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Crossing the Enterprise Chasm is a podcast on how high-growth startups prepare to build with enterprises and Fortune 500 companies. Each week WorkOS founder Michael Grinich is joined by founders, early-stage team members, and product leaders who lead the charge to go upmarket. In every episode, you'll find tactics, strategies, and actions on how to successfully sell to and serve your crucial early enterprise customers.
Michael Grinich (00:02):
Welcome to Crossing the Enterprise Chasm, a podcast about software startups and their journey moving up market to serving enterprise customers. I'm your host, Michael Grinich. I'm the founder of WorkOS, which is a platform that helps developers quickly ship common enterprise features like single sign-on. On this podcast, you'll hear directly from founders, product leaders, and early stage operators who have navigated building great products for enterprise customers. In every episode, you'll find strategies, tactics, and real world advice for ways to make your app enterprise ready and take your business to the next level.
Today, I'm joined by Ceci Stallsmith, partner and co-founder at Calyx Consulting and former director of platform marketing at Slack. Ceci has spent most of her career thinking about developers and how to reach them, first at Box, and then at Slack. Her company Calyx focuses on companies and their journey becoming platforms. We're delighted to have her here on the podcast to chat about a particular area of her expertise, marketing to developers. Ceci, welcome to the podcast.
Ceci Stallsmith (01:05):
Thanks for having me, Michael. I really appreciate it.
Michael Grinich (01:07):
All right, let's go back in time a little bit. We'll start there. Tell us about your time at Box, first in the Developer Relations role, and then later as the Platform Product and Ecosystem Manager, where I know Box went from zero integrations to over a thousand eventually.
Ceci Stallsmith (01:22):
Yeah, it was so fun. This story could be so long, so I'll try and keep it short. The journey at Box to platform was fascinating. I joined at about 200 people. Box had always had an API because they had always been sort of platform first, but Aaron was really great at sort of capturing the zeitgeist at various moments in order to grow the company, and so mobile... Do you remember 2011, Michael, mobile was really, really hot and exciting?
Michael Grinich (01:46):
Oh yeah, it was the AI of the early 2010s. Yeah.
Ceci Stallsmith (01:50):
Absolutely was. The iOS app store, and also the Android app store, were where VCs were mining for new companies and everything was really exciting. So I had the opportunity… I was doing developer relations for Box, trying to get people to build with the API, which didn't really make sense because I'm not an engineer, but I was able to because the API was straightforward enough, so props to Box. Aaron one night pulled me and my manager into a room. This is like we would work at 10:00 PM, and it was fun, and had this idea for this mobile ecosystem and I got to go and build it with them. So it was really fun. I just literally was scouring the app store and cold emailing all of these people who were building these apps in the productivity and sort of business space.
And I just got them to integrate with Box, and then we would do these big marketing launches to sort of blow out the excitement about our ecosystem, and it worked surprisingly well. We started and launched with 10 apps, but we got a ton of press, and then grew it to 50. Took on the Android app store, grew another 50, and then grew to well over 200 apps and stopped counting. So it was a very, very fun, crazy ecosystem journey. There were also a lot of lessons learned too I can share as well, but that was the experience in Box.
Michael Grinich (02:58):
Yeah. Going back to that, the very first set that you did, that first 10, do you remember what the kind of catalyst was for actually doing this? What did you see, or what did Aaron see? Was it a thesis bet, were people already starting to use it? Platforms are always the hot thing. Everyone wants to be a platform so everyone wants to do it, but why did you know it was the right time to do it for Box?
Ceci Stallsmith (03:18):
Platforms always were the hot thing, but I've worked with a lot of companies since then launching their ecosystems, getting their platforms together, and it is a little more playbook-ized at this point. There wasn't as clear of a playbook in 2011, I would say. Microsoft and Apple had done it, but there wasn't anyone recently who had done a really cool ecosystem that everyone was sort of jealous of or wanted to be like. So one, it was still a little bit novel. I recently worked with launching an ecosystem for a pretty big company, and getting partners to want to build to our platform was really hard. Everyone's been playing this build to my platform or I build to your platform game for the last decade, and people are a little tired of maintaining integrations. Back then, this was sort of new and exciting. So that was one thing.
Two, there was still some novelty to this whole effort. Mobile was the wild west at this point, so it's sort of like I would say AI is right now where everyone's just scrambling to build to figure out where the little growth angle's going to be that's going to make them into a big company by building with this new technology. Mobile was that at this moment in time, so there was this question of how are files going to move on mobile? And how is mobile going to play out? Remember Paper, it was a really beautifully built note-taking app? It was the hottest thing. It took tons of money from big VCs. They had this beautiful office in New York. They were a mobile app. They ended up selling to the New York Times. It didn't end up being a huge outcome, but everyone thought that that was going to be the future as you're building on iPads, and it was really, really cool.
So there was also this moment of hype around mobile and lots of opportunities, so people were very willing to work together. And then the last thing was we were totally exploiting issues on the native operating systems, so there weren't secure ways to pass files between apps at that point on the operating systems, especially on Android. Android had some weird protocol thing that they had, so I actually got a patent in my name when I was seeing product, which is hilarious because, how did that happen? Yeah, so it was really fun and there was a lot of green field for exploring how to take an API that was about moving files around securely and applying that to mobile, which then changed over time as the operating system got everything locked down and I think you're going to watch that play out a lot right now with AI because it's the wild west.
Even with the announcement that OpenAI made, I don't know when this will air, but this was yesterday November 6th, they're kind of resetting the ecosystem repeatedly because they're bringing out so many new tools. And as those tools change, it's going to really change the games for what apps can do. So it's kind of like the flashlight app on iOS where everyone had that app, and then they added it natively and it changed. So that was part of the way things played out.
Michael Grinich (05:55):
That's a really interesting comment about how those things end up becoming in-house native to the platform. I was literally just talking with a friend at lunch today about how all of the AI work he's been doing in a startup for the last six months is sort of no longer relevant, given what OpenAI has announced, but you just kind of keep moving the goalposts and they're working on the next new thing.
Ceci Stallsmith (06:14):
I have a wonderful mentor who did a lot at Microsoft, and we talk about this stuff a lot. One of the things he always says is, when you're building with a platform like that, especially if you're a smaller player working on top of them, you have to always be trying to see around corners, because the assumption that we're all just friends and we're all just trying to only make each other's businesses grow is the wrong one. If you're going to be a really cutting edge winning company built on top of a platform with an ecosystem like that, you kind of always have to be seeing and trying to find out where they're going to cannibalize your business eventually and building ahead of it. And we thought a lot about this at Slack because we didn't want to offend our ecosystem at all or really destroy them. So we would do a lot to basically communicate in advance if we were going to add features, which we obviously did, all the features Slack has now that would sort of directly impact or compete with our ecosystem.
And I think that just doing that sort of one-to-one outreach, or even group outreach, it did a lot to help the ecosystem stay healthy.
Michael Grinich (07:08):
Let's talk more about Slack. I think that's a great segue. Obviously, a very different platform, different kind of type of developer, and different timing of the market and industry. What was the marketing motion there? How was that different or similar to Box? Can you talk about that, maybe what drew people into building the Slack platform? Then we can talk about some of the specifics.
Ceci Stallsmith (07:25):
Totally. So Box was interesting because if you looked at Box... Dropbox was in the space, and we were the enterprise option, but we were also more of a number two. We weren't the hottest kid on the block. Whereas Slack, we were the leader in the category. We were the thing that everyone wanted to use. We were growing like gangbusters. When I joined again, I joined around 200 people and got to watch a ton of growth for the company. I hate to say it, but I think I could have been pretty bad at my job and we would've done perfectly well and succeeded. I think that my team was amazing, and I think we did a good job. So I think we hopefully had an impact on making things even better at Slack, but there was just simply product market fit. So one of the biggest things I've observed, especially in developer marketing, is you can out market, especially products that you are trying to bring to, in a sales led world. And you can often out market things in a very consumer oriented world by having influencers push stuff and things like that.
But with developer products there's just a different level of BS filter, I would say. I don't know if you feel that. Do you feel that in your world?
Michael Grinich (08:24):
I think developers, they have a very refined sense of smell for when things are just a little bit off, and it's almost a sense that other non-developers don’t have. They don't even know that they're doing something wrong
Ceci Stallsmith (08:36):
And I actually really love that about the developer audience. There's more discernment there, so it's pretty hard to beat product market fit. So Slack had product market fit. When I joined, we didn't have a third party developer API. So we had APIs that you as a customer could use for your own Slack. That was it. So it was insane because we were growing so fast. Developers wanted to build these third party apps to reach our big customer base and our very fast growing customer base, and they would have to ask customers individually for their API keys to get them an app, and they were doing it. So they were just doing backflips and climbing over really impossible to scale walls in order to get apps built. So we were just, as fast as we could, shipping the API to work, and then launched it. And we're basically managing growth, I would say at Slack. And then a lot of the stuff I think we did well in terms of developer marketing was... We just had a really high bar for how we marketed, like the way we used words and what we would do.
We were really equipped to do awesome events and just bring a craftsmanship to the work that was really fun that I think people resonated with. We had an awesome BD team and developer relations team, and we really knew our ecosystem. I still know the ecosystem pretty well and lots of work through that ecosystem well still. So I think there was also a lot of personal touch that we did that made a big difference in terms of how we worked with the ecosystem overall. There's a lot of basic tooling stuff I could talk about with just opening up developer communications was a really big deal when I joined. We hadn't been saying anything. We just started sending a newsletter. We just started doing some really basic stuff, which made a big difference. So those are the highlights for me. I think a lot of it has to do with how you talk to developers, and that's a lot of what I learned there and then had to teach the team in terms of you can't just cut the fluff, cut the marketing stuff, get to the meat and get it across.
Michael Grinich (10:20):
Let's talk about that a little bit more because I think you're totally right that product market fit that Slack had really propelled the company. My current definition of product market fit when I talk to other founders is when you can just keep screwing everything up and yet keep succeeding. It is just you keep tripping over your shoelaces and yet you keep scoring goal after goal with your customers. And that's an amazing thing to have and a magical place to be, but there's so many companies that have had that and then screwed it up, or they've had a product and then tried to launch for developers and totally missed, whether it's on tone of voice or the way they launch their platform or how they connect. And the benefit of a developer platform is huge, so everyone really tries it. What would you say are the things that companies should look out for that's a great way to market or voice to developers, and maybe what should they stay away from or common pitfalls that you see indoctrinated as they try this?
Ceci Stallsmith (11:10):
I work across so many different companies now that I get to see and then edit the work of a lot of different marketers or people who are thinking about working with developers. I don't want to sound too mean, but the first one I see is that you take someone who doesn't like classic B2B marketing, and then you plug them into developer marketing and they're just using the language of B2B marketing with the developer audience. And this is such basic Marketing 101, but there's this understanding of who is your target user or your persona, and part of being decent at developer marketing is understanding what developers will react to. So I am getting to fractional CMO right now. It's really fun. And I love working with our CTO at this company because we'll work on some stuff and then he'll look at it and he'll be like, "Ugh, I hate this. That's such an overstated claim."
And developers, like we were saying, there's just this desire for things to be very honest, and maybe even a little bit humble in the way they're stated, because when you're building software, you are building net new things and there are things that are really impressive and cool, and then there's stuff that's pretty straightforward and basic. And it's easy as a marketer to be like, "Oh, I'm charged with trying to make people excited about this feature of the API, so I'm going to go act like it's so thrilling." And it's like, no, it's actually just basic and useful and just state it as that, and stop trying to hype this thing up that's actually just normal. If you're building OpenAI, they're not even being very hype even, that's really changing the world and how we think about things. If you're building an endpoint for a feature or access management controls, that's a nice feature and you should just say it in a straightforward way because it's not so impressive and amazing.
So taking one, reducing the hype unless something's actually really cool, two, watching out for just regular business jargon and lingo, I would just give it to an engineer on your team if you're trying to practically do this and be like, what do you gag at? And just let them redline it. Take someone who's a little bit snooty about stuff and just literally let them redline your blog or your website, because they will take that language that just feels fake to them and cut it down. Those are the two big things. I think the last one that is important here, and I think I learned this at Box, which was really fun, there is a danger… It's really hard to find real technical marketers, obviously. Usually people who go into marketing are not technical, or technical people stay in technical roles. You occasionally can, but you can't bet your farm on that.
If you find a marketer who needs to market technical things, they need to be able to sit down with the person who developed it, the engineer, the product person, whoever it is, and really understand how it works because the work of tactical marketing or marketing to developers is being able to explain how this thing works without having to be extremely technical in the explanation. So distilling the hard thing into something simple is really important. And often, I think you see, I'll work with people who don't really understand how the product works, and then the marketing is just very bad because it doesn't clearly communicate what's possible.
Michael Grinich (13:55):
Let's talk about brand a little bit. You haven't touched on this, but I know it's a big thing. We've talked about it a bunch one-on-one. And with developer products, these iconic products that developers are drawn towards, like Stripe, brand is such a huge part of it. How do you see that fitting in? Slack obviously had an amazing brand too, and so does Box. How does it fit into that developer angle and the platform building narrative?
Ceci Stallsmith (14:17):
I have a funny and weird perspective on this one. So these types of companies, a lot of it is just determined by the founders, and I think I would actually point to that for WorkOS. I feel like you have a very strong perspective on how the brand should look and feel, how the API should work, how your product should really work for people, and that impacts how it literally looks and feels. I would say at Slack, so much of that marketing brand is just Stewart, or was Stewart. It's hard to talk about Slack now because just, in your brains when you're listening to this rewind three or four years and then think about Slack then, that was just Stewart distilled. And he really did get into those marketing choices. He was in all the brand conversations. He blocked brand stuff left, right, and center.
I think when you look at Stripe, again, the Collisons are notorious for being very careful about what gets out the door for that company's marketing. And I think that a lot of their brand, and I would say this for your product too, it's the product that is the brand. It's not just the marketing stuff that is the brand. And I think there's something to, they have a good sense of what aesthetic they want to be getting across. They have a sense of the palette and some of the look and feel that's going to come across in the actual marketing brand stuff, but I actually think a lot of the brand experience that developers care about is literally the ease of use of the API or the ease of use of the different products or how great the examples are in the SDK. I think that's a huge part and a way more important part of the brand experience for developer products.
And hey, as a marketer, that's actually a little hard to control because I don't write the docs, but I can bother people to make sure that they're managed well, and have good IA and have good examples and are doing cutting edge things. So I think that actually the docs are one of your most important brand experiences, and I think a lot of this comes to your CEO or the founder DNA and the feel the founders want to get across in the company. I have not seen a lot of marketers successfully get around CEOs who have strong feelings like that. And I do see a lot of companies that are kind of meh on brand, and it's just because the leaders don't care that much.
Michael Grinich (16:19):
And you can build a successful company without doing that too. Many folks do. You just don't get that. The je ne sais quoi, kind of supercharged on top of it.
Ceci Stallsmith (16:26):
You don't get the sparkle. And I think the biggest piece to it is you want people to want to be hanging out with you. I think the value of that brand piece is like, I look cool if I'm associated, whereas you don't look as cool with a company that no one cares as much about.
Michael Grinich (16:41):
Not as aspirational, sure. I can definitely tell you WorkOS, it's not just me, we obsess around it across the whole company, even down to error messages being thrown by the API, every single customer support message, trying to make it on point. It's not just the gradient on your home page or the color of your logo.
Ceci Stallsmith (17:00):
Oh, I would say a disproportionate amount of it at Slack was the product, and then the voice. I think that more of it was the voice than the imagery, or the coloring schemes or anything. And that's a combination of Stewart and this woman, Anna Pickard, who is one of the most amazing voice and tone people, or the most amazing person I've ever worked with on that front. She just has a real talent for this, and it was so hard, this is a little inside Slack story, so hard to train marketers in Slack's voice and tone. It was almost impossible because people would always come in and be like, "Oh, Slack's voice and tone is so playful and fun," and then try to replicate it, and then just sound really hokey and lame. But Anna had this great... She's British, I feel like there also was this element of it was a little extra sophisticated.
One of our tone things was we're not above a joke from English literature. We would just throw in little random sophisticated tidbits. I'm actually sitting on a piece that I want to publish that's like this overview of what you're allowed to say and not say as a Slack marketer, but it was so painful. We would have to put people through the wringer, and then just realize a lot of people couldn't write for the company because of that.
Michael Grinich (18:01):
I want to switch gears a little bit and talk about what you've been doing since Slack with Calyx, which is I think generally focused on helping companies that are building platforms navigate this, whether those are developer platforms or ecosystems or just ways of working with other companies. Tell me about what being a platform means to you. How would you define that? What is a platform?
Ceci Stallsmith (18:22):
This is an interesting one. One of my favorite companies that I invested in when I was in venture, I printed this shirt that was a toaster, and it was like, "I'm not a toaster, I'm a platform" was the caption of the shirt. Everyone says their platform. Everyone is not a platform. At Calyx, I don't only work with ecosystem players anymore. I actually also just work with straight up developer products because there are a lot of them and there are not a lot of people who do marketing for them. So I work with both. I would say a platform, especially in terms of the ecosystem, I like Bill Gates' measure of a platform. I don't think I've worked with tons of platforms who have become that his measure is a platform... It's a true platform, you've built a true platform product when the value of the things built on top of it in sum is greater than the platform itself.
That's a pretty hard and high order, but I actually like that as the goal because it helps you understand that you're trying to build something that's much greater than the core underlying product, and that the platform is going to take that core underlying product and bring it to really new heights in terms of what's possible. So I'm really into that concept. And then when it comes to dev tools, I actually think it's totally cool to be a really useful tool. And you can make lots of money that way and have a really good business. And then if people extend it, awesome.
Michael Grinich (19:35):
Well, I want to also ask about something you've written about, which is your go-to-market philosophy. You have this approach to it, these seven principles. Can you give us a quick summary of that? What's across the seven principles, the seven points, and maybe a little bit of color around it, what are your favorite ones or what do people not usually adopt or recognize?
Ceci Stallsmith (19:52):
Yeah, they're all over the place. The first one is that Bill Gates principle, the platform, everything built on top of it, in sum is greater than the platform itself. The second is this concept of a flywheel. So basic. I've been at so many companies where I have to teach people about how flywheels work, and I think that's getting more understood as people listen to Lenny a lot and people like that. But basically, a platform makes your core underlying product more useful to more users, and therefore grows it. But you have to kind of get the flywheel growing by yourself first, and then it kicks and starts to do it itself as you grow. So that's the second one. The third one, a lot of the work I do is figuring out messaging and value of platforms. And as I've done that work, I've realized there are only actually three ecosystem value props, and two of them are nearly the same thing.
The first value prop is you can make a lot of money with this platform by building on top of it. The second one is you can get a lot of users, which usually translates to money. And the third one is, this is really, really useful technology that you can use and do brand new things or really important things with. So usually, you're focusing on one of those three value props. The fourth is that developers are first-class citizens. I've worked a lot of places where people just don't see the developer as an important user because the customer that's paying in a B2B scenario is often the higher priority. But if you're really trying to build a great platform, you need to treat your developers well to keep them around and to make it sustainable. Fifth one, I think it's fifth, is that, I've already mentioned this, take your marketing lingo, synergy, or seamless, things like that, just stop saying sort of classic B2B marketing words.
Developers don't want to hear it. The sixth one is that ecosystems are really messy. The term ecosystem comes from the outside kind of ecosystem where you have a pond and a bunch of stuff is dying within the pond, and there are a bunch of animals and bacteria that are eating that, and then growing up and other things are going to eat those. It's messy. It is important, but the growth is in the mess, and you do need to have people in place to kind of safeguard that and make sure it's not too inhospitable for people. So I think that's important. And then the last one is very basic. Everyone wants to be the center of the wheel. Everyone wants to be the platform. Not everyone is, and that's okay. It's okay to say this is not the moment for us to build an ecosystem.
It's the moment for us to build a set of really useful integrations for our users. And that moment of tipping into becoming the core ecosystem could come in the future, but I've seen that kind of forced before. And I think the ones that are most important... The developers being first-class citizens one, if your product is not a developer product, gets missed a lot. And you often throw them bad APIs with bad documentation and expect them to build stuff, and that just simply won't work. It will work for a minute, and then it will fail. So I think that's one of the most important ones.
Michael Grinich (22:34):
Last question for you before we wrap up, a lot of folks listening to this podcast are probably earlier in their journey, maybe just getting started, maybe haven't hired their first marketer yet even, or just are early in that journey developing their platform or product, or what have you. What advice would you give out to an early stage founder maybe looking to build that initial go-to-market team or go-to-market motion? What would you say to them?
Ceci Stallsmith (22:56):
I'm working with a really early stage marketing team right now. I'm doing the part-time CMO thing, and it's been very, very fun. I think the biggest stumbles I see people make is trying to say, "Oh, our marketing motion is going to be that thing that you're not doing at all right now," and then trying to hire someone. Let's say you don't actually have a lot of content going, but you're like, "I think we need a content team," and then you hire this standalone content person who is disconnected from anything else you're already doing. That just doesn't work. The biggest thing I'd say is if you're seeing some growth, if you're getting users on the product, getting paying customers, you're doing some marketing. It's just a question of who's doing the marketing at the company, who doesn't have the title, and what are they doing? And I want you to find those people.
It's often probably you, CEO, or the product person, it's often one of those people, and write out what those jobs are, and then go build the job description around that by giving that to someone who's experienced and who's done it well. Because taking your existing motion that is working, and then scaling that is going to grow you, but trying to artificially place marketing into this thing is a huge fail. You end up firing that team, and it's not fun.
Michael Grinich (24:03):
I have definitely heard that story time and time again. That's all the time we have for today. Ceci, thanks again for joining us. This is really, really great.
Ceci Stallsmith (24:10):
Thanks Michael. Appreciate it.
Michael Grinich (24:16):
You just listened to Crossing The Enterprise Chasm, a podcast about software startups and their journey moving up market to serving enterprise customers. Want to learn more about becoming enterprise ready? The WorkOS blog is full of tons of articles and guides outlining best practices for adding features like single sign-on, SCIM provisioning, and more to your app. Also, make sure to subscribe to this podcast so you're first to hear about new episodes with more founders and product leads of fast-growing startups. I'm Michael Grinich, founder of WorkOS. Thanks so much for listening, and see you next time.