Twitter and slack or two of Technologies most popular products, but you rarely hear about 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 confounders learn about the strategy Frameworks focus and Leadership that turned to unknown apps into Global phenomena. April joins nfx. Partner, Pete Flint share what she learned about world-class product development.
Welcome everyone to the NFS podcasts 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 joining the board. And and so we've stayed in touch pretty much since then turn it on and off, you know, I've just had really enjoyed the conversation about product and Entrepreneurship and investing and you know, April is just had one of these
Amazing careers leading product teams initially at Twitter and then slack where she was Chief product officer and so seen firsthand kind of the transformation of an evolution of those businesses consumers ation of the Enterprise and you know, those are obviously category defining businesses in themselves. So our audience that nfx is this age Founders that I think would really benefit from your product leadership and insights. And so, you know, I think today we're going to have a fascinating conversation about product and platforms and and network and maybe touch
Touch on a few other things at the end so welcome. It was so good to have you so eight for you've LED product teams of both Twitter and slack and and both of them are category defining businesses. I think worth north of 20 billion dollars or more. I guess that's sort of you know, the one hand there's a lot of similarities but are perhaps in your mind like what are some of the differences being inside there's organizations scaling that those product what are some of the core things that you've seen that a different that perhaps you learn through that experience. Yeah. I mean, it's it's an interesting.
question because I think the reality is there are there are a 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 transition from Twitter over to slack was just how different they were and you know, they're pretty systemic differences, you know, slacks and enterprise software company you build software you make it as good as you can and you charge
Judge 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 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 as part.
Lie still true in 2020. I always described it as a trading room floor because it was so loud when he 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 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 everyday things that
would happen on the service 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 2015 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 is 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 this concept of doing your best work and working hard, but also people were literally using the service.
No that 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 ten or a hundred 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 they're so it's really quite different even though communication is really at the core of both of those products, but it's amazing how communication so fundamental that it can go a lot of different directions in terms of
business culture product experience and more. Yeah. Yeah, that's so different the kind of b2c side and sort of the that 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 in my perception is that you know, Enterprise software was typically aggressively sold, you know, you can imagine the kind of like Enterprise sales people the word knocking on cios doors and kind of send this product at
It's sort of scent felt 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 Twitter. Would you feel the same thing at the same way? I got some curious. How did black kind of engineer that growth or was it was it just happened? Yeah. Well, I mean, even it kind of 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 like run like don't walk and I've had the opportunity to do that twice mean. So when I joined Twitter in 2010, you know is 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
Is to express them more Express themselves more freely in a public forum. And so when he came to Twitter, you know, the you know, that was a mobile app and you know, people are 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 was a 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 and 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 felt the same when I joined slack, but with slack this shift was it was BYOD, so 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 there often times. They were at a point where the fragmentation of tools for the workplace.
And was so vast that it departments are we're giving you know, especially 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. So just 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 at 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 distracted. It was actually instead really cultural.
Her
and connection moving from the 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, you know, I see a connection to that all the way back to what I experienced it 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 in 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 that 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 in a 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 outset 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 instead 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 are a bunch of growth tactics that were used. There were, you know, 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 you know connecting to that broader cultural shift in Market 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's it's so true. They were just at the tip of the spear.
About those stairs 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 this this early adoption and there's a sort of like very special product magic that kind of appears in these platforms where you know, this early stage. There's perhaps this tightly defined group and then cut the later stage, you know, slack it CEOs as well as the kind of like the summer intern who are kind of using these platforms.
At forms and then the Twitter's it's you know, it's obviously pretty much everything in the world. How do you think about just sort of tightly defining or not tightly defining the kind of audience 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 platforms. Yeah. Absolutely. I mean, I I have experienced this sort of I don't
Confidence curve that sort of grows early on and then Wayne's for a bit and then restores to like a happy balance around you-know-who over that initial audiences. So, you know with Twitter it was it was influencers. It was journalists Etc. 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 too.
Mainstream folks and then there's you know, you can kind of 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 challenge 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
Thanks. And so it was 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 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.
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 often times are sort of like the tastemakers for technology selections within the entire organization. So, you know, we could have spent time thinking like, oh, we've got a really like poor 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 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 it's early users are the pathway to the other users. So I think that was true for both Twitter and slack and but it but you know, it's always a challenge you don't want to box yourself in but I
It's oftentimes a PR challenge in terms of how you frame it and how you tell your own story more so than you know that then it should be taken as some sort of directive that you need to react against in your product roadmap. Yeah, and and and just going back to we said the beginning to it seems to be this Eeveelution from early adoption to kind of like some period of kind of you know challenge or kind of negativity of Bank some of the early adopters then a Resurgence over time. Like if that happened in both these organization what I guess what was 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 often times shows up because platform developers are often times some of your most vocal, you know, your sort of one of your most vocal constituencies, and if you get confused about your developer platform and
well, I've got to 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 your circuit 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 that leads you to ensure that your 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, if with both Twitter and slack we befell what I believe is sort of 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 the really unhappy down the road when you realize that some of the 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 you know, your platform is going and so, you know, I'll call up one example with Twitter. We had both the Twitter API, you know, it had been out for a while and you know, a thousand flowers were 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
Calpers could plug it in and 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 and 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 their 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 as 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. And so when we built that feature and we built it with Publishers a specific slice of sort 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 it there.
Our need they saw you know this I usage they saw you know, they're 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 as 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 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
At 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 them on the platform and having that reflected through our platform features started to really frankly mind.
Give the platform some shape and a purpose that it lacked when it was just an API by the yeah, it's so interesting so so often we make companies that they aspire to be a platform and then they you know, building the platform from day one, but just forget to build a product or most which kind of drives drives the platform and then, you know, clearly articulating. What is the hierarchy of needs or was the hierarchy of constituents because when you have more constituents then there's more complexity and if there's not Precision on that kind of hierarchy all things
it's can kind of fall apart. I'm curious is like it's this Eeveelution from product to platform. I guess what it's like there are any other things that people get wrong about that kind of evolution to building a platform as opposed to just building a product. I believe you have to earn the right to be a platform. I mean a 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 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 you offer and so, you know, when I when I think about platforms I often times sort of draw like almost like a Maslow's hierarchy of needs and to have a really meaningful platformer 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
Ation, 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 got to 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 run all of 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 of 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 workplace tools. And so
You know we could have decided. Well, why don't we just keep everybody in slack all the time and let's build a basically build a browser into slack and just have you experienced 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 we never needed to take that approach and the reason was because you know, it's from a means 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 eight hours in slack versus seven hours slack and so, you know, there was no driver like you might see on an ad base platform for us to have these sort of incentives that misaligned us with the developers and 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 are 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 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 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.
To help route you off there, but we do what we do want to do, you know enable as are those handoffs because those handoffs between people which are ultimately communication, you know, we're best suited to be in the place where people could already be found. Yes. It's so interesting. Maybe maybe just changing tax a little bit. Maybe this talk talk a little bit about dogfights. You know, when we first kind of connected it was the sort of post the Trulia and Zillow dogfight and then, you know, obviously it's slack as major competitors with atlassian and
Microsoft and you know, there's this sort of adage around like focus on your customers, not your competitors, but it's a tightrope walk. You can't be sort of two kind of myopic. I'm curious is as a product leader going through those periods of sort of intense battle. What did you learn and how and what was the some of the guidance that you gave the team and they're in imagine this this hyper-intense competition that happens in all technology companies. This question is such a good reminder for me that and that it needs to be stated.
explicitly that a product is not just the code, you know, it's kind of remind my team that pushing CO2 production is not a launch 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 stance has 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 and it like in an Earnest honest pure 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 to because Twitter is you know, ten years later. I'm very very proud of Twitter and how its 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 that 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, you know their Market valuation would suggest that the world and customers are understanding that
at better and better every year so, you know, I think you know, I just think when it comes to dog fights they 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, and I I, you know, I
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 those can be sustainable businesses with a long life ahead of them. And that's generally what I'm always aiming for. Yeah. I couldn't agree more. I think the, you know, the the focus combined often with network effects and sort of
Of as you say kind of like a clear clear leadership just can really make seemingly subtle differences, but important ones over perhaps the incumbent is 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 we're doing many things and perhaps couldn't do the one thing that was really valuable extremely. Well, you know, obviously social networking and you know, lots of Twitter like companies, but there's only
On
Twitter and they did it better than anyone else. Yeah, and I mean both of those companies that I am 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 company 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 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 there 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 exoticness event. I would say
To really create a shift in the need but but man talk about being the right company and the right place the right time and you know, and I think their success as well to serve. Yeah. Yeah and took it took me about Network effects. So, you know, I at least in my experience that kind of scaly marketplaces, you know, Network effects was kind of important but it was, you know, I know just like in 2008 it was like we just want to grow and we want to survive and then coming out of that you
Why's that? Oh my God, this network effect thing is just like incredibly powerful and Incredibly defensible for a business and created something very valuable and I'm curious how much a network effect is, you know, we obviously love Network effects here 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 cork core product of the beginning and there's a function of scale.
It created these sort of Highly defensible and highly valuable businesses. Is it something that product teams think about day in and day out. I think that it is, you know, whether they are 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 some of the sort of first order growth drivers when I think about Twitter we didn't necessarily
we talked 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 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 growth strategy the work that Chloe sladden and the media team
To convince the broadcaster's 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 an online conversation about this on-air experience. That was that was disconnected from the network. And 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 login with slack because they realize that once people that if teams actually used 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 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 that get used in service of growth, but I think they're also table Stakes for good product experiences now too and so so I think you know in this gets a little bit too how you sort of think about structuring your product organization. You know, it's not I think it's no longer the case 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
Or 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 quickly engage with other people through that service and all the all of those things Drive growth and network effects you touch their own just like Building Product teams. So, you know, you've been in some of the sort of greatest product teams in Silicon Valley, you know, if you're giving advice to early-stage Founders who are looking, you know major
Kind of a couple of Engineers and themselves or something a little bit bigger. Like what advice would you would you give from early Founders to help as they think about scaling their product teams? And so 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 first p.m. And my answer to that is actually pretty similar to the answer that I would give to a group product manager.
Juror, or IPM director deciding whether or not she should hire one more p.m. 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 p.m. Not for one day. Maybe not even for one week, but if you know, especially as a Founder if you find if you if you need to pull your team and you regularly find that people are waiting for answers.
Are waiting for guidance to be able to make forward progress? Then you really have no choice your hand is forced and I think that often times 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 slowing your team down. There's a lot of value in founder and being very close to the product and close to the team.
Aim for as long as possible, but you also you had any Growth Company whether you're in zero to one or later. You always have to be thinking about how your fiery firing yourself from various aspects of your job. And this is one that I think people get quite emotional about and you know, Darius a Territorial and so or, you know even have some ego tied up in owning this piece and I think that that can do a teams a disservice. So I'd start by asking your team.
Now we see that we see that all too often try and transitioning from kind of product leader to company leader is just a often a very tough thing to for found us to do and so, you know, you you must have hired hundreds. If not more good kind of product leaders over your time. Like are there any sort of tells that you have that or areas of someone sort of Personality or the way they think that you dig into to help to sort of identify really strong product.
Talent that you think might thrive in that culture. Yeah, so I have a pretty structured way that I think about p.m. 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 you know a p.m. 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 realize
Graduate college project product managers with a very very few exceptions where maybe they have some coursework in the topic. And so it is a it is a learned skill that you learn on the job and ultimately everybody comes to product from somewhere else, you know, 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 three axes that I think about our functional subject matter expertise and growth stage experience and 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 three and a half years there. And so I you know functional is it starts?
Just what flavor of p.m. Are we talking about here? Because if you go to one company, you know, maybe every p.m. Is a CS degree and 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 PM's are the same but very specifically if you're looking to hire a product leader because PM's sort of have this, you know, they have their their, you know, their their lineage of you know, what functional background they came.
M2 came from before product. You can often times 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 as having some challenges scaling you might hire a more technical a more technical product person because maybe they can help fill that Gap. Maybe you don't have anybody running marketing and so actually want to product leader who can just take that on and run the ball.
With the ball for a little bit until you reach a scale where you hire somebody for it, whatever the case it. Did, you know, you should think about it because you should be looking for Fairly. You should be looking at PM's from Fairly different companies and cultures and based on the answer that question. Number two is subject matter expertise. Sometimes it matters. Sometimes it doesn't, you know, you you know, especially more Junior rolls. You can just hire generalist PM's that can they can kind of work on anything and they're hungry to learn new problems and new audiences. But as an example at slack when I was hiring
Being 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 a lan 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 levelled all of us in the product organization up around what it looked like to be a product leader for large customers.
You need to show up for them and Pitch to them and in face objections from them as well. As you know, just deep understanding of the audience and their needs and then third is gross stage experience, which I think you know oftentimes gets discounted but there are people that have worked in 20-person companies. They're 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 22 2008, you know.
Oh, there will be some roles that will just require somebody who can scale and sort of morph and level up so quickly every 6 months. We're actually finding somebody with growth stage experience is more important than the subject matter or even what flavor of p.m. They are because they just know how to lead through that kind of change. So so this strengthen the 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
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 p.m. Well, okay, that's super helpful thing. That's like 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 touched on it earlier just around the sort of interaction between product leader and and perhaps fell and founder and you know, I imagine both Twitter and slack the inventors of the product of the CEOs of the product.
Who had deeply passionate about it rightly? So and I'm curious. How did how did you navigate that or any sort of tips for product leaders coming into an organization navigating pre-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 in really I'd say our approach with for me and Stuart at slac was was to have a pretty extended.
Operation period And I think that that was really a key to success for us and that when I became VP of product about six months and 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 you know, ensure that over time. We were consistent in the vision that we are sharing with the organization.
And the guidance we're setting in the role definition between our teams that we were you know, in total lockstep around that and so we were all you know, three of us except for the CTO who is Cal Henderson, the amazing engineering co-founder of slack when the four of us came together. It really just unlocked this Rhythm where we could start to get we could start to get things done. We could build our teams we could hold them accountable, you know, we could review products and establish a road mapping process.
Isn't 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 of come out of 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 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 six. 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 how the you know how you 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 it up, you know a few years ago. It was hundreds of hours of calibration time, but I think was absolutely critical and I think that you know, a lot of product leaders come in and they want to get the CEO out of the room as quickly as possible or the co-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 vision or the spark or
Or 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 going to it is going to evolve over time. That's natural. It should but I think that Islam for you know to 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
Time. Yeah, I've also I've also seen the opposite as well. We're founders of like, you know, they perhaps come from a kind of business or engineering background and they and they hire an amazing head of product and this person's run it at kind of Google or or Facebook or you know, ran massive engineering teams or product teams and and they Jet and they basically transition a delegate far too quickly and they kind of create this sort of incredible turbulence in organization because the alignments not there. So yeah.
Yeah, in my experience a hundred percent the same if you're going to onboard or as you say calibrate, then it's just like your way you'll make your in a very strong British. If you do it a little bit longer than perhaps feels comfortable as opposed to less comfortable. If 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 organizations. It's any advice that you would give your former self to like things to do or
Or not do or perhaps skills that you would have wish you'd learned earlier or perhaps unlearned, 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 in 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, I haven't spent a lot of time officially doing product marketing and you know, what I have found is that having experienced of stepping a little
Outside the lines of traditional product management has for me been incredibly incredibly valuable. Its it makes 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 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 we're 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 sitting, 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 career and I do think that there's probably a gender element to this as well where I had
To sort of defend that I was really a p.m. And you know, I think I ended up spending, you know, too much energy in my early career kind of having to constantly prove myself and just so you know put to put a, you know specific example on it when I was a Travelocity. I wanted to transition into p.m. And I was doing a lot of the p.m. 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 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 CSS undergrad degree. And so these goal post 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 have these
Is 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 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 p.m. And fortunately I've got a you know, the story turned out great for me. I've gotten to do product at Twitter and /malabarismo.
Back over the last 10 years. 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 career p.m. 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 in gender. Is there any you know now that I've just seen
Kind of firsthand how to sort of differences of opinion and perspective and background lead to just far better outcomes, you know, particularly on the product side and across the board. It's at any advice you give kind of early Sage teams as they're thinking about this about the things that they should be doing that there 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 Investment Group hashtag Angels is focused on actually putting real.
Germont 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 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 about equality and Equity, but it's all focused on salary and like, you know
Of the stories that you hear about people making it big and 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 zero, but when it's worth something it can be quite big and it can go on to position a person to have 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, you know this stuff really matters. And so, you know, so, you know, 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 are 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.
That 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 in 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 City that 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 as
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 Latin X Founders. I mean, I mean, it's all out there. There's no excuse to not find the talent because it's never been easier than before. It's a to find talent that is going to help you have that diversity on your team and your products going to benefit from it. Your customers will and certainly those employees will yeah, so true.
Couldn't agree more and you know, you've been very successful and obviously a huge amount of kind of personal ability and drive and commitment. But also, you know, you've been surrounded I'm sure kind of mentored and had advice from a number of amazing people throughout your calculator. The people that you've been have had a significant impact on your kind of own personal growth throughout the years that you'd want to highlight. 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 and so I was just you know, I you know, 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 sort of connect the work that I was doing for hit for today's 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 got to know him, you know 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 him I wanted sponsorship. I wanted him to spend time with me and help me be successful. Not just a sort of
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 organization. And I think you know since that time has very much done that for me, but 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.
Answer being on the other side of the table, but it's absolutely something I want to do. And sometimes you need to be sort of 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, you know, some of the other people that I've been really grateful to to, you know call what is called friend tours, you know, all of my hashtag hashtag angels are women with whom I have worked with whom I have angel investor the you know, we've backed over a hundred twenty companies together, but
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, you know now for five years in five years going on, you know, six of having those people that I can I can call at any time. It is a really important that work for me. And then finally I'll say, you know working for Stewart Butterfield for three and a half years, you know, I learned more about product.
T' and about, you know a care for the craft and the you know 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 people and I love the word friend tools. That's definitely a definitely 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 sort of enterprise software is kind of wrong word because it's
Like if you think of this sort of starchy daus like environment of kind of bit badly designed experiences and we've seen this evolution of the consumerization of Enterprise and I know you've touched on this reporter movement here, I guess. What do you what do you like? It's from your Vantage Point. What do you see as going on on perhaps the the kind of business side of software how that's evolving. And and how do you think is perhaps different or or very similar to what's going on the consumer side of things? Yeah. Well, I'd say it's it work.
Getting started, you know the work that we did at slack over the last three and a half, you know over over my time there, but the that the company has been doing for the last five years, you know really addresses, you know 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 and you know 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. So it should you know, it should just sing and it should just, you know be an in an effortless experience to communicate and defined information 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 ganache and the founder is building and her team are building software for for Farm Workers, you know, a lot of them still used.
Punch Cards to punch in and punch out. They need to track the new 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 process less detrimental to the environment. There's so much opportunity for evolution in agriculture. But you know, it's it's just such an 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
Doing it just reminded me that like there's still so many cards to sort of turnover with this consumerization. And even I would stay 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 you know, 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 is an angel.
Investor. Yeah, and I'm sure and it's clearly accelerating right now is as everything is going digital and more remote than 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 six months ago and I think they're way more interesting opportunities today. I think that's true. I mean that 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 in 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 there
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 square space, 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 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 for sure we and you've talked to previously about how
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. How do you manifest that in a product organization? It's a great question. It's almost 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.
Suppose, you know product principles that you use you can you know use storytelling as product leaders and is 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 build 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 smarter.
how you put your talent to use and that Talent includes the individual, you know, the the PM's and the designers that maybe have the you know, they have just demonstrated the greatest ability to take something Beyond just meeting a set of needs but actually like going further to actually meet unmet, you know, 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
and so, you know there, you know, I don't expect that every single p.m. Or designer within an organization is always going to hit it, you know 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 into 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 whether its Founders or sort of
That almost like product culture Keepers 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?
Stout comes 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 a pro like, you know, this is a fascinating conversation so many terrific insights for our audience. So I want to 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 was it was a lot of fun?
