The story behind Slack’s marketing and the leap from marketer to CEO — Abstract’s Kelly Watkins

 Thanks so much for having me, Brett. I'm stoked to be here.

 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.

 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 I've always felt like as soon as you bake those plans, they're pretty irrelevant and outdated, the moment they're completed.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this idea for me around optimizing for trade-offs is that, um, it's really about, rather than create these monolithic outdated, long running plans.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?

 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.

 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.

 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?

 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,

 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?

 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.

 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?

 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,

 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, 

 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.

 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.

 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.

 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.

 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?

 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.

 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?

 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

 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.

 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.

 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.

Today’s episode is with Kelly Watkins, CEO of Abstract. Before joining Abstract, Kelly ran top marketing teams at Slack, Github, and Bugsnag. She shares her biggest lessons from her first year as a CEO and then she pulls back the curtain on some of the most critical marketing milestones in Slack’s ascent, like developing the “where work happens” tagline.