SaaStr 874: From 0% to 83% AI-First Customers in 2 Years. How Owner's CEO Rebuilt a $100M Vertical SaaS Company

0:00In order to benefit from agents, you've got to build an extremely opinionated product.

0:07Adam Guild:Because the thing that makes agents magical from the perspective of the user is this idea that it is the first time that software is able to drive the outcome that that user wants without them having to manually intervene and try and figure out how best to configure the software in order to get the outcome. the time savings and fewer expertise requiring insights that are required to engage with the product. Let me take you back to three years ago, because the past three years has been a huge roller coaster at Owner. Three years ago, Owner was crushing it. We were building this Shopify for restaurants thing that was working.

0:44Adam Guild:It was a website builder, online ordering system, marketing automation system for restaurant owners. And from a growth perspective, it was going great. We were exceeding the triple-triple-double-double-double trajectory that the SaaS lore says eventually leads to building a unicorn. We'd raised more than$89 million in capital from all of these incredible investors. Things seemed great. But beneath the surface, we were facing an existential risk starting in early of 2023. That risk was the chat GPT moment that was cascading throughout the tech industry and putting huge pressure on us in two different ways, each equally terrifying.

1:26Adam Guild:The first way was all of the AI native startups that were being born in early 2023, doing things that previously weren't possible, like vibe coding website generation and AI phone answering and ordering for restaurants. and the risk that they posed was that they were growing like wildfire and directly could disrupt our product. The other risk was coming from maybe even more terrifying direction because all of the massive companies in our space, publicly traded companies, had taken notice of our momentum and were as aggressively as they could trying to stop it. Throwing hundreds of engineers on trying to clone our product and then distributing it into their customer bases of hundreds of thousands of similar customers.

2:10Adam Guild:it became obvious that unless we adapted in this moment and took advantage of it, that we were going to get crushed from both of these directions, that we were going to slowly bleed out and die and that we wouldn't have a business in a few years. The hard part wasn't realizing that. The hard part was all of the smart people around the table that disagreed. Major investors saying, Adam, this is CEO thrash. We can't just invest millions of dollars in this new product direction. and take people off of this thing that is working. It's working well, it's growing efficiently. We can gradually layer these in over time.

2:48Adam Guild:Or team members, product managers and engineers saying, Adam, I know a hundred customers personally that are asking for the product to do this thing. And if we're gonna take people off of that to build this new thing that hasn't even worked or been proven, it's just going with the AI fad. How could we possibly do that? Or the industry experts, the folks that had spent their lives and careers in our industry of restaurants, that were saying, Adam, if there's one thing I know, it's restaurant owners. And restaurant owners are terrified of AI. If you start to pivot your company in that direction, you're going to alienate your customer base.

3:25Adam Guild:It was brutally hard, but we pushed through all of those reasons not to. And if we hadn't, then this wouldn't have happened. And this glorious tweet from the godfather of SaaS and the king of SaaSter AI, Jason, one of our incredible early investors and board members, on the first of this year talking about how we grew faster in 2025 than we did in 2024, and how more than 83 % of our new customers, up from 0 % just two years prior, started their journey by using our AI products. Talking about the caliber of talent and momentum that we've been able to accrue, that we wouldn't have otherwise. So that is what the next 30 minutes is going to be about.

4:09Adam Guild:About all of the ways in which we had to reimagine our product and our business to adapt to be AI native in the way that we build product, the way that we operate, and the way that our whole customer journey works. I'll also touch on psychologically all of the challenges that came from making these sweeping changes across the business. You're listening to the official Sastra AI podcast brought to you by...

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6:09Adam Guild:And to make it extra helpful, I'm going to be demoing for you the five most impactful things that we built, both the product and how that changed, and all of the internal systems that do things like automate the busy work for all of the builders and engineering product and design, what it looks like to have an AI native finance function or sales function and the tactical things that I learned from the psychologically hard challenge of convincing a team to move in a completely different and unproven direction. So let's dive in. I'll take you back to the moment in early 2023 that we got up the courage to go all in on this direction and push through the industry experts saying it was a bad idea.

6:50Adam Guild:That moment was at the International Pizza Expo there, where I'd gone in very excited, showed up early to do my usual thing, showing these restaurant owners, the Shopify for restaurants that we'd built, the website and online ordering product. And I show up that day, amped, very early, get my laptop set up right before the showroom doors open and pizzeria owners start coming in. And as that happened, and pizzeria owners start walking in to the showroom floor, the first few passed me by. And then one, he cranes his head. he looks at something behind me and he walks up to the back of our booth and pulls out his phone.

7:30Adam Guild:I'd never seen this happen before. So I walk up and introduce myself. Hey, I'm Adam. How can I help you? And he was scanning something that one of our PMs brought to the show as an afterthought. It was this poster that was describing one of our upcoming products, which at that point was a terrible MVP, very embarrassing. But it basically said, analyze everything that is broken about your restaurant line and fix it with AI with a QR code to scan so that they could try using this experience. And this guy, Joe, was fascinated by this. He was so excited by the idea of using AI in his pizzeria. His 55-year-old pizzeria owner from Pennsylvania was really excited by AI.

8:08Adam Guild:And what was so interesting about this to me is it was the exact opposite of what I'd heard from the industry experts. And even what I'd heard in customer discovery interviews three months prior. What I realized in that moment is that the chat-GBT moment hadn't just taken the tech industry by storm. It had also been used by all of these small business owners. They'd read about it and they'd gotten excited by the idea of using AI as an advantage in their businesses. Over the course of that day and talking to all of these pizzeria owners, it was the number one most common thing that they wanted to know about.

8:38Adam Guild:Even though it had nothing to do with the vast majority of our booth or collateral and what we were there to demo, I was getting questions like, how can we use AI to drive new customer discovery? How can we use it to drop our labor costs and become more efficient? And it was that day that we got the courage to go all in on this direction and actually neglect some burning fires in other parts of the product in order to do it. So to give you a demo of what specifically changed, in early 2023, we were 100 % sales-led growth. It was an inbound motion. People would book a demo and then have to talk to a salesperson, an onboarding specialist in order to buy the product and then get started with it.

9:16Adam Guild:And we re-imagined that whole journey in an AI first way, asking ourselves how much easier and better could this become for the restaurant owner now that we have generative AI. What it led to is this experience that you might have seen went super viral on X about two weeks ago. We got more than 2 million views on the tech community announcement of Greater. But what wasn't on X is that in the restaurant world, this has been growing like wildfire for the past two and a half years. because the way the whole thing works is instead of having to go through a salesperson and an onboarding person to build out this new website and online ordering system for the restaurant, we asked ourselves, can we use AI to automate all of this and just have the restaurant owner type in the name of the restaurant and then have the AI figure out everything that is screwed up about it online and then fix it for them as the restaurant owner.

10:02Adam Guild:So the way it works is you type in the name of your restaurant, which in this case, I'm typing in a restaurant that I saw last week, really needs a new website. and within seconds the AI jumps in and starts crawling every place it can find that restaurant on the open web pulling in all of their nearby competitors so it can show them how they compare and contrast to their competitive landscape going into their Google business profile and scanning to make sure they're following all the right settings descriptions and keywords that drive Google discovery reading all of that restaurant owner's reviews so it can figure out what customers love about that restaurant and rebuild the experience with that in mind.

10:40Adam Guild:Doing a photo quality analysis, an AI photo shoot, where it's not only ingesting all of the photos that it can find, but then upscaling the images, increasing the lighting conditions, the color, making it look much more professional. So then it goes from this website before, which is hilariously barren, to say the least. It's a very confident restaurant because the photo is just a picture of napkins on the website that says, welcome to Thai Thalé. So this is the before to give you some color. Here were all the things that were wrong with the report before, where images were missing, alt tags on the website, bunch of other SEO things were screwed up.

11:13Adam Guild:It's checking like 90 different factors in SEO and CRO. And then in a matter of less than five minutes, it went from that before to this after, which initially blows the restaurant owner's mind because that video they've never seen before. What we've done in that five-minute period is we not only did an AI photo shoot for the restaurant of upscaling all of their images and making them look much more professional, but then we added motion with VO3 and created this compelling initial video. In addition, we've built out all of that restaurant's content to perfectly reflect what people on Reddit, Instagram, Facebook were saying about that restaurant and make sure that it represents the value proposition well.

11:52Adam Guild:It's got spotlights around the most popular dishes, the Thai samplers, one of them, photo gallery, details on the cocktail, sake, and the bar, so that in less than five minutes and for free, a restaurant owner can have, go from a really bad initial website that is actively hurting their sales and creating a bad initial first impression to a state-of-the-art amazing website. And it isn't just a flashy demo. This has had a profound impact on our business. It is why more than 83 % of our new customers are starting their journey by using this product. It is why we grew faster in 2025 than we did in 2024 and a huge part of why we are now accelerating as we're about to cross$100 million in ARR.

12:38Adam Guild:So what are the most important lessons learned on product from going through this experience of building a product to disrupt our prior thing and reinventing the customer journey? lesson one is that in order to benefit from agents you've got to build an extremely opinionated product because the thing that makes agents magical from the perspective of a user is this idea that is the first time that software is able to drive the outcome that that user wants without them having to manually intervene and try and figure out how best to configure the software in order to get the outcome, the time savings and fewer expertise requiring insights that are required to engage with the product.

13:20Adam Guild:That is the thing that makes that Thai-to-lay website so powerful from the restaurant owner's perspective. It's not just that it looks prettier, it's that when they activate it, it quickly grows their sales by increasing their conversion rate and SEO discovery and having the best practices that we've learned from powering thousands of restaurant websites and the experiences of tens of millions of consumers that are using those websites. Interestingly, this also connects to the second major takeaway on product, which is that in order to insulate yourself from the dreaded getting screwed over by Claude effect that is terrifying so many startups right now, that opinionation ends up providing that insulation.

14:01Adam Guild:What I mean by that is if we were to go in today to Claude Code or Codex and say, build me a beautiful new website for Ty Talay, it would already build a much better website than what they had before. And yet the website that it would build is based on the corpus of all of the restaurant websites on the internet and all of the other UI best practices, but it is missing the insights around exactly what components on that restaurant's website are correlated with sales growth. Exactly what it is about the restaurant's call to action or placement of the nav bar or the rest of the homepage content that causes it to show up on the top of Google.

14:37Adam Guild:And that means that through having this very opinionated product approach, where we enforce that all of the restaurants are following the same system and same best practices, that we've got this unique data advantage in being able to consistently drive that outcome for users and this moat that ChattyBT or Claude can't exactly touch in order to deliver the outcome for our users. Which brings me to lesson number three. In the old world of SaaS, the way we thought about high quality products was we were measuring things like daily active, weekly active, monthly active users in the dashboard. That was a sign that our user base was engaged and that the product was working.

15:15Adam Guild:And now I think that closer to the opposite is the signal of the product really working. Meaning that if agents are powerful because they drive the outcome for the user without their constant manual intervention, then every time that somebody's logging into our website builder to manually intervene with the way that it is setting up their restaurant online, it means that we have failed. It means that we haven't created an experience where the software drives the outcome because the user is the one that is trying to solve the problems that were created by the software and that instead what we should aim for is an experience that is as low touch for users as possible, where they don't need to log into the dashboard and constantly intervene with what is happening with their business, but instead the software just knows what the best practices are and is constantly executing them on their behalf.

16:02Adam Guild:Okay, now that we've covered the reimagining of our product, it's also worth covering the way that our product development and engineering process changed as a result of this product change. This one actually starts with Will, who is a genius builder, a one in a million unicorn who's an excellent product mind, design mind and engineer in one person, and the first person that we had on building Grader. As Grader took off, Will found himself suffering. Suffering because the thing that energizes Will most in the world is building awesome products, being deep in the code base, and continuously making things better.

16:43Adam Guild:But as the thing took off, we started putting more and more engineers and product folks and design folks in that part of the company, and Will found himself having to incur all of these coordination and communication costs in managing a bigger team, doing things like keeping linear up to date and notion and daily standups and all these things that we've just kind of accepted as part of the product development lifecycle to keep the team aligned, but that are really a huge cost on the very most leveraged ICs in the company. No great builder wants to do the builder busy work of staying aligned with the team and showing up to the standup meetings they all just want to build.

17:18Adam Guild:So we asked himself, could we apply this same line of thinking that just led to this product breakthrough in the way that we actually develop product. And so Owen was born. Owen is our internal agent that does 90 % of builder coordination work. Owen is constantly listening to GitHub, Slack, Notion, Linear, Google Meets, grabbing the transcripts from Gemini to understand the work that is already being done by builders and keep the team aligned automatically. so that Will no longer has to show up to the meetings and ask people for status updates and Slack them back and forth to understand the status of any given project in leading this part of our platform, but instead just has all of that intelligence in real time at his fingertips.

18:02Adam Guild:This is saving us a huge amount of time. And another awesome thing that it can do is automate all of the really boring front-end work. What I mean by that is if you look at that screenshot, Owen is constantly listening to Slack, where when somebody submits a bug or some visual thing that seems off, like in that case, he's showing a screenshot of our agentic chat and saying that the bullets look too small. Previously, that would require somebody creating a ticket in linear and then a front-end engineer taking up that ticket, finding the part of the code base that controls the size of the bullets and updating it.

18:36Adam Guild:And across a massive product area, there's all sorts of things that come up constantly and it is taking the time of some of the most leveraged people in the company. So he asked himself, could Owen actually do this? Could Owen call CloudCode, which has full visibility into our code base? And just immediately when a Slack message is posted from a product person, a design person, a support person reporting a bug, jump in and do the first draft PR. So now Owen does. You can see that he immediately responded and linked the PR that he wrote, which immediately fixes the visual issue. This saves a tremendous amount of time across engineers and keeps them focused on the highest leverage engineering work versus the very boring and monotonous front-end fixes that come up.

19:17Adam Guild:another breakthrough on this front of leveraging our builders came from our brilliant co-founder and CTO Dean. Dean found himself with a similar version of the problem that Will was facing. Dean is also an amazing builder and hates unnecessary meetings and stakeholder alignment stuff and trying to distill context from big groups of people. A lot of you probably relate to that. So what Dean asked himself is, is there a way to get the signal that is currently costing me hours every month where I have to interview our customer support folks and our sales folks and our customer success folks and read all of the different tickets of things that have been submitted by customer facing teams and talk to customers in order to understand in this lossy way, what it is that would be most impactful to build in any given sprint.

20:06Adam Guild:and that is what led to the product insight command center the product insight command center is constantly pulling insights from every place that our customer facing interaction occurs salesforce intercom momentum talk desk all sorts of others and then grabbing those transcripts and any time it notices a prospect asking for a feature that we don't have or somebody reaching out for customer support as a result of a bug or something that is missing it develops this dashboard that gives Deem immediate and real-time visibility on where the biggest opportunities are to take friction out of our customer journey or to improve the product in order to drive our revenue.

20:42In addition to having our more technical teams,

20:46Adam Guild:traditionally, engineering, product, and design operate as AI native, we've also started to operate as AI native in finance and sales. And this next example is one of my personal favorites because it saves me a tremendous amount of time and occasionally embarrassing moments. It came from our brilliant CFO, Will, and Mira on the finance team, who about a year and a half ago started operating in Claude instead of Excel as our primary financial artifact. And what that enables is the situation that many of you are probably very familiar with, where you're catching up with an investor and they ask an extremely detailed question about a metric and exactly what ladders up to it.

21:26Adam Guild:And it's not something that you would just have at the top of your head about how the Q3 rule of 40 compares to the Q4 rule of 40 or the different ways in which CAC is changing over time. It requires you saying, great question. We're going to check with you and get back to you versus being able to just spit it off on the top of your head. So what we'll build by having our financial model and all of our most important financial artifacts in Claude is the ability to just query our financial model with the types of questions that you would get. That's AI Native finance. Another game changer is making our sales team and go-to-market team AI native.

22:04Adam Guild:Few epic things to demo on that front. Credit for these go to our awesome CRO Kyle who you might have seen yesterday. Our go-to-market AI lead YG and our awesome VP of BizOps Jonathan Shankman. Kind of awkward but what they built is not. What they built is amazing. They identified a problem that you're all very intimately familiar with, I'm sure. Reps were losing a huge amount of time every day and manually doing research before every demo in order to show up understanding the prospect's needs and the current situation and not waste a bunch of time with discovery questions so that you can get right into the meat of the benefits of the product.

22:41Adam Guild:In addition to saving a bunch of rep time, the other thing that they were solving for is our buyer, restaurant owners, are extremely busy and overwhelmed and skeptical. So if you don't show up extremely prepared, there's a good chance we're getting hung up on or not taken seriously, which is why our reps were spending so much time on this, 20 to 30 minutes before every demo. In addition, it was hard to quantify and qualify restaurant leads in real time if they wanted a demo within a couple hours. So what they built is the following. AI-PCR, pre-call research, and eGPV. The way it works is the moment a lead is submitted in our system, booked through our website or added in by a sales rep deploys a bunch of agents to research everything that that rep would do manually.

23:23Adam Guild:Not only running the greater report that we saw for Ty Talay, detailing all of the different issues with their existing online presence to drive problem awareness, but also pulling in things like who is the nearest, most successful customer to this restaurant that can be shared as social proof or EGPV, estimated gross payments volume. Within about$250 now, we're able to triangulate around how much in gross payments volume any restaurant is going to drive on our platform, which is a major driver in being able to prioritize the highest value leads and automate qualification so that it's not just up to the BDR going through a detailed qualification question.

24:00Adam Guild:It saves both the rep and the prospect a huge amount of time. And over the past three years or so of implementing and continually fine-tuning this system, we've seen a more than 90 % increase in call volume and rep time with customers. And they're basically out of having to do all of this extremely monotonous research work ahead of each opportunity. We've also seen close rate increase by a really substantial amount.

24:26Adam Guild:So that solves the practical problems of reps, saving them a bunch of time before every demo. It's also worth talking about one of the game changers in solving the emotional problems of sales reps. And that emotional problem that I'm referring to is intimately familiar to any sales leader or founder in this audience, which is that it is brutally, brutally hard to be a salesperson. Even when you have a great product, you're just getting rejected constantly and reaching out to people who don't respond. And so the insight from our marketing folks, Hannah and David, was if we could automate any time a customer says something positive about our product and share that with our sales team and our broader team, it's going to increase the amount of confidence and conviction that a salesperson is able to show up with because they're constantly being fed examples of the positive impact that their product is making.