So I think I grew up in, um in New York City when I was really little. So I lived in the Bronx. Um, until I was about five years old when we moved up to the Boston area. Andi, When I moved up around there, I wound up becoming friends with a kid whose dad owned a machine shop and that machine shop had some programmable tools. And so hey, taught me when I was about eight years old how to dio some really, really simple stuff on the command line. Eso things like, uh, yeah, Ask some question. How old are you? If you're over 21 you can drink a beer. If your lesson 21 you can't drink a beer. And so that was that was part of my intro to programming was, you know, just hanging out at my friend's house when I was, like, eight years old. I kind of gave up on a bunch of that. Got focused on all of the other things that kids focus on from age 10 11 12 13. And then when I was 13 it was 1995 which was really like the big year when the World Wide Web became a thing. And I realized that, you know, the Internet was going to be, you know, this huge part of life going forward. It was really interesting. And I had a little bit of programming experience, so I started teaching myself a little bit more about how to code. And I made that my hobby. So it's my hobby for all the way through high school. Tell us about 18 years old, and, uh, in parallel to that, my uncle had been an I t person at this, Uh uh, This this travel agency and the founders of that travel agency went on to found Priceline dot com in the nineties and brought him along. I was like, their I t person. So all of a sudden I see my 27 year old uncle, um, you know, go from, you know, just any other member of my family toe all of a sudden having overnight fortune, and so, frankly, this like, yeah, this this really, um you know, simple minded, like teenage fantasy formed in my head of like, you know, I also wanna get rid quick, just like you know, I think a lot of people fantasize about that type of thing. Andi, I think that caused me toe realize that I should lean into technology. And then that was a good opportunity for that. Well, I know I would actually find it a really rewarding career, and there would be a bunch of, you know, interesting twists and turns after that. Um, that initial fantasy of you know, setting myself up for life, coupled with my by doing my hobby, was kind of the thing that that motivated my teenage brain in that direction. So I set in my mind I'm gonna go be CTO of company. I started a couple of companies right after high school, both of which failed miserably. One was an online barter trade platform. One waas bike maps integrated with, uh, you know, live street maps. But this was in the year 2000, so Google, of course, ended up doing this in in 2010. Quite well. If you wanna map your bike group eso, both of those failed. And then I went Thio wound up going toe night school and studying computer science at Harvard. Andi in parallel, was developing software for a bunch of local real estate agencies in Boston. So that kind of became my knee show. Is running a software consultancy for them? Andi, I always fantasized about, you know, getting back in tow. Startup world, you know, started by cos again. But frankly, after failing a couple of times, and I was, like 18 I really felt scared about it. Like, you know, the I I put myself into a zoo much debt as you can when you're 18 years old at the time. In order to do those things, you know, I was skipping meals to make stuff happen because it was it was so stressful on then afterwards, you know, the fallout was was quite difficult emotionally. So it took me a little while toe get into a good headspace to go dio something like that again. Um, after college, I went and started at a startup that got acquired, you know, just a month or something. After I joined on DSO that only lasted a short while and I started realizing like, Yeah, I'm getting a little bit older. I should maybe try to figure out, you know, a real career for myself went to a big company worked there for a couple of years, and in the process, I learned a bunch of things about how you know, a big real company works, and it was really awesome. Thompson Reuters, you know, big Global global Company. But I also learned that I didn't really want to be, um you know, one small part of a really big machine I wanted to be ableto feel like I was making really meaningful contributions. And so, um, that set my eyes back out into the startup world on DSO I started having coffees with a bunch of people talk about companies. They were starting from scratch. And about my 7/30 conversation, I wound up meeting Dan Cheat, who had been the founder of Lab 49 which is ah, technology consulting firm in New York that grew to a few 100 people. Onda had a ringing endorsement from from a close friend of mine. And so, you know, he told me what he wanted to Dio and I was hungry to get started with something. And so, um then started greenhouse. And so now if we flash forward about 8.5 years, Greenhouses over 300 employees. We have over 4000 companies using our software, including lots and lots of brands that you would have heard of. My team is about 100 people or so. Andi I'm involved in everything from business, technology, strategy and product strategy. So that's my longer dancer from childhood Thio.

So I think it kind of depends a little bit on scale in time of year. Those air, probably my two faceted answers. So when I was CTO and there was a 15 person team, I think I was really? And it was a brand new company was responsible for figuring out. What's the culture gonna be like? What engineering practices do we need in order to be ableto scale up successfully? How do I recruit people into this company? Like, what's the reason they should want to come work here? Um, you know, and how do we respond to incidents in the night there, Tons of sort of tactical problems to solve everywhere. And I think the strategic direction was relatively clear and the strategic direction could be related through one on one conversation. So when you have, like a 10 or 15 person team, you could meet with every single person and, um, you know, relate the same message and have deep conversations with them form deep relationships that starts breaking down. Um, certainly, by the time you get to 40 and by the time you get to 70 or 80 people, you know gets gets to be logistically impossible to communicate one on one Thio, folks. And so then you have to start thinking about what are the most leveraged activities Aiken Dio, in order to effectively coordinate and retain and higher at scale all of these people. So, um, the thing I found interesting when When you sort of move up the up the curve in terms of size of organization is that the problems become in some ways, like even though they are human problems, a little bit less human and mawr systems problems because you're then trying to create a system for fair compensation, not just, you know, tell somebody what they're, you know, comp changes for the year. You're trying to create a system of, you know, how you'll handle vacation policies. So I you know, whatever it is. And so I think I took each one of those people problems and and thought about it as an engineering problem which I think actually helped me really engaged with, you know, my brain in the way that software engineering had engaged, engaged my brain as I was doing that type of work. Um, Then I think the other thing is, you know, you get towards the end of the year you're rolling into the next year. There's questions about budgeting. How are you going, toe? Spend your money. How much money do you need would spend it on Andi? All of that rolls up Thio the strategy and so as a seat, you're also a member of an executive team. Eso I'm the department head and have a counterpart in customer success to counterpart in sales counterpart Um, you know, in in people function a counterpart in marketing and, of course, the CEO and other business leaders. And so you're trying to figure out collectively, what is it we should be doing with our business? And how does that plan translate into specific things that I'm going to do inside of my team? So in some ways, your, uh contributing to defining the top level business strategy is part of an executive team, and then you're responsible for translating that into a form that can then be action by your department. And if your department's a good spies, you know, you have 100 people on your team, whatever it is, um, it's almost like that process has to be layered through filtered through a few different levels. The top level thing might be make more money next year. You know, in the next level, thing is you have to then have ah by doing something right. So make more money next year by building a new product and then the next level down. You have make more money next year by building a new product, Onda new product will be X and then the next level down it's and this team is going to work on it, you know? So you end up with a re sourcing plan that's aligned Thio, whatever the overall top level objective as it cascades through through the organization.priorities. I think number one is always create a healthy work environment for people. Um, you know where people feel happy to come toe work, cause or as happy as they can be? I mean, there's, uh, you know, days for everybody where they would rather be doing something else, Of course, but I Azaz kind of a core responsibility of any leader, too. Create an environment. Um, that feels good for the people on the team. Allows them Thio do really great work, allows them to feel like they're learning from the people around them, allows them to feel treated fairly. Um, you know, when they come to work, Andi allows him to feel respected no matter who they are. So I think that's probably priority. Number one is ensuring that culture is set. Number two e think it's always, you know, bringing in and trying to harness the best people toe help make the company better over time, and so recruiting is always a top priority. I think anytime you have talk Teoh, a senior leader, recruiting the best people into the company is probably the most leverage thing that you can do it because you recruit an awesome person. They do great things without you having toe do much. You recruit a terrible person, require lots of attention and don't do their work. And so who you hire is is most impactful. Decision on Ben. You know, I would say the third one is really ensuring that there is clarity in what we're doing. Onda coordinating the actions across the group to make sure all the right stuff happens. Um varies pretty considerably their periods. So I think from year zero through three of greenhouse, it's probably working 70 our week. Um, that was the really early start up phase from years three through six of greenhouse or your seven. Maybe even I think I was probably working 55 hours a week or something like that on then, you know, then I think I steadily dropped a little bit. And during co bid Right now I realize that you know everyone trapped at home, I need to prioritize other things in my life on top of work, in order to be my best self when I'm at work, because there's so much else that sort of you get out of going to an office or, um seeing your friends outside of work. There's a lot of things that you don't you don't get during this period of time. That e think you have to replace or something. So I probably worked very normal work hours now, like 40 hours a week. I spend more time with my daughter and my wife. I spend more time exercising. I spend more time cooking Onda. Frankly, I think I'm bringing a much better version of myself to work. As a result, eso if I were, you know, if I were starting and like, you know, you got to do whatever you got to do with the beginning. So sometimes that means throwing hours at the problem. There's no other way. But I do think that you know, it's a recipe for burn out toe. Continue working long hours indefinitely. Um, and you become a You still go out for work. But you're your worst version of yourself. If you don't do the stuff that restores you when you when you get to work. Yeah,

good job is challenging in part because, you know, for for those who might be listening who have a technical background, you know, everything is called deterministic. Like you take action A and B happened. That's not the case. When you have big groups of people, every person has different way of understanding what you say a different way of internalizing what happens in the world and work, eh? So I think there's a perpetual challenge that people manager in dealing with all of the variability and people are a work with, um Well, uh I think, uh, the next biggest one is probably just logistical. You know, the consequences of the decisions that you from competing predictive, and it's costing millions of dollars bond, you know, a really big deal and set the course of the business one way or another. And so if you don't make those decisions in the right way, uh, you know, they making read about them. So I think I take that very seriously. It's a major challenge. Um, in terms of the most painful stuff, I think any time you have to deal with, you know, a performance issue of some sort or a layoff. You know, something that really winds up impacting people's lives in a negative way. And you have to be the sort of bearer of that message. Yeah, I think I think that Zoe's made forced by their job e share that view, um, approaches effective and overcoming them. I mean, I don't know. I think that maybe for that last one, which is, uh, you actually have to let people go. Um, I think everyone has this first experience when they end up having to let someone go, and then the team is better on the other side. Depends on the reason when he ends up like let go. But like somebody who's not pulling their weight is that sometimes didn't motivating team Having that experience even once, then teaches you the light at the end of the tunnel. So let's put it in a little bit more context, E b emotionally helpful. And you do have to deal with something like that, Um, but fundamentally like human and understanding that, you know there is. If you ever end up having to let somebody go from a team that it is painful, it's painful for them. It's much more painful for them than it is for You have to do it. And just to be a sympathetic human is possible during the process. That's that It's the worst part of the job.