The Exchanges

Q I just want to wrap up where we always do, which is when you think about sort of product building, product orgs, all the stuff we've talked about, is there someone in your career that's kind of most imprinted themself on you?

A I think the two people that have had the most impact on me are Gokul Rajaram and Alyssa Henry, both at Square. Gokul was leading product and engineering when I first got there. Gokul was extremely focused on speed and moving quickly. We were spinning up most of Square's product suite. He started in 2013. When I came there, it was basically like exactly how you described it. Like we've got this wedge product. Great. We're gonna build this business operating system on top of this wedge product. Payroll launched, customer engagement launched, appointments launched, invoices launched, all these things just like bam, bam, bam, bam, bam, bam. He had such a drive and sense of urgency to him. He was so humble and like kind, and he's been a mentor to me and my, my whole career. And like, I, I just like, I love that guy. He's a beautiful human and he, he's, and so teams felt supported, but like moving quick.

AI assessment note: “I think the two people that have had the most impact on me are Gokul Rajaram”

Q do you want to verticalize and in what ways do you want to sort of invest in some sort of common platform or operating system? When you think about that in the context of Gusto, when you think about it in the context of Square, were those decisions made by product taste and intuition, or, or did you develop like a structured way to decide on those types of things?

A Coming back to Gusto, I mean, I think what, one of the things that we really benefit from is that our thesis of helping folks with starting, growing, and running teams is those jobs, I think just inherently are much more shared across industries. So if you break down our customer set and we have north of 300,000 small businesses on Gusto now, And you look at them sort of by traditional industry segmentation, it's very evenly distributed across a lot of industries. And I think we, the reason for that is some of those, uh, jobs that we've done for starting growing and running teams are, are very shared. So benefits administration, being able to hire off board employee handbooks, payroll, the paying hourly workers, so on and so forth. There's nuance and we, and we try to, you know, try to build into that nuance so that it form fits various industries in the right way. But, but a lot of it is shared. If you juxtapose that with Square, Square is trying to do much more. I mean, that's one part of sort of the SMB stack, and they're trying to do that and sort of all other parts of it. And I think in parts of the sort of the SMB stack, if you will, there's just more, more like vertical nuance that shows up faster. You know, come back to your question. I mean, I think it just was kind of apparent that for the number of ways that we are trying to serve small businesses at Square, There wa…

AI assessment note: “I think it just was kind of apparent that for the number of ways”

Q some ways, if somebody is the most career oriented, maybe they go make the core two percent better every year. And that's going to be the best way for them to grow. And maybe that's fine. Maybe somebody with that personality should just focus on that. But is there anything else you've, you found or figured out over the last decade in sort of this theme that we're talking about?

A Yeah, we talked about the Hack Week example as a service of innovation. There are, you know, there are, we have a few across to right now, but there, there are teams, you know, that it's nice to kind of spin up and be like, look, we're going to try this for a little while. You know, or you kind of have free reign in this space to try some things. We believe that you're shooting at a real problem, so we buy the problem articulation. And a lot of times, if you find a leader that can convince you on the problem, that's where my, a lot of my like, okay, I trust the intuition on this because I can, they can reasonably articulate to me why they believe, we might not know this all yet, but like why this is worth charging at. And if the logic checks out and I buy the intuition behind it, as well as like how they weave together the story, that kind of checks that, that can help check the judgment box for me to be like, yeah, let's have at it for a while. So carving out teams and giving them sort of the space to, to attack and knowing that going in, like this is a unknown area. We may or may not find success and trying to set the expectation up front that like, if we don't find success, we need to just be able to have an intellectually honest conversation. At some point we can have a Rough sense of when that might be where we're like, okay, we might not be here with this one. Try to find…

AI assessment note: “carving out teams and giving them sort of the space to, to attack”

Q think to talk a little bit about building products specifically in the context of small businesses as the primary user. And I was interested given you've done it in different roles across different companies for a decent portion of your career. Are there specific things you've figured out as it relates to building products specifically for SMBs that might be different than building for any other type of potential user?

A I think when you work in technology, it takes a while sometimes to find what part of technology you're really passionate about. I've worked in a variety of tech settings throughout my career. I was so excited to start at Square and working with small businesses back in twenty-twelve or so. I've always loved small businesses. It's been a part of my life. My grandfather owned a bowling alley. I grew up going there every weekend. I just think they have a valuable, Part of making a good community. So as a customer, it's a great customer to serve. And I, and I really felt more at home at Square than ever before serving that customer. And there's a few reasons. I think the first was, boy, if you get it right, they love it. You know, you're working at sort of the core of helping them with their livelihood and with something that to them is, you know, kind of make or break for their life and for their, for their wellbeing. And so there's a lot of heat on the customer when they sort of respond to like, How's it going? You know, if you did it good, you hear a lot of love and praise. If you did it bad, boy, you're going to hear that. And, and I really appreciated that. There wasn't much ambivalence to how, how the product works with small businesses. They're very direct on like, this is crushing us or it's like super helpful. So that was one. I think a second, you know, really treating a …

AI assessment note: “There wasn't much ambivalence to how, how the product works with small businesses.”

Q Do you think sort of product taste and intuition is something that is like a learnable skill or a muscle that can be exercised and, and, and improved over time? Or at a certain point, does somebody just have that type of sensibility and other people don't?

A No, no right answer. I do really value what I would call good judgment. And good judgment is something that is best screened for at the point of interview. And that doesn't necessarily have to mean like this, somebody is an expert in all things product and they've used a million products and they can articulate, you know, use a lot of like product vernacular to articulate things, but has reason, you know, construction problems in a clean way, has reasonable ways that they would sort of break down how they would go about solving or getting to a conclusion on something ambiguous. These are some of the things that I want to see in, like, somebody that's trying to take up the product management role in particular. A characteristic we're looking for is somebody who's curious and, like, somebody who, ideally, they have gone out and, like, played with a whole bunch of products and, like, can bring in examples of how product X did something well or product Y did something well. Even if it's not in the same domain, that helps know, like, okay, the curiosity sort of vein is there, and you pair that with good judgment, and they seemingly are You know, excited about just the product arena in general, like those kinds of conditions lead, I think, to success with product managers. So yeah, I mean, I think it can be developed, but like, we certainly want to see folks that are coming into that…

AI assessment note: “So yeah, I mean, I think it can be developed, but like”

Q Can you explain that in a little bit more detail in, in sort of how you use horizons or like how you would explain to someone the way that you think about resource allocation in terms of investing in the core, enhancing the core? Taking on new high conviction bets, high risk bets, sort of those types of things.

A Yeah. So we're, we're right now we're like in the first cycle of my time at Gusto of going through, um, annual planning and working through, um, what we're going to be doing over the next year. Annual planning for us is a little bit offset. We follow like the, more or less the tax year calendar. So our fiscal year ends, ends in April. I, one thing I really like about our approach at Gusto is we keep We keep a rolling three year vision of where we want to go. And so we're working through that right now, like stepping back from just next year, what does the next three years look like? And what does the customer deserve? And what, where are we versus where we think we should be for the customer? And we use that as an opportunity to kind of think big. It's constrained in the sense that it's three years away. So that's not 10 years. I mean, there is some constraint on that. We try not to get too nitpicky about like, well, how are we going to resource that? And all the questions that inevitably Will come up when we talk about a shorter timeframe, but we want to think, you know, think bigger in that timeline. And in doing that, you know, that allows, that kind of gives us the space to both go like, what would it look like to go deep? What would it look like to go wide? And a lot of new concepts and thought and thinking comes out of that, of that process. So we're in it right now, whic…

AI assessment note: “we keep a rolling three year vision of where we want to go”