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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 Adam Gross, who is currently the interim CEO at Vimeo. However, before Vimeo, Adam has a long history in the SaaS industry with a lot of companies you might recognize such as Salesforce, Dropbox, and he was actually also the CEO of Heroku. He's co-founded two companies and mentored and advised dozens of different founders. We're super excited to have him on the podcast to talk about his experience here and especially with developer products. Adam, welcome to the podcast.
Adam Gross (01:04):
Michael, it's a pleasure to be here. I'm glad we got this scheduled, and also thank you for the mug.
Michael Grinich (01:08):
Absolutely.
Adam Gross (01:10):
That was the best thing I got for Christmas.
Michael Grinich (01:11):
The wonderful WorkOS mugs. Well, we have a ton of stuff we can dig into. We've known each other for a while. I want to go back in time, to well before we met, back when you were at Salesforce in the early days of Salesforce now. You spent seven years there and when you were there, you were the VP of Platform and Developer Marketing, before its IPO. Talk about that. What was platform and developer marketing at Salesforce at that early phase?
Adam Gross (01:34):
Yeah, thank you for that question, and as they say, when dinosaurs roamed the earth. So this was the early days of Salesforce that was starting in '03, and there are a couple things, I guess, for all the people interested in now, what is the history of the tech industry would be helpful or interesting to know. At the time, Salesforce was small. It was a couple hundred people. The entire product development organization fit on a third of a floor at One Market. The platform team, I think was maybe two or three people at the time, and what I think people forget, or at least maybe don't have as much experience with, is SaaS and Cloud were not considered things. And they were actively opposed by at least what was the conventional wisdom or mainstream of the industry. I remember famously at the time, Gartner recommended that you only consider SaaS as something you do temporarily while you're waiting for your enterprise software to be installed and deployed.
So it was, one, less of a fait accompli, in a way that we kind of think about technology changes we experience today perhaps, or at least in retrospect, which in some ways made it more fun because we got to be the defiant pirates with a mission. And that very much infused the spirit of the company, which you still see today. It was a mission and we were literally there to evangelize. We had a fundamental new model that the conventional wisdom rejected that we, in our hearts, believed and knew was the right way, was going to be better, and we were in a position to tell the world about it.
And the part, at least in the history of Salesforce, that first decade was very much about platform and Salesforce, as some of your listeners may know, has its roots in the database and platform world and Oracle in particular. So the fact that it had such a platform orientation is maybe not a surprise, but maybe for people who experienced the product or company today, that whole era, Salesforce was very, very much about the platform capabilities, arguably more so than the applications.
If you go back and look at the marketing, if you look at what we were really talking about, it was all of those platform capabilities because really what we were talking about was the evolution and journey of SaaS. And one of the many things that made it so fun is each time we were kind of creating a new platform capability, we weren't just expanding what was possible with Salesforce, we were expanding what people's consciousness and understanding of what SaaS was capable of. That was hugely exciting and still is.
Michael Grinich (04:26):
It's funny, thinking back on that time. I mean, I've read Marc's book about the ‘no software’, just the idea of that it's almost hard to imagine today given that Cloud and SaaS is the default way that people build software.
I want to talk more about platforms actually, something you said. So at that time, Salesforce is growing. It's pre IPO. It's still early days, certainly compared to today. Everybody wants to be a platform. It's like platform this, platform that. Every startup thinks that they're going to be a platform someday and yet to become a platform to earn that right, there's a lot of other things you have to do along the way and actually have the adoption or something to, I don't know, have the legitimacy for people to come and build on top of what you've built.
Can you talk about how Salesforce and just you have approached this? You've worked at a lot of companies that have built platforms or gone after that. How should folks approach that? Should they not do it too early or should they get started early?
Adam Gross (05:13):
As someone who's done platforms most of their lives, I'm a big fan of the idea that there are no such thing as platforms.
Michael Grinich (05:22):
All right.
Adam Gross (05:24):
I think especially technical founders, and I say this as somebody who's been one, can get lulled into the developer tools and platform business by the illusion that it allows for an abdication of what the value is. Here's a bit, here's a widget, here's a compiler, here's a thing. It's up to you to imagine what it is and what it's useful for and how you should do it. And we have this illusion that kind of happens in the market, and that's what we want to do because it spares us all that messiness of actually having to go to market. Which is of course the thing that technical founders tend to be least enthused with.
The reality is that there are no such thing as platforms. They are always domain-specific. Pick your favorite layer of the stack. Look at semiconductors, right? Intel ain't NVIDIA ain't AMD ain't Apple. There's always engineering tradeoffs and by virtue of that, there's always some measure of domain specificity. That was true of Salesforce platform, that was true of Heroku. It's why we accept a degree of heterogeneity in databases that we have, because we have different tradeoffs in a different fit. So I very much think about platforms as being adjacent to a limited and well-defined set of problems, rather than this broad horizontal thing. Dangerous territory in that framing.
Michael Grinich (06:55):
I mean, you're talking to somebody who has started a company with OS in the company name, so I'm definitely in the category of loving platforms too. We could talk about that some other time. Tell me more about marketing around this. So the category creation step. Salesforce really was defining really a new framing of what software was and how this platform could be used by customers. How did you do that early on? I mean, being thought of as a temporary solution is almost ludicrous to think of compared to today with Salesforce.
Adam Gross (07:24):
Yeah. I'll put in a plug here. I did a talk 10 plus years ago that you can find on YouTube. It's called Platform Marketing for Developer and Platform Companies. So I go into a lot of this in detail and it's mostly about what I learned from the Salesforce era. I did it with Heavybit, I think you can also find it as part of the Google Lab stuff. I put that talk together because I think so many entrepreneurs, startup founders, struggle with how to even frame what positioning, what category creation, what does this task even mean? Does it mean being really good at buying Google ads? Does it mean getting stories about my college years and creation story into the media? What am I trying to do here? I helped frame that and certainly what I believe at the core, certainly true of Salesforce, is what you are always aiming for is some kind of industry transformation narrative.
How is what you're working on helping create, aligning to, contributing with, motivating some fundamental tectonic shifts that are happening in the industry? Because what you get with being associated with an industry transformation or if you're really lucky, creating one. Of course the examples tell themselves. When you are synonymous with an industry transformation, Open AI, Salesforce, and to some extent, these things happen. To some extent they're created. I would argue with Salesforce, it was very much created. When you get that, you get this key intersection of company and brand attributes that are so important for every startup trying to achieve the next level of maturity. Which is, you are strategic, because of course you're strategic if you're aligned to some broader change in narrative. And being strategic is core to getting any enterprise opening up their wallet, and you're emotive. You're important in a way that resonates spiritually with how people think about the world, their problems and their opportunity. With emotiveness, you get people to give a shit and when you get people to give a shit and open up their wallets, that is usually a pretty profound recipe for success.
I literally think about this as a two-dimensional space. How strategic are you? How emotive are you? And everybody starts at the same place, way down at the bottom. Salesforce started there, Open AI started there at the very beginning, WorkOS started there, my startup started there. And it's how you're navigating this two-dimensional space, sometimes becoming more strategic, sometimes more emotive. That is so important to thinking about what you're building, how you're telling your story, the value you're creating for your customers.
Michael Grinich (10:21):
Is the goal to be both strategic and emotive?
Adam Gross (10:24):
For sure.
Michael Grinich (10:24):
Yeah. As you're talking about this, it resonates with a lot of stuff I've learned and heard from people who are experts at selling. It's like, don't just say what the widget does, but say the impact it drives, or you're not buying the drill, you're buying the inch-sized hole in your wall or something, the outcome.
Adam Gross (10:40):
Yeah.
Michael Grinich (10:41):
Yeah. Talk about that, how this impacts the sales.
Adam Gross (10:43):
Really great salespeople will be effective at working on that strategic dimension, which is how is this thing empathetically related to a customer's or a company's most important goals? Being able to read companies, and I talked to them on the board of Buildkite and I talked to the team over there about this a lot. Imagining a company like Sims, with little thought bubbles over their heads, like I need food or I'm bored. Companies are like that too and being able to read the thought bubble that's on the company's head in that succinct, quick way that you can then relate whatever you're doing, that's their core strategy. That's how you become strategic to them.
It's not what they necessarily say. It's having the empathy to allow that to be revealed. So that for sure is an important thing that's important for salespeople. The emotive thing is, and I don't want to make this too marketing and sales, but maybe this works a smidge, the emotive piece maybe is, and it's marketing's job to do both, but it's going to be more of the company, the product, the experience, the brand than just that sales component.
But absolutely. When we think about the brands, the companies, the products that we respect, we love, we want to emulate the most, what are they? They're the ones that are highly emotive and highly strategic. What could be more Apple? I've got this incredibly emotive thing that I communicate with all of my friends with all the time, and it represents my connection to the world and how I consume media and all these kinds of things. And it also is transforming industries just left and right, just mowing them down. Incredibly potent combination.
Michael Grinich (12:28):
You said something around this, I remember we had a conversation a year or two ago, when we were talking about people that are really great at doing this. As founders or people building companies, they start to think about who can I hire in or who can I collaborate with? I think you described this as the difference between poets and librarians. Do you remember that?
Adam Gross (12:47):
Yes. Yeah.
Michael Grinich (12:48):
Can you say this again or touch on this a little bit? It's one of my favorite things. I wrote it down.
Adam Gross (12:52):
I got to tell you, we're shifting gears a little bit, but this is probably my core organization building principle, and so I'll tell the medium version of this story. So in the nineties I started a company, it's a web analytics company called Personify, and there was a gentleman there named Trevor Rubel who told me this, and I give him credit because he doesn't know this, but he changed my life. Basically it's understanding that there are two kinds of people in the world. There are poets, people who are creative, people who you look to for the originality and quality of their new thinking. And there are librarians, they're process people.
Another way of thinking about that is there are content providers and there are process providers, aka poets and librarians. Now, here's the thing, librarians need poets, poets need librarians. They need each other. It's not that one is better than the other, but the number one mistake in hiring an organization building is having a librarian in a poet's job or vice versa.
This is like a classic engineering management... It comes across the board, right? This debate permeates every conversation about every hire that you make, most of them. Your VP of Eng: are they a poet? Are they going to be the person that creates the most popular new open source project because they came up with this new architecture for x, y and z? Are they a librarian? Are they a process person that's going to be really good at getting the trains run on time?
Same thing with a product person. You can hire a CPO. Is your problem that you need genuine insight and customer-driven creativity to drive new forms of value and pioneer a new path? Or is it that you can't ship anything and you got to get some process and some organization and structure?
Same thing with marketers, especially true of marketers. This is one that happens all the time. You hire a CMO, a VP of marketing, process people, they're going to optimize your ads, like librarians. Poets, they're going to come up with your new positioning. Which of those do you need? And yes, in the fullness of time, I'd like to think we all develop both. I'd like to think I've worked on my librarian inside. I'm more of a poet. Poets are the kinds of people that appear on podcasts and tell stories like this, but just being mindful because just like the quickest way you see it, once you think about the world that way, you see it as clear as a bell.
You're in a meeting with somebody and you're asking them to create a blog post for a new product launch, and you just see them stumble all over it and you're like, "Okay, trouble, right? This is not the person who does that task," but it's also important because, especially technical founders. I mean the core hacker ethos is dismissive of process. It's dismissive of librarians. In the core hacker ethos, everybody is a pirate and a creative, and we don't need no stinking anything else. These are just stupid managers who waste other people's time.
You have to respect that providing context, providing structure for providing process, is a really important capability and skill in your organization too, and you are equally screwed if you are exclusively librarian or exclusively poet.
Michael Grinich (16:01):
What does that distinction look like for people in sales? Sales is such a process-driven, numbers, CRM, forecasts, even paid based on performance. There's a high emphasis put on legibility in a sales process.
Adam Gross (16:17):
Yeah. Salespeople should be, by and large, librarians, because if they're too concerned... I'm sure, I don't know, I've seen this a million times. A salesperson who's too concerned about what the product is or too concerned about what the message is or has too many comments about the website, I'm like, "Eh, that's a problem. Maybe you're not in the right spot."
I don't want to dismiss the art of, again, that customer empathy, the psychology of the relationship building. There's poetry in there, for sure. And we've seen it when we've experienced the natural skills and sales capabilities of different people. But at the end of the day, that's a machine that you're running in very highly structured process and that's what it needs.
Michael Grinich (17:07):
You mentioned Apple and Steve Jobs. I feel like Steve Jobs was the poet seller, the reality distortion field.
Adam Gross (17:12):
Yeah. That's why you get a little bit of... It just goes back to confirming that hacker ethos, like, "I'm Steve Jobs, I don't need anybody else," but let's look at Apple. What is Tim Cook? He was the COO, right? His whole skill was... And what is so unbelievable about Apple among its other capabilities, that it can mass produce these things, incredibly complicated devices. Although, we're going to be in the semiconductor business. Great. All of a sudden they can do this at global scale. I mean, that's pure librarianship, right?
And Tim Cook was the librarian to Steve Job's poet, at least in the late stages of his tenure, and that earned him the top seat, and that was right. Tim then had to say, "Okay, well how am I going to augment my librarian nature and bring the right kind of creative people together so they can drive that innovation?"
Michael Grinich (18:00):
I wanted to go back and touch a little bit on developer platforms. So you led Heroku for several years, which still is this legendary company that a lot of people admire and are in some ways trying to recreate the ethos of that. And a lot of Heroku, the marketing and the messaging and the product design of it was so just crisp and clear. I think it's why it's been so durable. Can you talk about that, the marketing a developer product like that, versus some other type of SaaS? What's different about it?
Adam Gross (18:26):
Well, I'll take plenty of credit for some of Heroku's success, and I will shun responsibility for anything that people don't like, but I won't take any credit for that marketing or the original product creativity. All the credit goes to the founders, who were uniquely obviously brilliant at that. This was an '08 ish era thing, but at its core, again, back to strategic emotive. People viewed developer tools as being non-emotive, non-experience driven, right? Experience wasn't a consideration. Maybe developers knew it. Of course developers knew it. We knew about the ergonomics of tools. We didn't have a word for it then. We didn't have a word for developer experience, and with Heroku and some of its brethren, GitHub, Twilio, it was the first time you had a defined idea of experience as a primary product attribute, and that was revolutionary.
And it was so dramatically different. It was so radical, almost like in any kind of revolution, the pioneers of the revolution embody the thing to a fault, and Heroku and GitHub both, especially in the early days, embodied this experience centricity to a fault. They were too rotated on it in a way. I mean, talk to anybody inside of Heroku. It took a year to ship a t-shirt. T-shirts were amazing, but they were slow.
Michael Grinich (20:00):
They're good shirts. Yeah.
Adam Gross (20:02):
Same thing at GitHub. So it was that just radically different. Again, it seems obvious in retrospect, but you just have to empathize with what the world looked like then and how unique and, to some extent, lonely a position it was to say, "No, we are going to stand for something very different in the stack rank of value propositions that has been previously asserted, and we believe it and we believe it so emphatically it's going to infuse everything up into including our coffee mugs."
Michael Grinich (20:34):
Adam, we could talk about this for hours, we have in the past. I'm going to let you go. We'll link the other talk from Heavybit and some of the other material and the talk notes for folks. Thanks again so much for joining us and sharing a bunch about this.
Adam Gross (20:45):
It was my pleasure. I wish everybody on the call, the founders, startups out there, enormous success in 2024.
Michael Grinich (20:56):
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.