What happens when a SaaS company blows up its roadmap and rebuilds around AI—top to bottom? Homebase CEO John Waldmann shares how he restructured product, pushed his team into AI adoption, and rewired the company’s culture to move at prototype speed.
In this episode, John Waldmann, CEO of Homebase, shares how the 10-year-old SaaS company blew up its roadmap and rebuilt around AI—from culture to code. He walks us through the shift from 20-page PRDs to lightning-fast demos, reclaiming product leadership, and pushing teams into their “oh shit” moment with AI.
We explore the leadership reckoning, cultural resistance, and practical playbook behind the transformation—and what it means for the future of SaaS, small businesses, and human-centered AI. If you're leading (or bracing for) an AI shift, this one’s packed with hard-earned lessons and honest insight.
Key Takeaways:
LinkedIn: John Waldmann | LinkedIn
Homebase: All-in-one Employee Scheduling, Time Clocks, Payroll, & More | Homebase
00:00 Introduction and Initial Reactions to AI
00:31 Meet John Waldmann and the Story of Homebase
00:53 Reinventing Homebase as an AI-First Company
01:46 From PRDs to Prototypes: Building Faster, Learning Smarter
05:02 How AI Is Reshaping the Customer Experience
09:19 Culture Shock: Resistance, Skepticism, and AI Adoption
14:03 The End of SaaS as We Know It?
19:34 Leading Through Disruption: Ownership, Urgency, and Org Design
25:12 Forcing the Shift: Getting Teams to Embrace AI
27:50 Hiring the Unemployed—and Other Nontraditional Talent Bets
28:56 Curiosity > Credentials: What to Look for in AI-Ready Teams
31:57 New Expectations, OKRs, and Holding Teams Accountable
37:10 Serving Small Businesses Better with AI
44:52 Final Thoughts: Team Dynamics, Founder Risk, and What’s Next
📜 Read the transcript for this episode: Transcript of Rebuilding from Inside: How John Waldmann Led an AI Shift Without Breaking His Team |
[00:00:00] John Waldmann: I talked to her about what we wanna do from an AI standpoint. I'm like, right out of the gate, I'm like, I wanna talk to you about ai. And her initial response was, I hate ai. I hate the companies building with AI companies, building with ai, don't care about humans. And it was like a fundamental, it was like, I'm coming from a place of living in hospitality.
Everything I do is about the human interaction. Putting an extraordinary amount of weight and pride on that. And that was like a very impactful thing. But I'll tell you by the end of the conversation, it was a. When can I get access to what you're building? Hi, I'm John Waldman. I am the founder and CEO of Homebase.
We are the leading team management platform for local businesses, serving over 150,000 of your favorite local businesses and over 2 million workers. Uh, we have spent the last year reinventing ourselves as an AI first company.
[00:00:52] Jeremy Utley: Wonderful. Well, maybe one thing that I've really been excited to talk to you about, John, is I know when we reconnected recently, it was because you had posted on LinkedIn about how you are reinventing the business from the ground up with ai.
And so I thought it could be fun just to kinda hear you talk, maybe first home base historically, and then what has changed for you as you've thought about rebuilding the business.
[00:01:19] John Waldmann: Yeah. Um, it's, that's a big topic. Uh, 'cause I think right in this moment of time, it cuts across everything. What are we building?
How are we building it the way that we operate as a company so we can talk about any and all of that. Um,
[00:01:31] Jeremy Utley: okay. Uh, well, I like, I like even those, that distinction, right? The what and the how. What are we building? Yeah. How are we working and how are we, maybe let's start with the how, because I think that's probably more essential to the DNA, so to speak.
And then let's get to the what after that.
[00:01:46] John Waldmann: I would say, you know, the, what, what are we building is an evolution. And, and that part has been very consistent over the 10 year life of our company. And what I think about for, uh, forward, you know, the North Star there doesn't really change, but I think the, how we build is changing so dramatically.
And you, Jeremy, when I reached out to you, I was sharing some of the thoughts that I was having of like, wow. Uh, at this moment in time, I feel like I'm going back to D School. Type building and kind of foundational founder mode, thinking about product and how to build product, uh, as much as I have in the last 10 years.
And it was super exciting and fun in that moment. And I think what I. I'll just, I'll, I'll take the way that we build product as an example from like a product and design standpoint. I think getting to the part of like, okay, we're back into the rapid prototyping, working closely with design partners, the pace of iteration and learning, you know, all that stuff has been radically accelerated in the ways that we're building any product.
Uh, and that's been, that's been one of a hundred ways in which we are, are changing how we work to kind of meet the moment.
[00:02:56] Jeremy Utley: When you talk about getting closer to the customer and the speed at which you're prototyping, what's enabling that?
[00:03:03] John Waldmann: Yeah, so getting closer to the customers, you know, I think that's something that we've always been super pride of ourself on.
You know, we serve local businesses, we serve a lot of local businesses. They're an incredibly fun customer to serve, right? You can go walk into and talk to him live. Their problems are so tangible, their stories are incredible. They're the best possible customer that you could hope for. You get to a certain level of scale though, and like some of those interactions become a little bit abstracted.
You know, you, you've got 150,000 plus customers. You can launch a, a feature in the product, and you get hard data back pretty quickly. On, uh, how are people responding? Did the AV test hold, did it drive the outcome that you wanted? You can, you can now get survey, like, launch a survey and get answers back from a thousand plus people so quickly.
You know, we've got 4 million plus people we'll use home base this year, but you can get incredible amounts of data from that. I think the thing that gets lost in that is like, we're in a moment where we're trying to create magic, and like that has, that's a little bit more qualitative than, you know, how did it perform on the AB test?
And for that, it's like the, okay, let me take a prototype early in how we're thinking about something, put it in front of you in person and see like, what are you reacting to? You know, the, the most basic, take it back to the roots of building product and design. Like take it back, see what the reaction is.
Come back a week later with a slightly different version of it, like a slightly more expanded version and just like keep pulling on that, that thread. And I think the, the great enabler here is all of these new prototyping tools. You know, we, we are now probably, uh, pumping out prototypes on bolt new or lovable, uh, or so, like all of these things have to be some co so core to the way that we do product and design at home base.
Uh, and has really changed the way that we're able to interact with customers and each other
[00:04:55] Jeremy Utley: well. Well, let's, one thing that's fascinating here, John, and I love that you went this direction, is I think when folks who maybe aren't so familiar with collaboration with ai, leveraging AI tools, when they think of AI conceptually, they think it's gonna get you farther away from the customer, and it's going to put you more towards abstracted AB test.
But what you just said is, now that we're using prototyping tools. We're getting back in front of people more quickly. More rapidly, which I think is a very counterintuitive impact. Right. So what's changed there or why has that led to more in-person almost, you could say analog interaction.
[00:05:32] John Waldmann: Yeah. I, i, it, it, it totally is that analog interaction.
Uh. I think part of it is the, the pace of development and learning. You, Jim, I go back to like, one of my favorite frameworks from the D school is that very, very basic looks like, works like, uh, you know, framework and, and like, are you moving a prototype? Are you moving a learning or a product on both of those dimensions?
And those two dimensions are. Correlated, but they're not the same thing. And I think in this moment where, uh, you can be behind the engines working on prompts and working on kind of how the AI is interacting, what's possible there at the same time where you're rapidly prototyping on what is the front end of this thing, how is this gonna show up for users?
What, what are the ways that people want to interact with that? I think you just get such a faster pace of learning on that. Versus, Hey, let's build Figma prototypes that are so high resolution on the, what does it look like, but are maybe not giving you the same cycle times on just the customer feedback.
[00:06:34] Henrik Werdelin: Do you take a bolt kind of like, uh, prototype or lovable or replicate or whatever and you throw it straight to the customer? Or is that like, is that more for testing? Like do you throw it in production already?
[00:06:47] John Waldmann: So we've done all, all sorts of things. Like this is the thing we're evolving through in real time.
Uh, yeah. I sat through a, a roadmap review meeting last week where it was every single item on the roadmap had a lovable prototype attached to it. And so instead of talking about like concepts or, or designs or anything like that, it was, let's talk about, let's just go through all of the prototypes and spend two minutes on each of these prototypes.
And these were like out there ideas, right? It allowed us to kind of like pressure test of thinking.
[00:07:17] Henrik Werdelin: It's the whole of if a picture is worth a thousand, a thousand words, then like a prototype is where it's a thousand pictures, right? Yeah.
[00:07:23] John Waldmann: I I think it was like the joke is true, right? Of like nobody sat here and was like a 20 page PRD doc is the best way to talk about product.
We kinda like ended up there accidentally and probably to the detriment of everybody involved. But like now you can go back to the prototype and everybody can kind of click on the idea super fast. Uh, so and that's and that,
[00:07:41] Jeremy Utley: sorry, just to be sure. Yeah, just, just to make sure I understand, John, you're saying that's where we were prior to unleashing our product and development teams with ai, we had kind of devolved, you could say, even though you started by the way, such a wonderful place.
But you kind of evolved to the point that the way we communicate with each other is 20 page PR docs. I can imagine even the bandwidth required for a human understanding to get up to speed. I can't get in the field. I got all these PR docs I gotta read. Right, exactly.
[00:08:09] John Waldmann: Like, you know, and you think about just like for me as a CEO, then sitting there and being like, well, shit, to stay current on what we might build that, that requires so much reading and.
The process had become incredibly linear. You know, we pride ourselves in like our cultural value is oh, day wasted. That's one of our three cultural values. And yet, like we had fallen into the trap of very linear kind of product building, very stepwise product building in a way that was leading to these very, very heavy artifacts that were great and served a purpose.
Don't get me wrong, like we got there for a reason, but at the same time was leading to very slow cycle times on feedback. And leading to very big checkpoints for us getting customer feedback. And I think the thing that this has allowed us to do is just blow that up, uh, and allow anybody to kind of go out and get feedback in a new way.
[00:09:03] Henrik Werdelin: I think as an entrepreneur, obviously you're, the people that you serve are incredible fascinating because to your point, like these are these incredible people who. Maybe don't get like the glory and the fast company articles, but like they are the one who keep the economy alive and the American dream alive and a lot other things.
Where do you think, where are they on AI at this moment in time?
[00:09:24] John Waldmann: That, that is a, a good question. I think it's a wide range. In two years ago, um, I was doing just like a random zoom catch up with six customers at the time. And I remember at that time being blown away of like, oh, these, these businesses have moved away faster here.
Than I thought. Uh, and I, I would remember, uh, there's this incredible business, Brooklyn Tea, uh, great tea shop in Brooklyn. Uh, and I remember her telling story super early on. She, she has a e-commerce site that she runs too. And she was talking about spending the weekend, uh, using chat GPT to generate a bunch of descriptions for all of the tees that she was gonna like put on her her website and how long that would've taken her before.
Honestly that was probably like May of 2023. It was relatively early on, maybe even earlier March of 2023, and she had like found a very specific use case in it. Now I think of like there, there is still a technical gate to like really unlock the power of AI and to push really hard on some of these applications and use cases for which that's very, very hard for a small business owner.
That's, that's where we come in, right? Is how are we bringing AI at scale to make building and managing a team incredibly easy so that you don't have to think about all of the minutiae and tasks that come with it. Uh, and I think there, there, there is an interesting dichotomy. You know, I, I always remember the, the conversation with, uh.
A friend who, uh, ran restaurants very plugged into kind of hospitality scene broadly, and, and I, I talked to her about what we wanna do from an AI standpoint. I'm like, right out of the gate, I'm like, I wanna talk to you about ai. And her initial response was, I hate ai. I hate the companies building with AI companies, building with ai.
I don't care about humans. And it was like a fundamental, it was like, I'm coming from a place of living in hospitality. Everything I do is about the human interaction. Putting an extraordinary amount of weight and pride on that. And that was like a very impactful thing. But I'll tell you by the end of the conversation, it was a, oh, when can I get access to what you're building?
Uh, because I think as you, like, talk through it and people are not afraid of ai. They're not, you know, in this context, they're not scared of ai. Uh, when you get into the practical applications of, Hey, how are you handling no shows today? Like, do you really need to spend your time on that? Or is that a thing that AI could do for you?
Do you really need to be screening the hundred cashier resumes that you got in the past week? Could AI do that for you? You know, you bring it to these very tactical applications, it's like, oh shit. I would love the help actually. Like I spent hours on that and I hate it. Uh, but you know, just
[00:12:13] Jeremy Utley: connect from, I hate AI to these hated or dreaded workflows.
You go, oh, I didn't know it could do that. Right? Yeah.
[00:12:21] John Waldmann: Yeah. And so I think that's a little bit back to our, our. Job as product builders is to like bring it back to the real problems that they're dealing with every day and not make it some like philosophical, uh, technology. Some grand debate around, uh, technology and back to like the, hey, we can make your life easier.
I.
[00:12:40] Jeremy Utley: Could we go back to that conversation? 'cause I think that's actually kind of a really cool use case. So you're talking to this hospitality leader who's really, I'm sure, uh, prides herself probably in this kind of handcrafted artisanal care right in, in the hospitality space. I'm familiar with some of those folks.
Um, she starts the conversation by saying, I hate ai. What? Is your approach, I mean, 'cause you're not like an AI evangelist, it's not like you're trying to sell her on ai, but what was the conversation like that moved her in? It seems like relatively short order from, I hate AI to When can I sign up?
[00:13:16] John Waldmann: Yeah. I think, um, moving is, is like the most trite answer imaginable, but moving it from the technology to the problem, right?
Which is like, okay, let's not talk about ai. Look, what I actually want to talk to you is about. How you build and manage your schedule. I wanna talk to you about the challenges of hiring and then with that, introducing solutions into the conversation of, okay, now imagine of home back homebased at X, uh, and getting those like, oh, that's possible moments.
So bringing it back to the things that she's actually dealing with, the things that she's seen firsthand as opposed to the let's lead with the technology. But I think that's always true.
[00:13:59] Henrik Werdelin: I have a weird question that's kind of like popping up in my brain. Um, I was talking to somebody else who was kind of talking about the demise of SaaS.
Um, and of course you're doing many like a SaaS product for specific customers. Where do you think the companies like yourself, and I definitely have like a, you know, like a, maybe a suggestion, um, where do you sit in the question of how concerned you should be? That a chat GBT becomes so powerful that the uh, yeah.
That the features that you provide are kind of like, uh, just something that people will just do on that app.
[00:14:40] John Waldmann: Listen, I, I'll be the first person to say, I think SaaS is dead. Uh, I said it in, you know, we had our leadership offsite in May of 2023, and I sat there and like the theme of the presentation was.
The age of SaaS is over. Uh, here's how we have to think about our company going forward. Uh, I totally believe that. I think at the end of the day, if what you are doing is, uh, if, if your advantage is the code base that you had built up over however much time the size of your code base, the surface area of your product.
You are in a bad position, uh, because it's pretty obvious that AI tools are gonna be really good at writing code and therefore the barrier to entry of just building product is going down incredibly fast. Uh, that the moat of a code base is pretty much done and that the relative ease of expanding our product and things like that is going to.
Come down dramatically. That's true. Before you even get to the, Hey, what is the role of agents in the future? Just like fundamentally the cost of building software is coming down. If that is true, then like there's not as much value in software as there was before, so I don't even think you have to believe in agents to believe SaaS is over.
Uh, now if you abstract away from what software is and then he, can you tell me what your, what your solution here is? Uh, I, I think if you extract away from what software is, it's like, well, fundamentally this is about helping a specific type of user make their life easier. And if you can totally transform that from like, Hey, let's make that work easier by bringing it online, designing some relatively easy workflows and building some automations into that to like, Hey, let's use tools to just do the work for you.
You are a profoundly more valuable company to your customers, and that customer hasn't changed. You have just evolved the way that you serve them. And I think that is the jump that every software company needs to make. I don't think every software company is in a great position to do it, but, uh, I believe that we are.
Uh, so that's gonna be our focus.
[00:16:50] Henrik Werdelin: Yeah, I think, I mean, like, I think you are too, which is why I dared asking the question. Uh. I'm biased. I have a book coming out on the subject, uh, August 5th called me My Customer in ai. And the thesis is basically that entrepreneurship is gonna be much easier. So you're gonna see more types of entrepreneurs to companies are going to look different, right?
So the object that is a company is changed. And, and then thirdly, when now more and more people can do it. How do you stand out? And we talk a lot in the book about this thing we call relationship capital, which is, you know, how do you create the authenticity and the authority? To understand a customer so well that you can be predicting what are kind of like the problems that we can solve with technology, and then exactly what you're doing, kind of bundle that up because at the end of the day, it requires real cognitive kind of resources to figure out how do you take this specific problem that is in the real world, and then how do you apply an LM model to it?
And another event is that I think you will have is that. While it's not a network effect, there's network in this effect in that when you serve so many of the customers that are the same, then obviously you see what works And you know, like a, a two person team, you know, can't have an innovation team. Um, but you then defacto through the product become kind of like the people that can take those kind of insights and apply it down to, to them.
[00:18:12] John Waldmann: I, I a hundred percent agree with that. And one, like I, I listened to the autos, uh. Uh, interview you all did. And you know, I absolutely believe in the thesis around what AI unlocks for entrepreneurship and how great that is going to be for the world. Totally believe in that. Uh, and two absolutely believe that so much of the long-term value of a company is ultimately in the customer focus and the understanding of a customer.
And I think one of the underrated powers of AI is that it allow, including reducing the cost of building software. That it allows for verticalization and purpose-built software in a way that it never existed before. And that was true whether you're building software, but I think, or AI agents. But I think it's doubly true going forward.
And I think like, you know, you still end up with these massive pockets of the software economy that are completely horizontal. Serving wildly different types of business and users with subpar solutions for all of them. And I, I think that is a thing that we should all be optimistic for, kind of the flywheel accelerating on of giving more purpose-built solutions.
[00:19:23] Jeremy Utley: I, I love, you had said a second ago, John, not every company is positioned to make this shift, but we are, you know, from, call it your advantage being your code base to your advantage being your customer. Can you talk about. How you, 'cause now it sounds like you've been undergoing this transformation for, call it the last year.
What were some of the key early moves you had to make as a CEO to shift your kind of company mindset? From our, the basis of our advantage is blank to the basis of our advantage is this other thing.
[00:19:53] John Waldmann: So I think, uh, I can sit here and say this, you know, give change is really hard. Uh, I sit here and say, if like.
We were so far ahead in our thinking of this in May of 2023, we're talking about the end of SaaS. I gave that presentation we talked about as a leadership group. Guess what? A year later, nothing had changed. Like nothing. Uh, you know, we kind of continued on our roadmaps. We were shipping the things that we were shipping, we were working on the, the projects that we had laid out.
Uh, I took a very bottoms up approach of like, Hey, what's. Let's communicate a vision for where we want to go. But I'm such a, I was a big believer of like, this changes everything. This is gonna change every part of our product. It's gonna change every part of how we work. Let's push this out to the entire company immediately.
Wrong strategy in a moment of change. Uh, looking backwards, I think where we really started accelerating in that change and getting the, the flywheel going was actually when we started to be more directive on it. And that, that was, I don't know, nine months later, uh. Coming out and saying of like, okay, actually we're gonna pick some very centralized teams and we are going to, uh, use them to prototype in different ways, whether that's internal operations or the products we're building.
We are gonna take the people that we have seen the natural curiosity for around these tools, and we are gonna elevate them to different positions where that curiosity and kind of experimentation can spread throughout the organization. We were going to recognize that and reward that more publicly in the things that we're doing from a show and tell standpoint, from a team learning standpoint.
And then ultimately just being far more directive on you have to use these tools, you have to change the way that you work. And ultimately of like, this is what the roadmap is. And I'll tell you as a part of that, I took over product again. Uh, so, you know, I hadn't been running product, but I took it over about a year ago for that reason was like, we gotta be more directive.
[00:21:48] Henrik Werdelin: I think it's. Incredible important point you are making and, and I think a lot of the companies I'm involved in, we've seen exactly the same, where there's kind of like been this invitation to start with from the founders often and then, you know, like business as usual, uh, because you know, people don't like to change that much.
And I also thinking like a lot of people who kind of had worked themselves into middle management in various organization were kind of very comfortable with the way that they've kind of like learned to do stuff. Um. And so, uh, I, I definitely hear from a lot of people the same that you're saying is that we had to kind of do that.
Um, Jeremy and I was talking just before you got on, um, on something that Kevin Kelly was talking about in an earlier podcast Yeah. Where he was comparing artificial intelligence with artificial power, and then he was talking about how you couldn't just apply artificial power to kinda like the. The wagons that you had, you know, that used this hols with, and so you, you had to kind of rebuild stuff from the ground up on that stack.
You had to build factories. And with autonomous driving, you probably can't use exactly the same roads and signs. Suddenly you have to rebuild stuff. And so what I hear you say is in many ways the same, that if you want to take full advantage of ai. You kind of have to kind of almost rebuild on a quote unquote AI stack, not technology stack, but kinda like technology acceptance stack.
Is that, is that what I hear you say? A
[00:23:21] John Waldmann: hundred percent. A hundred percent. And I, I, I do think, um, I. That most people will get to an oh shit moment using these tools and realize how powerful they are, and then kind of the natural curiosity can kind of emerge around it. But I, I do think at an individual level for change, you, you kind of have to get people, help people get to that oh shit moment, and then give a lot of the tooling to your point and infrastructure and change and be directive of how different the world is gonna be in a, in a post world share.
Um. One of our board members said something really profound, uh, probably a year ago, uh, when he was talking about trying to get the company up the, up this learning curve, and he said is if you want to get people who are, uh, further ahead on thinking about ai, hire some people that are unemployed right now as point was one.
They're the people who have the time to tinker. They're not day to day in the, uh,
[00:24:28] Jeremy Utley: they're not steeped in the status quo.
[00:24:30] John Waldmann: They're not steeped in the status quo. They're not busy writing PRD docs. Uh, but the other part of it is those people realize that they are not hireable anymore if they don't have a skill set here.
And that's in a very important thing. And I think if you are a leader in this moment and you care about your team, you care about the people working for you, you're doing a huge disservice to them if you don't kind of push them into the deep end of the pool and nudge them to learn these, these tasks, I, I think there's a lot of people that are kind of doing it by invitation and suggestion, but at some point it's like, yeah, I just feel like I would be doing the team a disservice like.
This is where the world is going. And if they're not developing the toolkit here, we have not served them. Uh, we should be the place where you can get up that.
[00:25:12] Jeremy Utley: How specifically. So say somebody accepts that premise, John, and they, and they hear you say, I wrote this down. I'm, I'm taking diligent notes here.
You're doing a disservice to employees who aren't up the curve if you don't push them into the deep end. If a leader accepts that premise and they say, well, where do I push? How do I push? What are the kind of levers that you use to push people?
[00:25:37] John Waldmann: Well, so there's a lot of, I think things that are not gonna surprise here.
It was things like lunch and learns and trainings. It was. Hackathons. But I'll tell you the thing that made all the difference in the world. We did two hackathons, uh, six months, maybe nine months apart. First Hackathon was like, Hey, we highly encourage you to use ai. Second hackathon was you have to use an AI tool.
Like that is the theme of the hackathon. And we do company-wide hackathons. So it's not just engineering. A product design is company-wide. Uh, guess which one was more impactful for the change management? Right. It was like, I can get people over that inertia a little bit of the, the fear and all of that.
'cause everybody's got like, well I got all these other ideas that I'm really excited for. And they're not bad ideas. They're always great ideas, but, but they're not getting people out of the comfort zone in, in the way that they need to be. And, and I think part of that was, you know, you start to get the people they can that had some of the natural curiosity and were tinkering on it and getting them kind of within those teams, sharing what they're doing and building the agents and showing how they can build prototypes.
Uh, and kind of leveraging some of those, uh, bottoms up examples, well tops down stuff of like, you know, take cogen of like, you will use a cogen tool, uh, and going from like, Hey, this is like an optional thing for you to, Hey, we, we expect you to use this as a part of your workflow. Uh, so I, I do think some of it is back to, you know, being a little bit more directive.
In some of this. And then frankly, it's a lot of the commitment of like bringing the tools in. Uh, yeah. Making the investment of third party tools as well.
[00:27:14] Jeremy Utley: Yeah. And then how you integrate, 'cause I wanna circle back to your board member's comment. I think it's so profound and so astute. The comment that higher people who are unemployed right now, I.
One of our favorite, one of the, one of probably the most popular episodes of this show to date is A CMO named Russ Summers, who was a, is a very pragmatic episode about how he basically unleashed what he calls a GP team to do the entire marketing function of his new company. And we get deep into the conversation, we go, Russ, where did your knowledge come from?
And you know what he said, I was laid off. That's so funny, right? I mean, yeah, and he basically had, and, and I think one thing there, there's two really important aspects to what you're saying. One, somebody who doesn't have a job actually has time to invest, whereas somebody who has a job has plausible deniability.
Like, when am I supposed to learn this stuff? Yeah. I'm shipping PRD docs. You want me to stop writing PRD docs, right? It's like this weird chicken and egg problem. The other thing is that, that I think is really profound that you said is this person, say Russ or the unemployed that you're hiring, this person knows it's unacceptable.
They're no longer fit for the new world, and they are approaching their season of unemployment probably differently. So my, so Juan, I just wanted to affirm what you said there. How did you integrate those people? I mean, what did you, how did you go about finding the unemployed people who are re-skilling themselves, and then how did you integrate them into an environment where you got a bunch of folks who are, may, you know, some varying degrees have caught up with the status quo?
[00:28:46] John Waldmann: Yeah, I mean, I'm running, I'm running product right now, so I see it a lot on those front lines. You know, I'm, I'm interviewing the PMs coming through as we, as we hire, uh, and. I think is in, in the context of an interview and, and talking to candidates first, you can see who's curious, who's been exploring the technology, who's spending their time on it, whether they're at a company or not at a company.
And, um, you could unpack the motivations around that, but it almost doesn't matter. It it, it is about the curiosity. And I think we're at a moment in time in a, a period of profound technology change where like curiosity is rewarded disproportionately. Uh, and so I think that is part of it, is making sure that we've got the, those people coming in, uh, and folks who have been tinkering and learning with the tools and all of that.
I think that's true across every single discipline. Uh. One of our, one of our core operating values is around mastering your craft. And like, if you're not thinking about how AI can help you in whatever you're doing, you're probably not mastering your craft. Uh, there's just too much going on. So I, I, I'm like a big believer of like, a lot of this is top of the funnel and just kind of like the signal through the front door, then bringing 'em in.
I think it actually kind of happens pretty naturally because I do think that there is like a lot of latent energy people want to learn. They want to. Figure this stuff out, but I think just seemed to be shown, you know, they need to get to ship. Can can we just double click on
[00:30:17] Henrik Werdelin: the, like to learn? This is a question I'm not sure from who owe you it might be best.
Um, and John, you probably from experience in, in Jeremy probably from, you know, academia. But, um, I was talking to a friend of mine, I was Kaman who was like a, you know, a high end coach and I was trying to understand why is it, it's so complicated for some people. Um, to kind of like starting to adapt these new tools, you know, where is it and why is it that some of these kind of like curious kind of, I wanna learn feelings, kinda like why are they not there always talking?
And he was talking about what he called the self-authored mind and the socialized mind. Like basically you had some people who kind of like falls into these categories and the majority falls into the socialized mind. Like, like to do what we've always done in an, in an age where. You'll probably see more and more of our team members do more and more different types of work.
Because like the classic boundaries is kind of, I guess, being also torn down by ai. Yeah. How do you think as a manager that we encourage that? Or is it purely in selection of candidates that we can kind of do that?
[00:31:30] John Waldmann: I, I think both, and this is as much to do with the experience around AI as it is the last 10 years of running homebase.
But I, I think in the recent experience, I do think, um, first that you have to give permission to your team and like really unlock that latent curiosity in the things there. Uh, and part of that is establishing a framework and setting the expectations higher of the previous way of working is, is not gonna cut it anymore.
We were very intentional when we kicked off this year. That it's day zero. We are a new company. We are approaching everything in a new way, and that is our expectation going forward. We have a a, a counter in Slack every day that just increments up from January 1st on what day is it at the company to just kind of instill of we are not this company that we were in the first 10 years of our life.
So I think part of this is setting the tone as a leader and that enables your team to do the same thing that enables your leaders to be more aggressive and. Kind of expand the Overton window of what was possible in the company again, 'cause that's that, that tends to get narrower over time. I think the second part of it is, you know, hiring a lot of people over time, managing a lot of people, seeing a lot of leaders, manage a lot of people.
I kind of think now that there are a set of traits and things like this, that it's not that it's not coachable, but it's probably not worth the time to coach. I think like we have to be honest with ourselves sometimes of like what we are as a company and kind of where we should be investing our time to bring people along.
And that may sound really harsh, but actually I think it is just like a, hey, sometimes we are trying to fit a square peg into a round hole, and the type of company that we are is just not the right fit for the person that's here. The cultural values that we want. Whether that is like where we are today or aspirationally where we want to be, just may not be the same fit for the person there.
And I think it's back to like, if you actually care about the person, stop trying to like hammer them into the round hall and instead just like acknowledge that it may not be the, uh, the fit that it once was.
[00:33:32] Jeremy Utley: Can you talk for a second about, I mean, let's get super pragmatic. Let's just geek out for a second.
Yeah. Things like KPIs, OKRs. What is the evidence? And it, it could be soft, right? They, they just have demonstrated they aren't curious. But like, if you think about managing people and you've gotta manage their performance and in some cases help them find a better fit, what are the specific things you've baked into the system to alert you to when it's become clear someone's not a fit?
[00:34:02] John Waldmann: Um. I think, you know, we do use OKRs. We've used a different variants of OKRs the last few years. Uh, for better or worse, we use OKRs. Uh, and, and I do think some of this is like increasingly the objectives, uh. Are very clearly aligned to the future AI driven company that we want to be. I think it, it, you know, back to roll the clock back, it was like we're setting objectives for which, like this solution to it probably requires AI to now the OKR is explicit on it will require, uh, ai.
And so at some level you have to set the outcomes to require the things that you want to see. And if you're then not seeing it. The gap is quite clear. You know, it, it becomes less around kind of like the qualitative traits and things like that and the outcomes that those qualitative traits would lead to.
So very tactically, it's like, well, you know, we believe that AI can make our support interactions better. We're gonna bake that into an OKR. We believe that, uh. Code gen tools can increase our product velocity. Two years ago it was about like setting the goal about engineering velocity. Now that goal is about adoption of code gen tools and the number of lines of code written by, or the, the percentage of our code written by AI tools.
So it was like a very clear example. Now it's like the light is very clear on who's using the tools and who's not using the tools. So. I don't know if that's actually like a good answer for you. Did
[00:35:40] Jeremy Utley: you to that? That's great. No, it's great. I big, I mean, I think, I think part of the challenge with, and, and you're, you've got the benefit of being a more nimble organization, more agile, et cetera.
Mm-hmm. I think part of the challenge, if, if I look across especially larger organizations, the reason some folks aren't, um, you know, collaborating with AI tools is because it's okay not to, inaction is an acceptable action, so to speak. I think what increasingly has to happen is leaders have to take inaction off the table at inaction has to become the punishable offense, and that doesn't mean success is required, right?
For example, I can imagine a KPI where you say, Hey, I wanna see 10 AI driven experiments in six months. If you show up, all 10 can fail. That's perfectly fine. I we're gonna high five, whatever. But if you show up and say, I only did two, we're gonna put you on a performance improvement plan. And if that happens again, you have to look for a new you.
We can't have people who aren't constantly experimenting on this team. Right.
[00:36:40] John Waldmann: That that's exactly right. That's exactly right. And I think what we had to do was make sure that we were being. Um, clear to the team on the journey that we were going on and giving them the support and tools to make that jump.
Like I, I, I want to make sure that we are a place where people could be trained and developed and find the resources available to make that, but at some point it does have to be pulled,
[00:37:03] Henrik Werdelin: I think. I think all this is incredible and you're so kind to be kinda like so honest with the journey and so really appreciate that.
Um, I was curious if we go back to your customers, let's say that we have you, I have a friend who's a tree cutter or has like a small restaurant besides obviously use Homebase as a vendor. That seemed to be doing a lot of the thinking for him. Yeah. What is some of the stuff that you, like how we, we now talked a bunch about how do we suggest.
That, you know, midsize to big size companies, kind of like a doing this. What would be your recommendation if somebody sat down and said, Hey, I run this restaurant, I do this thing. You know, how should they think about like doing the same journey as you've done with your company through this
[00:37:47] John Waldmann: change?
That's a great question. Um. I'm sitting here as a technology company, and it's very easy for me to say this as a builder, as a company full of builders of like, how am I unlocking the, the best version of the team that we have who are incredible, who are curious, who have learning mindsets? H how am I giving them the, the, the room to run?
You know, I am all about like, let your wild stallions run. Uh, like that's who you want at the company is the people that are just like born to run at a certain speed and accomplish great things. Tech is full of that, right? It's very easy for me to sit here as a, as a company and say of like, that's what we're gonna culturally be as a company.
I think you're running a local business. The nature of your business is so different, you know? And, and I think that is why like company like Homebase can be so successful because I think for the longest time, uh, technology frankly did not honor these businesses in what made them so special. So.
Important to the world, what made their teams so unique in what they provide to the world? We are absolutely doing a disservice to our customers if we're saying, Hey, in order for your team to take the next step in the journey to be a great restaurant and serve, you know, deliver incredible customer service, they should be spending an hour in front of software every day.
That's a failure of us as a company. That's not a failure on them. Like we should be doing the exact opposite, which is like in this moment in time, deliver solutions that are allowing them to get to the thing that they are uniquely good at. And the thing that allows them to be a thriving local business today.
Ultimately that is about the experience. It's all the things that exist out outside of the tools and how the business runs. Uh, it, it is about the ways that they're using tools to kind of accelerate their, their special and unique advantages. That's almost always about kind of the company they're building, the way that they serve their customers.
It is almost never around the ways that they choose to run payroll. Uh, there is no unique advantage in that there is just time spent. Uh, the thing that we can hope for as a company is we give them that time back. The other thing we can hope for is like, give them the tools to be incredible managers and leaders and automate some of that work for them too, because.
A lot of 'em are not classically trained managers and are coming at this as a first time manager or first time leader. So I think we have a role to play there, but I, I think the part of the world we serve is like, should be more enabled than kind of technology first.
[00:40:22] Jeremy Utley: Is there a world, John, where your recommendation, uh, I dunno if this is a statement or a question or what, it's possible that your suggestion to these folks, if, if they ask you, how can I become augmented with ai?
To your point, it's not about them automating their own payroll or whatever, but is there something about thought partnerships, strategic thought partnership? I think one of the comments, and there were kind of recurring themes on this show in these conversations is. There's something about kind of workflow augmentation and automation and all that stuff, but then there's just the thinking partner.
Like for a small business owner, basically they've got trillion dollar coach Bill Campbell in their pocket who if they know to provide Chad GBT, that context. I want you to play the role of Bill Campbell. I want you to ask me Tim questions about my business, just like you ask Larry and Sergei, I want you to be brutally honest.
Poke holes in my thinking. Give me non-obvious strategies, right? All of that's available to somebody. Is that how you would recommend, you know, a small business owner kinda leverage AI or, or what's the, what's their immediate, uh, low hanging fruit opportunity.
[00:41:29] John Waldmann: Obviously the lowest hanging fruit opportunity is use homebase. But we'll, we'll take that as an assumed. Of course. That's, but that
[00:41:35] Jeremy Utley: fruit is like on their lips.
[00:41:36] John Waldmann: The second thing that they should do, uh, yeah, I,
[00:41:40] Henrik Werdelin: you forgot to say that. You're, you forgot to say that. UL prove entrepreneur. I do the,
[00:41:43] John Waldmann: yeah. Join home base.com. Uh, start for free today. Uh, perfect. We are a freemium product. Uh, no. The after, after going through that journey. journey@joinhomebase.com and getting set up. The next thing. Yeah, I, I think that's a great point around using chat GPT and just the, the amount of coaching and support available in that, uh, founding a business is a lonely journey and it is an incredibly hard journey. And I don't think the work and uh, kind of courage that every single local business that exists in this world has, is demonstrating, gets the amount of appreciation that it should. Behind every single local business. There is an incredible story. Like that's one of the best parts about serving these local businesses is like that.
The courage that it took for this person to put a big part of themself out into the physical world, serving their community and the people that they know. That is a very, very profound statement of entrepreneurship. It's vulnerable. Yeah. Yeah. So much vulnerability in that. Forget about like the financial, uh.
Risks that people are taking and doing it, but like the emotional risks that people are taking that are profound and yeah, I, I think chat, GPT or whatever, LLM of choice, dude. Dude.
[00:43:02] Jeremy Utley: Okay. Okay. I just have to interrupt 'cause I like, okay, Hendrik and I did this the other day with Blair. Let's, let's just brainstorm on your business for a minute.
What if there's a series of home-based branded or home base recommended GPTs that are all about small business coaching, right? You could encode. Some GPTs based on world-class coaching as you understand it. Right. Um, and I wonder if there's like the top five, I mean, Bryce Shamal from Moderna who we interviewed a while back mentioned AI as assistant, AI as coach, AI as expert and AI as creative partner.
So we even take those four things. It's like, yeah, what if there's home base assistant, which is just a custom GPT. I wonder if that might be a really interesting way to kind of build trust with small business owners. It's like you can act if you pay what, you may not even have to pay open AI to get access to GPTs, but we've built these tools to demonstrate the power of, you know, coaching expertise, creative assistance.
[00:43:56] John Waldmann: I think that is a wonderful and provocative idea of. You know, there, there's so much of this that we are putting in and building home base around of how are we bringing help to the tasks and the things that you have to do and the regulatory risk, and how are we offloading all of that from you to us in your brain.
Uh, but I do think that there is a part of this that is emotional too, and being able to provide that coaching and support in a way to a, to a business owner or a leader. You know, we all know as, as. Leaders and managers. So much of what we do is the support that we're providing other people and yeah, it's a hard thing.
Uh, so yeah. I I like that idea.
[00:44:40] Jeremy Utley: Well, that's o one thing that we aim to do on this show is always give a gift back to our gift. There you go. There's your the My friend. So thanks so much for joining us, John. This is an awesome conversation. Okay, Jeremy, professor. I know you're, this is catnip for the, for the BarkBox guy.
Huh?
[00:45:01] Henrik Werdelin: I see what you just did there. See what I did? See what I did. We 1st of April, uh, the day yesterday of this recording, um, announced our cat box, uh, where we're just sending out an empty box to people, to the cats to plan. Um, 1st of April though, so there you go. Um, that's,
[00:45:18] Jeremy Utley: that's so funny.
[00:45:20] Henrik Werdelin: But, um, okay, so I mean, like, there.
A lot of things obviously resonate a lot with what John was saying. A, I mean, like he's just an incredible leader and I think it's so cool when people come in the pot and talk so honestly about some of the issues and I think this problem of like, how do you get my team to kind of embrace this new technology is something that.
Every founder is now trying to figure out. And I thought he had some incredible suggestions. And, and I think also just kind of, it was nice to hear somebody else who kind of like is, is trying to do the same thing and find it complicated. Um, so I think that was one thing I I I love that you're, you had a quote on, uh, inaction is an acceptable action.
And I think for people who run this organization that thrive to be more AI first just will have to stop accepting that, uh, 'cause there's just. You know, and I think, you know, as we've been doing this podcast, I think we also started with this curiosity mindset of like, how do you do this? And how do you get people to walk through path and how do you inspire and make sure you do the Slack channel and stuff?
And I definitely, I think interestingly, you have. Failed a change of tone in the last year and a half where a lot of people come on now and a little bit have the attitude of like, okay, playtime is over. You know, like, we, you got access to it now you actually have to use it. Well,
[00:46:40] Jeremy Utley: I, I mean, you, you know that I'm obsessed with play, so I won't say playtime is over, but I will say, uh, it's no longer optional.
I don't think playtime is over. I mean, not to, not to mince words, but I think playtime is now mandatory. Yeah. Whereas perhaps before it was optional.
[00:46:53] Henrik Werdelin: Yeah. Right. I think that's it. Well put. Um. And then I kind of like, uh, I dunno, this a very practical thing. Uh, I just like the idea of having more people say, Hey, that's great.
Gimme 10 ai Examples of that, I, I mean like if with. Uh, rep or lovable or you know, like all these different tools that are available for people to make their own prototype. There really no reason why even like teams that may be a little bit slower to adapt this thing like, uh, finance team, legal team, whatever it is, uh, uh, except we've heard many examples of those teams being the first.
But besides that, I mean, I just say, you know, you need to come back with 10 examples of something tangible of how you solve this with a product. And just get into the rhythm of practice. The vax on vax off, kinda like motion or ate kind of, uh, reference, but the, to just practice in productizing solving the problems with ai.
And that is, I think, increasingly also just something that we should just ask people to do.
[00:47:55] Jeremy Utley: Well, no, no time spent kinda building with AI is wasted time. So even if that product doesn't ship, even if that lovable prototype doesn't go anywhere. You're building kinda muscle memory and familiarity with tools that you, that will become more indispensable to you over time.
Therefore, play and build, and I mean, I love the example that he gave at the beginning of the show, which is the product review process. The roadmap process has totally changed now instead of reading a bunch of 20 page documents, which basically becomes the job. Now we're doing two or three minute demos of real live prototypes, and all of the time that we were spending reviewing our plans is now been redeployed in the field.
We're able to be learning and inspiring and getting feedback. It's just this incredibly counterintuitive reality. I think that an ai, I. Augmented workforce is far more able to be more human than the workforce without. And I think the fear of kinda cybernetic organization and cyber, like all of this vernacular, is actually, there's scare tactics that keep people from being able to be more human, to spend more time with their customer, to find better problems to solve, and on and on.
I also loved, um, I think he mentioned the cultural value is mastery of their craft, and this idea that, um, AI must become a part of what it means to you to master your craft. That is a really well stated point, that if you have a craft that you are mastering, if you aren't incorporating AI into further mastery of that craft.
I think what he said was, if you don't see that you're blind, or at least that's what I wrote down, maybe that was my interpretation, but to me that it's a great reframe of what does it mean to have a craft and master it. You, you now gotta incorporate ai.
[00:49:42] Henrik Werdelin: Is that it? Not as in, is that it? But like, is that all that was that, that's
[00:49:46] Jeremy Utley: all, that's all you took out?
Uh, I've got, I mean, I have like nine pages of notes here. I can't read and speak at the same time. I think, you know, one thing I will say that's pretty, uh. Was was great is, you know, the, the irony of, I dunno if it's irony, but the hospitality person, you know, who hates ai, who, once you start to imagine what you go, oh well I don't really want to do that.
Oh, and I don't want to do that. And I thought John's kinda clever shift from, it's not, the conversation should be about the technology, it should be about the problems we're solving and the the how is up to us. Right? But if you can help someone. Be clear on, you know, the fact that they've gotta screen a hundred resumes for the hostess jock.
Nobody's raising their hand and saying, I can't wait to read all these resumes. They're saying this, these resumes are actually keeping me from running my restaurant. Right? Think shifting from a focus on the technology to the problems that it solves, I think is really brilliant.
[00:50:45] Henrik Werdelin: I think that's it for this wonderful episode.
[00:50:49] Jeremy Utley: Henrik, what's our, what's our, um, what's our code word?
[00:50:53] Henrik Werdelin: What about, uh, small local business? Because I do think that, like what he said about how important it's, and how little credit they get is just a hundred percent right, like it is you walk down all through these small stores and they're always friendly and like, at least like the ones that are around me and they're always like, just makes you feel welcome and make your day and it must be exhausting having to make sure you stand up there and restock the store and get it ready every day or coffee shop or whatever it is.
[00:51:21] Jeremy Utley: I think that's a great code word. I will submit another so people have two options and they can just decide what they agree with. I say distraction because while I was saying what stood out to me, Henrik was sending me a meme. He wasn't even listening. So I think the code word should be distraction, but.
It's not to you, you're good to choose. Do you wanna say, you know, support small business? That's because
[00:51:43] Henrik Werdelin: I think you look like data from uh, star Trek today. And so for people who watch it on YouTube, they can un unbelievable. Unbelievable.
[00:51:52] Jeremy Utley: I'll leave it to you to wrap this program.
[00:51:55] Henrik Werdelin: Okay. And with that, thank you so much for listening to another episode off Beyond the Prompt and as always incredible.
Incredibly just ex incredible. We just really appreciate that you're staying to listen all the way to the end. And. If you are here, will you please, please, uh, give us, like, give us a subscribe, send it to a friend so that we can grow our, um, listenership, uh, would very much appreciate that. I totally killed that one, but
[00:52:20] Jeremy Utley: there you go.
I love it. No, leave it. Leave it. Thank you. Leave it. Thank
[00:52:23] Henrik Werdelin: you so much for everything and we will talk soon.
[00:52:27] Jeremy Utley: Aio.