Chet Kapoor: Allan, welcome to Inspired Execution, and thanks for being here.

Allan Leinwand: Thanks, Chet. Great to be here.

Chet Kapoor: So you've had an incredible career in technology, right? Setting up HP's first Ethernet and Cisco's early networks to leading teams at Shopify, Slack, ServiceNow, it seems like all companies with S, but, you know, all companies have been very, very successful in our household names, right? I mean, from a tech industry perspective and so much more. What has been an unexpected lesson that you have learned through your career?

Allan Leinwand: Yeah, that's an interesting question. Unexpected lesson. I think maybe the one unexpected lesson that I probably wouldn't have predicted if I had thought about it early in my career is you have to spend a lot more time finding and interviewing the right people for the roles. As you build a very strong engineering organization, I just sort of naturally assume by working at companies that are household names in the tech world, you'd be able to find these amazing people that just show up and walk in the door and sort of just kill it for you. And early in my career, I got some advice about you need to spend a lot more time interviewing than you think you do as soon as you get into management. And I thought, how hard can that be? But the truth is, I spend a lot of time interviewing these days, especially the great rate that I'm currently at Webflow. I'm probably spending four, six, eight hours a week interviewing.

Chet Kapoor: Wow.

Allan Leinwand: And I think if I go back to my early career and something that I probably should have learned earlier is hiring the right people makes you a better leader, makes the team stronger. And honestly, if you hire the wrong people, you spend all this time doing things that don't move the product forward, don't move innovation forward, and are just like a chain, a ball and chain on sort of like your ability to execute. So I guess if I think about something that I wish I'd learned sooner, that'd be it. Hire the right people, spend more time interviewing, and kind of always be closing in the people world.

Chet Kapoor: Can I double-click on that just for a second? There's many techniques on hiring, right? And you would agree when you were a first-line coach, I use coach and manager interchangeably in this case. . Your first-line coach, your hiring techniques are probably different versus when you're a senior executive and you're a CTO, right? And so do you have you on both situations when you were a first-line coach and now? I'll give two contrasting styles, glass is half empty or glass is half full. Have you found that to be that you've changed your styles as you have gotten more senior or is it still the same?

Allan Leinwand: I think I've gotten to be a tougher interviewer as I've gotten more senior. I think I gave people a little more grace and a little more latitude and a little more of, oh yeah, I can see how they could grow into the role. And I think as I've moved up the stack from, manager to senior manager to director to VP up the stack, I think I've gotten to be a harder interview because I'm really taking a look and thinking, will these people make a difference? Will they also attract talent? Will they bring the right innovation culture? Are they a cultural fit in terms of their style and how they lead teams? And I think the other thing that I do sort of honestly with just the grace of my title is if I find someone that's sort of in the org that we really want to hire, say a really interesting individual contributor or even a manager or even a tech lead somewhere in the org and the team's really excited about them, what I generally do is I reach out via an email. So just a cold email and say, hey, I understand you're interviewing with our company. We're really interested in you for this role. I'm Alan. I'm the CTO. I will make time on my calendar today or tomorrow if you want to talk about anything about the company. And I usually send that email for folks that are, you know, maybe we want to push them over the edge. We want to hear if they're really serious about us or not. And you'd be surprised, like I said, maybe just with the title that comes with it, about 70% of the time people send me a note back and say, yeah, let's talk. And I consider myself a pretty good closer, but I also consider myself a pretty good judge. And a couple of those people have gone into those interviews or like those casual conversations and I've gone back to the hiring manager and said, nope, kill it. And it's pretty rare, but I do do it. And I think that becomes part of the process in order to help figure out if that person is going to be the right cultural fit and the right technology fit. And I haven't, I didn't do that early in my career, to be clear. I've only done that maybe in the last five or 10 years.

Chet Kapoor: I have, if I can add a couple of things, I've found that one is more and more I am looking for purely understanding the individual and their childhood issues is like my number one priority. Right? Because by the time I'm interviewing somebody, they have gone through skills. They have gone through the basic clock speed, skills, teamwork, integrity, all those things have actually happened. And now we're like on the final touches. So the thing is, you know, what are the issues that they will have beyond the dating game? And the second thing is, what is the potential of them making this place better than it already is?

Allan Leinwand: That's right.

Chet Kapoor: Right? And so those have been my two focus areas, but it's really interesting how much of your culture is based on the people you bring on. Right? Because the saying that, A's hire B's and B's hire C's is actually a very true statement. Right? I mean, it just, you cannot keep compromising. And I think I am an absolute sucker for speed and thoughtfully go through this, but not when it comes to hiring. Because I think a lot of these things are far more one-way doors than most people believe.

Allan Leinwand: Yeah, that's exactly right. Thinking about how do you hire? How do you bring on the right talent? How do you make sure they have the right cultural fit? Because like I was saying before, if they're the wrong fit, you're probably going to know pretty quick as well. I think you'd probably agree with that, Chet. And then you've got a long tail on how to, manage them out, go through a process, do everything respectfully. I also tell people like, treat people on the way out in the same way you treated them on the way in. So you have to like, you're kind of dating as you were describing sort of on the way in, and you're trying to charm them. And I'd like to say if, I'm interviewing a VP of sales candidate and they don't sell me, like how do they get to that role? I expect them to sell me perfectly, right? But then if you think about how do you treat them on the way out, I think you have to be professional. You have to be respectful. And a lot of times people that move out of an org, probably move out of an org to a better place at the same time, right? They probably just weren't a good fit.

Chet Kapoor: No, I agree. I agree. The saying that I use is, everybody you see on the way up, you'll see on the way down. It's a different context, but it's essentially the same concept, right? Especially people who are being successful at a very young age. I love seeing that because they're obviously at the right place at the right time, but a lot of their success is because of who they are and what they bring. And just every now and then to know that everybody you see on the way up, you'll see on the way down. So you've said there are two types of CTOs. They are thought leaders and they're builders. What do you think is the difference between them and which one are you?

Allan Leinwand: Yeah, I think there are two types of CTOs. There are CTOs that are really focused, setting industry trend, being a thought leader, being someone who really drives the entire industry forward. And then there are CTOs that are, maybe more internally focused in the details, working through the projects, maybe still coding, maybe still working on individual contributions on their own. Yeah. I like them kind of a blend. I do events like this where I get to talk publicly and I get to advocate for what Webflow is doing and how we're innovating and how we're sort of like bringing web development superpowers to everyone. But my next meeting is going way deep in the details of some of the projects that we're working on and doing a code review. So that's literally what I'm doing 20 minutes from now. Yeah. So I think the happy blend is kind of my happy place. I still do PRs. I'm still in the code. I have Visual Studio up right now. So it's just a matter of being able to do both. And that's really hard and it does stretch you and it does make you kind of, I don't want to say Jekyll and Hyde-ish, but have to compartmentalize. Like I'm doing this podcast now, which I think is great and I love advocating and I love doing this work. And like I said, my next meeting is I'm going to be in a code doing a code review.

Chet Kapoor: It's really interesting, Alan. I call it range, right? Which is, you know, you got to be able to write code and then talk about the industry and where you think the industry is going over the next two or three years and modify your perspective, right? Do you think, have you met many of your colleagues who have that range? Because it's really hard, right? Once you're there, it is damn addictive, right? It's very hard to deal with one or the other, right? Because you really do want both.

Allan Leinwand: Yeah, I think you're right. And I think I want to be in the details. I want to understand the technology at a certain level. Because honestly, if I don't have that technical depth, it's very hard for me to be credible with the teams I'm trying to lead and trying to set the objectives for and trying to innovate. Inside of Webflow, you say you like speed. I'm Mr. Can we ship this sooner? That's like my question in every single meeting. Can we ship this sooner and why not? And if I don't have that depth to go into the code and talk about the architecture and talk about the systems we're building and how this data structure needs to be rebuilt so I understand why we have another sprint's worth of work there or, hey, don't we already have that function and why can't we just call it over here and save ourselves half a sprint's worth of work? If we don't have that ability to go in and do that investigation, don't have the ability to go in and actually understand things at that level, then I think you lose the credibility with the teams you're trying to guide and innovate with.

Chet Kapoor: So let's talk about innovation for a second, right? Very different now than it was 20 years ago, right? Very, very different now. I am of the opinion, I'll put this out there, and then I'd love to get yours and we can talk about it at disagreements. I'm of the opinion that you get innovation out as soon as possible because I think facts are outside and opinions are inside. Having said that, both your company and mine are focused on building developer products that delight developers, right? That they have to delight. So look and feel, and the beautiful APIs and the beautiful experience don't come by going super fast. You have to be super thoughtful. And I find experience and getting innovation validation and things like that are actually at odds with each other. How do you resolve some of that with the teams?

Allan Leinwand: Yeah, it is at odds. And you're kind of talking about the tech debt versus innovation balance, right? That's a thing we think about a lot. So what I tell my teams, and I tell them this every single month repeatedly, sort of on a loop, and I think they're probably branded and knowing this now as I say, engineering priorities are this. Number one, and I learned this from some of my previous mentors, so I'm just completely blatantly ripping it off. But number one is fix high priority customer issues fast. So that means if something's broken for a customer, P0, P1, whatever your sub one sort of definition is, you run to that fire, you fix that. Number two, you make sure you allocate resources to make sure that FCU doesn't happen again. And that sort of avoids the compounding tech debt that breaks innovation. And number three is you innovate like hell. So what I say to every sprint and every scrum team is think about those three priorities. Do you have any P0, P1s that are outstanding? If you do, allocate some resources to solve that right now. Second, are there any outstanding, bumps in the road or potholes that you left from the last set of P0s and P1s? If so, allocate people to that. And then spend more time and allocate the rest of the team to innovation if you have any, allocation left. And what you find is that engineers generally, when something breaks, they run to the fire, they fix the issue. They completely forget about fixing the potholes in the road and they go right back to building product again, right? Because that's the long part. So if you get people on the pattern of every day at your 10 a.m. stand-up, got any sub-zeros, sub-ones? Nope, great. Got any outstanding incident remediation action items? Nope, great. Whole team's in on innovation. And if you get those first two turning really quickly, you end up with more time to innovate. So that's kind of how I tend to balance it. I tend to think about avoiding tech debt up front, and that leaves more time for innovation as opposed to, okay, let's go innovate for a while and then let's swing to tech debt and then let's go innovate for a while and let's go swing to tech debt. I mean, sometimes that's necessary, to be fair. You just have stuff that, you know, a long-running architectural change that's a big tech debt project. But the general principle of fix things, make sure they don't happen again, and then allocate for innovation is how I try and balance that.

Chet Kapoor: That's a great perspective. And actually, I like to be very specific. I like the order, right? Let's not do a demo of the latest feature first. Let's talk about the issues, the potholes like you talked about. Let's talk about what's the resolution for those. And let's talk about the really cool feature after. So people can all drool and goo and gah and go from there.

Allan Leinwand: And to be fair, we do end-of-sprint demos. We do do like demo time and get people to stand up in the virtual Zooms and show off their features that are half-baked, that are getting ready to launch two or three sprints from now. So we do like to do that as well. But we also celebrate the fixing the incidents and fixing the tech debt along the way.

Chet Kapoor: Let's talk about AI. This is, both of us have been through many different technology waves and Gen AI is the latest. What do you think is the same around this time and what's different?

Allan Leinwand: Huh, well, I've been a workflow and automation person for a while. It's sort of like been in my DNA. And what's similar this time is, you know, whether it was the internet or the browser or networking is it's all about moving us forward faster than we were before. That's how I think that's the similarity in my mind. So I'm really sort of excited to see what people are going to do with AI. We use AI inside of workflow engineering to write code, innovate faster. We're building lots of AI into various surface areas. We've launched some products. There's a lot more to come in that area. We're really focusing on, products for developers and designers and marketing and brand people. And we'll think that, AI can leverage, sorry, AI can be useful and help those people gain leverage as well. Now, when I think back on, the past and how the innovations that we saw in the past, I think back to the early days of the internet. I'm probably going to like really like date myself, right? Thinking about Waze and Gopher and things like that before the browser came out. And then the browser came out. And that was like a new UX paradigm. And that new UX paradigm really allowed us to explore the backend protocol, which was, HTTP at the time. But you remember, there was a lot of browsers. We had like a whole ton of browsers we're all playing with. But eventually that sort of sussed itself out and we ended up with sort of a, a good set of browsers we all use these days. I feel like AI is sort of on that cusp. It's like the HTTP side of things. The protocol's there. We don't quite have the UX worked out exactly right yet. There's probably some innovation. We're all trying various ways to interact, whether it's an API or a text-based chat or integration with a document store or something. But I get this feeling we're like at the beginning of the browser war sort of thing. And I see that pattern repeating. Really cool technology, lots of potential, like the guts of it we all can get into and look at. But the UX is what I think is going to be the next evolution. I'm not quite sure what it is because I'm not a UX expert, but I'll know when I see it.

Chet Kapoor: I'll tell you the two paradigms. I mean, we just came off a leadership team discussion on this and we were, since we're all server-side middleware folks, right? And one of the things that we talked about was are we in the Tomcat era, not even the web server era, or are we in the J2E era? And we think we're in the Tomcat. We really do think that this is really early, right? As that happens. I do think that whatever UX, I do think there's a massive evolution on UX that'll come. And I do think that the two things will be is I think voice will have something to do with it. I am now getting mildly irritated when I do not type when I have to type.

Allan Leinwand: Interesting.

Chet Kapoor: I'm getting to a point where I, and especially on my phone, right? It's very specifically on my phone, right? It's like, I'm just like, why am I doing this? I should just be able to speak to my device, right? Not when I'm working and writing and things like that. But I think those two things, but whatever happens on the UX side, I know it'll be something that generative AI will also generate for us. I think that part is very clear.

Allan Leinwand: The one thing I think about from a UX perspective, again, I'm not an UX designer, but I think about geolocation and GPS making the content more relevant to me. There was a point back in the time, eight, 10, 15 years ago now that people were talking about, hey, walk into a store and a coupon will show up on your phone for that store. And people thought it was creepy and weird. But now like I have teenage daughters and they share their location with their entire friend group and everyone knows where everyone is and GPS is kind of built into their daily lives. I wonder if there's something around GPS meets Gen AI to make the content, almost instead of you having to ask your phone, it just gets pushed to you. Again, I'm a workflow automation person. So I'm thinking about, I'm at the restaurant, you know, calendar's right there. Gen AI knows where I'm going. Can it just tell me the next thing to do?

Chet Kapoor: That is by the way, that would be awesome as well as, I think I know some of the people that are the leaders that are building G Suite and they are, I saw something very interesting. They're doing a lot of work on getting Gemini and Gen AI into it. And I'm sure the Microsoft folks are not holding back either. So I'm looking forward to like my agents knowing enough about me to be able to do lots of things for me. And the example I keep using with people is that if you use maps, you use agents. I mean, it's just there. So it's not like a new concept, right? That's right. It's a person without maps versus a person with almost maps, right? If you remember that from a long time ago.

Allan Leinwand: I was going to say, you and I are doing each other. I'm talking about Waze and you're talking about paper maps. That's all good. I know.

Chet Kapoor: So your goal at Webflow is to bring web development superpowers to everyone, right? And at Datastacks, we're really focused on helping developers build Gen AI apps, right? And we also went off and got some no-code stuff that we're doing on the Gen AI stuff, hard as it might be. So what do you think? You talk to developers a lot. You're building products for that. What do you think is one of their biggest challenges they are facing right now?

Allan Leinwand: Yeah, I think from the developer point of view, it's trying to, as you were saying earlier, consume the APIs, consume the patterns that I think are emerging to build the next set of, in our particular case, it's website properties, website optimization, website personalization, analytics, everything around that. We have a headless CMS, a content management system that people can tie into and build out their entire marketing stack on Webflow. So I think in our world, Webflow started as a website design tool ending with publishing on the web. And now we're really a website platform. So it's optimizing your web experience versus mine. It's personalizing. It's doing analytics.

And in our particular world, just trying to give developers an easy way to access all that data, easy way to get data into the platform and out of the platform in an endless way, and really just trying to expand what developers can do. I think developers have been sort of siloed into, I'm a front end, I'm a back end, I'm a web dev, but I mean, the reality is it's just development of something that's useful for your customers. So as long as you, yeah, as long as you think about how can you make the surface area for developers accessible, easy and performant for whatever customer needs they're trying to address, I think you'll be successful.

Chet Kapoor: Do you think, and do you think Gen AI helps them, Alan?

Allan Leinwand: I know it helps our developers generate the right amount of code. I know, we're looking at sort of the open API specs and we're publishing things in that world as well. So that way Gen AI agents can read our APIs and then move them and leverage them going forward. So we are thinking about all of those things. I think Gen AI, at least internally, has helped us write automation, write tests, think about how do we do PR reviews. We actually have a Gen AI product that we're looking at right now that sort of reads through our JIRAs and then prioritizes our stack rank of product priority. So there's a lot of things that we're doing that I think are gonna help us as a company. So it helps my developers. I have to assume that a similar paradigm helps other developers as well, but that's how I think about it.

Chet Kapoor: Yeah, no, for sure. We definitely think that internally, it's much easier on new projects, right? But even on existing projects like Apache Cassandra, we still think it's a 20% or maybe even higher uplift.

Allan Leinwand: Do you find a lot of your developers are actually writing PRs with Gen AI or are they using it for code reviews? And how are they using it?

Chet Kapoor: They're actually using Copilot a lot. And we have a great partnership with GitHub. And so we were one of the early partners for Copilot. So they've actually, we're working with them closely where they're training their Copilots on our code. And so it is very specific to us. And so that's where we get a lot of benefit from on how quickly can people get things done. And so you talked about, SEV1s and SEV2s, we call them P0s, P1s, and how quickly can you get through them, right? Because the fun part is actually doing the next big innovation, right? But you want to pay attention to the customer. So Copilot helps a lot. We do a lot of, we have a very strong, Alan, a very strong data group that actually spends a lot of time analyzing data and providing insights across the board. And so we experimented with, ML and predictive stuff, but just too brittle. Just too brittle. Now, very rarely, we'll go into a weekly meeting. We run a daily cadence and a weekly cadence at the company. Very rarely, we'll go into something where we do not have some insights from some AI tool that we're using.

Allan Leinwand: Yeah, very cool. No, I agree. I think, like I said before, to me, it's a workflow automation accelerant more than anything else for us right now.

Chet Kapoor: The piece I will tell you, and we'll talk about bold predictions, is what I'm really looking forward to, just like the browser, I'm really looking forward to what is the retail banking for Gen AI, right? I'm looking for when does somebody's P&L change, not just top, bottom line kinds of improvements, right? That's what I'm really pumped up about. And I don't have a prediction on what it is, but I do think that people are thinking about it in a big way.

Allan Leinwand: Yeah, that makes sense. I'm curious to see what happens. And whatever happens, I'll be a consumer.

Chet Kapoor: So before we do, before we go into a rapid fire round, I wanted to ask you a couple of questions. Sure. One bold prediction that you have for the future of web development.

Allan Leinwand: Well, I think the interesting thing about web development up to this point is it's been a constellation of products that people have used. They've published their website, they've thought about how to optimize it, they've used AI, and we have an AI product called AI Optimize that allows people to figure out which variants work for various markets and various demos. They've added analytics onto it, maybe they've added some tracking, maybe they've done some work in the marketing stack. And my bold prediction is I think all that's gonna start to consolidate onto platforms. And I think, you know, when I think about my days at Slack and I think of my days at ServiceNow and Shopify, having a platform that has a set of data, then that data is in leverage across multiple different applications in a consistent, reliable, coherent way. It's just so powerful having that single data model that you can then leverage across multiple apps. And right now you see these people I call it the Franken platform. You get like these various APIs and someone will change something over here and, you know, product X and downstream lineage problems in a product Y. And we gotta get away from that. We have to get into an environment where we're solving solutions. We're not spending time architecting third-party products all work together. So I'm really looking forward in the web platform space to seeing things coalesce around platforms. So my bold prediction is you'll start to see that in the next two, three years and I'm gonna do everything I can to make Buffalo part of that.

Chet Kapoor: One unpopular opinion you have about AI.

Allan Leinwand: Alexa should have won. Cause you're talking about voice and things like that. And how long has Alexa been out? Five, 10 years now. So it should have already won that game. And my unpopular opinion is, we've had it for a while. Just wasn't very good. So I don't know why.

Chet Kapoor: Or Siri, or Google, any of those, right? Come on. All right, rapid fire questions. Sure, let's do it. What one thing do you want AI to automate most in your life?

Allan Leinwand: Vacation planning.

Chet Kapoor: By the way, they do, it already does a good job of it.

Allan Leinwand: It does, but it doesn't book the tickets and figure everything else out. Yeah, it doesn't do the execution, just does the planning, I agree.

Allan Leinwand: Yeah, I gotta work for the automation. You can tell me what to do, but not just do it.

Chet Kapoor: I know, I love that. Most inspirational book you've ever read.

Allan Leinwand: I don't know if it's a book, but Brene Brown listening to her talk and say clear is kind. Amazing, just amazing. Like I brought that into my life. I talk as transparently and clearly and matter-of-factly as I can to people. Clear is kind, being transparent, being just very direct in a human way really affected how I think about things. That's

Chet Kapoor: awesome, I'm a fan. If you could have dinner with any tech legend, dead or alive, who would you choose?

Allan Leinwand: Oh, wow, any tech legend?

Chet Kapoor: Yeah. Oh, wow, that's a hard one. So many to choose from.

Allan Leinwand: Yeah, I'm thinking about Richard Stallman up through Zuckerberg in college. So anybody in that camp, let's go with Zucker at Harvard. That'd be kind of fun to hear what he's thinking about.

Chet Kapoor: Yeah, what three words describe great leaders?

Allan Leinwand: Transparent, high integrity and focused.

Chet Kapoor: What's the best piece of advice you've ever received?

Allan Leinwand: Just be myself and bring my whole self to work and don't be afraid of saying things in a clear, transparent way. Don't hold back. The way somebody said this to me 20 years ago is, Alan, just be Alan.

Chet Kapoor: I love that. I absolutely love that. I keep telling folks that I can only be the best version of myself. I cannot be somebody else. And so I love, that's phenomenal advice. Alan, this has been phenomenal. Thank you very much. Our listeners are going to love this episode. We really appreciate you coming and joining us.

Allan Leinwand: No, thank you so much for the opportunity. It's been really a lot of fun.

Chet Kapoor: Thank you. Thank you.

Inspired Execution

Allan Leinwand

CTO, Webflow

Next-Gen Web Development: AI's Role in Shaping the Future with Allan Leinwand

Episode Transcript