https://review.firstround.com/build-products-that-solve-real-problems-with-this-lightweight-jtbd-framework
KELLY WATKINS
Brett Berson: Well, thank you for joining us Kelly.
Kelly Watkins: Thanks so much for having me, Brett. I'm stoked to be here.
Brett Berson: So the area I wanted to start was company building in general management at a high level, and then we'll kind of explore a bunch of adjacent topics. Um, and maybe a great place to start is some of your, thinking around the concept that there really aren't right. Or wrongs. Uh, but rather everything is about optimizing for trade-offs.
Um, and so we'd love you to sort of explain that idea in some of the things you've learned about it.
Kelly Watkins: Sure. I think that really came from a place of going through these big planning processes that every company goes through. You know, you get to the end of your fiscal year. you've got to pull together your goals and your plans for the next year. And I always have felt like those processes weren't that helpful?
Um, I think largely planning is guessing. Um, and if you're trying to put together a huge year, long plan before a year has even started, it's serious guessing, right? There's lots of things you can't predict. I've always felt like as soon as you bake those plans, they're pretty irrelevant and outdated, the moment they're completed.
Um, and so I've always been looking for alternatives, like rather than having a business revolve around high-fidelity plans that have to constantly be revisited and constantly be changed. Are there ways to optimize more for decision-making in the moment? Um, I am a huge military strategy nerd. Uh, love John Boyd.
Uh, think he's absolutely brilliant. And he's the, uh, individual who came up with the OODA loop and the OODA loop is shorthand for this process of decision-making, uh, that he sort of created going through stages, which are observe orient, decide and act. Um, and he studied fighter pilots. He was a fighter pilot himself.
And what he saw was not only could people who went through that loop faster, be more successful, but the thing that really mattered was orientation. Like what filters and lenses did you use to make decisions? So I've always thought of like, how could that translate back into a business context and really this idea for me around optimizing for trade-offs is that, um, it's really about, rather than create these monolithic outdated, long running plans.
How do we approach decision making in the moment and real-time decision-making and how are the questions that we ask not about getting it right, versus getting it wrong, but more about unpacking from a first principles perspective, what are the trade offs like, what will go great in scenario a versus terribly same with scenario B and then how do we think about really what we're optimizing for?
Um, and then it gives more opportunities for participation in decision-making from all sorts of people. Uh, and it's really about what's the data that we're looking at today and how do we keep charting the best path forward?
Brett Berson: So, can you give us kind of a case study or an example when you think back, maybe over the last year to kind of bring this to life in terms of actually what you're doing at your company.
Kelly Watkins: Sure. So. I think a really important thing with abstract is about this new product that we've taken to market recently. So when I took over, um, a CEO about a year ago, we've had a really thriving and incredible business to date, um, abstract for folks who don't know, really serves product designers and product design teams.
And we launched in 2019 with a product really focused on version control for design files, which has grown leaps and bounds. Um, since then more than 7,000 companies use it today. It's a really high value, awesome product. And as I came in, I wanted to figure out how did we build upon the success of that?
Um, you know, design teams are starting to use more browser base and cloud docs based products. And I wanted to figure out, you know, if version control, wasn't the job to be done in a high fidelity way with those types of design tools, what was something that we could do?
Could we take a second product to market? And I think over the course of that journey, all sorts of trade off decisions made. Um, you know, one that really stands out to me was really thinking about, how did we think about timing and how we wanted to take it to market? there's all sorts of ways that products can be launched.
Folks will send stuff out and do very long. Private betas, for example, another path is to work on something for a really, really long time, you know, make sure that you feel internally really solid on it. Um, and then do a general availability release. And, you know, I think if you look at these options, there's not a clear writer, they're right.
It's not right to do along the beta. It's not right to do a lot of internal work. And then a massive GA it's really about the trade-offs and what are you optimizing for? And so for us, as we thought about this decision, there were a handful of trade-offs that we considered. Um, how do we think about speed?
There's no product on the market today that exists that does what notebooks does, which is our new product. so as we were thinking about, uh, notebooks and taking this product to market, um, you know, we were really looking at not how do we make the right decision? Um, but how do we make the best decision and how do we think about the trade-offs, uh, between all sorts of issues and, considerations, there was a number of trade-offs that we wanted to optimize for, there's no product that exists like this on the market today.
And to speed was an important. Consideration for us getting something out soon, um, and getting something out quickly so that we could feel fill this existing gap in the market. Um, I think the second place was really optimizing for feedback. Um, you know, putting something out, but wanting to continuously have the opportunity for customers to say, you know, this additional thing would be great, or if you change this thing, that would be great.
And so, you know, as we thought about those trade-offs and how to optimize for them, that really helped us pick the best path forward, as we took it to market, we put it out in a public preview launch that was really optimized and oriented toward getting feedback from cohorts of people. So, you know, I think that's really what I mean when I talk about this, how do you think about trade-offs rather than, you know, the binary of right or wrong, it's really about, you know, what are you trying to achieve?
And what's the optimal path to get you there.
Brett Berson: Do you have a ritual or. A set of practices that you do before you start anything that, that kind of gets these trade-offs out in the open, or is it more organic or what does that look like?
Kelly Watkins: Yeah, I think there's a couple things I think rituals are important, but I also think it's a combination of rituals. And how do you operationalize company values? Um, we've done a ton of work internally, not just to put down our values, not just to say what they are, but to figure out how to operationalize them.
And so our values are more than just words. You know, we obviously have values that are words, things like, uh, craft and curiosity and grit and service and inclusion. Um, but I think it's, it's really hard to live those as really nebulous ideas. And so we've tried to operationalize them, you know, in ways that can reinforce behaviors.
For example, um, you know, we have saints internally, things like data is better than opinion, you know, really looking at how, when we're making a trade-off decision. Do we look at data. Uh, as a real source of guidance, um, things like we make our own weather, you know, really the idea that the, the power of decision making in a choice lies with us and lies internally.
So I think that's one important dimension of it, the other side. And I think a big reason why we built notebooks is because one of the rituals we do around making decisions is, uh, documenting and putting stuff out there. I think oftentimes you have to unpack the context you have to talk about. What's the goals, what's the purpose.
And so, you know, one of the things that we use notebooks for is really documenting those things. Every team internally uses it. So when we're going to start an effort, folks are writing out, um, the context behind decisions. They're writing out what the trade-offs are. Notebooks, come with templates, baked into them.
Which is really great, cause you can utilize those, but oftentimes it's just, you know, how do you think about, um, the checklist of information that needs to be documented so that a decision in a discussion can be made? Okay,
Brett Berson: And so can you give an example of a standard template, you know, you're getting ready to kick off pick any arbitrary new project. What are the sort of the different parts of that doc or what might that look like?
There's a couple pieces to it, you know, when you're articulating what something is going to be or what something could be. I think there's basic stuff in here that probably wouldn't surprise folks. You know, how do you clearly articulate what the goals are, what you're trying to achieve?
Kelly Watkins: Um, I think articulating success and. What failure would look like are important distinctions. So, um, that's an important trade-off right? what are we optimizing for when it says their success? But like, how do we get clear on what failure would look like to, um, I think, uh, demonstrating open questions and putting those down is, is important as well.
You know, so there's all sorts of pieces to this that I think are useful. Um, but I really think it's that upfront context. So if I'm going to kick something off, if I'm going to start something, I'm starting with writing these pieces of information down, here's what I'm trying to achieve. Here's why here's what I think success would look like.
Here's what I think failure would look like. Here are the open questions that I have and aligning first on that sort of information and context before getting into a specific solutioning.
Brett Berson: Got it. So how does this sort of worldview translate to how you operate the company is sort of a click higher meaning? have you done away with sort of annual goal setting and all the classic things that we would think of exists in a SAS company? Or is there some version of that? Or how does, this sort of thinking translate to the higher order bit of how you broadly, um, set goals as an organization?
Kelly Watkins: so we have goals. Um, we have specific things that we're trying to achieve that are time-bound. Um, but. There are there specific and it's a pretty short list. So, you know, we, for this past year have really oriented around three core ideas. One is how do we ship a platform that people love, um, and that not only includes notebooks, which is the new product we've taken out to market, but it also includes our previous product.
Um, Which does version control for design files. So how do we really, with both of those products, um, continue to ship platforms that people love. Um, second is how do we own our market? How do we continue to have great growth traction? How do we continue to have people using and paying for our products?
And then lastly, how do we think about doing the best work of our lives? So those are our three key focuses for the year, um, of the things that we're trying to achieve and that every team's work ladders up to. But when we look at how the company works, I think there are two things that stand out one. Um, we focus on work really a quarter at a time.
So I think it's the longest range that I've found to work is looking at a quarter and even sometimes a quarter can feel long. Um, but I think beyond that, the kind of fidelity of planning gets slow. And particularly in this moment in time with COVID and just other things that are coming up at every moment, I think it's, it's tricky.
There's a lot of, uh, contingencies that you can't plan for. Uh, so we look at planning at work a quarter at a time, and then the second ritual, and I think the second thing we've put in. Is how the company is broadly managed. So there's an exec team at abstract folks who report up to me.
Um, but we've intentionally broadened the sphere of folks who participate in strategy and decision-making. And so, um, managers across the company, we meet, uh, every week in a meeting that call operations and intelligence, which is very, um, uh, specifically stolen from Stanley McChrystal's book. Uh, and that's really a meeting where we talk about strategy.
We talk about the data that we're seeing, shifting course, all sorts of specific pieces like that. one thing that I'm curious about it and thinking about for us is, you know, it doesn't make sense to look at more of a sprint based model for how we're doing work. But I think, um, we haven't specifically implemented that yet, but it's something that I'm looking into. Sure. So a handful of things go on in the operations and intelligence meeting. And so it's a combination of top down and bottom up conversation. So, you know, things from me that are coming down where decisions need to be made, strategies need to be decided on, uh, we need to plan specific pieces. And so how do we bring folks together to really give input and make decisions?
There's also bottoms up conversation that happens. So our, our managers, um, and folks who are running various parts of the business are a lot closer to the day-to-day work. So there's space for them to surface issues, space for us to problem solve. One of our, um, kind of core operating principles for the business is this idea that different minds see more parts. And I think that meeting is really an expression of that, you know? even as CEO, I think my.
Perspective is definitely limited. It's limited by all sorts of things. Um, and I'm aware that I am a fallible person. I think the same goes true for the broader exec team that brought our leadership team. And so there's a real, um, sort of perspective of not just humility, but collaboration that we've tried to instill in what successful leadership looks like at the business.
And it's this idea that you need different minds to solve the problem. Um, you need perspective from other people, and we've tried to be really intentional about having this ritual around this Monday morning strategy meeting, where people are getting to talk about the different things that they might see in a problem and help push everyone toward the best possible, you know, set of trade-offs around the decision.
the idea that kind of different perspectives? Um, generate better outcomes. can you think of an example or, or from maybe the past few months of that just illustrates that really well,
Brett Berson: of the things that you mentioned, both in this meeting and kind of at the beginning of our conversation is the impact of military strategy on the way that you think about both. I think, general management and sort of company strategy, business execution. I was interested. Are there other, specific sort of frameworks or ideas that you've translated from a bunch of your reading or learning about military strategy?
Stanley McChrystal's book was really illuminating for me. And I think there was interesting bits in there about how the military reoriented itself around this concept of frontline teams. if you think about how and why we built this meeting, um,
Kelly Watkins: If you look at traditional structures of how business or, or how the military has worked, it's a lot of command and control a lot of top-down directive. So we're going to go in this direction. We're going to do these things. Here's what that means for your work. Um, and I think the truth is that the world is moving too quickly for that type of pattern of decision-making not only because it takes a lot of time to disseminate that information.
Um, but also because the folks that are making the decisions in that model are so detached from what's going on in the world. Um, and so I think, with military strategy with Stanley McChrystal, with work, that's come out from Deloitte on frontline teams. It's really this idea that the businesses today that are the most successful.
Are the businesses where people who are on the front lines are empowered with the information that they need to, to make the decisions, um, in the moment and to do the work. if you think about. How many companies work. There's often a big chasm between the locus of power at the executive team decisions that are made there. And frontline managers are people managers who are doing and running the work day to day. Um, and I think that chasm can be problematic for all sorts of reasons.
It can lead to a lack of trust. It can lead to misalignment. And so with this meeting that we have internally at abstract, a big focus has been to cross that chasm and to have the people who are, were involved in participating in strategy, and decision-making being more aligned and to have more trust, um, with the people who are going out then and going to be responsible for executing on that strategy and executing on those decisions.
The other big piece for me here is, um, Having a big emphasis on transparency and how do we make sure people internally have access to the information that they need to, to make decisions and do their job.
Kelly Watkins: Um, and that's something that's, uh, been a big priority for me, uh, in this role. And I think a big priority for how we run the business is, you know, making sure that we share metrics with people. We share how the businesses doing. Um, I not only write a letter to the company every Friday on things that are top of mind for me, but we share.
Other information as well. Uh, you know, we share our board memos with the company so that people understand what we're talking to the board about and, and how we're talking about our progress and what we're seeing. Jen Olsen, who runs finance for us, is really transparent around numbers and budget.
And, you know, when I've worked in places where, um, that information wasn't accessible and I think it created, you know, more harm for people not to understand those dynamics of the business. So we've really sought to treat people like adults, um, and, and make that stuff apparent so that it's not having to be escalated to me when a decision needs to be made.
People have the same context or nearly the same context that I have, so that they're more equipped to make the decision themselves.
Brett Berson: On that point. How do you think about contextualizing information? Um, I think like one of the downsides or one of the critiques that some people have around kind of radical transparency or sharing all the numbers. Is that, for example, as a, as a CEO or an on the executive team, you can take any number and you can understand it's quite contextualized and you really understand what it means and what it, why it matters.
And so I assume part of the way that you run the company is not just here's some data dump every week, but there's a lot of contextualizing or maybe educating. And I'm curious if you have any thoughts or lessons learned around that.
Kelly Watkins: I love that you bring that up because I totally agree. I think it's so important. the point isn't just access, the point is understanding. Um, so yes, we make metrics and information available. Um, but. We have other avenues through which we educate people. So for example, we have a weekly, all hands, every Friday where we talk about numbers, we talk about things that we're seeing.
Um, sometimes that's me giving my, context and interpretation on things. Oftentimes that's other folks talking about what they're seeing. Um, we have every Friday, a demo Friday where anybody in the company can demo stuff that they're working on. Again, Jen, who runs finance. When we wrapped up, uh, some budget stuff.
Recently, she went to demo Friday and demoed the budget, um, to give context and explain various decisions and stuff to people. Um, we also make use of, you know, writing things down. Uh, one of the things that we just rolled out. That I'm really excited about is what we're calling an internal change log. Um, and so it's almost like I'm running RSS feed internally where anytime a decision is made across systems that's relevant for the broader business.
We can point to those pieces there. Um, so it might be a link to something that was posted in Slack, or it might be a link to an all hands recording or a link to a meeting recording, or a link to a notebook where a decision was made. Um, but really connecting the dots for people around, not just something happened, but something happened.
And I can go to the source and understand the context of how and why. So, you know, again, always more to do there, but I totally agree with what you brought up that. We're not just putting information out there for the sake of information, but we're trying to level folks up, um, and their own sophistication of understanding how the business works across multiple avenues.
Brett Berson: Have you noticed any downsides? You know, we started the conversation talking about trade-offs. Um, and it's about optimizing for trade-offs. When you think about the way that you engage frontline teams and frontline managers, when you think about, uh, transparency and contextualizing, et cetera, et cetera, have you noticed there, there are downsides or issues with this approach?
Kelly Watkins: I don't know if I would frame them as downsides necessarily. I would frame them as. Considerations that you have to think about if this is going to be the approach that you're going to take. So for example, um, when we hire one of the things that we prioritize is people who are comfortable with ambiguity, um, because we strongly believe that.
Being a successful employee at abstract requires folks to want to take ownership over problems and want to be folks who can, um, help figure stuff out rather than necessarily having decisions dictated to them. And so I think that's an important trade-off here, right? If you're going to run a company in this way, you have to be optimizing for comfort, with ambiguity and hiring.
Um, I think another piece is how do you tolerate and, have space for failure? Uh, obviously not everything would go right if I was making all the decisions. So just to put that out there, that that's not the alternative here. Um, but. You know, people are imperfect. And even if they're closer to a situation they're often working with imperfect data as well.
So I think part of, um, one of the conditions that has to exist inside our company, and I would also argue other companies that operate this way is that there has to be a high degree of tolerance for failure and failure has to be oriented toward learning. but you can't give people responsibility for owning a decision if you're not willing to allow them to not be perfect, a hundred percent of the time. So again, not necessarily that there are downsides, but I think there are trade offs that you have to consider. If this is the way that you want to operate.
Brett Berson: A couple of things that come to mind based on what you just shared. Um, the first is one of the things you mentioned was the importance of hiring people that are comfortable with ambiguity. And so I'm curious if you're interviewing someone or, you know, you have a 15, 30 hour long zoom with someone or maybe a hiring manager is, and you're trying to understand their comfort level with ambiguity.
What are you doing in the meeting or what are you asking to get signal around that characteristic?
Kelly Watkins: There's a couple of questions I ask. Um, one of the ones that I found to be most helpful is asking folks what sort of things they need or would need from abstract and in order to be wildly successful on the job, and really listening and digging deep for the answers there. So. When folks are able to articulate things like, you know, um, I, I really need to be pointed toward, things that are broken so that I can fix them, or I need access to information so that I can make the best decisions.
You know, there's a handful of ways that I think people can articulate the environment in which they will thrive. for folks who need a high degree in a high sense of sort of direction, um, and very kind of clear marching orders for stuff. That's not a bad thing.
Um, that's just not the company that we are at this stage. I think it's true for a lot of startups that, that they're not at that stage. Um, but that's, that's one question that I asked. Um, I also, uh, ask people to walk me through, um, How they solved a particular problem. So, you know, I'll ask them to talk to me about a time that they were faced with a decision or faced with a trade-off or faced with a time where they were moving forward with a plan and new information came up that suggested they should change course.
And I'll ask people to kind of walk me through their thinking and what they did. You know, I think that that can often be a really practical example of how do people, um, deal with data in the moment, their ability to shift their ability to make decisions. So those are a couple of things that I.
the other thing that comes to mind is, is how broadly do you think about incentives as you run and scale abstract
you know, the Charlie Munger, ism incentives rule the world, um, and incentives show up in all sorts of different ways, right? One of the things you were just sharing is the desire to create a culture of high, high risk tolerance and high willingness to fail.
and I'd love to talk about sorta aside from telling people it's okay, how do you actually create a culture that embraces failure
Kelly Watkins: Yeah, I, you know, I think there's a couple ways that I think about this and a couple of things that we've done. Um, and I think my sense is this matters in multiple directions. So obviously there's, top down incentives that can reward behaviors, right? This could be, uh, how we think about promotions.
One very specific example here. Is that when we do performance reviews, which we do twice a year, we ask specific questions of individuals on how they feel like they lived the values. But when they're asked for peer feedback and asked for manager feedback, it's really rooted in the values, um, you know, is somebody showing up curious, are they demonstrating grit?
Um, how are they really living iteration? And so, you know, the feedback in this very structured performance review is really centered in those valuables and principles that we want people living. Um, I also think that the feedback like. less formal matters. So a small thing that we do is we have a kudos channel and Slack and anybody, and everybody can pop in there and give a teammate kudos.
And it's a really popular channel. There's a lot of shout outs in there. Um, when a person who works at the company created custom emoji, uh, based on our values and principles. So folks will call out when they do CODOs, what value somebody lived, uh, and people emoji react with that, uh, with that emoji value.
So I think those are small things. We shout out those kudos and talk about those people, um, at every all hands on Friday. So I think those are more, um, ritualistic things. I think there are other, components that we've worked in that, that enable people to have that sense of safety. So for example, retrospectives, um, and this isn't just something that our engineering team does, you know, our marketing team, uh, our product team, other folks do these as well, where, uh, when something's done, we'll have a conversation about what worked well and what didn't, what do we want to start, stop and keep.
And I think that enables, um, more blameless dialogue around things that worked and things that didn't. So those are, those are some of the things that we're instituting, um, to try to really, make this something that people can live. And then lastly, I guess the only other piece I would call out is manager training really matters here quite a bit.
We invest a lot in training. Our people managers, um, we, we partner with a company called life labs, uh, to do manager skill training. We also, one of the things I'm really proud that we've done, um, internally is democratized coaching. So oftentimes the folks who get coaching inside of a company are folks like me, right?
So I'm, I'm assigned an executive coach. Uh, I I've been working with executive coaches ever since I got into leadership roles. And I can say firsthand that that's been a life-changing experience, but I think that. One of the ideas that we had, um, was that if we democratize this, could it have an outsize impact on our company?
So not only do you know, um, folks in leadership positions like myself, get access to coaches, but we've partnered with a company called lingo live, um, who has an incredible coaching platform. And there's folks all across the company, individual contributors, all sorts of folks that have access to coaching, um, to try to really help them level up in how they're working internally and how they're being successful at the company.
Brett Berson: So I wanted to shift gears and spend a little bit of time talking about some of the lessons you've learned around marketing. you spent a decent chunk before you've been running abstract, working on some of the most interesting marketing challenges. I think of the last 10 years in technology.
Um, and maybe a place to start is, is just talk about, um, some of the different insights and things that you've picked up across a couple of these, uh, companies and marketing challenges. And maybe we could, start with Slack. Um, and maybe how you thought about the role of story and messaging and marketing and positioning over the, the early years of the company's life.
Kelly Watkins: sure. I feel like we could spend an entire, like three hours, five hours talking about this. Cause it's such a fascinating question. Um, and my time at Slack, uh, was just an, a lifetime of education. So. To start with a Slack journey. You know, I came into Slack when the story was really rooted in features and functionality.
So it was really about a messaging app for teams. That was the story that was the positioning really centered on messaging. And there were a handful of problems with that, um, that we saw at the time. So first and foremost, when you looked at the data of how people were using Slack, um, It didn't seem like channels were widely understood.
A lot of folks were using direct messaging. So you tell people it's a messaging app. Um, when people think of messaging or at least when they thought of messaging then, and in a work context, it was a lot of direct messaging rather than this open, transparent, you know, conversation that takes place in channel.
So that was one data point. The second was feedback from our sales team when sales would get into conversations, uh, with customers around purchasing Slack, um, There was a lot of sticker shock around price, because for a messaging app, we were at the very, very, very top end of the market. And then you had Google, HipChat, you know, which were a couple dollars a user, and Slack was, you know, multiples of that.
And so the storytelling and the way that we were positioning the product was wildly disconnected from the price and what people thought they were getting. And taking all of this stuff into account, you know, one of the things that I wanted to try to solve was how could we tell a story that expanded people's minds about what was possible with Slack, but did it in a way that was centered more on them and more on their sort of orientation than ours.
And there's a couple of key beliefs that I bring to the table on this. So first and foremost, is that, um, jobs to be done. It's just such a incredible framework for thinking about how to do strategic storytelling. Uh, and that's because I think it highlights the fact that what people are looking for and their orientation is the job that they're trying to do.
Um, not the features and functionality of your product as a first order thing. So for example, if I'm trying to hang a picture on the wall, that's my Headspace, right? My Headspace is how do I hang this picture? And yes, like a hammer can help me and a drill can help me. And, um, I don't know, all sorts of tools can help me.
Um, but I'm not approaching life from thinking about hammers versus screwdrivers versus drills. I'm just thinking about how do I get this picture on the wall? And so that I think was something that I really took strongly into account. Um, the second was when I think about products, um, I've always had this framework in mind around what wares and house.
Um, and I think that matters when it comes to storytelling. So what base products are. In my mind, much more transactional. So you think about something like an exception monitoring tool? Um, it's a pretty transactional product, not to say that it's a negative product, but it's transactional. Right? the experience of monitoring exceptions and an application, isn't that wildly different one user for another right.
It's surfacing data about errors. Um, it's very much a what, um, conversely, I think there are products that are housed that are really about workflows and really sort of opinionated processes to get things done. I think this was certainly the case when I was at GitHub, it was very much about an opinionated stance on how software should be built.
Slack though. Was really aware. Um, and I think there are lots of examples of great wear based products, but Slack was really about this operating system for doing work. Um, so when we took those two things into account, that was how we came up with the, where work happens, story and the where work happens, message.
Kelly Watkins: It was really about. Centering the value of Slack on people and their work. Um, almost setting us up for this kind of where blank happens, kind of a opportunity to do storytelling. and we really want it to shift people's behavior and have them see that it was more than messaging. It was relevant for them.
And it had a lot of incredible knock on effects. in this case landing on a tagline or a positioning, how do you build confidence to kind of finally ship it and say that this is what we're going to spend the next X months or years building our brand around.
so I think there's two ways to come up with positioning very broadly speaking. And I think that matters and I can talk through those. Um, I think the other piece is there is like a bit of an art and science to this as well. Um, so when you think about the two ways, I think there's an outside in and an inside out approach to thinking about how to tell the story of a company.
Kelly Watkins: So, uh, outside in is looking at, what's the market, who's our audience, what do they care about looking at all these externalities and then figuring out based on those, what's the story that we have to say in response? Um, I don't, it's not necessarily a bad path to go that route. Um, but I think that, um, oftentimes when you go that path, you're working less from a place of internal conviction and more from a place of, you know, how do we like explain something in a convincing way, given where.
The market or our user base stands at this particular point in time. The other path at which is, as you can tell, my more favorite path, um, is to go inside out to really figure out how to distill clarity about what's our core purpose. What's the thing that we're trying to achieve in the world. And then how do we talk about that in a way that, um, is not only relevant to people, but differentiated from other folks in the market?
well, before I went to Slack that I think the core purpose of the company had been established and this really came from Stewart. His vision for Slack was to create the operating system for work. It was really about how do you take advantage of the shift that was taking place in computing, away from, you know, documents as the kind of center of work to people and how people work together.
Kelly Watkins: And I think his vision for the company was that Slack could be this container, this, this operating system, um, in which like all sorts of work could take place. Um, it's an incredible product vision. I don't think it's a particularly great tagline. it's kind of wonky and, not really, uh, as inspiring, um, as where we landed with where work happens, but that was really the core purpose that we were working from.
And I think the clarity around that core purpose enabled us to figure out ways to talk about it that made sense to people and that took them along for the journey.
Brett Berson: In the case of where work happens. Do you remember what the runner up ideas were and why you decided not to pursue them?
Kelly Watkins: It's kind of funny. So, "Where work happens" didn't come from a big sort of branding or brand strategy project, to be clear. I woke up in the middle of the night and said, this is the story. And started scribbling furiously on, you know, what were the parameters of "where work happens"?
Iwas reading this book at the time about the importance of place for humans. This idea that as human beings, why does place matter and why do we need a place? And so this concept of "where work happens," the "where" behind it was really rooted in the fact that we had lost that sense of place for work.
yes. At the time, people were still going to offices, but there was a lot of distributed companies, big companies, even in an office experience, you're moving to different rooms, you have a desk here or a conversation there, there, wasn't a clear where there wasn't a clear place for work.
Kelly Watkins: Um, and you know, the kind of rise of digital products, I think perpetuated that when it came to happens, you know, I think it was really the sense of the fact that as humans, we want to achieve things, you know, we want to make progress, we want to move stuff forward. There there has to be momentum to our work.
Um, and so, it really was this middle of the night idea. I pitched it to people internally, uh, and it, and this is where I think about the art and science of these sorts of pieces was, you know, it wasn't like. We did a ton of market research and, stress tested this as a brand promise and a core tagline.
It was really the fact that every person that we talked to about it, um, we all would get chills when we would think about the story and it just felt so timely and so real for the thing that we were trying to do. Um, so yeah, I mean, there, there weren't really specific runners up. Um, you know, it was like this idea that that was like a lightning bolt that, that struck, that just had such incredible power that I don't think it was ever a question of not going with it.
Okay.
when you think about some of the different marketing challenges you've taken on. One of the things that I've noticed is that many of them, uh, we're focused on products in pretty competitive markets or market that there are lots of substitutes or alternatives or similar types of products. Um, and I was interested. Is there anything that we haven't talked about as it relates to marketing and positioning that, that you found is particularly important when you're working on a product that has a lot of competition?
Kelly Watkins: Yeah, I think people's experiences with the company and with the product have such huge effect. Um, and this is where I think that my systematic theology sort of lenses come in, um, because I think by and large as humans. We're trying to constantly build systems that explain the world to us, um, and that explain ourselves to other people.
And so we're constantly signaling, um, this is who I am. This is what I'm a part of. This is, you know, my, where I stand on particular things. We're constantly looking for those signals and others and companies at the end of the day are collections of humans. Right? So it makes sense to me that the people inside of companies, aren't just trying to signal those facts or search for those facts.
The companies themselves are doing those things. Um, And so if you're an individual and you choose to wear a particular brand of clothing or drive a particular brand of car, I think ultimately you're telling a story to the world about yourselves, about who you are and if you're a company and you make choices about products that you use, or all sorts of things, you're trying to tell a story to the world about the type of company that you are.
Um, and so I think that dynamic in a competitive market, you know, is, is really strongly there, obviously yes, there's competition on price. Um, you know, there's all sorts of dynamics of competition, but at the end of the day, you know, how do you really align with who that company is trying to be? How does your story align with theirs?
Um, and, and how do you think about having experiences that reinforce every part of that? So. On the one hand. Yes. At Slack where work happens was a tagline, but it was so much more, it was, a way that we thought about so many things. Uh, it was a way that we thought about how we showed up in the world.
What was our office experience? Like? What was the experience like at conferences? Um, all sorts of pieces. I can't give enough credit to folks like Anna Pickard and other people who worked tirelessly to develop the Slack voice, um, and how it was so human and authentic and real, uh, you know, and I think.
All of that stuff matters. Um, there's such craft and courtesy that I think has to go into all sorts of decisions if you really want to stand out in a crowded marketplace.
Brett Berson: That's super interesting. the tie in with, your studying of broadly how humans, uh, think about the world and themselves. Do you think about marketing to to get everybody to want to use this product? Or do you think about creating a set of values that resonate with a subset of people and maybe, um, repel others, for example?
Kelly Watkins: There's two ways that I think about this. Um, first I think marketing is well, three things, I guess three, three, there's three things that I think about in response to this question. Uh, the first is I don't like everyone is not an audience. It's I talk to folks all the time about this, that, uh, it's not possible to serve everyone and it's certainly not possible to serve everyone simultaneously.
Um, you know, I think the theory of adoption curve is. An absolutely brilliant framework for thinking about this. Um, you know, when you're talking to early adopters, that's different than talking to the late majority and it's not possible to have a conversation with all those folks at once. So being specific about who is your audience at a particular point in time really matters.
Second, I think marketing is an expression of a business strategy. And, you know, in, in work that I've done on the consulting and advising side, this is an area where I've really tried to push other CEOs that marketing can't be successful. If there's not a clear business strategy that marketing can can drive against.
And I think that business strategy has got to be really focused on, uh, who are we going after at what volume and why? Um, you know, uh, being more clear about w w w you know, what our goals like, yes, revenue is important, but, um, you know, what are the like, inputs that really matter to achieve that revenue output?
So I think that's too. and then the third thing that I think about, um, is that all humans, when they're considering a new product, go through awareness, consideration and intent, um, and at any point in a product's life cycle and in a product journey, you have folks at various stages of that process.
So you have people who are just becoming aware that a product exists. You have folks who are just starting to consider its utility for them. And then you have folks that are getting to the place where they believe that your product is the right solution for them. And they're ready to take action.
And if you, if you look at all of these pieces together, They're not really three separate things like awareness, consideration, and intent is just the dynamics of how humans make purchasing decisions. Um, but you can't effectively work people through an awareness consideration and intent cycle. Unless, you know, specifically who's your audience, um, because you want to be able to tell them specific stories at each stage of that process and to like, what's the business goals that you're trying to achieve, um, as a, as a marketing team, because it matters if you're looking at volume or it matters if you're looking at various components.
So they all kind of layer together. I think to help marketers build the right strategy is for achieving not just growth, but I think, uh, growth and like loyal users who understand the product and care about it and believe in it, which to me is like the ultimate thing we're trying to achieve.
Brett Berson: So with that framework as a backdrop, do you think you could walk us maybe through how that expressed itself in the launch of notebooks?
for folks who didn't pay as close attention as, as you did fret. Uh, when we looked at taking notebooks to market, for our preview launch, we did three things in a row. Um, the very first thing that we did was put out a state of design report. Um, and you know, this was because we really wanted to take a moment and start by articulating the problem, not in our words, but in the words of our audience.
Kelly Watkins: So we, we had interviewed more than a thousand designers, um, you know, about all sorts of things. Uh, and we found. You know, really incredible data that pointed exactly to the product thesis for notebooks, um, you know, 50% of designers, for example, really believe that having their workflow work well with teams and products and engineering is critical to their success.
two thirds of designers said that the biggest challenge that they face is getting feedback on a work. Um, 95% of the people we surveyed said that. If they could find a way to communicate the value of their time spent to the company, that would be a huge differentiator to their work internally.
Kelly Watkins: And so we pulled all this data together and put this report out because we felt like, um, it was the most critical way to really think about, starting with awareness and starting with awareness, not of abstract and not of our solution, but awareness of this problem right now that design teams are facing, um, this problem that designers have incredible tools for the functional aspects of their job for producing screen design and UI.
Um, but design has no tools really for like collaborating effectively with other people and collaborating with the aim of making decisions. And they have new tools for measurement, no tools for saying. To the company. Um, here's how we know that we're doing our job. So we started with that piece. Then we moved to, uh, an open letter to design, um, which was really rooted in our point of view.
So we wanted to move the conversation from sort of awareness about this problem to putting a stake in the ground and getting people to really consider abstract as a possible solution. Um, and, and we didn't. Push all the way here. the open letter to design wasn't an articulation of the product or the product features.
It was really our beliefs. It was about the fact that, um, right now design teams suffer from a suboptimal process, um, that we felt like it's the time for a platform to exist, where, um, designers can be in control of the feedback process. Uh, they can have, you know, focused and open dialogue about the things that they're trying to achieve.
And so that, that was the second step. Um, and then the third step was kind of getting people to this place of, of, uh, initial intent, which was putting notebooks out in the world, um, and enabling people to sign up and request access. I'm really proud of the team who worked on this one, two, three, um, each of those pieces was so artful and well done.
In two days after we launched, we had more than 2,500 companies who had signed up to request access. You know, we, we far beats, uh, our internal kind of goalposts around people wanting to use this product. And yes, I think there's a real sense here of like this moment in time matters and the world needs a product like this, but at the same time, we were really intentional about taking people through this journey of, of awareness, consideration, and intent.
Kelly Watkins: Okay.
Brett Berson: The other thing you were mentioning a few minutes ago is sort of the influence of both jobs to be done. And the idea of understanding if this is a, what, where, or how product can you maybe talk a little bit about how those two ideas maybe showed up in the way that you ended up positioning and, and marketing the launch of notebooks?
So when I think about abstract, What we are building with this product. What we're building with with notebooks in particular is really rooted in, uh, how, um, you know, it's really about giving, um, people, a workflow for reviewing and making decisions on design. And yes, there are elements of the product that have a high degree of customization because we know that teams and companies have invested a lot in their design process.
Kelly Watkins: Um, but it's taking, I think a lot of, of ways of working that are implicit and providing a platform or those workflows can be explicit. So I think hugely influential in the product strategy, um, was kind of this, this what, where, how, um, you know, at the same time with jobs to be done, You know, uh, a lot of the, the once we got to the stage of really talking about the product and what it was, um, you know, we were really trying to thread the needle there.
So that first piece that came out with a state of design report was really about the jobs that people are trying to do that are hard today. Um, things like review, design, work, get feedback, um, get on the same page as other stakeholders who aren't deeply involved in the design process measure work. And so it was like, here are the jobs in people's own words that they want done that they're struggling to do today.
And they wish we were better. The open letter to design was us really. Putting a stake in the ground and putting our point of view out to say, it's timely solve these, like it's time that we not just let these things linger, um, as, as needs that aren't, um, addressed. And then when we got to the launch, a lot of the ways that we talked about things that you can do with notebooks was really rooted in those.
Um, how do you think about reviewing work? How do you think about different pieces? One of the choices that we made, um, and how we talked about the product is, you know, when you look at the page on our website, that describes what notebooks is, it's really written from the perspective of the design process and how the features of notebooks align with the design process rather than just here's features.
And here's functionality, um, really rooting in design is doing this job with, you know, with this particular steps. Um, and this is the platform that can make those steps possible and a fundamentally more. Efficient, um, uh, fun and transparent way.
Brett Berson: So with these kinds of marketing concepts, as a, as a backdrop, I'm interested in, in learning more about. You know, uh, a founder reaches out to you and you, you obviously did a bunch of amazing consulting work, before sort of your current role. So like a founder reaches out to you, they have a product in market.
Maybe they have a hundred K and ARR. So, so there are people paying for this and they like this thing that they've built. Um, but they haven't really thought much about marketing, right? The founding team kind of put the landing page together and figure out how that, how they would describe it. And they come to me and they say, we want to take this much more seriously.
We think we have, um, early signs of product market fit and we haven't really done any quote marketing. Um, how would you coach them in terms of where to start or what to do, or what are the next steps to, to kind of be successful in this area?
Kelly Watkins: Yeah. I tend to have this conversations a lot. And I think most of the early part of this conversations is trying to ask a lot of questions. Um, you know, I think there are many folks for various reasons who approach this type of work with not just frameworks, but playbooks. And I think frameworks and playbooks are very different things.
I think a playbook is a, you know, a set of steps that if repeated, regardless of context, lead to the same outcomes and I, I don't love playbooks. I don't think they really work that well because I think context matters where I think a framework is a lens for seeing the world through which information can be filtered, um, and can help with decision-making.
And so, I'm often trying to like have conversations with CEOs and with these leaders to really help fill in frameworks that will be useful for them. So, asking them a lot of questions about, you know, who is their audience, what is their business strategy? What are the things that they're trying to achieve?
Because I think the solutions when it comes to marketing matter for those. Right. Um, you know, there are lots of different ways to build a marketing organizations, ones that are rooted in product marketing as the center ones that are rooted in growth or demand generation, you know, there's all sorts of ways to construct a marketing organization.
And what I'm constantly looking for is. How can I help a CEO get clarity on what's the kind of organization and approach that they need? Um, I also, I wrote a piece some time ago about this on medium, on how to think about hiring your first head of marketing. Um, and a lot of the stuff that I put in there at least for early stage companies was thinking about things like, um, somebody's ability to do experimentation.
You know, when, when you're at that stage of early signs of product market fit, you've ostensibly gotten there because you've done a lot of prototyping and iteration with the product to really find what works marketing isn't dissimilar, right. Um, to really nail the playbook for your company when it comes to marketing, um, you know, you, you, you need to have somebody who's willing to come in and do that same little level of iteration and experimentation to find channels that work and approaches that work and, and all sorts of pieces, um, really looking at how do you.
Have a bent toward hiring somebody. Who's curious. Um, cause I think curiosity really, really matters for people who are coming in, who are initial marketers. really though, I, you know, I think to answer your question, it's about how do I help people connect the dots between, you know, their particular business and what they need from marketing?
Because I, I don't think it's abstract. Uh, I think it's gotta be purposeful and intentional.
Brett Berson: I wanted to switch gears a little bit in the last bit of time we have together. how do you think your marketing career has influenced the way that you, operate as a CEO?
Kelly Watkins: It's such a good question. Um, I think a strong arc to my life is the power of story. You know, everything from my early days in the nonprofit sector to work in tech marketing, I just think that human beings are creatures that make sense of the world through narrative and make sense of the world through story.
And so I think I've brought that into being a CEO. Every Friday I write a letter to the company called a weekly digest. And, you know, sometimes it's about data that we're seeing in my interpretation about it. I wrote one one not too long ago, that was about imposter syndrome and like how that's impacted me and how I've tried to think about imposter syndrome in my own life.
And so, I don't know, I think that I'm trying to remember that even in a different position, even if I'm not the Chief Marketing Officer, if I'm in the CEO role, like I'm still a human telling stories to other humans who work at the company about life and what matters and how I think about things. So I don't know that that's probably the strongest thread of connection between the two.
Brett Berson: On that point. one of the things that I personally found that I think a lot of people under-appreciate is the role of story and narrative internally at a company. Um, I think a lot of people think about mission and vision goal setting alignment, and then a lot of people think about external narrative.
What is the positioning of the company externally? And, um, one of the most powerful forces, at least I think is what the internal narrative is and whether you like it or not, there is an internal narrative at your company either you're in control of it, or you think about it or you understand it, or you don't.
And so I was interested. Do you have any thoughts about that idea of internal narrative.
Kelly Watkins: Yeah, lots. Um, I totally agree that internal narrative matters so much. And one of the things that I learned really early on as a leader is that internal narrative happens through repetition. Um, somebody once said to me that. People will finally hear you when you have said something so many times that if you say it once more, you feel like you're going to vomit.
Cause you're just so sick of saying it. Um, you know, and I think at the time I was like, Oh, that's cute. You know, but then I realized, no, that's actually true. Right. it takes a lot of effort for people to internalize, a narrative. Um, you know, uh, it's a reason why, when we do our all hands every week, we start with like, what is the point?
What's the thing that we're trying to achieve? What are we here to do? And this isn't just like, remember everybody, our mission statement is, is X, but it's really like talking deeply about, um, you know, what's the goal, what's the purpose? What are we here to do at this company? So I think that repetition really matters.
One of the biggest jobs that I think a CEO has an accompany is to set the tone. Um, you know, I think people might think it's to make a lot of decisions, but like really what my job is is that at least I see my job as to set the tone internally.
Kelly Watkins: Um, and. To set a tone that is like focused and calm and resolute. Um, I think people look to leaders to gauge their own reactions in a situation, right? So if I'm running around like a headless chicken, or if I'm stressed or I'm freaking out about things, or my tone is like on a really high frequency people graft off of that.
Right. And so I think the, the thing that I'm constantly trying to do is figure out how to have a tone of approachability, a tone of we can solve anything, you know, a tone of like, I dunno, just grace under pressure, because I think that filters out into the organization and really important.
Brett Berson: So to wrap up, I'm interested in, what have you found surprising in being a CEO for the first time? And you spent, uh, a huge chunk of your career working really closely with different founders and CEOs. And now you are a CEO and what sort of stood out or what's been the most surprising, uh, part of actually being a CEO.
Kelly Watkins: There's been a handful of things, honestly. Um, I think if you would've asked me, when I was leaving Slack, if this is where I would have ended up, I probably would have laughed at you. Right. There are very few examples of marketing leaders who become CEOs. Um, and so I don't know if I even thought that this was possible for myself, which obviously is a, a whole another conversation.
But, I think there's a bit of been surprised at like being here and, and, and getting this opportunity. And when I really unpack that, I think where it comes from is like the examples and the archetypes of what great. CEO leadership looks like I find them to be so narrow. Um, you know, we often think of the enigma Matic product founder, or, MBA finance leader.
Um, and there's not a lot of examples I think, of, of diversity in CEO leadership and how we talk about it. And this is everything from the qualities that make great CEOs to, um, who these people are. You know, I, I started when I took the role of reading, um, books by other CEOs and I found them to be very frustrating.
Um, oftentimes because I didn't feel like they were very real, I think, these books are often written from like, you know, a, a very Rose colored glasses perspective, looking backwards. Um, you know, but also I didn't see myself reflected in them. Um, I'm a really introverted person.
Um, I like thinking about things, you know, I'm not this like extroverted bag ananymous leader. And I think the thing that surprised me is that that's okay. Um, that the superpowers that I have and that I bring to the table are just as relevant for executive leadership as the ones that I think are most commonly touted as, as what makes somebody a great CEO.
Um, and the thing I think I've tried really hard to do in this role, um, is to not change myself, to not push myself, to be, um, you know, this, this, like. Person that I'm not, but to try to figure out how to be the best version of myself in this role, um, how can I show up vulnerable? Because vulnerability and leadership is something that's really important to me.
Um, how can I be my authentic nerdy, introverted self, so I don't know. I think that's the thing. Um, and, and I, if, I guess if I had one wish, I would wish that like we could expand the kind of conversation and the parameters for what people in this role look like and who they are.
Brett Berson: Great. Well, that's such a wonderful place to end. Thank you so much for spending this time with us and sharing.
Kelly Watkins: Thanks for having me,
so a specific example of, this Oni meeting that we run, uh, and how it surfaced something that we needed to make some decisions on, um, was really around how we were using Slack internally, which sounds like a small thing.
Kelly Watkins: Um, but you know, as a fully distributed company, uh, you know, we hadn't been super explicit on how to use it. Um, you know, is it for decision-making, is it for water cooler chat? Is it for all sorts of pieces? Um, what's the expectation of response time. Um, and this wasn't something that came down from me, you know, I spend a lot of my day in, you know, in zoom, uh, on meetings.
Um, but this really came up from our people managers who said. One of the biggest challenges that we see right now for our teams being successful is really figuring out how they can work with other people effectively. Um, and what tools we use that can really.
provide more clarity for where they should be doing work and how, and what that led to was a handful of folks, um, in this kind of broader management group, volunteering to pull together a, how we work document, um, and a document that was built in a really collaborative way openly with that group of people that really articulated first principles on how we use tools.
Kelly Watkins: What's expected of people in terms of, um, what they do, where and how, and, you know, I felt like it was such an incredible. Um, thing to see this group of people coming to solve this problem, but also like I didn't have anything to do with it, which was so cool. Right. I, it, we didn't have to wait for this thing to become so painful that it got to the level of coming up to me, which I think would have taken a long time.
You know, we had people who were close to the work and close to their teams and really were able to identify that this lack of clarity on how we work with something that we could fix. And I think we got to it a lot more quickly, um, and in a lot more thoughtful and well-formed way than if we didn't have this group of people working together and surfacing issues and solving problems in a highly collaborative fashion.