little bit until you reach a scale where you hire somebody for it.
Whatever the case it that, you know, you should think about it because you should be looking for fairly you should be looking at PMs from fairly different companies and cultures. Based on the answer to that question. Number 2 is subject matter expertise. Sometimes it matters. Sometimes it doesn't. You know, you, you know, especially in more junior roles, you can just hire generalist PMs that can they can kinda 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 Morgan who had built and sold enterprise software.
And so I hired Elon Frank, who continues to this day to be, the leader for the enterprise, product and team at slack And he is a fantastic addition to the team because he was somebody that really, you know, 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 show up for them and pitch to them and and face objections from them. As well as, you know, just deep understanding of the audience and their needs.
And then 3rd is growth stage experience, which I I think you know, oftentimes gets discounted, but there are people that have worked in 20 person companies. There are people that have worked in 2000 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 2000.
And, you know, there will be some roles that will just require somebody who can scale and sort of morph and level up so quickly Beller 6 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 kind of change. So so this this structure for me, all it does is it forces me to pick which one of these 3 axis is most Morgan.
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 sort of attribute of this product later that is most important for this job. So it's always a bespoke process for me to hire a PM. Right. Okay. That's super helpful. Thank you.
That's a that's such a great framework for kind of thinking about how to how to hire a product managers and product leaders You know, you you touched on it earlier just around the sort of interaction between product leader and and perhaps found and and founder and you know, 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 how did you navigate that Morgan sort of tips for product leaders coming into an organization navigating Pete existing founders with kind of deep seated passion for for their own products. Any advice for people doing performing that role? Yeah. Absolutely. I mean, my approach, with, and really, I'd say our approach with for for me and Stewart Slack was, was to have a pretty extended calibration period. And I I think that that was really a key to success for us.
And that when I became VP of product about 6 months in, I did 2 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, you know, ensure that over time, we were consistent in the vision that we were sharing with the Morgan.
And the guidance we're setting in the the role definition between our teams that we were, you know, in total lockstep around that And so we were all, you know, 3 of us, except for the CTO who is is Cal Henderson, the amazing, engineering cofounder of of Slack. When the four of us came together, it really just unlocked this rhythm where we could start to get we we could start to get things done. We could build our James, We could hold them accountable.
You know, we we could review products and and establish a road mapping process and just get the engine going. And so that was really fun work and, you know, going off and doing that in a vacuum as a product leader, would have been one way to get it done and sort come out of come out of the cave and be like, okay, team Pete 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 had we brought Stewart along for that process. And so, you know, for for at least four quarters, and if I remember correctly, it might be might have been 6 we had Stewart in the room for for all of those processes so that that would be an opportunity for the team to hear feedback directly for him from him.
It would be an opportunity for him to observe the team's progress as well as just get a read on on how the, you know, how know, how this organization was shaping up and give feedback to me and give feedback to, my engineering and design peers as well. And so this calibration period, I counted up, you know, a few years ago. It was hundreds of hours of calibration time, but I think it was absolutely critical.
And I think that, you know, a lot of product leaders come in and they wanna get the CEO out of the room as quickly as possible or the the CEO founder. And I think that's a failure mode. I mean, that that's That that is it's too abrupt for the organization and for the humans involved.
And it also means that there's it's just inevitable that some amount of the the vision or the spark or the, the, you know, the commitment to quality just the way of thinking that made the company successful will get lost in the process. And that's always you're gonna it is going to evolve over time. That's natural. It should. But I think that as long for, you know, 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. Yeah. I've I've also I've also seen the opposites Beller we're founders of, like, you know, that they perhaps come from a kind of business or engineering background, and they and they hire an amazing head of product. And, did this person's run it at kind of Google or or Facebook or or, you know, ran massive engineering teams or product teams.
And and they Pete and they basically transition and delegate far too quickly. And they kind of create this sort of incredible turbulence in Morgan because the alignment's not there. So, yeah, in my experience, a 100% the same. If you're gonna onboard or or as you say, calibrate, then it's just like your way your may you're you're in a very strong position. If you do it a little bit longer, then perhaps feels comfortable as opposed to less comfortable.
Curious, like, you've talked about your kind of own evolution, and that evolution the early days of slack. I'm curious, like, as you think about your own professional development in these Morgan. It's any advice that you'd give your form itself to like things to do or or or not do or or perhaps skills that you would have wished you'd learned earlier or perhaps unlearn?
You know, I started my career as an engineer, you know, 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 and 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.
You know, 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, you know, haven't spent a lot of time officially doing product marketing And, you know, what I have found is that, having experience sort of stepping a little bit outside the lines of traditional product management has, for me, been incredibly, incredibly valuable. It's me.
It James me who I am today, which is, you know, 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 and what's 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, you
know, they can they can do their best work and, where they walk away with fond memories when they do decide to move on. And so, you know, those, those are things I aspire to. I think my experience setting, you know, not only in the product management organization has been a huge asset for that. The challenge that I face, though, is that that created a number of different times in my Currier.
And I do think that there's probably a gender element to this as Beller, where I had to sort of defend that I was really a PM. And, you know, I think I ended up spending, you know, too much energy in my early career, kind of, having to, to constantly prove myself. And just to, you know, put to put a you know, a specific example on it. When I was at travelocity, I wanted to transition into Pete, and I was doing a lot of the PM work for my project to be clear. But I was told I need 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. It was I just didn't totally understand exactly where I fit within the organization until I got there. Post MBA in 2007. 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 goal posts sort of kept moving around for me.
And, and I think a lot of people have this experience, and I definitely think that a lot of people of color and women have had this had these stories of sort 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, you know, more confident and more, questioning about those barriers that were put in my way.
I I think I pushed them a bit, but it's easy for that sort of feedback, I think, to to get into your head and make you think, well, maybe I'm not a PM. Unfortunately, I've got a, you know, the story turned out great for me. I've gotten to to do product at at Twitter and slack over the last 10 years.
I I, you know, I absolutely, characterize myself as a product, product leader today, but I that would be my advice to some of the folks out there, who are earlier in their peer 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. That's super helpful. And you mentioned diversity and gender.
Is there any, you know, not I've just seen kind of firsthand how sort of differences of opinion and perspective and background lead to just far better outcomes, you know, particularly on the product side and and across the board. Is there any advice you give kind of early stage teams? Is there thinking about this, about sort of things that they should be doing that they may not be doing? I mean, I think focus on diversity as early as possible.
I mean, some of the work that we 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. And so, you know, we initiated we wrote a blog post in 2017 called the Pete 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, about, equality and and equity but it's all focused on salary. And, like, you know, none of the stories that you hear about people making it big in Silicon Valley have anything to do with salary. They're all focused on that. It's all about the equity.
And of course, oftentimes equity is worth 0, but when it's worth something, it it it can be quite big and it can go on to, position a person to make different choices in their Currier, 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, you know, This stuff really matters.
And so, you know, so I, you know, I I mentioned that in the context of 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. Flint software companies, in or 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 already thinking about diversity because, you know, that decision that you delay by 6 or 12 or 24 months in the best scenarios can be orders of magnitude and difference, for those employees in terms of their outcomes. And money is nice but what it can do and what it can, you know, the downstream effect of that to the 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 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 Beller you find amazing black designers, amazing black engineers, founders that you can back, Latinx founders. I mean, I mean, it it's all out there.
There's no excuse to not find the talent because, it's never been easier than before to to find talent that is going to help you have that diversity on your team, and your product's gonna benefit from it, your customers will, and, certainly, those employees will. Yeah. It's so true. I couldn't agree more.
And, you know, you've been very successful and, obviously, a a huge amount of kind of personal ability and pride and commitment, but also, you know, you be surrounded, I'm sure, kind of mentored and had advice from a number of amazing Pete, throughout your current cure. So the people that you've been have had a significant impact on your kinda own personal growth, throughout the years that you'd you'd wanna highlight. Yeah. Absolutely. I'll I'll call out a a couple of folks.
One is Dick Costello 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. And so I was just, you know, I, you know, he's he's 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 sort of connect the work that I was doing for hit for tiz business strategy to sort of close the loop, with this otherwise sort of cost center type work that I was doing around content acquisition. And so I, so got to know him, you know, had the opportunity to work for him for 5 years at Twitter and near the end of those 5 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 him I wanted sponsorship. I wanted him to spend time with me and help me be successful, not just to sort of react to me if I sort of came to something with him. And so I approached him about it and and he, 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 optimization.
And I think, you know, since that time has very much done that for for me, but for for others from the X Twitter network, And, you know, 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 wanna do. And sometimes, You need to be sort of called into service, to do it.
And when you are, you gotta answer that call, and and that was what Dick did for me. You know, some of the other, people that I've been really grateful to, to, you know, call what I was called, friend tours, you know, all of my hashtag angels are women with whom I have worked, with whom I have angel invested. You know, we backed over a 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, for, executive experience that they can lend me. And so maintaining that tight network, you know, now for 5 years and, in 5 years going on, you know, 6, of having those people that I can, I can call at any time? It is a really important network for me. And then finally, I'll say, you know, working for Stewart Butterfield three and a half years.
You know, I learned more about product and about, you know, a care for the craft and the, you know, in in 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. You know, learn 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, you know, I've been really 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 with the folks that are just, you know, coming up behind me. Yeah. It's such an amazing group of Pete, and I love the word friend tours.
It's definitely, definitely if if you can find mentors or friends and find that balance, just wonderful. And I've certainly seen that myself. So I just wanna touch touch on a moment about how you see the evolution of enterprise software and sort of enterprise software is kind of the wrong word because it's like if you think of this sort of starchy dot like environment of kind of bit badly designed experiences, and we've seen this evolution of the consumerization of of enterprise.
And and I I know you've touched on a broader movement here. I guess what do you what do you like, as from your vantage point, what do you see us going on on perhaps the the kind of business side of software, how that's evolving, and and how do you think it's perhaps different or or very similar to what's going on the consumer side of things? Yeah. Well, I'd say it's we're just getting started.
You know, the work that we did at slack over the last 3 and a half, you know, over over my time there, but that that that the company's been doing for the last 5 years, you know, really addresses, you know, a a large and growing market and yet there are still so many different tasks and, you know, significant work streams and audiences that still are untouched by, sort of this movement.
And so, you know, when we were building slack, you know, it just made sense that, of course, the app that you have to use 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.
So it should, you know, it should just sing and it should just, you know, be an an an effortless experience to communicate and Flint information in inside slack. And so, you know, we were always striving for that. You know, 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, you know, when I think about, you know, a completely different vertical, so you get outside of knowledge workers and you think about agriculture. You know, I, one of the companies that I backed recently is called Ganaz. And the founder is building, and her team are building software for, for for farm workers. You know, a lot of them still use punch cards to punch in and punch out. They need to track, 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, detrimentals the environment. There's so much opportunity for evolution in agriculture But, you know, it's it's just such early days in digitizing that industry.
And, you know, 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, like, there's still so many cards to sort of turn over, with this consumerization. And even I would state just basic digitization, there are still a lot people that go to work every day and don't have tools to use, for their daily activities that are, you know, even on the same, you know, playing field as the ads that we have for consumer use.
So I think there's a ton of opport 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. Yeah. And I'm sure and it's clearly accelerating right now as as everything is going digital and more remote, then, I mean, the sort of trends have been going for a while. They've just been, you know, ticked up a few years.
It seems so that they were interesting opportunities 6 months ago, and I think they're way more interesting opportunities today. I think that's true. I mean, the the area that I've been just absolutely captivated by is just watching the local businesses here in my India, 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, you know, a sense of urgency and, like, 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, you know, under duress, and, under a bunch of different constraints because of shelter in place. And and they're doing it.
And So I've been, you know, incredibly focused on that part of the market, a part of the market where there there are tools like Shopify and Square and Squarespace. But I think that, you know, 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, you know, this is something that I just can't stop thinking about and, is an area that I expect to see, you know, a lot of evolution in the coming years. Yeah. Yeah. For sure. And and we and you've talked to previously about, how to make enterprise software more delightful curious if there are any learned, like, properties of user life that you can break down, or when you say delightful, what how how do you manifest that in a product organization? It's it's a great question.
It's it almost it it almost ends up resolving to, you know, can you teach taste And, I would say, I haven't answered that question for myself yet. I think you can try.
You can certainly, you can seek to establish principles, you know, product principles that you use, you can, you know, use you know, storytelling, as product leaders and as executives in the way that you give feedback to teams to help them sort of trace back their steps and potentially find another path forward when they when they when they Beller something that has an absence of delight. But, you know, but I'll be honest.
I mean, 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 individual, you know, the the PMs and the designers that maybe have the, you know, that have just demonstrated the greatest ability to to take something beyond just meeting a set of needs, but actually, like, going further to actually, you know, Pete unmet, you know, un unstated needs or even, start to stoke the idea that there are things that people want out of the experience that they they didn't even originally come there for.
And so, you know, they're, you know, I don't I don't that every single PM or designer within an organization is always going to hit it, you know, and and find that moment of delight 100% of the time. I think 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 the the Beller it's founders or sort of just the almost like product culturekeepers within the organization to have, some amount of editorial review, to help bring some consistency. So I, you know, I'd love to figure out you know, 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 sort of, like, implant a chip in every single person and get the exact same results every time. April, like, you know, this was a fascinating conversation, so many terrific insights for our audience.
So I wanna thank you once again, for sharing with us today. And, looking forward to hopefully seeing you in person before too long. Absolutely. Thank you so much for having me. It was, it was a lot of fun.