ALLAN LEINWAND

>> Craig Gould: Allan Leinwand thank you so much for joining me today on the podcast. Allan you’re the Chief Technology Officer at webflow, the platform bringing web development superpowers to everyone through no code design, AI driven personalization and enterprise grade hosting. Before webflow, you helped shape some of the world’s most influential technology companies as CTO of Shopify, ServiceNow, Zynga, and as SVP of Engineering at Slack. That is quite the resume and there are lots of places I want to dig in and there, there are things they haven’t even listed there that I love to talk to you about. But Allan I’d love to start these conversations by asking folks their memories of their first job. What, what are your memories of your first job, Alan?

>> Allan Leinwand: Okay, thanks for having me aboard and very kind words. I’ve been very fortunate in my career so far. my very first job, I’m going to really date myself, but honestly I was a paperboy. I rode a bike, which, well, don’t think was a 10 speed. I think you, you know, stop the pedals in order to break on it. And I, deliver papers. So, that is my memory of my very first job. And I, it wasn’t the delivery of the papers in the morning that was the intimidating part for me. It was the going up every two weeks to the houses and asking for them to pay the, I want to say two or three dollars that we. For the monthly subscription. That was the intimidating part for me. I learned quickly I’m not in sales.

>> Craig Gould: You know, it’s maybe it’s not surprising how many C level people I’ve been talking to that that was their first job. I don’t know if it was just the, the prevalence of that first job, you know, or if there was something about that job that kind of prepared people for the realities and kind of set them on course for a trajectory. I mean, I mean you’re learning pretty early that you, you gotta get in at the crack of dawn and you know, and kind of hit it, you know, rain or shine. Right?

>> Allan Leinwand: Yeah, I mean, I think, I think the thing I learned in that particular role, if I reflect on what you just said, is responsibility. I felt the responsibility of getting up early every day no matter what. You know, the throwing those newspapers in the canvas bag and riding around the neighborhood. And I also think I felt a sense of pride, like I was the one that got to do it. I was the one that got to deliver that I was up to your point before everyone else, before I went to school and there Were people that actually, you know, might be so hard for some of your listeners to be, but that they waited for the paper every morning. They were dying for the paper, for the news. And I sort of felt the weight of that. and it was pretty important. I felt important, I guess, and I felt like what I did was important. And that was very gratifying.

>> Craig Gould: Did you have pretty good aim? Did you break any windows?

>> Allan Leinwand: Don’t recall breaking any windows. this was in Connecticut when I was much younger. And there’s big yards and big, big lawns. So it wasn’t like I was riding on the sidewalk every 10ft throwing a paper. It was like riding up a gravel driveway, throwing the paper on the stoop, going to the next house, you know, maybe 500 yards down sort of thing.

>> Craig Gould: So, Allan you know, like we said, you’re, you’re currently cto in the last four or five jobs have either been, you know, head of engineering or CTO at some of the country’s biggest brands, but back before these leadership positions. But after the paper throwing, you know, your first engineering jobs, HP and the very earliest days of Cisco, I think if, if I understand the story right, you were within that first 15 to 20 engineers at Cisco. I think you showed up before John Chambers did. Right.

>> Allan Leinwand: so technically I think I was like employee 100 something at Cisco. And there’s probably about 40 people in engineering. And I did show up before John Chambers. John Morgridge was the CEO at the time, but I’d actually been interviewed by Len and Sandy, who are the co founders of Cisco. and I actually took an interesting role. My first role, believe it or not, wasn’t in engineering. I took a job in the training department. And the reason I did that, because I want to learn everything. I want to know about every protocol, every single thing. And I figured the best way to do it was stand in front of 35 strangers every week and teach them everything you knew. So John Chambers was in one of my training classes and, when he was a new hire, he was a director of sales at the time. And he came in and was, I think he’s director of sales, I don’t know, regional director or something like that. And he came in and sat through one of my training classes. That’s when I first met John. So, yeah, Cisco is quite small. But I eventually did, go into the engineering department at Cisco and I wrote code for both router code and network management code early on in my career.

>> Craig Gould: One of the interesting things I’d like to talk to you about in your career is that it seems like you’re a really curious person. I want to come back to curiosity at some point, but it seems like when you got into network engineering, you really dove deep, and you dove deep for a really long time, and then there’s a point in your career where you started to kind of apply this collective background of knowledge to going in new directions.

>> Allan Leinwand: Yeah.

>> Craig Gould: And so can you kind of talk about that, that evolution of going from really, really deep to, you know, applying that knowledge in other ways?

>> Allan Leinwand: Yeah, I think, I think you kind of got it exactly right. I really believe that as an engineering leader, you have to be able to go deep and you have to be able to get into the details. And I was fortunate enough to start my career in a pretty hot technology, which was networking at the time. You know, there’s a saying, and I’m going to get it wrong, but there’s something like, you know, 10 algorithms in all computer science, and everything’s a derivative of that. and networking has graph theory in it, it has array theory in it, it’s got mat in it, it’s got queuing theory. There’s all these things that apply to networking in various ways that you’re right, I went very deep in NETworking for probably 5, 7 years of my career. But then I realized I could take those algorithmic learnings, the metaphors, or even just the, algorithms and how they’re deployed, and look at various other parts of the business. So I really saw my role as going beyond what technology does, but applying that technical knowledge into a strategic part of the business. And, you know, my very first leadership job was a management position at Cisco. I remember thinking that now I needed to not necessarily be the most deeply technical person there, but be able to be a sounding board for people that were deeply technical, to be able to have that deep technical conversation and at the same time help people pull back slightly and understand how that technology applied to the business. And that’s really something that I, I’ve loved doing. You know, you, you, you rattled off a bunch of companies I’ve been super involved with, but I really have never really been an expert in anything. I wasn’t an expert in E commerce, I wasn’t an expert in, you know, communications at Slack. I wasn’t an expert in workflow as a service. Now what I was really, really good at, I think, was hiring great teams, understanding technical patterns and algorithms, and then figuring out how to apply those to the needs of the business. One thing I like to say is, like, I take what I do really well, I learn a market really well, and then I kind of pivot 10 degrees every time just to learn a new market, because I’m curious about it. And when I joined webflow, we run millions and millions of websites across the planet. you know, hundreds of thousands of people logged into webflow at any point in time. I didn’t know website development when I got here, but I knew I could dive in and learn, and I knew that I could take what I had in my backpack of knowledge and apply it to a new market space. I also don’t want to go do what I’ve done before. I want to learn new markets. I want to understand how I can bring that knowledge to teams, help them set the right strategic direction and help them get the right clarity on what to build next. Because it kind of does go back to those algorithms every single time.

>> Craig Gould: You’re talking about pivoting 10 degrees, and I just imagine being in your shoes and coming in and leading engineering organization. And I’ve worked alongside engineers in Silicon Valley before, and there’s some personality quirks, eccentricities, in. In my imagination, it. It seems like one of those challenges would be walking in and garnering the engineer’s trust, especially if you’re coming into a new product category that you haven’t been in before, being able to establish that you know enough about what they do and that you know enough about where the company’s headed that they can trust your leadership. Am I imagining that scenario correctly? And if so, how do you go about establishing that trust with your engineering team?

>> Allan Leinwand: Yeah, I mean, that is a challenge every single time. I think you started this conversation mentioning curiosity, and I think being deeply curious is something that I really like to do. Sometimes people get intimidated by that. I’ll come in and I’ll drop into a Slack channel, or I’ll drop into a meeting and I’ll just ask what I consider, like, five whys. Why are we doing it this way? Why do the Architect that way? What’s the history behind that? Why did we not consider? Or, did we consider something else? And sometimes people, you know, bristle a bit. It’s probably the nice way of putting it. Like, what’s this new guy coming in with this big, fancy title and m, why is he asking questions about what we’ve been doing for the past five years? But I. Hopefully they get to learn my personality enough to really realize that. I’m just curious because I want to understand. I want to understand How I can then help architect the culture. Because, you know, at the end of the day, my role goes beyond technology, and it goes into figuring out how you can build a culture tied to the technology. And sort of at. At each stage, I’ve learned that scaling teams requires more than just building the right answers or building the right systems. It’s about building an environment where teams can be curious, do the best work, have that intellectual debate. Because at the end of the day, it’s like when you have that honest, open, intellectual debate, you can deliver the most impact. So another thing I do is, you know, it’s Triton. I’m sure I can remember who said this in the past. I’m going to butcher the quote, but somebody said, you know, praise in public, you know, skull in private sort of thing. I’m, a very, very strong believer in that. So if people are doing the right things, you’ll see me in sock channels highlighting what they’re doing. If they’re doing something maybe that’s as culturally incorrect or maybe not down the right technical path. I’ll, maybe talk to them privately. So I think, you know, to answer your question very directly and concisely, I’m deeply curious. I go deep into the code, I read the code. I want to make sure engineers can trust me with the decisions that they’re making. I don’t ever pretend to understand the intricacies of everything in a 5 million line code base, but I think I am skilled enough and have been around enough to ask the right questions to earn their respect and then make sure that I praise them when I see them heading in the right direction and sort of, like, guide them when I see them head in a different direction?

>> Craig Gould: Privately, can you talk about some of the things that you touched on there in terms of some of the challenges you face in having a distributed workforce? How do you effectively establish, set up, and manage teams? What are the challenges of managing technology versus managing people?

>> Allan Leinwand: Fortunately, in my role, I get to manage both, which is kind of the fun part. I think you have to love the technology, but I think you also have to love managing people. challenges in today’s remote workforce are one, trying to build that connection. Because, you know, we’re all in 2D, right? We’re all in this, like, zoom interface all the time. And, you know, when I get people together in person for the first time, I have to play about how tall are you? Game, because you never know how tall you are because you’re just a little zoom box. but I think that one way to manage that is to take the time to communicate clearly, to take the time to over communicate in whatever medium you’re over communicating with. I happen to use Slack a lot, so I spend a lot of time communicating in Slack. I think that the other thing that we do at webflow, and we did it in some of my previous companies as well, we encourage people to get together periodically in person. And this isn’t purely social. I think there’s a lot of power in people getting together and getting something done. What I mean by that is I’ve asked teams if they’re going to get together, have a goal, yes, you want to do dinners, miss some social times and things like that, but deliver something, get together and build something together. And there’s something just so communal about that, that, hey, we all got together. I have a team just this week got together in Washington D.C. i think they said 18 or 20 people got together and the output was a new feature and function that got shipped into production today. So it’s just really, really invigorating for people to see that. It also is super powerful to like have that human connection and to deliver something together. And I think that’s been sort of a little bit of a secret sauce that we’ve deployed at various times.

>> Craig Gould: I’ve worked as part of a remote team before and you know, there have been times where I’m just like, I wish I could just walk into a room, these people and go up to the whiteboard and just start. Because I’m a very visual, very, you know, let’s, let’s chart it out on the board sort of person. And it’s great that you provide those opportunities for your team.

>> Allan Leinwand: I think that’s true there. You know, it’s funny, I was just talking about this meeting that they just had in the nation’s capital just an hour or two ago, and one of the people in the meeting was like, yeah, those two days were great. But then I just really want to go back home and like, just have a little bit of quiet time. So there’s, you know, there’s different personalities with different types. And this person was commenting, I can’t wait to get home and sit in my quiet space and just code for another two days because I. My social battery is kind of drained. I was like, that’s great. But you know, they also saw the value in that. So I think it takes, it takes all types maybe is probably the best way to think about it.

>> Craig Gould: Craig, tell me about Webflow. What are the main differentiators for Webflow versus somebody like WordPress.

>> Allan Leinwand: Yeah, I mean really the difference is Webflow is building sort of this website experience platform. And what that means is people can design beautiful sites, build those beautiful sites both visually and in code, and they can launch full stack websites and web apps. So you know, when you think about WordPress, it is a different sort of environment that people are allowed to build. We think about building visually, we think about building both for the marketing Persona as well as developer Persona and bringing it all together. So we see people that are, you know, building the sites, designing the sites, launching the sites in seconds, getting them delivered globally with, you know, incredibly good SEO scores, incredibly good performance scores. And then we see people doing things like optimizing the site, such as AB testing, personalization, localizing the sites into multiple languages, having analytics on the site, having a very powerful, CMS or content management system behind the site. All that is possible on the webflow platform. So at the end of the day we think of it as like an AI powered website platform builder that allows brands to really deliver amazing experiences. and you know, of course in this day of AI where we’ve leveraged AI throughout the product, we see sort of interesting thread of capabilities to do, you know, image generation, content generation, text generation, even to like surface different options for people when they’re landing on a particular website. Maybe wherever you’re sitting, Craig, and where I’m sitting, we have different views of the website when they appear. websites are more dynamically, they’re more dynamic properties than people think they are. And I think when you think about some of the older technologies out there, I don’t think they’ve really kept pace and where the web is going to.

>> Craig Gould: What is the spectrum of businesses that use webflow? I mean, is it, you know, is it everybody from the individual to the small medium business to enterprise, big brands, does everyone enter at the same point or are there different levels, you know, based on the, the size of your business needs?

>> Allan Leinwand: Yeah, I mean right now there’s, I kind of classify the website market space in three different areas. There’s kind of like very static, we call them presence sites. there are a lot of people that use webflow for that, but probably not our target market. There’s also very, very complicated websites. Think like integrations into backend ERPs and you know, multi millions of dollars of websites. that’s probably not our space, but everything in the middle is what we’re shooting for. So yes, it is individuals, it is agencies that are building on behalf of small to medium businesses. It is enterprises like the New York Times and Dropbox and you know, lots of other folks you can find on our website that are building as well on webflow. So it does very large portion of the market. But if you need like a one page website that you’re never going to change, it’s fine. Not us. And if you need like, you know, a $5 million build into some backend ERP manufacturing system of some sort, that’s probably not to see, therefore just kind of everything else in the middle.

>> Craig Gould: So let me ask you this. I, I feel like in researching and listening to you, speak to other people, I feel like I got the impression somewhere in there that we may be headed towards a place where these dynamic sites are capable of generating highly customized sites depending on who the visitor is that, you know, especially with how many cookies are out there and you know, our knowledge of who’s showing up to a site and where they’ve been and what their tastes are, you know, can you talk about that capability of serving someone something that’s really specialized to them versus a static, standard branded site that’s the same for everybody?

>> Allan Leinwand: Yeah, that’s in the vein of what we call optimization or personalization and sort of in the past, you know, the recent past, maybe two or three years ago, marketing teams would need to generate different landing pages or different views of the site based upon geography or maybe based upon a particular segment or demographic that you were landing on the site based upon your cookies or your language settings or whatever. but these days with AI, you can generate hundreds of different variants, hundreds of different potential views of that site dynamically. And the really fascinating thing about that is that, with AI also, given the fact that we host the sites, we see the traffic, we get the logging information, we actually know which of those variants, we call them experiments actually convert the best. That’s what a website’s for. In the dining website, at least in our world, is for converting something. It’s converting someone to buy something. It’s converting someone to fill out a form. It’s converting someone to look at a product detail page and call sales. Or you’re looking to land someone for your business. So then the question becomes, is the button in the upper right hand corner or down in the middle of the page the best? Should the button be red or should it be blue? Should it be in, you know, I don’t know, comic Sans font or, you know, Helvetica font? I have no idea. I’m not a marketing Person, as you can tell. But these sort of experiments and these sort of things that people are doing with websites are so powerful and they really are helping drive a much larger conversion. The other thing we’re seeing that I think is really fascinating these days is for the past couple decades, marketing teams have built websites, to convert and they’ve used SEO, you know, search engine optimization, and they spent lots of time understanding how SEO works and how Google rank algorithms work. All that’s kind of going out the window these days. So because, you know, you and I go to chat GPT and we go to Claude and we say, you know, tell me the best Italian restaurant in San Francisco and Italian restaurants, or tell me the best business software for chat in my company. those products want to know how they’re going to be surfaced in those, and in those engines and how those particular chatbots and answer engines we call them are going to talk about their products. So there’s this new thing called answer engine optimization or AEO versus SEO. And when I think about, you know, your question, personalizing website, I think about it being for two different Personas. There’s a human Persona and there’s the bot Persona. And how do you actually optimize that and set up the website in a way that all the experiments, all the variants, all the different things that come in that can feed that site and tell it how to respond, it’s just a fascinating world. There’s so much data and it’s changing so quick. It’s. It’s really, really fun to work on.

>> Craig Gould: You know, I think about the big LLMs looking for answers, and you think about the individual users landing on pages. But we’re in the middle of the boom of agentic use cases. You think about all those agents that we will be sending out on our behalf, and how does someone that’s managing a site understand and you know, respond to an agent that’s showing up on someone else’s behalf? And what, you know, what’s the most optimized way to respond in that category? I mean, we’re kind of in the thick of it right now, aren’t we?

>> Allan Leinwand: Yeah, we really are. I mean, the companies that define this next market aren’t just shipping like incremental products. Right? The thing about how they scale their organization, how do they build innovation, how do they make that part of their DNA? Because, you know, when the next model drops tomorrow or the next day or a week from now, how are we going to innovate? How are we going to like make the product resilient and able to handle that change. Because when I think about, you know, webflow’s mission, our mission is to bring, you know, development superpowers to everyone. And that means let people develop for the web no matter what they’re trying to do, and make sure that the thing they’re trying to do, which is get someone to land on the website or get a bot to land on the website and then have it convert into something for the business, is something that, you know, CTOs need to think about. They really need to think about not just building infrastructure, not just building technology for technology’s sake, but aligning it with the strategy the customer needs and making sure that delivers on behalf of the business. Because that’s, that’s the real fun part of it. In my job, I think I get to both be, you know, we started this conversation talking about diving deep into technology, networking and bits and bytes and packet formats and I love that stuff. We also have to think about all the hard parts of the business and bringing all that together is just, just really a lot of fun.

>> Craig Gould: Can you talk about how AI is touching your day to day, but also the day to day of your engineering staff? Right? I mean it’s, you know, 10 years ago the, you know, the day to day of the CTO and those engineers would have been a little bit different. And I guess, you know, I would love for you to respond to the notion of whether or not AI is actually replacing anyone or is it just enabling people to be more efficient with their time and move at a, at a different pace?

>> Allan Leinwand: You know, I don’t believe AI, ah, replaces engineers. I believe that AI augments the best engineers to be more productive. And from the moment an engineer joins Webflow, they have access to a complete set of AI toolkit. So we give them ChatGPT Enterprise. We use a, we use cursor. we have a product we use called Augment Code, which is a, a system that basically allows us to index our code base and talk, chat with our code. we are not replacing engineers with AI. We are absolutely letting people be more productive, have more power. Just to give you an idea like our cursor usage is up 80% in the past, two or three months. Our cycle time from the time it takes someone to put something into JIRA and actually ship to prod, is down 21%. Our deployment times, how fast we deploy, every single day, it’s up about 11% off a really, really high baseline. And all this while making sure. That, you know, change failure rate, which is the amount of time we push something to prod after roll it back, it’s less than 2%. So I am invigorated by AI as yet another tool in the toolbot of engineers. And the other thing that I think that is counterintuitive is people think that AI is going to place junior engineers. I don’t think that. I think junior engineers are allowed to uplevel their skill set faster with AI. And I’ve seen that personally, I’ve seen junior engineers or engineers just starting their career out of college sort of go up the career path almost six to eight months faster than they would have in the past. Because now, instead of like having to have a meeting to ask somebody about this particular system to understand how the company does X, Y or Z, they literally chat with the code using things like augment code. Hey, why do we do this in this particular, how does this work? How does this system tie to another system? And you see, these early career engineers just dive in, curious, and get the answers faster. Not, always 100% correct, to be fair, but it’s pretty close. And it allows them to move up that career ladder so much faster. So, I’m not a believer in that AI replaces engineers. I am absolutely believer in that AI augments senior engineers who do great work, and it accelerates career paths for more early career engineers.

>> Craig Gould: And it sounds like it can really help expedite bug fixes. Right?

>> Allan Leinwand: Yeah, we are actually seeing a lot of that here as well. I still do fix bugs. I’m still in pr, I’m still in it. And I do love going in and challenging the LLM sometimes. We have a channel here inside of webflow. We call it UX Papercuts. It’s like all the little nickname stuff that just drives users crazy. There’s a form. So you fill out a form and you say, you know, hey, this button clipped improperly, or this text looks like it’s formatted wrong, or the margin here doesn’t match the margin there. And like, all these little things that happen. And I literally take the text out of the Slack command, I posted an augment and say, fix this. And, you know, more times than you’d like to think, it just fixes it. Or I’ll go off and like, do something else while the agent sort of grinds in the background for a while. And then I’ll test it locally, verify the code, make sure the code looks right, make sure the code is not doing something wonky. And Then I’ll push it out and it’s, it’s pretty amazing to watch that happen. So yeah, bug fixes, particularly for the things that are just rudimentary work that, you know, that’s what agentic is for, is like take that grunge work away from people. seems to be very, very effective for us.

>> Craig Gould: I think I heard you say before that you guys had gone in and fed the transcripts of all your product videos into an LLM M. And now if someone is, I’m a user, I’m trying to use webflow, I hit a roadblock. I can a rudimentary question of, of whatever in a little chat box and it will take me to the right spot in the right demo video to show me the answer to my question. that’s, that’s a pretty powerful solution, right? I mean my, my wife’s an instructional designer and that’s a great use of those resources. Right.

>> Allan Leinwand: Actually that comes out of an intro hackathon. It was about a year and a half ago we ran an intro hackathon. I might have been on GPT 4 or 3.5, you know, back in the day, a couple years ago. And the yeah, it was exactly that. So we basically, you know, took the transcript of every one of our webflow University videos and there’s hundreds of them ran, to a rack. And then essentially if somebody asked a question like how do I do X in webflow? If the question, if the answer was available with a specific confidence interval, we would literally, instead of saying go watch this video, here’s your URL. We would say click here. And it would then the video would say if you’re trying to do so and so like literally give them the right spot in the manual, if you will. And it’s been super cool to see people use that. It’s a pretty highly used func feature.

>> Craig Gould: Tell me about innovation. You know, it’s gotta be top of mind. I mean you’ve been lucky enough to work with some founder CEOs that are just really rabid about product and you know, just being product consumed, you know, customer consumed, experience consumed. Who’s driving innovation? Is that collaborative across the top of the organization or you know, are you engaging, challenging your, your guys to, to figure out how to, to take the technology in, in new directions? How does one set that course and how do you, how do you manage it and how do you, how do you encourage it without, without putting a lid on it?

>> Allan Leinwand: Yeah. so thoughts of thoughts there. So you’re right. I have been involved with amazing founder CEOs that live, breathe, don’t sleep, just live their market, live their customer experience. And I think that is one of the more effective environments I can be in. Like I said, I, I don’t come into some companies being an expert in this space, but I generally look for founders who are still involved, very innovative, and can see around three corners faster than m anyone else. That is, that’s a great combination. So that, my job as a CTO is to really drive that innovation. Now to your question. How do we, like, not one, run after every shiny object on the planet and two, make sure that we do run after some shiny objects? so for most organizations that I’ve been involved in, we do carve out a portion of engineering for innovation. And I think the most important thing that I try to establish up front is we’re going to try some things and probably 8 out of 10 of them we’re going to stop. And that’s okay. So I celebrate both the success and the failures of those. I think it is. You have to take, you know, sports analogy. You have to take shots on goal, you have to give it a try, you have to try some things, and if it fails, that’s okay because it is our job to push the envelope and it’s our job to think about what’s next. And we don’t always get it right. You know, matter of fact, most of the time we don’t get it right. So very directly, I make sure there’s always a portion of the organization that is in what Jeffrey Moore calls the, you know, innovation zone. always trying to make sure that there’s a portion of the organization that is pushing us to the next level. Thinking a year out, really just pushing the company to think about what’s next. Whether we really see that market or not is kind of not really relevant. What’s relevant is we’re pushing ourselves to be innovative. The second thing I do is when that innovation does catch fire and it does go from 0 to 1, I’ve often put a process in place or a system in place to let it what I call graduate back to engineering. Because, you know, generally the people that are most innovative, the folks that, you know, wake up with a crazy idea that you kind of look at and go, maybe, you know, they’re great 0 to 1 people, but they’re generally not, you know, 1 to 100 people. They don’t think through how to build it for scale, how to integrate with the systems, how to do the Logging how to do the security implications, how to make sure it scales for performance at 10x, all that good stuff stuff. So there’s always a, like a demark point, if you will, and I literally call it graduation day or something, graduates from innovation into engineering. At that point it’s got to be fully staffed, it’s got to have product people on it, it’s kind of growing up, it’s kind of a maturity cycle. So to answer your question pretty clearly, always make sure there’s somebody or some portion of engineering that’s allocated for innovation, but that always makes sure there’s a way for that innovation. When it does catch fire, when it does feel like there’s a market there, there’s somebody that then gets staffed and allocated to pick it up and run with it. And scale. Because the world of like creating something from scratch, from 0 to 1 versus a scale, people that take it from 1 to 100, they’re different teams.

>> Craig Gould: Do you find that, that sometimes the, the original idea from that, that dreamer winds up being of a different scale than what is capable of being replicated and launched in a stable way. I mean it becomes right sized.

>> Allan Leinwand: Yeah, I think, yes. There is always an interesting challenge of taking a new technology, whether it’s a database backend, whether it’s a new UX paradigm, whether it’s the way you’ve recrafted the user experience, whether it’s the mobile side or something, or the desktop side of something, and thinking, okay, you’ve tried it on 10 people now, what happens when 10 million hit it? How does that actually work? and sometimes people, you know, the light bulb goes off and they go, okay, here’s what we need to change. Other times they go, I don’t know. And that’s where you have to redeem other people. I remember back at, you know, Zynga, we launched a game that went from zero, I want to say 40 million DAU in something like five days. You know, the team that built the game was not the team that scaled the game. you know, I remember back in, you know, the service nowadays we’d launch products that would have to handle quite a few transactions per second. Like literally out of the gate. We put something into production. Before you knew it, hundreds of thousands of instances were using it. There’s something so amazingly cool about that for the engineering teams to see that happen. But again, I think that the people that sometimes drive that innovation have that spark are not necessarily the teams that scale it. And probably they don’t want to Be.

>> Craig Gould: Right in the middle of your career. You spent time as a venture capitalist. You had Panorama Capital. Can you talk about that shift and what that was like for you given your past being deep in networking and maybe how that experience influenced your future and those CTO roles that you’ve taken on since that period?

>> Allan Leinwand: Yeah, ah, I did spend seven years in venture capital. It’s kind of like what I call the right turn in my career. I just. The honest to God truth of why I did it is because I had been involved in two vc, three, two or three VC backed companies at that point and I never understood what happened behind the VC curtain. I just curious again, I was like, why did they care so much about ownership in a cap table? Why do they think so much about depreciated cash flow? Why are they asking me these questions? And I was had the opportunity through somebody I worked with in a previous startup where he said, hey, come on over to the, come on over the dark side. Give it a try, see what you think. I will confess the force is strong in the dark side. But I learned a lot about how people think about business and it sort of educated me in terms of how to align the business outcome with the technology. I also learned that I think I learned to be a better hiring manager because in the world you probably see six to eight to 10 companies a week. You say you know, yes to three a year. So you learn very quickly to pattern match in terms of do you want to work with this person over time. So I think it’s maybe be a better hiring manager. It’s maybe be able to be a quicker judger of talent and it helped me understand the business model behind technology. But I didn’t quite get before as a venture capital was capitalist, was this is really cool technology. Why isn’t everyone buying it? And well there’s actually a lot more that goes into sales cycles, a lot more that goes into making the business case. There’s a lot more that goes into making sure the technology hits the market and has the product market fit. I don’t think I even knew the words product market fit before I went to vc. so it educated me on that. but to your point Craig, it got to a point where I was itching to build again. So that’s why I left VC and went back into being a builder. It just, yeah, the itch wasn’t scratched.

>> Craig Gould: Being a venture capitalist, I know that a lot of the bigger VCs will have operators in a network that they’re able to provide to founders as a sounding board, not. I saw that you’re currently part of a Norwest operator collective. And what does that look like for you? You know, how formal is that role? Is it, Is it where you’re kind of, you know, you’re on the other end of a bat phone for Norwest? Are there events that you show up and are able to provide kind of a roundtable? What does that wind up looking like for you?

>> Allan Leinwand: Yeah, ah, I do this for a couple different firms. That one’s one of my LinkedIn profile. They’re the more formal one, if you will. but yeah, it’s kind of both of what you described. It’s one being on a bat phone, because what VCs are trying to do is they’re trying to do technical diligence. So the question is always like, have you heard of this thing? Do you use it? Would you buy it? How much would you pay for it? They’re trying to do a, you know, a TAM and SAM analysis on the product, which I’m happy to do primarily because, VCs do see things sooner than us in the operation space C. So I will get a lot of, you know, technology flow my way and seeing new cool things that are just being launched, that’s kind of fun. Norwest, I do all three of those. I’m on the end of the bat phone for them when they’re looking at deals. There is a collection of us that get together on a regular basis, so there’s a cohort of us to get together and sort of build nice pairwise conversations with fellow CTOs and CIOs. And third, there are events where they’ll bring us all together and with companies and we’ll sort of like cross mingle and cross pollinate a little bit. those have all worked well for me. The ones that don’t work well is, I’ve been involved in some VC organizations. Where, did I say this politely? I won’t say politely. They bring you in for a day and they, you know, parade 15 portfolio companies in front of you with the, with the, with the, the question of which one are you going to buy from today? And, that doesn’t work well for me. different VCs, like different companies have different ways of doing business. I prefer to be more engaged one on one, more engaged with a peer group and more engaged periodically as opposed to it being a transaction discussion.

>> Craig Gould: How is that industry changing? Because, I mean, it, it seems like it’s you know, I think of, I’m trying to remember, I think I saw somewhere where, you know, 30 years ago the total, the total VC community was like 4 billion. And now you’re not even showing up, in the top hundred list. Well, maybe a top hundred if you’ve got a 4 billion. Aum, can you talk about what are the, realities that the VC community is having to face? Especially when it sounds like a lot of them are trying to chase down AI opportunities. Right. I mean it’s kind of dog eat dog out there right now. Right.

>> Allan Leinwand: I mean I haven’t been in the industry since 2010, so kind of dating my knowledge here. But from what I can see from the outside in, there’s a lot of money chasing great deals. valuations are pretty high from what I can tell. But maybe I’m wrong. Maybe there’ll be like, you know, outsized outcomes for people. but I think you’re right. My perception from the outside in is there’s a lot of folks that are finding a lot of different bets in hopes that the multiples will give the return that allows them to raise their next fund and continue investing. and there’s obviously a lot of really, really good investors out there that have been through a couple cycles. They’ve been through the cloud cycle, they’ve been through the mobile cycle, and now they’re going through the AI cycle. And like I said, I happen to have connections into quite a bunch of VCs, so I get a lot of calls and a lot of like, information coming my way, which I consider as an asset for workflow. And I also think it’s, it’s helping me stay intellectually honest and pretty curious about what’s going on.

>> Craig Gould: You mentioned earlier that being a VC you felt like made you a better judge of people and maybe help you figure out hiring, a little bit better. Can you, can you talk about the challenges of hiring the right people and how even just, you know, we. Again, you know, it seems like AI enters every conversation even, you know, for you, trying to hire engineers. How are you even able to, to judge whether someone, you know, at what level is someone using AI to, you know, or, you know, is that even a concern? I mean, is, how do you, how do you judge people in this day and time?

>> Allan Leinwand: I mean, AI just isn’t a tool. Webflow, it’s fundamental to how we do engineering capacity, we do velocity, how we judge our engineers. So we actually adapted our hiring to reflect this. AI fluency is sort of integrated into our interview process. We have AI challenges. We allow people to use AI. We look at that both from the individual contributor, the IC level and the manager level. And because AI is sort of central to everything we do here in our work, we’re actively seeking people who are excited to lean into this technology and push its boundaries and do the next cool thing with AI to deploy the, you know, bots of agentic AI and have a thousand agents out there running and try the best tools and the newest things. So we’re looking for those, those people that want to do that. one of the things we did tactically is, which I know a lot of companies are struggling with, is we set up sort of a test bed with a, ah, portion of our code base and a portion of our infrastructure. And we essentially allow engineers to like go try whatever you want in the world of AI, we don’t let it open to the entire code base because of course worried about security and confidentiality and that sort of stuff. But we want eng be able to go try the latest and greatest, sexiest thing out there. and then we just look for usage. So vendors bring in a tool and they want to sample it and they want to give it a try. And then we look at, you know, dau daily active use. And if people continue to use it, then we think about bringing in for an official trial, going through the security hoops and doing all the right things. we really tried to, you know, lean heavily away from the risk. So we, you know, we said we’re going to go for a higher risk profile. We’re going to set up an environment where people can test these tools quickly because we think that the best engineers are going to want to try the m latest and greatest. And what we don’t want to do is put a lot of friction in there. A comment I got just last week, the week before, which I thought was super gratifying, is a brand new engineer DM me in Slack and said, you know, I really wish I had known how much we were using AI before I got here. I was at a previous company and like I couldn’t touch half this stuff and it was so frustrating to me. And we just have it here for everyone and it’s really, really cool. So yes, AI enters the conversation every single time. But the way we think about it is it’s just going to be part of our lives and we want people to lean into that.

>> Craig Gould: What do you look for in employees? whether it’s at the engineer level or Even the lieutenants that you have right under you. What are the human elements that you’re looking for in the people that you want on your team?

>> Allan Leinwand: I, I, you know, we’ve definitely wanted to be curious. I definitely want them to be technology experts and be able to dive in deep and own problems down, all the way down, five, six, seven layers, down the stack from where they’re at right now, I definitely want them to be technology signing boards for their teams. Doesn’t mean they’re architecting everything, but they’re able to have the conversations I’m also looking for. People are very transparent. I’ll never forget Stuart, Butterfield at Slack had a little wooden plaque outside his door, which just, just used to be awesome. Every time I’d walk in, it said, bring the bad news, the good news can wait. And I mean, or, bad news first, good news can wait. I’m paraphrasing basically. You know, another person I used to work with, at ServiceNow, used to say, don’t hide the ball. Like, just, just, just come in and tell us, let’s talk about the problem. Let’s, let’s be actually honest. Let’s, let’s talk about it together. And I’m looking for people that, that do that. So when I’m interviewing people, when I’m going through the interview process or the hiring process, I’m really looking for people who can be technically deep, transparent, describe the complex in a simple way, and really want to just think about how do we move the business forward together. politics don’t really work well for me. You can probably tell just from talking to me for the last hour. I’m a pretty transparent person, and I really want my teams to exemplify that.

>> Craig Gould: If I were a VP of engineering, or, you know, a senior engineering manager, and I’m aspiring for, for a CTO role, what advice can you give me? You know, I mean, you know, you’ve climbed, that mountain. You’re also responsible for bringing people up that mountain.

>> Allan Leinwand: Yeah.

>> Craig Gould: What can you suggest to somebody? Who do you look for in terms of the leaders? And how can somebody kind of, refine those characteristics in themselves in order to make that climb?

>> Allan Leinwand: Yeah, I think technical skill is absolutely essential. But what defines great CTOs and great engineering leaders is the ability to align the technology with the business. It sounds so easy to do and it’s so hard to do. You know, I think the question I spend a lot of time with my directs asking is, that’s a really cool technology, but what problem Are we solving? And maybe the other question I ask a lot is how will we know we’ve solved the problem? Will it because latency will have gone down? Is it because product adoption has gone up? Is it because cost has changed? Is it because scalability has changed? Because queries per second is now 10x what it was before one third the cost? Why are we doing this and why does it matter to the business people in technology? Because we all love technology. We love to get in the bits and the bytes, love to talk about the bits and the bytes. I think great engineering leaders can take a step up from that and say, the reason we’re doing this and the benefit to the business or the benefit to the engineering organization or the benefit of the code base or, the benefit of the culture is in a very clear and concise manner. It’s just such a powerful thing that I’ve learned from so many great people in my career to be able to not talk tech, but talk tech and adoption and why. And I think just, it’s a really, really fascinating skill.

>> Craig Gould: Allan I really, really appreciate your, your time this afternoon. If, if people wanted to keep track of, of you, if they wanted to keep track of webflow, where, where’s the best place for people to keep an eye on what you guys are up to?

>> Allan Leinwand: Yeah, feel free to follow, me on LinkedIn. I’m also on X Twitter. Those are the places I tend to hang out most in social. so, yeah, feel free to reach out to me there. if you want to reach out to me an email. I’m not hard to find and I do respond a lot. So happy to, happy to take questions and comments from anyone. I think one of the best things people can do in this industry because is always changing, always growing, always expanding is share the knowledge and just connect. So, I think it’s a very powerful thing. back to networking. So it all starts to networking. Right? So I think going back to networking, networking humans and networking networks has always been fascinating to me.

>> Craig Gould: Well, again, I really appreciate you being my guest today, Allan

>> Allan Leinwand: Well, thanks, Rick. All right, well.