Ep. 18 - Eat Your Vegetables with Caitlin Siegrist | Devs:After Dark

Boom.

Hello and welcome. Another beautiful Friday, which means another beautiful episode of Developers After Dark. We are here with, uh, episode number 18. Um, I'm going to apologize ahead of time because I'm going to have to leave the stream halfway through. I have a lunch date with my son, uh, at school. So, um, but we do have a very awesome guest today, which I really want to get it. That's why I'm gonna go fast and, uh, kind of go through a little bit of the, uh, the bill paying quickly here, and then we'll get right into it. Uh, just a quick reminder that the Postman Developers Choice Awards is still going on. I believe you still have a chance to vote. I think you still have another day, right? So get on out there and vote if you haven't already. You can go to the homepage of our website here, and I'll give that to you. Messed around with the banners a little bit, so I'm a little bit unorganized on those.

It's okay, buddy.

Just go there and you'll be able to go to the scroll to the bottom and you'll be able to give you the instructions on how to vote, the same instructions that you would find anywhere else. And of course, Hannah and everyone else too, it was also been posting it on LinkedIn, so you have a really good opportunity there to check it out as well. And another thing I wanted to bring up just really quickly before we jump into everything is you wouldn't know it by looking outside here in the Midwest, but spring has sprung. And with that comes, as if you've been looking at the website for HubSpot in the last, I don't know, I'd say what, 24 hours, you will notice that the Spring Spotlight is upon us. Tell us more. Oh, I plan on to. I'm gonna get real specific on this one because along with the Spring Spotlight comes the actual highlight of the developer tools. And basically, and I actually have a nice little, I did this on the fly here. And for those on audio, it's gonna be developers.hubspot.com/ss25-dev-tools. In that, what you're going to see is quite a few things. I'm not gonna be able to go through all of it right now. That would take up way too much time. But you're going to see things like the UI extensions or the app cards. You're going to see things about basically there's upgraded certifications. We have— I'm just kind of going through some things here. The discovery cards, I know that's a big one too, especially with the app listings. And I've seen those with a lot of the updates that have come through. Just really fantastic stuff. Tons of improvements on the CMS side as well. And then updates to the CRM API. So there's There's a lot there. If you go to that, if you go to the Spotlight homepage in general, and then you can also take a look at this one too for, that's kind of like the developers highlights of it. Both of those things have like a tremendous amount of information that you'll be able to check out. The main Spotlight page too goes through a lot of the AI, a lot of the Breeze stuff. So there's tons of stuff in there too. And a lot of really cool videos from kind of like case studies, if you will, you know, with a lot of really cool businesses and developers and providers where you'll be able hear their story as well. So a lot of great stuff there. I do recommend if you haven't already, it just came out yesterday or just updated and you should go check it out. A lot of stuff there. So you'll really like that.

Yeah, that main site, Nick, is hubspot.com/spotlight, which should get you there.

Yeah, I didn't put a banner for that one, but yeah, that one's a little bit easier to remember. So you can just go to /spotlight there and you'll be able to check that out. The rest of the usual suspects, obviously go to academy.hubspot.com if you'd like to learn anything brand new. There's always new content up there, so go ahead and take a look at that. And then of course you have the developers changelog, which is going to be at developers.hubspot.com/changelog. If you want to know what's going on in the developer community amongst HubSpot, that's where you're going to want to go. Everything we do, you're going to find it there. So plain and simple.

I feel like this might be in the show notes if they get posted.

Interesting.

Hmm.

All right, go ahead. No, that's fine. That's fine. We'll take a minute. Go ahead if you want to. All right, that's— it's fine.

I get it.

They might be 6 episodes behind on show notes, maybe 5. But I have already— I've already promised to everyone that I will have those updated over the weekend. It's just, um, I have to go— you know what it is though too? You have to go and rewatch. I have to rewatch myself. I know, it's fine. And then I have to like—

Boom.

So mean. And I have to admonish myself like as I'm watching because then I, I see the stupid stuff that I say throughout. So there's a— I'm a little hesitant and reluctant to do the show notes sometimes because I'm like, yeah, I don't want to watch that again. But it's okay, I'll do it, I promise. But all that aside, Were no notes, I think, from last week. Last week was a good week. Didn't make too many mistakes, didn't say too many dumb things. So that was nice as well. At least not that I remember. So if I don't remember it, then it really didn't happen. But without further ado, as I said, great guest we have today, someone that I've worked with pretty much since day one of coming to HubSpot. So that's been almost 4 years on my end. So, but I will let her introduce herself. Kaitlyn, tell everyone who you are and what you do.

Yeah, sure. I am Kaitlyn Segrist. I'm also having some internet/cell service issues, so hopefully I don't cut out. I'm now just doing this from my phone, so hopefully you don't lose me. But I am on the Developer Relations team and I spun up a new team inside of Developer Relations late last year called Developer Product Success. And our mission is really to be kind of that bridge between HubSpot's development team and all the extensibility that we're regularly putting out and the partners who adopt it. So we're only about 6 months into this team, but we're already, you know, running some really cool betas. We are really starting to think through what should our strategy and process be for launching new extensibility with our partners. So I think there's a lot of impactful change that you'll see coming from my team as we, you know, we get a little bit further along in our journey of this brand new mission.

And that's the beauty of it, because you'll hear people say, well, wait a minute, wait a minute, this is Developers After Dark, but that's, that's not, that's not a developer. What I, what I really want people to understand is like there are so many other aspects and there's so many other kind of focuses that kind of interweave with that, right? You're not, you may not be developing code in ones and zeros, but you are developing programs, you are developing betas, you are developing things in which I pretty much walk hand in hand, if not side by side, if not lead sometimes the developer process, whether that's coding and so on and so forth. It's the same principle when people ask developers after dark, it's still daylight outside and it's only noon Central Time. There's things to it where you don't give away the secret.

To be fair though, we're in Illinois, it could turn nighttime at any point.

I mean, that's true too. We get 4 seasons in a week, so it's one of those things as well. But it's really important. And that was kind of one of the things when we first started doing this, that we wanted to make sure that we didn't fall into that trap of like, well, everybody has to be a developer, everybody has to code, everybody has to— not to say that you've never coded, Kayla, but I'm saying like, there's that thing where it's like, well, you have to be like, you're not doing React or you're not doing Java. Well, then that's not, that's not always the case because there's so much more that goes on that kind of impacts whether you're developing a program or just doing actual development work, like actual coding work, that it all has to kind of go together seamlessly or it really does make things like hugely difficult. So—

That's right, man. You can code alone all day long. You won't get very far if you don't have, you know, the whole picture in front of you.

Exactly. And I can say, working with Katelyn for at least the last 4 years now, there's been so many cool things that we've done. And there's like a lot of programs, a lot of beta programs and things like that that we've, you know, kind of worked through and like, watched through the process that it's like without having people that can actually like have the vision to see that ahead of time, um, yeah, it makes for a really bad time if you don't have that. I'll, you know, just be honest. But, um, tell us how you like— what, what first sparked your like interest in like technology in the overall in general? Like, was there, was there a moment where you kind of said, oh, you know what, this is, this is something interesting?

Yeah. So I actually— my, my path to HubSpot, although I've, I've been here for 13 years, um, I had a completely different career track in mind initially. So I started out in account management at, uh, like a traditional marketing agency, and I had, you know, a handful of clients in my portfolio. I was doing a lot of event management and brand strategy stuff, and I did that for a while. And then I thought, like, this is the career I want. I want to be the Don Draper of like this generation. And so I went to grad school and I, I got a master's degree in advertising and I was all set up to like, this is what I'm gonna do. I'm gonna be a brand manager. I'm gonna be a CMO. I was like really excited about that. And I came outta grad school and I had a job in brand management type, like I was for a big retail chain and my job was a marketing assistant, I think, or something like that, marketing strategy assistant, something like that. And about 1 year into the gig, I was like, huh, so we're just about to do the same thing again this year? Like the same, we're just gonna run the same strategy with like a slightly different flavor? I was like, oh, I got all these ideas, you know, I really wanna, I wanna be doing more than just planning out this, you know, the same strategy year over year. So I, I, at the time, Pinterest was like a hot thing. It was the new thing. And being a retailer that focused on fashion, I was like, we should start using Pinterest. Like, we could create these lookbooks that live online, and then they can be like inspirational for our customers when they'll look online, and then they'll go in store and buy. And it was sort of like, oh, that's like, you know, that's not really like a true marketing channel. I don't think we want to explore that. So That was really what sparked me starting to look for other things and being like, I'm seeing how technology and especially social at the time, because again, this was like 14 years ago, was really starting to be, you know, a huge channel. So I just happened to have a friend who was working at HubSpot at the time and, you know, like 200 employees or something. And she's like, we're looking for people with true account management experience who like to be scrappy, like to get creative, like to experiment. And I was like, well, that's 100% me. So I came into HubSpot, um, having zero software experience, like had never worked at a software company, had never even had like a software company as a client. I, I was just running completely blind on what this experience was going to look like. I spent about 8 years at HubSpot in that CS side of the business and then found that there was a good opportunity inside of product partnerships at the time. And then moved into that space. And that was really where I started to get the developer flavor of like, oh, there's a lot of value that I can add to our partners around this is how I think you should deepen your integration, or this is the type of app I think you should build from the ground up. And that really got me excited of, you know, how do I help partners think through the customer experience? What are the use cases that our shared customers are trying to solve? And it was a very untraditional path to how I landed on developer relations as a non-developer.

Was it scary? I mean, was it kind of intimidating, like, to have to rethink that, like, coming into an entirely new surface area that you've not really touched before than You know, pivoting.

Yeah, honestly, it was scarier to move from customer success into product partnerships than it was to move from like traditional marketing into account management at a software company. Because in the, in the CS space, you know, it's a lot of like marketing strategy and sales strategy. You know, that's really what that CS role can offer. Whereas when I was coming into product partnerships, I really had to teach myself about what was even technically possible. Because like in my early days moving, when I moved into product partnerships, I was like, we should add this feature to your integration. And then, you know, I'd be talking to a developer internally who's like, okay, but like, that's not possible. And here's why. And I'm like, oh, shoot. Okay. So, you know, it was like there was a There's a big learning curve for me of like, cool idea, Caitlin, not possible because of this. Or like, yeah, it's on the roadmap, but it requires like a huge restructure of how this part of the product is, is infrastructured. So maybe in a year or two. So that was challenging as someone who had like a less technical background at the time.

So let me ask you this question real quick, because I know like I, I've also done like regular customer service support. And then like being with, you know, DevRel now, the feedback that you get from the audiences, how is that different from your perspective? 'Cause like for me, it's like night and day when you're talking to regular customers versus developers who literally will rip things apart right in front of you, in my opinion. And they like, no, no cares in the world will completely trash a product in front of you. And you're like, yeah, about that.

So true.

AJ's made me cry so many times.

Yeah.

Yeah, I think there's a real balance between having empathy for, you know, the blocker that the partner is having and also being able to set their expectations correctly. You know, I'm thinking back of when, um, I used to run this program on product partnerships called the App Accelerator, and the objective of that program was we would look at HubSpot's green space And then we would go out to partners, or what we would call ecosystem entrepreneurs, which were developers who maybe had a small business where they were trying to tap into HubSpot's ecosystem to create some real SaaS revenue. And it was in that program where we would get these ideas back from developers. And I'd be working with someone like Jeff Russo on go-to-market, and we'd be like, oh, this This is such a sick idea. Like, I love this. I could totally see how customers would use this. And then we'd go back to the product team and be like, hey, how cool is this idea? Like, I think we should run with this. And then they'd be like, yeah, no, that's, that's not possible. And like, that's not aligned with, with what we're thinking from an extensibility standpoint. So then I'd have to go back and be like, we loved your idea, but— But there was a recurring theme that kept coming up. in the Accelerator, and it was objects. Partners really wanted the ability to customize objects, create net new objects. And so as we announced in— we've been talking a lot about renaming objects. That came out, what was that, like a month ago or something, the ability to rename objects.

Mm-hmm.

It was things like that where we had this bundled collective feedback where we could go back to product and say, Yeah, we get that you're not going to solve for every unique snowflake idea, but here's this common theme that we're getting. I think those little wins make it easier for us to go back to partners and be like, we're listening, we know there's pain and you can rip the product apart right in front of us, but we're also making really cool advancements and we're doing a lot to make the experience better for our developers. I think it's a balance of empathy, but also like, hey, don't forget all these really cool things we have done for you lately. Whereas on the customer side, it's a lot more— on the customer side, it's a lot more like, build this because my specific business needs it and I'm the only business that needs it.

Right.

Some of those use cases are a little bit harder to rally the whole group together and be like, here are 25 customers that asked for for it. Um, sometimes those use cases are just so granular and unique to that customer, um, that, you know, and if you only have like 25 customers in your install base, that it can be challenging to really grab that feedback as like a bigger unit and drive change through the product org with that.

Is it hard to like, because you've I'm trying to think of the best way to ask this, but like making that transition from brand marketing over to starting to deal with more, I don't wanna say more complex things, but it's a definite change of pace. Was there something that surprised you in that kind of move over that maybe wasn't, you may not have thought of it before, but it was like now that you're here, especially like when you first came to HubSpot, Like, was there something that like just kind of surprised you about either like the way things were done? Because like for me, I came from a small company, if you will, to HubSpot, which, you know, and even at the time when I joined was still— to me, that was big. That was like a huge place. So there were things that like I experienced or the way things were done that just completely were like foreign to me. Did you have anything like that that kind of stood out to you when you first got here?

Yeah, I think the biggest one, and it's, it's still something that I'm, you know, figuring out how to manage, is just the rapid pace of change and innovation.

Yeah.

And it's awesome.

I love it.

Like, we've always been a super active development company, and it's, it's incredible. But as the product gets bigger and HubSpot gets bigger, I'm still trying to figure out, you know, how do I keep a good pulse on what I really need to know to be very good at my job versus Like, what's a kind of a nice-to-know where if I have time, I'll go check it out? That balance is hard. And it's really hard when you're on a team like Developer Relations where we're touching every single part of the product. It's really hard to figure out, like, where should I focus my time and my energy so that I can set the developers that I'm working with up for the most success?

When you, when you first started, you, you said it was about 200 people at HubSpot compared to, I mean, Yeah. There's 200 people in the New York City region who are, you know, engineers now. So how, how were you, how are you able to, or I guess explain the difference, like priorities compared to when you started versus now? Because I'm assuming you had much more, your eyes are all over the place when there's only 200 people, you saw everything right now. It's so, I mean, how do you even know what you need to know? You know what I mean?

Yeah, it's hard. You know, you guys get it. There's like 1,000 Slack channels that you need to be in. It's definitely hard. We have found a lot of success in focusing on the strategic objectives that HubSpot sets for the overall company and then just saying no if what we're working on doesn't align to one of those strategic objectives.

Hmm.

That's been probably our biggest saving grace. And honestly, like we've spun down programs like the App Accelerator because at the time it just didn't align with the objectives that we had set for the product partnerships team. And so it's, you know, it's stuff like that where you have to understand, you know, understand like, okay, we're shifting our focus and we're going to spin down this program. And now I'm going to focus on a new program that does support one of those strategic objectives. And then just like staying hyper-focused on does this actually help me do better at the program we've set up that we're currently operating? Yes or no? And if no, then just like move on.

I've got one question before I wanna pull on a little thread before I pop outta here. But you talked about being able to say no to things. Was that a hard— were you always able to do that from whether the brand marketing side or onto product here at HubSpot? Were you always able to do that? Personally, I like— it's even a criticism of me at this point, even now, even after being here for 4 years, the ability to just say no because you can't. Like, I just, I have the hardest time doing it. Is that something that's difficult for you or does that come— are you able to do that?

It's— So I think everyone should start their career at an ad agency or a marketing agency because billable hours, right? Like I had to literally fill out timesheets. That said, this is what I did today and here's how much time I spent on it. And if you went over scope, you had your director coming at you of like, why did you do that? That— what, what is that doing for our bigger mission here? Now I got to go bill them for your time because you took on like editing a budget that we don't even own, you know? So like, I really early on got good at being like, Is this core and is it the core function of my job? Am I expected to do this? Yes or no? And then also like not letting really shiny, exciting things distract me because it's just burned into my soul of like the billable hours. Do the, do the work that's in your scope. I mean, we will certainly like find little things to, you know, that get us excited to kind of just like put a finger in there to be like, we might come back to you. Like, I love this idea. I might come back here and like try to see if maybe we can make this a little bit bigger. But I mean, you guys get it, like where we are with our size right now, we have to be so hyper-focused on what the task is at hand so that we can set ourselves up for success.

Absolutely.

Yeah, no, that's a good— that's a, that's a good— I did for, I think for, I want to say it was like, what was it, AJ? Like maybe less than a year contract work where it was at an agency where I started to do a little bit of that. And I just don't think I did enough of it for to make it to be impactful because I still had that mindset of just like, well, it takes as long as it takes, you know, as a, like starting out as a coder, I was just like, yeah, it's going to take a couple hours. And they let— they're like, no, I need to know how specifically how I'm like, it'll just get done when it gets done. I don't know what's wrong with it yet. Let me tell you.

Yeah.

So yeah, that was one of those things where I, yeah, I probably would've benefited from more experience like that, like you said. But I just, I wanted to say, Kaitlyn, thank you so much for coming. I'm gonna hop off. Dennis and AJ are going to take you the rest of the way home. But again, thank you so much. And anyone that doesn't know Kaitlyn yet, awesome to work with. One of the greatest people. Like I said, 4 years of doing, and you said accelerators, and the first thing that popped in my head was Steam Accelerators. And I was just like—

Oh yeah.

You know what I mean?

And I started going down like a, my mind went down a different track. But yeah, but no, thank you so much. As always, it's awesome to work with you and yeah, I appreciate you coming on, but I'll let Dennis and AJ take it from here and thank you.

Have fun at lunch, Nick.

So let me ask you a quick question, Caitlin, cuz I know this was something that I also struggled with when it was in the agency life of like the training part of stuff too, right? Cuz like you're working on a project and you sometimes the project around, you don't always know everything about the topic. Or like, I know for instance there was one where we were building a certain piece of functionality. I'm like, I don't, I don't know that stuff. And the hardest thing for me was figuring out how much billable time do I spend researching versus building versus all of these things. And I know for me personally, I ended up doing a lot of my research at night after hours of work so that way I didn't have to do it to the client because I felt bad charging a client for my own learnings. But then I had a boss who once was like, hey, it's kind of a 50/50, right? You are learning on the job, but some of that is technically work that you're doing for the client because it's brand new anyways.

So like, can I add to that, man?

Yeah, yeah, go ahead. Absolutely.

I'm just like, part of me is always like, if I don't know it, do I want the person to know that I don't know it, right? I mean, yeah, like, what do I need to do on my own so I don't look like a fool trying to, you know, get this client to work with us? So yeah, I I want to hear the answer to this. This is— yeah.

Well, I mean, my current answer is incredibly grateful for AI summaries, writing assistants. Like, the AI summaries has been— I mean, we're all using Gemini now at HubSpot, and like, that's the first thing I do when I get— someone sends me a Google Doc that they're like, hey, I think you might like— this might pertain to you. I just hit that AI summary first. And I'm like, oh yeah, okay, this is worth— this is worth a deeper dive of like reading through the entire doc and, you know, thinking through my comments. Or like, oh no, that's actually not like that. Thanks to the AI summary, like this is like a departure from actually what we're working on. Like, cool, thanks for sending it to me. But, um, yeah, I don't ever want to go back to a world where I don't have that because I love it. Yeah, it's a huge time saver.

You know, have you— have you used AI in ways that have helped, like, like with the jobs that you're performing? Because like for me, for instance, recently I've been doing a lot of Looker development. So it's like LookML, like I love their docs, but there's things that I need to do that are like particular to what I'm trying to do. So I will literally ask ChatGPT I used and I was like, hey, I need to create like a dimension that does this, this, this. And it was actually like helping me troubleshoot through a lot of the issues I was running into. So have you tried to do anything like that with AI or Gemini or whichever AI you're particularly using?

Yeah, I mean, I've been using ChatGPT to write a lot of stuff for me and summarize a lot of stuff for me. I've also been using it to just get like, you know, I— one thing that we're working on kind of behind the scenes is I think I mentioned at the top of the— at the top of the meeting, You know, we're really focused this year on like, how do we create a better framework and process for launching to our partners? You know, all of our new extensibility, like how do we make that a more streamlined process both internally, but also how do we set the right expectations with partners externally and provide a, like an enjoyable and helpful experience as they're helping us test? And, you know, my coworker Jackie and I are working on this and like neither of us have ever built like a software development lifecycle. We're kind of like, well, we're going to do a ton of research, we're going to talk to a lot of people. But like, I've just been running stuff through ChatGPT to be like, do I sound like I know what I'm talking about before I send this out to a whole bunch of developers and engineers? Like, I've kind of been using it as a gut check of does this language sound like I know what I'm talking about? It's gonna— a nice little—

I just wanna put out there, I was in Dublin with, with Caitlin recently, and I heard Caitlin talk very, very, very in the weeds about HubSpot's direction with AI. So you know what you're doing, and I will definitely be following you. Which leads me to maybe possibly a loaded question here. There's a lot of opinions on AI at HubSpot, and I know you need to have a direction to go. To send, you know, your— what you do with your job, right? How are you dealing or managing with all these opinions and figuring out which opinions are strongest and how, you know, you should look forward?

It's been challenging, but it's been really interesting too, because I think at HubSpot for so long, we, you know, we were really hyper-focused on like creating obviously our own product and We were maybe less— I wouldn't say less invested in the ecosystem, but there was less ecosystem opportunity. Where now that tide has really turned and there is so much ecosystem opportunity. And so where I've been really trying to help people form opinions or maybe shift their opinion a little bit is thinking through like, is this something where we could go we could take it to a certain degree and then let the ecosystem do the rest. And reminding our team as they're trying to innovate that there is an entire world out there in our ecosystem that could help us. So it's like setting up interviews to try to get people to feel more comfortable in their opinion, giving use case examples of like, this is how and an app partner's product could talk to Breeze. Here's a use case that Gabby, our customer, might use to go into Copilot or a workflow or something and say like, hey Copilot, summarize a Zoom meeting for me. It's that type of involvement with the ecosystem where I think we on the Developer Relations team need to continue to remind our internal developers like, There's a lot of power in the ecosystem. Maybe it's, maybe we can convince somebody that it's better to let the ecosystem solve it than HubSpot solve it and, you know, just create some more extensibility. Like, let's see what the ecosystem does with it.

Yeah.

So there are a lot of opinions, but, you know, as long as you give them some reasonable data on how the ecosystem could influence, it's been, that's been super receptive. I think people are realizing, like, it's gonna take a village to get this off the ground.

Following up on just, yeah, the ecosystem and AI and where HubSpot's headed, where the ecosystem's headed. If I'm an app partner, how do I know I'm not directly competing with HubSpot for a feature? Like, how do you— where's that balance?

I think, you know, healthy competition is okay. You know, like, we always say, I had a manager for a while here at HubSpot, Hugh Durkin, who said a good, a good ecosystem, a good marketplace offers choice.

Mm-hmm.

And that has like stuck with me forever. So there might be times where one of our app partners has a competitive feature or, you know, competitive product even, but people buy products for different reasons and sometimes that's okay. Like, we might have some feature overlap, but Gabby might have a use case for why she wants both. So it's, it's going to be out there, but I think competition is what fuels really good innovation. So I, I don't, I tend not to steer away from that. Um, yeah, I, I think it's, I honestly think it's a good thing. I think it keeps us on our toes and keeps us thinking.

Yeah, I totally agree with you. Do you ever find yourself to have to push a partner to say, you know, go ahead and pursue that? Don't, you know, just keep on going at it. be scared that you're competing with us because that, as you just said, this is good.

Yeah. And I think I, you know, one message I give to that ecosystem entrepreneur type developer is HubSpot's always going to go wide and shallow. We're never, you know, at least not in our direct future, are we going to have hypergranular use cases that solve for a very small population, but for an ecosystem entrepreneur, That might be okay. You know, having like 100 customers might be exactly what they need to keep the lights on. And so if, if I feel like the partner's done their research and, um, they think that they can add like a special sauce onto something that— a feature that maybe we already have, then I think that's okay. Like, that's—

Yeah.

You know, there's, there's always ways to add additional layers of context. and think about use cases. Maybe it's in an industry that we haven't thought about or that we don't typically serve.

Right, right. AJ, I'll let you ask a question. I could do this all day and I know that I'll just take over, so have at it.

Well, okay, so let's see here. Because I know you deal with a lot of the app partners and things like that, let's just say theoretically, like, what's the one thing that you would give as a piece of advice to every app partner that comes in that maybe they don't know right away? Because I'm assuming there's also a trend when people are applying to the App Partner Program or they're trying to do things where, hey, like, don't worry, you're not alone. You know, everybody hits this. You need to do this next. Like, is there that first initial step that you might say to somebody? Like, what would you tell them as their first initial step if they wanted to come to HubSpot with an idea? What would you say that they should do first?

Yeah, I mean, I always want them to have done research. So when they come to me with a concept, I typically kind of poke at them a little bit of like, all right, like, where, you know, have you looked at the forums? Like, have you gone to Reddit? Have you— is this an— is this a HubSpot problem that you're trying to solve, or is this like a SaaS CRM industry problem that you're trying to solve overall? So research is always one that I'm asking for. Like, a blind concept of like, I just think this is a cool idea. I'm like, yeah, maybe cool idea, but don't go spin your wheels on it if, if you don't actually have some some data that's going to back you up. I think the other thing, especially if you're smaller and just trying to start out in the ecosystem, is like ship your MVP into the marketplace. You don't need to have the most crazy feature-rich integration in there. That's going to take time.

Yeah.

Solve for a use case, get it in the marketplace, start to get some installs, see what's working, Get real customer feedback, get that exposure through the marketplace, and then continue to add more and more features as time goes by. You know, like we're constantly shipping new stuff, new extensibility, like keeping a— keep a good pulse on what's out there and what's applicable to your integration and just go in and touch the integration at least quarterly. Like you'd be surprised that some people just put it in the marketplace and then never go back and touch it. Like we really want developers to be regularly maintaining that integration. And we're hopefully going to put out some programming later this year or maybe next year to inspire that ongoing deepening of an integration, like going in and not just doing maintenance of like, oh, this is deprecated, or, oh, I need to do this, like make this one small change to my listing, but actually adding for additional use cases and thinking through what else those customers are expecting out of that integration.

Would you say there's any advice you would like add since in your tenure here for an app partner? I guess I knew you did themes as well, but like, is there, is there anything that's changed over the years?

I mean, the number of apps available in the marketplace is like, what, 6,700 now? So the competition is out there. So I think there's You know, I've seen a lot of, a lot of people have to find interesting ways to, you know, get their app in front of customers. I think that's been a big change. I think the other thing too is, you know, we hear a lot from developers that are like, I have to talk to somebody at HubSpot on the product team. I, you know, I need, I need their advice on X, Y, or Z, but There are so many developers in our ecosystem that know HubSpot like they built it themselves. I mean, a good example of that would be someone like Dax Miller from Happily. Like, Dax could come in and sit down at a desk at HubSpot and like crank out code, no problem. And so I always encourage people, like, build your own little community of really talented developers.

Mm-hmm.

Inside of the HubSpot community, you don't have to completely rely on talking to a HubSpot product manager about an idea you're having or a blocker you're having. You don't even necessarily need to talk to someone on our solutions architecture team. Like, sometimes the community can, can solve that for you. Hmm.

Yeah, I think you bring up a great point because honestly, like, in the community, that's what Dennis was, one of those people with me. Like, we, we actually had a chat with a couple of people where we did that ourselves is let's take some like-minded people in the community that are working on like-minded things and let's discuss like issues and outcomes and things that we expect. So I think that's perfect for that. That's a great piece of advice for people. So on that, on the direction of giving advice to people, what would you say is the best advice that you've ever gotten in terms of just general like work, whether it be from a mentor or like somebody just on the street yelling, either one?

Someone on the street yelling, eat your vegetables, is that one. I think, I think for work, the best piece of advice that I ever got was from a manager I had when I was working at the ad agency or the marketing agency who said, anytime you have an argument or a very strong opinion or very strong problem, Always come with a solution. Like, if you're going to go to your manager and be like, this is a problem, I am struggling with this, go with the problem. Like, you absolutely should be talking to your manager about roadblocks you're hitting and challenges, but go with a proposed solution. It might not be the one they choose.

Mm-hmm.

But at least you're being proactive in like, I've identified this as an issue and I'm being proactive and I'm coming with a way that I think we can solve it. That's gotten me pretty far at, uh, in life, really. But I guess the other thing I would say too is like, just be as like nice and kind as you can. I think people like that. People generally like working with people who are like fun and easygoing and nice and respectful. Like, yeah, you know, in the world we don't sometimes get a lot of that everywhere. Um, and we get so busy at work that even like You know, blasting someone in the Slack being like, hey, can you help me with this? Instead, just like literally take the extra 4 seconds to type like, hey, how's it going? Hope you had a good weekend. Or like, hey, how— like maybe when I talk to Nick next week, I'll be like, Nick, how was lunch with your son? Before I like blast right into a question that I have or like where I need his help.

Yeah, see, because I'm totally guilty of that. Like, hey, QQ, like quick question. And then, but usually I do end up like talking after the fact.

But yeah, that's—

I I definitely agree with you there. Like approaching with kindness and empathy, definitely. It just helps open the doorway to, to me, I feel like more transparent communication too, because it's like that level of trust almost immediately. So I completely agree with you on that.

Let's see here.

So we—

I do the hey QQs every now and then. I'm guilty of that as well. I do the hey QQs as well, but I try to when I can, you know, especially if like we're launching into something a little bit more complex. I might soften it a little bit with like, hey, hey human, I'm also a human reaching out to you. Like, let's be humans for a second.

Yeah, yeah, absolutely. Nick's got this question he likes to ask, and I think I want to augment it a little bit here.

He's not here, do it.

That's right, this Nick guy, let's get rid of him. Um, disconnecting, like you're, you're not working anymore, like how do you, how do you go through this transformation? And I know Nick likes to talk about how if technology was involved, what do you do to get away from it and just get outside of the tech world? But like, I want to go more like, you know, you, you're in the weeds all day long thinking about things like very deeply. You got kids, you got family, all that good stuff. How do you like make that transformation into, you know, the just getting out of it and having some, you know, personal space?

Yeah, it's hard. I'm actually not the best at that. Um, I, you know, when my kids get home, I stop. Although every now and then, like, I'll be on a call late or something, and my 3-year-old loves to come in and sit on my lap and look at everybody on the videos and, like, bring a toy in and, like, show it on the video. And I'm like, oh, I'm so sorry. It's adorable and also probably very annoying. Um, but I do really try to just, like, stop working after my kids get home. But then I, you know, I'm guilty of, like, Oh, like, I'll see a Slack come through at 8:30 at night and I'm like, oh, this is easy. I'll just answer this right now. So I'm actually pretty bad at it.

Well, this is terrible.

But I do. I know, I'm like, I'm the worst to answer this. But I do. I like my mornings for, like, disconnecting a little bit more. So, like, I'll drop my kids off and before I sit down at my computer, I'll go do something. Like, I'm a big Pilates. lover. I'll like go do my Pilates class in the morning, or I'll go for a walk, or I will like— I spend probably like 30 to 40 minutes from when I drop them off before I like actually go even into my, my workspace.

Yeah.

And that, that's been a little bit easier for me to be like, okay, I haven't even started yet. So like give myself a little bit of extra time. I'm better at setting expectations in the morning than I am after work.

I hear that. I, I've always— I'm just envious of anyone who can wake up early in the morning. So it seems like the perfect time to be by yourself and have your own space. But I hate— I think mornings should be illegal. I think, you know, they should be outlawed in, you know, most states if possible. So, you know, that's not gonna work for me.

Yeah, morning— mornings are— it's—

Yeah, it is. But like, when you have a 3-year-old— when you have a 3-year-old and a 7-year-old, like, you're up.

So yeah, yeah, yeah, you know, and actually, I wanna, I wanna, I'm gonna, I'm gonna pull a little bit from what you wrote in your questionnaire. Because one, I love that you wrote it because this is, I relate so hard to this. Um, you, you spoke to, um, some of the things you'll do on the weekend to like kind of sneak in a nap, right? Like you'll, you'll play a movie or something. I, I am 100% about naps. Like I never thought I would be that person as I got older. I'm like, oh, you don't need to sleep. Like, No naps all the way.

They're so amazing.

I feel like as a parent, like, you have to at some point.

Yeah.

It's like, how else do you like— because I'm very guilty of it myself of like, there'll be something on the TV and like, next thing I know, I pop up awake and the kids are like now in the kitchen doing stuff or whatever. And it's like, I mean, they're 9, so they can do that thing. But it's just one of those things where like, even when they were younger, it was like, yeah, here's Bluey. I'm going to take a quick 20-minute nap. Like, I feel like you need to do that stuff just to stay sane.

Mm-hmm. Yeah, absolutely. And I think, you know, our co-founder Brian Halligan is like very much a proponent of naps. I mean, well, back when we were all working in the office, we had a nap room, but also, you know, we'd be sitting there at our desks and they had like couches in the space between all of the little like mini cubicle kind of desks. And you would like walk by and Halligan's just taking like a 15-minute recharge nap. And you're like, all right, that's awesome.

Wow.

So, you know, I think he set a nice expectation of like, you can nap during the day. Like, if you need a 15-minute refresher, like, I think they say, isn't it like between 15 and 20 minutes is like the ideal amount of time to refresh you without making you more tired? Um, so yeah, I'm, I'm, I would nap every single day if I could, if that, if I had that luxury. Like, when I retire, there will be a nap every single Yeah.

So, what would you say are some other, like, non-technical things that you do to unwind, like hobby-wise or anything like that? I know you mentioned Pilates. Is there any others that you have?

I mean, with my 2 kids, like, it's a lot of driving them to sports and, you know, driving them to this, that, or the other. But I really love to go on trips. And I am like crazy obsessive about planning literally down to every single meal that we're going to eat and having researched the menu ahead of time.

What?

And knowing exactly what I'm gonna get. I'm at that dinner, it's like drives my husband crazy. It probably drives everyone I travel with crazy, but I always like to have something on the horizon.

I would absolutely love to travel with you because that is me. I have to like, in my head I'm like, okay, we're here. This is gonna happen at this time. Now this, now this, now this. I attribute that a lot to being a developer. Do you attribute the fact that you do a lot of that as the project management side of you, that you also are project manager?

Yeah.

Okay.

I was like born to be in project and program management. I mean, I love to organize. I'm a huge one for like, I have a label maker, you know, I'm like that person that like, I know where every single thing is. Yes. Yes, Dennis. Exactly. Everyone should have a label maker, by the way. If you don't, can we get like a sponsored link to label makers for this?

Yes.

But I just, I, I'm like, I love to look forward to things and I love to research. I love to look at like photos of the places we're going. I'll go on TripAdvisor and go down the biggest rabbit hole. I'll be like reading reviews from 8 years ago. You know, like, I'm just— I love to obsess over, like, being prepared and plotting out, like, what's the next experience? So I do a lot of time. I spend a lot of time just, like, looking at where I want to go next, where I think the fam should go, and where I want to go with, like, my best girlfriend on a, you know, a girls weekend. And so I do spend a ridiculous amount of time doing research on that. And then, um, I'm a big one for going on like really long walks. So especially when the weather gets better here in New England, I'll go on a 2-hour walk and just listen to all my favorite podcasts. Like Smart Lists is my favorite podcast with Jason Bateman and Will Arnett and Sean Hayes. It's hilarious.

Caitlin, Caitlin, Caitlin, you— what? No, your favorite podcast is Developers After Dark. It's happening right now.

You said, you said non-work stuff.

This is a work—

this is my work podcast. I mean, obviously, I've already listened to all the episodes, so you guys gotta start doing like one a day. I need, I need fresh content.

On it, boss. On it.

I actually— one of my rules I have is when I'm going on a walk on a weekend, like if I'm— it's Saturday morning, I'm like, okay, I'm going out on a walk. I never listen to a work podcast. Like, no offense to Developers After Dark, but I listen to you guys during the week. On Saturdays and Sundays, I'm listening to like Smartless or Office Ladies or a completely mindless, like silly little podcast. I'll listen to like Daddy Gang, um, you know, like those types of podcasts. So that helps me feel like I'm not taking up my own personal time with like something that's work related.

Let's just talk to Nick about starting a gardening podcast so we can get Caitlin on the weekends.

Okay.

Oh, you need to start a Pilates podcast, then I'll listen on the weekends.

Okay, noted. Well, count me out.

I'm just not physical. I just, I just, I, I'm a very lazy person recently just because of just things.

Like, I'm just tired.

If you want to talk, I'll do— well, we can do a napping podcast. Well, how about that?

How's that sound?

Yeah, the 20-minute intermission just to take a nap during the podcast. That's really the only way.

It can be sponsored by Calm, that meditation app that has like little sleep tracks.

Yeah. No, no.

Let's see.

Let's see.

Are there any other projects that you're working on outside of HubSpot and anything else that you're particularly like just like heads down in? Like, do you have a project going on at home? Like, I know like Dennis does chickens. He's got chickens. Which I'm very jealous of. And I should say my wife's very jealous of, which I still am like, we are never getting chickens.

They have hens.

I just, I can't. One, our HOA doesn't allow it, which I'm not going to go on about HOAs. I think we could all go on to that one. But yeah, like, I know you do chickens. Are you into farming life, Caitlin? Because it appears a lot of people are farmers as well.

You know, I'm not into farming life, but I recently ran for local office. here in Needham, Massachusetts, where I live, and I lost, unfortunately. But I ran for town meeting member in my precinct, and the election was this last Tuesday, and all incumbents won. So no new faces. Womp womp. But I'm kind of getting into that. I've been really interested in my local community. So a good example is I've been participating in the strategic planning committee for the public schools in my town where we're trying to plot sort of like what's our 3 to 5 year vision, but also what's our really long-term vision? Like what's our kind of our vision statement for the education in the town? So I've been using a lot of my free time for that. I am going to run again because you know what, I just barely missed getting one of the seats. And I do believe that at some point new faces will be embraced. into town government. So I'm not going to give up there. I'll keep keeping on with that. And then I guess I would say other than that, I'm really into interior design. So I'm like constantly changing rooms in our house and painting them different colors and like probably driving my whole family nuts. But I really like to design and, you know—

Do you finish painting a room or is it like half painted?

Oh God, I finish it, Dennis. Come on, you should know that about me. Like, I don't leave a job undone.

We got a kitchen that has still the painter's tape up from like 3 years ago, I think, you know, some sort of COVID thing we started to do. And it's still— there's painter's tape over this corner. So we're different people.

I've been saying I was going to finish this office for about, oh, as long as I've lived here now. But yeah.

That's not my art.

That's not my kind of style, by the way, up there. That came with— that came with when we moved in.

So he's literally been saying this to me ever since I've known him, and it's—

nothing has changed yet about it.

And it is your style now.

I do have a really awesome picture though that I'm going to be putting up, and hopefully it'll someday be able to be shown. It is from the Muppets, and it's the Last Supper, but it's all Muppet characters, and it is absolutely great. 'Cause I'm a huge Muppets fan. So like, that's, that to me was just like, that's like the focal point now that's gonna be up there.

Nice. I love that. I just feel like when the space, when I like the space, I'm more excited to be in it. So especially with my little mini office here, it's, you know, I painted it the color I like. It's super girly. I have 2 boys, so I don't get to like put bows in anyone's hair. So I put bows in my office, you know?

Oh, you get to put bows in their hairs anytime you want.

Absolutely.

If only they'd let me. I wish they would. I am taking my older son for a pedicure though on Sunday. So I've found things that he is into that I also really enjoy. So, you know, well, I do little activities like that where I'm like, I will infiltrate your soul to do some of the things that I like to do.

Yeah, as a dad of 2 girls, that's— I definitely understand where it's like, you're like, I gotta find something. And luckily one of them went into music and the other one's going into like a bunch of artsy stuff too. So like, I'm a huge art person. So to me, that was just like fantastic to be able to relate like that.

Yeah. Yeah. And it's fun to get like to influence them to like stuff that you like. I like to see how far I can take it. We've done a pretty good job. Like my husband and I both love college football. And now like my, my older son's obsessed with the Colorado Buffs where I went to college and he's like wearing the gear all the time and stuff. So, you know, you can find ways to really push, push what you like.

That's right.

I think that's— should we, should we wrap it up here?

Should we?

We should. Where should we find you, Caitlin? What's, what's the best way for people to connect with you to, you know, know what you're doing?

I think LinkedIn is probably the best, best place to find me. We can put a link in the notes recap that I know Nick's going to work feverishly on this weekend.

So yeah, yeah, exactly. He's probably doing it right now. He probably doesn't have a date with his son. He's working on the notes.

I hope he's got like one earbud in just listening to us. The whole time.

We're just roasting him the whole time he's gone.

Yeah.

Yes.

I hope my audio and video—

Yeah, as I was saying today, and I was joking with my wife that I was going to try and work this in here, but I mean, we got 2 of us. So as Milo says, 2 out of 3 ain't bad, right? Right?

That's right.

Boom.

I was worried that we wouldn't have a good quote at the end, uh, AJ, and you just fulfilled it.

Thank you for, uh, Not only did I fulfill it, I actually accomplished what I told my wife I was going to do. So that's the one thing that I've done that I told my wife I was going to do this week.

I think that's a successful week right there.

Yeah. Yeah, no, she does all the travel planning and everything else because she messaged me when we were talking about the travel stuff. She's like, yeah, way to not say you don't do it. And I'm like, no, yeah, I don't. I get too anxious. My anxiety just overtakes me and I get to the planning point where I'm like, I don't know if I'm overplanning now.

So that's Yeah, there's no such thing as overplanning in my, my mind. I mean, I do think you can over-force people to do your plans, but there— you can never plan too much. You can always cut out. But you know, you're gonna— if you ever go on a trip with me, you're gonna be handed a printout, a 30-page printout at the airport of like, here's the restaurant we're eating at and here's the dish I recommend.

Well, if you go to Inbound, then we must have a day of Caitlin taking us and doing what Caitlin wants to do. I think that would be so much fun.

San Francisco, here we come.

Let's do it.

Yep.

Let's do it.

Thank you so much for being on today. Like, we really do appreciate it. And as somebody who's also worked with you multiple times, love working with you. Like, very, very transparent, very passionate, very just— no idea is a dumb idea when you are approached. And I do appreciate that because there are a lot of times where like you have ideas and people are like, oh yeah, that's a great idea. On to the next thing where you do take ideas in, you do take people's feedback in very well. So any app partners that are listening who have ever talked with Kaitlyn, just know that your feedback is there and it is recorded. I guarantee you she has looked at it.

So seriously, preach. Yeah.

Yeah, you two are the best too. We have a great team. I love working with you guys. You're super fun and we always have a great time. And I apologize if my audio and video was cutting out. It's great when technology doesn't work.

You look better than we do, so don't worry about it. All right, y'all have a great day.

Yes, thank you very much.