Jon Dick: Out of the Box Marketing, AI Fluency, and the First Returning Guest

In this episode, HubSpot’s Chief Customer Success Officer Jon Dick reveals how mastering AI fluency can transform your business, and shares practical tips for developing AI skills, overcoming tech fears, and finding your niche in a crowded marketplace.

We take Jon "Out of the Box" and surprise him with questions and gifts about his improv career, his time at Harvard, his physics background, and his upcoming anniversary with HubSpot.

His unique perspective combines scientific rigor with creative spontaneity, making him a must-listen voice for navigating tech’s next frontier.

Check out this episode on YouTube and Spotify, and Apple Podcasts.

• Episode Transcript

  Aaron: Let’s play out of the box. Is that theme music, Jon? I think that music is just for you. You said you were a good dancer, so I think you gotta bring it.

  Jon Dick: The good dancer was a joke, Aaron. That was a joke. Let's be clear.

  Aaron: Wait for the drop. right, so Jon's gonna go ahead and grab the little box that we got actually sent to him a couple of days ago, and he has no idea what's in there.

  —

  INTRO

  Aaron: Hello everybody and welcome back to the Sound of Inbound. Today we have a very special episode because we have a two time guest joining us here on the Sound of Inbound. His name is Jon Dick and he is the Chief Customer Success Officer at HubSpot. We are so excited to have him here because when we were at Inbound this past year we had an abbreviated conversation and today we get to extend that.

  Mark: Yeah, it was so great to see him at Inbound. mean, he was really in his element there and he's in his element everywhere. I'm so excited that he's going to be our first recurring guest of the show because he thinks so differently about marketing, so differently about customer success and all the things happening in the marketing world right now. I'm really excited for this conversation.

  Aaron: He's very plugged in and that's really because of his background. He's got a very interesting background and you learn all about it outside the box. I'm just dropping some hints. So you're to want to stay tuned for our next episode of Sound of Inbound. Are excited, Mark?

  Mark: I am very excited.

  Aaron: Let's go hear it. OK, everybody stay tuned. Here we go. Jonn Dick here on the Sound of Inbound.

  —

  Aaron: Hey today we are making a little history with our first ever two time guest. He helps shape the customer experience for literally millions of users worldwide as the Chief Customer Success Officer at HubSpot. And if you've ever talked strategy with him, you will know he is wicked smart. That's kind of a clue to where he's from, endlessly curious and an absolute blast to be around. Please welcome back the one and the only Jon Dick.

  Jon Dick: That's wicked kind to you, Aaron. Thanks so much for the intro, buddy. Thank you.

  Aaron: Oh my God, we are so excited to have you here today. It is just so cool. I think a couple of things we wanted to get into, we're going to talk about AI, of course, we're going to talk about HubSpot. Would love to get to know you and where you're from. So why don't we just start off with where are you from, Jon?

  Jon Dick: I'm from Boston. I just want to take a moment. The Super Bowl is coming up here in the U.S. And I think I speak for everybody in the country that they are just glad the Patriots are back in the Super Bowl. Am I right? Like, it's been a while and I think everybody's pretty happy about it.

  Aaron: Yes, it has been a beat. But this year should be really good. have a good lineup. We have a good matchup.

  Jon Dick: Seahawks and the Patriots, so it's a little bit of a... to coast. The Seahawks, we'll see if they get a revenge tour. I don't think they will. I think we got their number, but we'll find out. We'll find out. I just know all of America's cheering for the Patriots. That's what I know.

  Aaron: I am too. I am actually too. Because you do have to do East Coast, West Coast on this as well. But I'm very much looking forward to it. Who's doing the halftime show? It's Bad Bunny? Oh, it's Bad Bunny. So it's going to be a dance party.

  Jon Dick: Yes, Bad Bunny. So yeah, I am from Boston, but I can also dance. And so that's rare for somebody from Boston. So I enjoy a dance party, but people from Boston not known for their rhythm. No, no, I grew up in Boston, Aaron, and I left Boston for a long time after college. I lived in Chicago for a long time. lived in San Francisco for a while, back to Chicago. And then eventually moved back to Boston actually to work at HubSpot. When I joined HubSpot back in 2016, 10 years ago. HubSpot was not a very remote friendly company. And so my wife and I moved from Chicago to Boston, which, you know, a little bit full circle for me back to where I grew up.

  Aaron: grew up in New Jersey, then moved to the Midwest for about eight years. Did high school and undergraduate in the Midwest. And I miss it. I miss it. But once I came out here to North Carolina, did not want to go back. So once you become an East Coaster, you just kind of like, you want to settle back out on the East Coast. I think it's our people, you know. And Boston is definitely our people too. Okay. I have something I really want to talk to you about. I think one of the things that you're known for is thinking outside of the box. So we're going to do a little game today. We're going to play, let's get out of the box. in the box. is that theme music, Jon? I think that music is just for you. You said you were a good dancer, so I think you gotta bring it. I mean, I-

  Jon Dick: The good dancer was a joke, Aaron. That was a joke. Let's be clear.

  Aaron: You gotta wait for the drop. Alright, so Jon's gonna go ahead and grab the little box that we got actually sent to him a couple of days ago, and he has no idea what's in there.

  Jon Dick: Look, look at this, look at this, wow. Cupcakes, I believe, with a 10 candle and some balloons and they're orange themed for... my 10 year anniversary at HubSpot everybody, I've been at HubSpot for 10 years.

  Aaron: For what, Jon?

  Aaron: 10 years, which is just absolutely amazing.

  Jon Dick: Thank you everybody, thank you so much, thank you, thank you.

  Aaron: So I think one of the things that we wanted to talk to you about is who these days gets to work in a place for a full decade. So we wanted to celebrate, you celebrate your 10 years with you. So what's it been like working at HubSpot for a full 10 years?

  Jon Dick: Thanks, Aaron. Yeah, I feel so lucky. I don't know. I've had just such an amazing decade at HubSpot. you know, there's a couple of things that have stood out about the last 10 years for me. think number one is that I just work with really great, kind people. And I feel like when, at the end of the day, I don't know, I've worked other places, you know, I've got friends who've got jobs and the number one thing, number one correlation with job satisfaction is if you like the people you work with. And I really, I like the people that I work with.

  Aaron: think that is actually the measure. It's the team.

  Jon Dick: Love the team at HubSpot. know, a couple other things that are great. You know, HubSpot, the second big thing I think is how much I've learned. And I think that, you know, HubSpot is, as a culture is like very obsessed with feedback, very obsessed with learning. We always kind of assume we could do it better. We always assume that there's something we could learn. And for me, that's been amazing because I'd love to learn. And every single year at HubSpot, I've had the opportunity to learn like really big, interesting things. And never more so than this moment. I say this to people on my team all the time, but like, I think, I hope that for the people who work at HubSpot, I hope that you feel like this is one of the greatest times in your professional development because you have the space and the opportunity and the tools to learn the skills you're going to need for the next decade of your career. and I feel like that's happening for me. And so I feel really lucky for that. And I mean, the third reason that I feel lucky to be at HubSpot for so long as I think the mission is really important and impactful, and particularly right now in the world, you know, the mission of HubSpot is to help millions of organizations grow better. really focused on SMB and I talk to our customers all the time, you know, multiple times a day. And the truth is they're just small business owners who are trying to figure out how to grow their business, have a successful career, serve their customers better innovate. And I feel so lucky and thankful that we get to be part of helping them do that, both through how we, you know, the education we provide, but also the tools we provide. I feel really lucky.

  Aaron: Yeah, something I want to talk about over the break, after the break is that HubSpot years ago was really the catalyst for inbound. And now I'm hoping it'll be the catalyst for AI when it comes to marketing. So I thought we'll talk about that in the second half. All right, go ahead, reach back in the box. me what else.

  Jon Dick: Okay, let's see what else we have here. We've got, it's something, something wrapped up. Hold on, I'm opening it. It's a cube spinner.

  Aaron: So we thought, you know, when it comes to applied physics, you'd be the man to know how to take physics and apply it to modern marketing. Because that's a little bit of your background, isn't it?

  Jon Dick: physics. Yeah, I love physics. You know, I studied physics undergrad and like really quick, like, think just really quickly, like I didn't necessarily hit with every science. I like science. I was curious about science, but physics, like, I just really hit with me.

  Aaron: For a second though, when you think about science in general, because we work in the life sciences, I think there's this safe space that scientists have where everything is very absolute, almost binary to a certain extent. It's either going to work, it's not going to work. And then they tinker, tinker, tinker until they can make it work again. And then at that point, we know it's working. And I'm wondering if in marketing, you really get that kind of binary relief of like that scientific, you don't get it. You know, it's a lot messier than just what you might have in absolute science.

  Jon Dick: You know, I feel like the thing about science is there are theories and there are laws and laws are well proven predictable. You know, the laws of marketing probably like, they probably transcend a little bit. you know, I would say probably like add value before you extract value is probably like a law of marketing, less testable. I think there are a lot of theories though, and those are very testable, very applicable to marketing. And I feel like the real thing is like the scientific method. I think is extremely applicable to marketing. know, particularly as marketing gets more complex. And I think the thing about that's so amazing about AI as a marketer is that you can just like dramatically ramp up your pace of experimentation and iteration. You can test things over and over and over over over over again. So you can get so many more data points, which I think allows you to just narrow in on results more.

  Aaron: So you are applying the scientific method through the work that you might do and that is kind of how you're pulling that that experience you've had through physics into the everyday marketing. This might be good for the next queuing up the next one. So go ahead. What is this?

  Jon Dick: This is a tie. This looks like a... Is this a Hogwarts tie? Is this Gryffindor?

  Aaron: almost inspired by it's actually a Harvard tie.

  Jon Dick: It is Crimson.

  Aaron: some of the improv groups might wear such a tie when they're out there doing improv.

  Jon Dick: That's true, that's true. Many improv groups like to dress up snappy and snazzy.

  Aaron: We are very excited that you're coming out of Harvard and of course having you here on the podcast, the kind of things that you might have gleaned. You went to master's degrees. We got an MBA from Harvard. Yeah. So what kind of things do you feel like are, let's say, transcending time? You went there number of years ago, but what kind of things did you learn in that experience that you feel like is still applicable today?

  Jon Dick: Yeah, I got an MBA from Herb. You know, HBS is not, and especially because it's a master's program and it's a master's program for general business. you know, it's not like you go and you take like accounting classes where you get quizzed on like credits and debits and like, it's all about how to think about business problem solving, understand markets, understand businesses, understand human behavior, understand frameworks that you can apply other places. And so honestly, like I've got a whole filing cabinet drawer full of the cases from Harvard and I pulled them out all the time. Like I was just prepared to give a talk on leadership and I was like, you know, I want to go back and look at my notes from like the authentic leadership development class. What's so amazing about the case method, which is, HBS is primary way of teaching is that it's all about stories. You know, you get a case and it's, it's written in narrative form with a bunch of exhibits at the end with data and other things, and it forces you to synthesize, but also because it's a story, can be more memorable and help you really like, I think internalize the learnings as opposed to just like, like I memorized that thing and I hope 25 years from now when I'm in that situation, like I remember the, like the formula ever.

  Aaron: Going through the paces and understanding more realistically what will work, what won't work is extremely helpful for folks. And I was going to kind of bring one other point up about your background with Harvard and then what came afterwards, because the tie is actually a twofer. It's that it's also being celebrated by folks that are into improv. And you are into improv. You actually did it for a number of years, right?

  Jon Dick: I did. Before HBS, I did improv. Yeah. I, it was super into physics. got an undergrad in physics and actually got, got a fellowship to go to Oxford university to study physics for a year. I was so pumped. Very excited. Very cool. That's why I thought it was a Hogwarts tie because I thought it's free. It's it's giving off Gryffindor color, you know, anyway. And although I'm not a Gryffindor, I'm a Hufflepuff. It turns out I got to England and I was all geared up to do physics and I ended up spending the entire year spending most of my free time with an improv group. I was part of founding an improv group in, Oxford called the Oxford imps. And, took what I'd done at UMass, which is where I went undergrad and, applied it there. And this group was so fun. It was so awesome. They're still performing, in Oxford and at the Edmund Refringe festival and stuff. They're like super cool. And, I just ended up being like, huh, if I went to like one of the best places in the world to study this thing, and I ended up spending all of my free time like doing improv, maybe I should follow that passion a little bit. And so that's actually why I moved to Chicago. Chicago is kind of the capital of improv. Yeah, I got, I got super into it. I think that's one of the reasons I got into HBS. think they have a quota for one improv person a year. So they leave one slot for the improv person just to add a little wackiness in the classroom, you know, who knows what's going to happen.

  Aaron: As a person who was in theater as well for a while, would say, and we had Ashley Faust on our show recently, and she was also a theatrical student of the theater, should say. One of the things I do think every single day that we need is to have that kind of spontaneity in our discussions and be able to be ever-present and be sharp enough to be able to pivot constantly. So I think that experience for you must be just something you might tap into constantly. Is that true?

  Jon Dick: Yeah, I I think if you generally follow the rules of improv, I think you're living a pretty good life and you're a pretty good human. Like, the number one rule of improv is the concept of yes and. What yes and means is that if you want to do a great improv scene with somebody where you have no idea what you're going to co-create with this other person on stage, then the number one rule is don't say no to them. If they give you a quote, gift on stage and say, you know, Here's the vacuum cleaner, like clean up the spill. If you say that's not a vacuum cleaner, that's a football, it's just going to be a terrible scene. The better thing to do is to say, yes, I will plug the vacuum in and clean up that mess, but you have to apologize first for spilling the vase and smashing the flowers. And now you're like escalating the tension. So, and I think that's like one of the best things you can do as a human being in life, especially in business is to just like, somebody, you know, brings an idea to you. And it turns out actually bringing ideas is like, it's hard and it requires vulnerability because you can be wrong about those ideas. And like the absolute worst thing you can do is be like, no, that's a terrible idea. The best thing you can do is be like, yes, and let me build on that idea and talk about how it could be even better and collaborate with you. you know, that's the number one rule of improv. There's other like good rules though. Like, you know, one of the goals of, of really good improvisers is you want to make everybody else look funnier than you. But everybody has that mantra, which means everyone's trying to set other people up for jokes. And so like, that's like a great, like, and I think that's good, good for teamwork, you know? So I think there's all sorts of lessons that, that came out. think Being comfortable with failure, improv, a lot of improv is bad. A lot of scenes are not good and you just have to be comfortable with the idea. And like, it turns out that's like a lot of things in life and business. So, you know, being comfortable with failure is also probably a good thing.

  Aaron: I've always wanted to take a class. I never got the chance to do it. I probably should still try at some point, but...

  Jon Dick: Feels like you've got improv in your bones, Aaron. You're giving me improv vibes.

  Aaron: Here's an observation though about improv. It's always humor though. Why isn't it like something like horror? Like why can't you do improv horror?

  Jon Dick: you can do improv horror. It just turns out it's really funny. So, I don't know, there was this amazing teacher that I always loved. Her name was Liz Allen. Actually, I have no idea where Liz Allen is in the world now, but she was this incredible improv teacher. And she used to talk about the sine wave of comedy and how like the absolute funniest improv scenes are the ones that are the most serious. Because an audience is sitting there and you like raise the stakes so high about like something absolutely terrible and awful or scary and horror. And as soon as you crack the slightest joke, the audience is like so desperate for a release that like it ends up being so funny. And so if you want to build a great improv scene, you need the sine wave of comedy.

  Aaron: honestly agree with that. Okay, all right. There's a couple more things in that box and they're all from Inventive.

  Jon Dick: nice, nice and inventive blanket.

  Aaron: We also included a couple more fun little things in there too. And it's all about yeah, you're very welcome We love working with you guys and we really appreciate you being on the show and everything So yes, thank you for taking part in wait, what do we call it? So I think that one of the things we wanted to you know Hear more about and we'll get to it after the break when we get to that point We'll be about you know AI in your every state day life and all that kind of stuff But you are probably like me. I think we're maybe a similar in age you grew up where there really wasn't even like a computer lab in a school yet. That's what I had. was one of the first people to actually add a computer lab when I went to the School of the Arts at UNC. And I was there watching everything grow with me, you know, and I'm sure it was the same for you. Is that true?

  Jon Dick: Pretty similar, yeah. I think my middle school did have a computer lab, but it was a very early computer lab. It was like five and a quarter inch discs. And, you know, to play Oregon Trail, there was like 14 discs and you like played like up until you bought supplies, then you swapped out the disc to the next one. And then like, you know, then you got dysentery and you swapped it to the next one.

  Aaron: One of my favorite things that we bought, well, I bought a couple things in the early days. My computer was by Gateway Computer. Do remember Gateway?

  Jon Dick: Gateway I wanted a gateway so bad you're so lucky I aspired for a gateway PC I wanted that cow to show up at my house

  Aaron: say their branding was just black and white spots when the when the box showed up it looked like a big old cow and they did lean into it. It was Prince. He put out these little you know like kind of choose your own journey games. Prince the artist and so I had like I don't know if that was like what you said it was like four or five CDs DVDs and you had to like each one like he would get to the end of a hall.

  Jon Dick: Prince the Artist?

  Aaron: you click on something and would like insert disc too and you'd that and play this amazing music video and you're like, okay, I'm in the studio now. It was great. I love that kind of stuff. But we've watched now the internet grow up and now we've watched course AI come through before the AI. I'm just curious because I want to talk about the yesteryear before we got into the next next chapter. But what was the thing you were most excited about when it came to what the internet really gave us before AI?

  Jon Dick: From a business perspective, certainly it was the democratization of reach. And this is a very old HubSpot and Brian Halliganism, but Brian used to say that the amazing thing about the internet was it was about the size of your mind, not the size of your wallet. And I always thought that was such a very captivating and powerful concept. And I think that actually holds true today. I think it's the same with AI, actually. I think it is about the size of your mind as opposed to the size of your wallet. because it's really about how much agency you have, how much creativity you have, how much you're willing to learn and build. And if you have those things, you can accomplish almost anything. but I think that was what was so cool about it was like any business in the world. And we used to see this at HubSpot, you know, a customer would come to us and they would say, I really want to get around a daycare center and I really want to get more leads. And you'd be like, okay, here's what to do to get more leads. Like here's how to rank on Google and here's how to publish the content and here's what to do. if you add that, you know, If you attract people to your blog and then get them to fill out a form, then there'll be a lead and they'll convert. And it just worked. It works so well. And it was so cool to see so many businesses and companies like grow. Yeah. And prosper because of it. It was just so cool. I think that's, mean, so cool.

  Aaron: So I wanted to mention one more thing is when you and I were together in Boston, you said to me, said, what's one thing that you feel like we should carry forward no matter how the technology continues to improve? And you said people just need to pick up the phone. And man, I am such in that camp all the time. Touching on derated tactic. And the human connection. I think that's the big thing that I feel like the phone does for us. And we do feel like that we just want to talk to people. It's not just about all the digital internet connections. It's just trying to get that human to human connection too.

  Jon Dick: Underrated tactic.

  Aaron: Okay, right when we come back, we're going to talk about how HubSpot has of course carried the flag of inbound for the last, I don't know how many years now, maybe we're getting on with 18 years now, plus, yep, 20 years. And now they're going to be carrying the flag of AIs. We're going talk about that with Jon right after the break. Everybody stay tuned.

  Aaron: Hey everybody, are back with Jon Dick with HubSpot and we're going to talk about what's on our mind these days and where we think the world's going to be headed in the next couple years. And I'm very excited to have him join us today. He is one of our second time guests, so very, very honored to have him here and learning more about how he applies AI every single day. I think one of the things that I was always kind of fascinated about with HubSpot is that they kind of lived the inbound theory and lived their brand from the very get go of the business. Connecting art and science is what I really think HubSpot's done so well. know, connecting the art of what Inbound can do for organizations and the science of building out a platform that can really put it in action. And it's been a catalyst for many businesses over the years about what we can do with Inbound. Here we are all kind of freaking out about AI. And now I feel like I have to rename my podcast, Jon, instead of the sound of Inbound, the Auditorio's AI. Okay, maybe I am good at AI, good at improv, I can do that. But I should have had a sound cue for that one, Jon, that would have been good. So what I wanted to talk about was, you you are really working with an organization that is at the forefront of applying AI into everyday business. And that comes from all the different touch points that brand can really impact from first touch point of brand awareness into marketing and then sales and then operations and then service and support and all the good things. And the way we see the world is, of course, is in that loop. of bringing those people back around and re-engaging with them and making them excited about a brand again. And now we have AI really kind of mixing it all up for us. So I think that AI will be HubSpot's next flag that you guys will carry for all of us and help us figure out the way to put it into everyday business. And I hope you agree. So let's talk about AI and AI fluency. So there's AI fluency and there's AI expertise. So just for a quick second before we get into some things that I would love to case studies with you, Jon. Tell me more what you think really AI fluency means, because I think that's a very important term these days that people are going to probably use a lot more and you guys use it, versus AI expertise and what is even AI expertise?

  Jon Dick: I think it is very hard to be an AI, to be like an AI expert, think is a really complex thing. I'm sure lots of people call themselves AI experts. I think most AI experts feel like they're not AI experts though. Like, I feel like, you you talk to like the smartest people, you know, in AI and they're like, I have so much to learn. you know, Andre Carpathy, Carpathy who, you know, is one of the more famous AI researchers, you know. Tesla autopilot, like open AI, all these things, like he's been posting about how he feels so behind as a programmer now because of cloud code and like how fast it's all moving. And you're like, okay, even the people who are experts here, like are, are just learning so fast. I think that's like, one of things you have to do with AI is just like, get over the fear that you like somehow haven't figured it out. And everybody else has, nobody else has figured it out. Everyone's trying to figure it out together. some people figure some things out faster than you, whatever, who cares? Like it is early days and you just have to be like, Everyone's in it together and we'est just going to try and learn all this stuff. And the more actually that you are willing to like share your journey, the more you are going to find that you are ahead of other people. And also you're going to find that people give you advice on how to speed up your process to become AI fluent. And for us, AI fluency is really just about the idea of understanding how to use AI to accomplish your job more effectively. And I think that's kind of the core of it. In fact, You know, it's like, you're like, really hope a HubSpot carries the flag for, for AI, for SMBs and like leads the way on that. And I do too. But the first thing I would say is like, I don't want to do that for AI's sake. I don't care about AI. I care about marketing, sales, and customer service. Like those are the things that I care about. And it turns out AI just allows you to do those things much better. And feel like a lot of customers I talk to about AI, their, their starting point is kind of like, and a lot of vendors, their starting point is like, but AI. Look at the AI. Have you seen the AI? There's AI here. There's AI there. What about the AI? you done the AI? And it's like, actually, like all the customers I talked to were like, Hey, that's really great. Like, I have a major lead gen problem. I am really struggling right now to figure out how to like, get enough leads to feed my sales team. And I talked to sales leaders and they're like, I cannot connect with buyers. I am struggling to increase my pipeline. I'm struggling to increase my close rate. And every service leader I know is like, I am getting so pressed by my company to do more and I don't know how to do it. I don't know how to do it. I don't know how to influence more deals while also supporting customers and keeping them happy. And so it just turns out AI is a tool to do those things. And I think that's like the most important thing for anybody to know about AI and go to market is it's like, you know, same problem, old problems, you know, new solutions.

  Aaron: There were some things that I've heard you on a few other podcasts and you guys have such great things to share with everybody. And I think you mentioned that HubSpot, there's human authenticity. Is it this way? Human authenticity and AI efficiency. Am I saying that correct?

  Jon Dick: Right. So I think that's actually, you brought up the idea of like loop marketing. I think it might've been on the break or the prep, but the thing, you know, we are out right now trying to figure out how to help all the marketers, sellers, and service professionals of the world figure out how to use AI to do their jobs better and accomplish their goals better. And really the first place we really leaned in hard was to marketing. That's our roots and our DNA is inbound marketing. And I think what you see with inbound marketing is that the tactics of inbound marketing are really changing very fast because consumer behavior and technology is changing very fast around how people shop and buy. And so we spent a lot of time thinking, researching, testing, experimenting, trying stuff. And what we came to was this idea of loop marketing. And there are a set of tactics in loop marketing, of course, but the foundational principle of loop marketing is you combine human authenticity with AI efficiency. And that's just what it is. And you apply that at every step.

  Aaron: I think you should emphasize the human in the lead. That's something that we say around here in our group and our agency and all the creative work that we do is that AI is a tool. We don't want it to lead on anything. We would like it to really help us in all the different steps as you're mentioning with loop marketing and loop marketing has a theory about how AI can really help each aspect of our engagement. I love that part and I think that is exactly where we all would see it.

  Jon Dick: are things that I think people will get comfortable with AI leading on. But I think that they, all needs to be tied to this idea of like based on human authenticity with the right way to collaborate with humans and AI together. you know, I think from a marketing perspective, I think that what humans are going to be great at in the future is, you know, people call it taste now. It's like people talk about taste all the time. Um, but I think, I do think it's taste and I think it's ideas and I think it's, um, you know, willingness to learn. And those are the things that stand out. then AI can lead on content creation, iteration, whatever. But as long as you are like super clear as the marketer about like number one, who your customer is. Number two, why your customer cares about your brand. Number three, what your unique ideas are about why your customer should want to engage with you. That's the only way for AI to work. If you don't give AI that stuff, it kind of just ends up being spam.

  Aaron: When I think about achieving what you just said, trying to figure out our target audience and then our unique selling proposition and all that kind of stuff, the thing that lot of agencies are challenged with and we are too is when you're working in a niche and you have organizations that might have similar roles in that niche, so we're working with a drug research organization or something like that, they say exactly what all the other companies are saying and it's really hard to find that spin. Do you kind of feel that too with things that you work on as well? These organizations that you talk to are actually all doing the similar things. So how do they all find that little niche that would be their unique selling point proposition when really it's the same as four others or five others or 100 others.

  Jon Dick: I mean, I think if you are in a category where your product is completely undifferentiated, which there are many places, then it really comes down to your ability to win mind share, win hearts and minds, you know, and that's, that's your brand. And so that is really where your ideas have to shine. why you have to have ideas that attract people to your brand more than, than your competition.

  Aaron: which is all about inbound marketing, about sharing that thought leadership and that personality. Yeah, like you said earlier on the podcast, I do feel like it's about who you want to work with. You also mentioned something else in a couple other interviews I read about was the explorer mindset and just being really hungry to learn right now. Is that going to be the thing that differentiates talented folks, like the people who are just willing to learn?

  Jon Dick: I think it is a certainly a part of it. Yeah. I mean, if you're not willing to learn right now, I think that you're probably going to get left behind in a pretty, pretty dramatic way. and what I love about that is it's not about how many resources you have or, know, again, it comes back to Brian's old saying, it's not, it's about the size of your mind, not the size of your wallet. And I think that's like, those are the best fights that I want to be in. It's just things are just changing so fast and capabilities are emerging so fast that like you have to be willing to learn and change and adapt and something and you have to be okay with it is some things are going to work some things aren't going to work, which is why you want to experiment even more so that you can find the signal from the noise much more quickly. I think if you are a learn at all, I think it's, I think it's a great time to be a learn at all. And I think it gives you a real advantage.

  Aaron: Okay, you queued me up wonderfully for the next question, which is really a lot of folks talk about AI, and my team knows I just can't stand the words talk about. I like to see things actually in action. I like to deliver on everything we're working on and show deliverable results. So I'm curious from your standpoint, give us a use case of how you're leveraging AI and not just, hey, we're being really productive with it, but give me something that you feel like has really been amazing for you or transformative, or even just if it's just a... I shouldn't even have to it's transformative. It could be something that you're like, didn't know AI could do this before, but now that it's doing this, I now have it doing this activity for me and it's helping me out every day.

  Jon Dick: I I like, you know, as a leader at HubSpot, use AI all the time because I do a lot of strategy work. do a lot of, you know, content creation, a lot of presentations, and it's an amazing, amazing aid to help with ideation, building ideas, going from ideas to structure. It's like so good at that. And so, I mean, I do that every single day. Absolutely. I think though, you know, the two probably most successful examples from my team this year, you know, one of them is customer facing and one of them is rep facing. And, you know, the customer, the customer facing example is obviously customer support and customer support has really good product market fit for AI. And the reason it has really good, you AI has really good product market fit within customer support is that it is mostly about content consumption. That's what generative AI is really good at and LLMs are really good at. And if you give LLMs the right content, they're really good at, you know, interpreting questions and mapping content against it. So it's like, they're really good at it, but I think what's so interesting about customer support as a use case for AI is it's really like the amazing trifecta of what you want to see for AI. The first thing is that it's better for customers. AI support is better for customers because it can give any customer a faster answer that is more informed and more accurate. Now, that requires you to put in the work to make your AI support good. You may encounter a lot of AI support that is not good, but you know, one of the big lessons we had when we first rolled out AI support, for our customers was we really obsessed about like resolution rate. That's the thing we cared about. We're like, you know, how high can we get the resolution rate on tickets with AI? And it turned out we weren't paying nearly enough attention to CSAT of AI. And we pretty quickly realized like, whoa, like we are doing great on resolution rate, but the CSAT on it is just not good. It's just not a good experience. So we really have invested most of our calories over the past couple of months on getting the CSAT customer satisfaction score. And so really put a lot into improving that. And so, you know, Number one, it's better for customers, assuming you can make it really good for customers, which you can, you can make it really good for customers. does take a little bit of work, but you can do it. Number two, it's great for reps, because for our support reps at HubSpot, they want the opportunity, of course, like anybody to learn more, work on more challenging problems, do more interesting work, and AI allows them to do that. You know, we look at what our support reps are able to work on now, and like they're working on really challenging problems, and they're able to be more proactive with our customers, which is really huge. Um, you know, shout out to our support team. think they're, I think they're one of the best in the business. Um, and I love that they're kind of getting the opportunity to work on a new set of problems increasingly. number three, it's good for the company because it allows you as a company to, to save money. And really the way that that plays out at most companies is it means that you don't have to hire as many head count in the future. That's actually the way that it works out, you know, is that you say, okay, cool. It used to be there was a ratio of like, I need one support rep for every thousand customers. I don't know what the ratio is, um, at your company, you know, but. And now it's like, actually like I need one support rep for every 1500 customers. And that just means that, you know, you have more capital to invest in other things, as a business. so I think it's a great trifecta. Good for customers, good for reps, good for the business.

  Aaron: You've mentioned this a couple of times, you've to put the work in, and I think a lot of folks are confused or not even realizing how you train these things. Now we recently put out, we put out a deployed, I should, that was the word I'm looking for. We recently deployed the customer service agent on a couple of websites to test things out. And so I just want to let everybody know how this works. So in HubSpot, when we say we have to put the work in, that training starts off with just giving it a reference point. So in the little wizard kind of screens. You can say, wanted to just look at our website and don't look any further. Like just look at the website and it'll crawl the website, pull the data in. You can also have it reference information that you upload. So if you have any business docs or customer service docs or knowledge docs, you could upload that like you do with any other LLM. And you can say, just reference these docs. Don't go anywhere else. Just look at this. And you can also have these customer agents set up in such a way where if there's something it cannot answer, go ahead and hand it off to a human or just ask for the email and don't try to make things up. So you can give it some guardrails. Now there are other ways you can let this LLM really go way beyond just your website and look at all the references that coming from the outside world too, but you can't narrow it. And so I think people say like, Aaron, I don't understand, put the work in, what does that even mean? These things are black boxes to me. And I do want everybody to understand it is actually really accessible.

  Jon Dick: AI training sounds like really scary. Like how am I a mere mortal going to train in AI? And it turns out all you need to do is just give it documentation. And I think what's really cool about, you know, our customer support, you know, our approach to help desk and our customer agent is that we actually make recommendations of places you can improve content, which is how you improve the training of it. So it might just turn out like it's really bad at answering a certain type of question and you just need to upload more content into the knowledge vault for it. And that trains the AI. think that's what we call it. The knowledge vault. The ticker.

  Aaron: is a good term. To your benefit, I think there were other organizations, I won't name any today, but other organizations that made big announcements during inbound last year, where they had to lay off a lot of people because they were going to bring in AI. And what I think of it as it opens up another type of opportunity for the humans out there. Like there's one kind of job you no longer have to do. And that might be the stuff that we don't want to do, but then there could be a whole bunch of stuff that we can do. So I'm just curious from your standpoint, what kind of folks would HubSpot be looking for next? I know when you guys out there, I heard this again in some of the interviews, was that AI fluency is now going to be one of those prerequisites. Like, we're going to look for people with this on their resume. Is that one of those things that you feel like people are going to be looking for or more than that? Or you feel like you're looking for those folks that are really in the ideation phase?

  Jon Dick: Yeah, it depends on the role. think anybody who joins HubSpot now needs to be on a path to AI fluency. And you might not be like fully there, but you have to show your willingness to certainly be on that path and learn. And that is important for us because I think we deeply believe that the people at HubSpot are going to need to learn a lot over the next few years because it's just a time for learning. And so I think that is a key criteria coming in, but I think what's happening in the world of skills, it used to be that, you know, there were generalists who really struggled to have a lot of impact and there were specialists who could be considered a specialist if they were at like a seven out of 10 skillset. I think what's happening now is that generalists have the capacity to do way more and accomplish way more. And so if you come in as a generalist, you need to be of the mindset that you can accomplish all sorts of things and have the agency and the willingness to tackle all sorts of problems and figure out ways to solve them, et cetera, because you can accomplish so much more. We kind of call them super contributors. And then you've got your specialists. think for special, know, specialization, again, you used to kind of be able to be a seven out of 10. Now to be like a real specialist, like you kind of to be like a nine out of 10, 10 out of 10, which just means you need to go deeper. And again, the good news on that is like in both cases, I think that is achievable if you were willing to leverage AI in your role. and leverage the tools and learn and grow. Like these are not things that mean like any single person is like locked out of the market. Like not at all, actually. It's like totally in your control, in my opinion, to, learn these things.

  Aaron: Yeah, there's been a lot of conversations we've had with people, especially because my daughter, my younger daughter is still in college and she wants to get into our world. I don't know why she's thinking that. But I was thinking about my daughter quite a lot because the industry is changing so much from year to year to year. And so I'm curious from your standpoint, if you had to speak in front of a whole group of folks in business school today, looking at getting into marketing, what's some of the things that you'd be looking for? Outside that AI fluency, what kind of core skills do you think they mean to have?

  Jon Dick: Number one, I do think that you need to have a willingness to deeply understand your customer, probably more than you had to for the last like 10 to 15 years when you could just kind of buy ads on Facebook or whatever. And so I think like insight and insights about your customer probably matters a lot. you need to really, and that's like not, people feel like it's like Mad Men and you just like sit there and like. It actually takes like a lot of work. I did an internship doing like account planning at an agency. It's like really hard to come up with brand insights. It actually takes a lot of work, requires a lot of research, a lot of data, a lot of observation, a lot of brainstorming to find something that's really good. And so I think that's something as a marketer you need. think refining your taste and some people do have probably more natural tastes, but I do think tastes can be learned and refined for anybody, but it does take work. And what's so hard about taste is you are always, I think it requires, it's subjective. and subjective things are scary because you might be wrong or not everyone will agree with you. And so like, that's where you have to like take that stand. And then I do think like your ability to understand system like combine that, that taste and that deep understanding of your customer with a modern approach to, systems to develop an outreach program.

  Aaron: You Mucky, you mentioned something I would not have brought up before, and I think it's important to kind of focus on it for half a second. As an agency, we have a focus, and I think we need to own that focus because we used to think of ourselves as we could help anybody anywhere, anytime, and that has really changed quite a bit. And I think you're right, if you're coming out of a marketing or business school program at this point, finding something you're really passionate about, if it's agriculture, if it's pharmaceuticals, if it's healthcare, or if it's retail, whatever it might be, pick your lane and learn your audience, as Jon is saying, learn your audience. Because I think that's going to differentiate you as well, not just coming in like, I'm willing to do anything, but actually knowing your audience. And we're going to be talking to folks this season about the retail side and other elements of marketing and how people do that kind of user research and on the digital side. And it's remarkable what organizations will do to go out of their way to learn what it's like to be in that position of the end user. And so if you can learn that niche, that's really good, think. Personally, think that's a great recommendation, Jon, that people can think about that and get to know it, get to know it really, really well. And why would we do all this work if we didn't enjoy it? So bring that personality that is part of you into your work and embrace it. Yeah.

  Jon Dick: Absolutely amazing what data is available now, how easy it is to get, how in control you can be of it, how personalized you can get, what kind of flows you can build. Like, you know, we're doing like agentic workflows now, like, which are so cool. When I started as as a, as in marketing automation, a long time ago, like I never would have dreamed that we could produce this kind of thing. You know, it's like what you always hoped. You're like, I'm going to create these like personalized emails and like literally all I'm to do is stick a first name in and be like, bam.

  Aaron: Yeah, it is incredible how far it's come in even the last six months. But here's what I was going to do. So I'm sure you're a fan of Late Night 2 and maybe David Letterman. So Robin Williams was one of the most frequented guests on the David Letterman show. And I'm hoping, Jon, you become one of our most frequent guests to spin poetic. Wax poetic, is that the word? Wax poetic on everything that's happening with technology because I'm so excited about where things are going. And I hope you and I get to check in at least once or twice more this year because I can't imagine how far it's gonna go. Just looking at last six months, what are we gonna be in six months from now?

  Jon Dick: I know, I know. It's exciting. It's exciting. I'd love to come back. I'd love to talk to you again. Thanks for having me, Aaron.

  Aaron: Hey, all right, everybody, Jon Dick, he is available on LinkedIn. And he's also available. You can find his profile on the HubSpot.com website under leadership section if you want to learn about more about him there. And of course, if you want to bump into him, you can join Jon and I at this year's inbound 2026 going back to Jon's hometown Boston.

  Jon Dick: Austin, see ya, see ya around town. Yeah.

  Aaron: Yes, we're very excited to come back to Boston, go back to the hometown of HubSpot and have a wicked good time. It's.

  Jon Dick: Good. Park the car at the Boston Convention and Expo Center.

  Aaron: We're very excited to be there and this will be my 12th year going to Inbound. Yeah, so very excited to rejoin you guys and hear about all the next greatest level stuff that's going to be coming for us in the marketing world.

  Jon Dick: Thanks everybody. Any HubSpot customers who are listening, thanks for being a customer. Reach out if I can ever help you and thanks so much, Aaron.

  Aaron: Yes, no, this has been fantastic. Thank you, Jon. Okay, everybody, please stay tuned for more episodes of Sound of Inbound. You can check us out at soundofinbound.com also on Spotify, Apple podcasts, YouTube, LinkedIn and Instagram. We love to see you there. Thank you so much for joining us, Jon. We'll see you guys there soon.