Courtney Sembler: Bias, Breakthroughs, and Becoming a Leader | Women of HubSpot

Welcome to the Women of HubSpot podcast, the show that celebrates the voices shaping marketing technology and the ever evolving HubSpot ecosystem. Hosted by George B. Thomas from Sidekick Strategies, each episode brings you the stories, strategies, and superpowers of the women driving this industry forward. It's their time. It's their mic. This is Women of HubSpot.

All right, so again, we're back. If this is the first time you're watching one of these Women in HubSpot videos or listening to a podcast episode, just know that this was born out of a very interesting situation. It was Super Bowl Sunday, by the way. 2025, I think whatever. Doesn't matter. You. Who knows how long these are going to be on the shelf life of people listening to. But to give you some context, Philadelphia Eagles. My daughter brings up to me that the quarterback has a team and that the team is all women and how she loves this. And it's amazing. And I. I start getting emotional, and I'm like, why am I getting emotional? And so, as a good, you know, dad of daughters, I go to LinkedIn and I'm like, you know what? And I do this post, and I didn't mean for it to be anything special. I was like, let's shine the light on women in HubSpot who do, you know, tag them in. Courtney. The post went bonkers, like nutsoids. I'm like, what in the what? And so immediately, my daughter and I, we looked at each other and we're like, we need to do something with this and about this. And so we started interviewing the powerful, amazing women humans of HubSpot. And it has been a great journey thus far. Just the conversations have been incredible. So I can't wait to dig into it with you today. But first of all, how the heck are you doing today?

I am great, George. I. I'm coming off of probably one of the most amazing weekends of my life. My partner of almost four years proposed to me over the weekend. I said, yes, it was my birthday. Like, I. I am just on cloud nine. So the fact that I get to talk to is even better.

I love this so much, man. Congratulations, by the way. That's like.

Thank you.

Amazing, amazing, amazing stuff. All right, so let's get into this. Courtney, If. If we could go back in time. Don't you love when questions start like that? By the way, if. If we could go back in time and meet young Courtney Sembler, just starting out. One, what would we see?

And.

And two, what would she be most surprised by? About where you are Right now, young.

Courtney was still very ambitious. So I think if you went back and told her where I am today, she'd be like, but we're not a CEO yet. Like, she. She'd be like, come on. Like, get. Get with it. She was incredibly ambitious. And, you know, what you would see is a couple of things. I started my professional journey very young. I was working for a nonprofit. We were focused on land conservation in South America. I did this interesting job where I was sort of like the admin to the admin. We had a small organization and it was mostly based in South America. So the, like, few of us that worked in the US There was a lot to do. There's coordination, there's all of these things. And the group of women that I worked for, it was actually a very female dominated space. I ran our CRM, which is funny now to think about. And so I think if you went back to her, that would be like, oh, we continued that. Like, it was useful. I used a environmental nonprofit CRM called eTapestry. They do not exist anymore, but that's okay. And that was my first sort of like, jump into the professional space. And I think if I went back and told her where we are today, I think the thing that she'd be most surprised at is how much we really enjoy where we are. Like, I think there was a lot early on where I was like, oh, this is hard. And it, like, feels hard, but, you know, oh, it's okay. Like, I'll just kind of push through. And I think she'd be really excited to know that I have a huge smile on my face every day that I come to work and that it gives me energy and that when I go on vacation, I come back from it, I'm like, yeah, okay, these were things I missed. And like, this is what I'm excited about, which would be really fun to talk to her about.

I love this so much. It's almost like you're leaning into. You have arrived at a place because you went through what was difficult to get to. What now feels easy, that you almost get to play every day instead of work every day, which I love that mentality. It is a magic place to get to. So Courtney, along the way and you started to allude, like, even by the way, starting out nonprofit had zero clue and CRM, by the way, zero clue. But you've had this journey and you even started to lean into, like, this group of women. At the beginning. When you sit back and you think about your journey, who are some of your Biggest inspirations or biggest mentors along the way.

There's so many, and I'm sure I won't be able to name all of them. So if I. If I miss them, I'm. I'm so sorry. You have an impact on my life, I promise. The biggest inspiration I have is my mom. My mom was a CFO at 30 years old in the late 70s, early 80s, and has just took the financial space by storm. She was kind of the first of her kind CFO at the time. You know, for women to be on the C suite now is still hard. Back in the early 80s, almost unheard of, particularly in the financial aspect of it. Like, maybe you had, like, a cmo, but a CFO to be a woman, particularly such a young woman. And I saw that growing up as a young. As a young girl, seeing my mom be in this leadership space and to own her voice. And I still remember being really young. I went with her on a trip to New York. She had, like, some meeting with some investors, and she took me with her, and I sat in this huge boardroom. You know, very classic, right? Like, all windows, we're in New York, everyone's in suits, and my mom is the only woman at this table. And me, I'm sitting there, and I'm, like, coloring. And the space that she took up for herself so unapologetically, like, just, I am here. I'm in charge. And, like, if you don't like it, that's your problem, not mine. And I know now that all of those early images and feelings make it possible to be where I am today. And so Debbie Reicher is the most. The biggest inspiration I have, and she inspires so many other women in our space, too. I grew up, I had this amazing friend, mentor, Eliza Durkin, who spent a lot of time with my mom. She worked for my mom when I was young. And she. She was, like, always, like, your mom is so great. Like, oh, yeah, like, she's my mom. Like, I know she's great, but she's like, you don't know what she's given me of, like, this confidence in this inspiration. And I think as a young girl, the fact that I never even question it, like, well, of course, like, girls belong in all these spaces. It now clicks to me, like, how much of that came from my mom in the space that she was giving me. And so those two women, huge inspirations for me, I would say, in, like, the HubSpot realm. The first boss I had at HubSpot, I came in, I was in Technical support, like, helping our customers every day. And I had this wonderful support manager, Nancy, and my first one on one with her. God, I was young. I was super ambitious. I'd just been like, coming to HubSpot. And she was like, what do you want to do? And I was like, oh, well, like this week she goes, no, no, no. Like, what do you want to do with your life? What do you want to do with your career? And I was like, oh, I can. I can answer that. And she was like, yes. I was like, oh, okay. Like, great. And she gave me this space to be like, what do I want to do with this job that's going to get me to somewhere else? It wasn't just about the day to day. And like, you cannot underestimate that impact, particularly when talking to young women. Like, that question is so, so powerful.

Yeah, I love so much of this already. Just the fact of, like, thinking ahead, this idea of. And we. And it's a reoccurring thing of, like, stepping stones to get where you want to be and. And having these goals to get there. Also, when you talk about your mom, I started to get emotional. I'm like, my gosh, like, come on. Like, because you don't know until you know about your parents, right? Because it's just. It's like you're normal until you realize that it's not everybody's normal. And so that's super, super powerful. We kind of talked about your. You. You're in the place where you go to play versus kind of work. You're definitely empowered and, like, you're empowering others. But I have to, again, dig back into the journey. Have there been any hurdles or. Or biases that you've had to overcome in your career? And if so, how did you actually navigate them as they were going on?

Yeah, there's. There's two very distinct experiences that I have that I'll share. The first is very early on in my HubSpot career, I was asked to go and present at a HubSpot user group, which we still have today. And it was a small HubSpot user group in Virginia. I flew down there. It was like my first big business trip. Like, you know, on the plane, like, have my bag, like, so excited. And I was pumped. I'd prepared so hard for this event. Like, I had decks, I had worksheets. I was so excited. And I got into the room and it is all men, all older than me. And one gentleman, he stands up as I began presenting and was like, oh, no, thanks. Like, I'm not interested in learning from a child. And he left. And you know, at the time like HubSpot user groups weren't just customers, they were like people who are like in the space. So you know, I, I don't fault this person for that. That's his experience, that's his, his belief. But there was that moment of being like, I still have like 45 minute presentation and I've just lost the trust of every single person in this room. And you want to cry, you want to hide, you want to like crawl underneath the table. And something that I have found to be really powerful for me is humor, particularly in those difficult situations. So he leaves the room, I sort of take a beat, take a glass of water and I'm like, does anybody else not want to learn today? Or like you good. Like, do you like, your, your businesses are fine, right? Like, you don't need to learn from me. And like everybody laughs and like relaxes a little bit. Like to me that was a really important moment of. You also don't have to make fun of yourself. Like I think self deprecating humor can be really challenging and particularly for women can be a really slippery soap. But like having that space to be like, if you don't want to learn from me, I'm good. Like, you are the person who will be impacted, not me. And actually that group that was there that night, they took me out to dinner. And some of those men in that room who learned with me that day are still connected with me on LinkedIn share how their businesses are growing. And we had such an amazing experience. But I think about that, I actually wrote an article about it at the time of like, you think I'm too young? Fine. You think I'm too young, I'm too much of a woman, I'm taking up too much space. What does that say about you? Not what does that say about me. There are moments I still get up on the inbound stage in front of large groups and I think about that person, I think about the impact of those words on me and it could have really gone the other way. That was definitely. I experienced that a lot early on. Presenting I'm young, I'm a woman, I'm blonde, I'm from California, people don't wanna learn from me. And you kind of have to come over that hump for yourself of you can either change and be not who you are and not authentic or you can lean into it. And so that, that was definitely difficult. The second, oh gosh. And like I might Cry. Like, it was. Oh, it was really hard. But I. Very early on at HubSpot, I was probably like a year, year and a half in, and I thought I was just on cloud nine, right? Like, I loved it. I was working really hard. I was doing a trainer role at the time where I was onboarding our new support rep. So start of, like, the leap to academy for me was like internal training. And I loved it so much. Oh, my gosh. It was like I woke up every day and I got to inspire and do front of room, you know, facilitation. I loved it. And I was doing the work of like, multiple people. We were pretty short staffed. And I went into my performance review with my manager and I'm like, I'm a four. I'm so great. I'm doing all these things. And she was like, no, you're a two. You're, like, struggling. And I was like, what? She goes, I'm, like, really concerned about your performance. You're not doing what I'm asking you to do. And I was just shocked. Like, I can still remember the walk back from that conference room. Like, I had to cross the street and I was crying and I was like, oh, my God. Like, I'm so off from where my manager is. I. I didn't think, like, all these things are going through your head, right? And like, the biggest word that's just right there in front of my face, like, I failed. I totally failed. I've been here a year and a half and I'm failing. Oh, like, what am I gonna do? Should I quit? And I got back to my desk and someone's like, are you okay? I'm like, no, I think I'm gonna go home, like, just, like, not feeling great. And that night, I, like, wrote a resignation letter. Like, you do all the things right. Like, you go through all the emotions. You're like, I'm going to quit. I hate it here. And I woke up the next day and I'm walking back to the HubSpot office and I'm like, I really like this job and I really like all these things. And so I decided, I was like, I'm just going to pull the band aid. I'm going to embrace every single piece of feedback that my manager is giving me. I'm going to look at it in a different angle and I'm going to try hard. And if in six months, like, I'm not doing it, like, then fine, like, I'll leave and I'll accept the fact that I'm not Doing well. And it was two and a half months later that I got an offer to join the Academy team. Like there was actually something in that moment that clicked for me that what I thought was a good job wasn't and I needed to carry myself differently. I needed to talk about my work. You can believe it. That first performance review that was a like low rating was. She uses I a lot. She doesn't talk about the team, she doesn't talk about we. Because I was, that's where I was in my career. I was so self centered and I have gone back to that person who's given, who gave me that review and I've thanked them so, so much because it, it changed the rest of my career really in how I deliver reviews and how I get reviews and how I get feedback. Like, it, it really changed me.

Yeah, I love this like the ability to use humor, that was one thing I'll pull out of there because it is a super hour. And the other thing is just the, the ability to take feedback and it not be a failure, but it be a lesson. And then the last thing that I, I kept thinking as you're telling the story, I'm like, oh, thank God she gave her the space and time, the space and time. Because at the end of the day, imagine if you didn't stay and you didn't end up at the academy and you didn't impact the lives because honestly this guy right here, I've been learning from you and the team for years. Like the impact that you've been able to make as who you are and what you're doing now is like, it's maybe not even measurable, to be honest with you. And so like giving yourself that space and time. I think a lot of the HubSpot ecosystem would say thank you God, like, thank you that that didn't end up being the path that we took. So very cool. All right, so, so let's keep going here. Courtney, here's my, my next question for you. Have you ever experienced what we would call a significant failure other than the story that you just told or setback that you just thought it's over and then what did you learn from that in addition?

Oh, such a great question. And I'm sure I could share a lot of different ones because I, you know, I do believe that failure is such a gift. Learnings that come from it, taking that ownership, one that really comes to mind is early on in my management career. So I loved being in ic. I was doing the professor thing, got the opportunity to take on a management position and, you know, super junior manager, very green, you know, had learned a lot, but, you know, kind of the first time I was going to manage people. And with that there's the people management piece and there's also the strategic piece, right? You get to take on more of that strategic learning. And I was putting together a strategy for our content development and like, content plan for the next year. And I had to get a lot of people's buy in, had to go in, you know, to executives. And I thought I'd put together. Gosh, I thought I put together the perfect plan. It was amazing. I loved it. It looked great on paper. I had no idea how to present it to someone who didn't understand the education piece. And I went into it with my classic educator brain. I'm like, here's why it's important. Here's how it's going to work. And they were gone in five seconds. And we're like, this doesn't make sense. I don't get it. And I was like, wait, but I have 50 other slides. And like, we don't care. And it got just turned down, rejected. They were like, absolutely not. And so then I tried again and it still didn't work. And I tried a third time. There was this moment for me of like, I might not be good at this. Like, I might not have the skill set to do this. I was a great ic. I feel like I'm, you know, nailing the, like, empathy, know, support as a manager. But this strategic communication, I don't know if I'm nailing it. And in that moment, there sort of felt like the two paths of, like, one, go find someone who agrees with you, right? Like, go find the person. We're like, well, you get it right? And like, kind of use that as an excuse. Or go to the person who is turning me down and flip the conversation, be like, how could I communicate this better? And I'm very fortunate. That person actually was John Dick, who is the SVP of customer success. I'm sorry, John, if you listen to this, you had made me cry, which I've told him before when he had turned me down the initial time. But we had this really great conversation where I was like, I feel like I'm communicating clearly, but it's not resonating. So how, like, help me understand. And he did what I think so many amazing mentors do, is he just broke it down really simply. He was like, try to communicate this in three slides. Try to communicate this in two. Talk to Me, like, I'm five, like, just get it really simple. He's like, I believe that you can educate anybody about the inbound methodology. That's a very different way of communicating than internally to stakeholders. And wow, like, that one conversation changed, changed me. But it was many weeks and months where I was in this sort of repetitive motion and I wasn't figuring it out. And there, there is no secret on LinkedIn or anywhere that can help you also separate out like the belief that you're not going to be able to be good at something and then being good at it. And now when I see that in conversations, be like, oh, you're a great communicator. And like, you're so strategic. I'm like, yeah, Courtney of five, six years ago was not. And it, it was a problem that I had to really go internally on so that I could fix it externally.

I love that. Go internal to fix it external. I also love the understanding of difference between external education and internal education around getting the things launched. There's so many good pieces there. So. So, Courtney, I'm, I'm super curious. Let's kind of keep chugging along here. What does empowerment mean to you and how do you actually pass that on to others in your field?

I love the word empowerment. For any women listening where empowerment has been used as like a dirty word for you, please just get that out of your head. Empowerment as a female, however you identify is a really powerful word. It's a powerful feeling. You have to be self empowered. No one can empower you for you. You can't sit there and just be like, yep, let me take all the lessons. Like, it has to come from within and people can create space for you to be empowered. And I think that's a really important distinction for leaders and for mentors is I think a lot of the times, particularly allies will be like, well, I want to empower women. I want to empower someone. And like, well, that actually takes away from what that word really means. You want to create this space for them to be self empowered. And an early mentor told me that and I, it sort of like knocked me on my butt a little bit. I was like, wait, I thought that's what I was here for. And they're like, no, I'm just here to create this space so you can self empower. And I'm looking at my screen because I have a bunch of little sticky notes that I look at every day and one of them says, you are enough. You can do it. And that is something I go Back to a lot. When it comes to that word of empowerment of you just have to give yourself permission. You have to give yourself permission to, to say the wrong thing, to try again, to stand up, to not do it right the first time and do it right the second or third or fourth, however long it takes you. And to me, that's a lot of what empowerment means, is you're going to be enough, you're going to do it. But if you don't believe that sentence when you say it out loud, it's going to be really hard to kind of move through those spaces.

I love that so much. So, so much. And I love the fact that I'm not the only human with sticky notes around their computer, by the way, as well. So there you go. So with that said, can you share a moment in your career where you felt especially empowered or proud of something that you achieved?

There's a lot of things that come to mind and so many of them are team efforts. So many of them included other people. I would say the one that really comes to mind is I was working with, of course, the Academy team and some other internal teams at HubSpot. And it was right before I got promoted to be director I'd been working really hard for. It was obviously a personal goal, but it was also a recognition that, like, Academy deserved to have a director. There was in that internal story of we are important enough, we do drive enough retention and usage for our customers that like, we need to have someone at the helm here that's going to represent us at the director level. And I was working at the time with Matt Barbie. He was leading a lot of acquisition and network driven elements and sort of this like, hump we needed to get over of. Like, well, why is Academy so important to the business? And I knew it and I, like, could communicate it and I had data points, but it was about putting together this story about why Academy was so important to HubSpot and what we were able to do for our customers. And it came together really beautifully in a strategy for, I guess, what was it like 2022, I guess was the year of how HubSpot Academy was going to like close this retention gap. Essentially. We, we wanted to be able to be the thing that moved this number and there was a bunch of other pieces that were going to come together and we'd have to work with all these teams and it happened like 2022. Is this like accelerant for Academy internally for myself. I got promoted. I was so excited. We then partnered a lot with the community and we started working with these other teams and. And I look back on that year and I'm like, it felt like the finish line. It was just the beginning of where Academy this, like, next generation. And, you know, the team just did an incredible job with what I will say was very ambitious goals. I was like, we're going to do all this and, like, maybe not have all the resources to get it done. They're like, are you sure? I'm like, I'm sure. And I believe in our grit and I believe that we can do this. To me, that was like, that moment that I sort of, like, wanted to hug them all and be like, like, we've got this. And it felt to me just like the Cloud 9 experience of being able to achieve something that I was really looking forward to.

I love this idea of belief. We believed in our grit. I also love the. The idea around this, Courtney, that it's like you said, I thought I reached the finish line, but it was our starting line. And so many times in life, those two things are such the same moment. And being able to understand that, embrace it and be prepared to run again for what is the next version of HubSpot Academy. Whatever you're doing in life or business is so, so paramount. And so it's interesting because it leans me into, like, there's people who are going to be watching this that are in the HubSpot ecosystem. There's people who are going to be watching this that have. Are not in the HubSpot ecosystem yet, just because of the nature of the type of content that we're creating, the conversations that we're having. And so I'm super curious, Courtney, if you could change one thing about how women are supported in this industry, what would it be?

I think there's a little bit still of that double standard around emotion. And I've experienced a lot in my life. I'm a very emotional person. I cry very easily, my cheeks will get flushed. And I can also be very passionate. And it can sometimes come off as overly passionate, overly ambitious. Like, all these words you throw overly in front of any normal word. And like, you describe how women are talked about, and I think there is still a push, a desire to. To bring women to the middle of that emotional barometer of saying, well, this is kind of how we want, you know, we want people to act. And we start to use those words like people and like, oh, like, this is how a professional would present themselves. And I think we do forget something about human nature. Men and women are different. However you identify, we're different. And that comes down to the individual level. But it can be very gendered. And I would like that support to show up in those middle spaces of when you're coaching with a woman or you're, you're a mentor, whether you're a woman yourself or, you know, you're, you're supporting in that way, you're being an ally. I think taking out that language of like, you need to change your emotional reaction to things. Happy, sad, angry, defensive, in between. Because we very rarely still audit men for the same thing. And I see it on LinkedIn, I see it in videos. There's still that desire to make us all kind of closer to how a typical professional will show up. And with that we actually lose some amazing things. Like with my team, with my incredible management team, I'm like, I do want to cry with all of you. I do want to be upset with all of you because that's a human emotion and I want to experience that with you because I care about your journeys and, and I care about who you are as people. And I don't think we're doing a good enough job caring about women as people, instead being like, oh, well, like, we'll just coach them on how to be this like, typical professional, often very male dominated characteristics. And while I'm not personally a mom, I do think that moms in the workforce get that even more of like, being happy about your child and like sharing pictures. Like, we have to normalize those things and we have to normalize them for dads. We have to be able to be like, share a picture of your kid and like, be emotional. Like, if we're bringing anything into the middle, I think we need to be able to create that normal space on both sides and support women for all of their emotions.

Yeah, there's so much going around in my brain right now. First of all, the thing you don't want is typical because that's mediocrity and that's just a strategy for like failure. Like real quick, real fast. And if I'm being completely honest, like, as a man, we were basically trained to bury our emotions. And there are, are many days that I just wish I could get them back, like, that they would be, you know, easily activated. And, and the other piece of this is like, we can be emotional if we're more willing to get out of our comfort zone. And so many of us are not willing to get out of our comfort zone and reach those magical moments of life. And so I love that piece that you just shared, I wish that we could be a little bit more emotional along the way, all of us, because that's what humans should be and can be. So this is obviously the women of HubSpot. So I've got to ask this question, Courtney. Are there any particular tools, strategies, trends in HubSpot that excite you right now as we're recording this conversation?

Do I just say AI a bunch of times? Like, does that help the algorithm? Like I'll just Repeat that word, AI, AI, etc. No, there's, there's a lot of exciting trends that I think are happening right now. The first is I, I think the world is finally waking up and realizing the power of the video content, the opinionated content. I'm so excited to see that be now part of so many more marketing strategies. It's something Academy has believed in from day one. I know it's something you've believed in from day one and you know, we're now seeing that the tools, the support, yes, the artificial intelligence that's happening around that. But my goodness, like looking 10 years in the future, I think this is the moment where that finally like clicked for everyone of, hey, you can use HubSpot to, yes, do all the traditional marketing, email, et cetera, but you should be using it also for that opinionated video content. So that's something that gets me really excited, I would say also in like the HubSpot world, everything that's going on with Breeze and our go to market strategies, like Holland at this moment, Nicholas Holland, who is our GM for AI at HubSpot, just released this great blog post that's talking about all the different ways that you can use it and I think in a really human and helpful way, bringing back to that center of what HubSpot's always believed is that human and helpful resource. And it doesn't have to be like a replacement, it doesn't have to be getting rid of jobs. It's how are we going to use these best practices to, to power our businesses moving forward. And it gets me excited because as someone who's tried to stay on the top of technologies, AI is scary for a lot of reasons and from even an environmental perspective. I started my career in the nonprofit space worrying about land conservation. AI is a sustainable conversation. We need to figure out the environmental impact. But it excites me that we're starting to see, I think the actual best practices start to flow out. It's not just like use AI and like try it out and like almost like the white knuckling of anxiety of like, you're at a dinner party and someone's like, you're not using AI, like, what are you doing? It's like, I don't, I don't know how to use it. Like, there. I think we're now at this place where we could actually start to talk about, like, well, here's how we'd use it. Here's how it would be good for your business. And I love that moment. And last, but, but certainly not least, I mean, I will give so much excitement and credit to the HubSpot Academy team right now. They're innovating on a dime from short form content to scalable onboarding to figuring how we're doing live content in all these languages. Like, I mean, I will always say that we're on the cutting edge of customer education, but they are doing some incredible things right now that are getting me really excited.

I love it so much. So let's shift gears and let's talk about networking and how important, Courtney, is it when it comes to networking with other females to you or just networking in general? And what strategies do you use to kind of build connections along the way?

Yeah, so I use the concept of I always have a board of directors. So I have my sort of board of mentors and people that I follow that all serve different, like, areas of focus for me. And my board is always growing, but it's also always changing because I think that's something that we forget as a woman in general, but like, just in people in general that, like, what you need from your mentors changes pretty rapidly. Like, what a mentor gave to you six months ago might not be where you need them today. So it sort of have these different categories of, like, I want someone on my board of directors that's always supporting my, like, public speaking, that my brand. Are they helping me with that? Someone who's helping me think strategically, Someone who's also supporting me personally. Like, don't forget about that. I am a big believer in work life integration, not work life balance. Like, you're a person, I'm a person. I need a coach that thinks about my nutrition, that thinks about my health and wellness as well as my professional life. You want to make sure you have all those things. As for, like, best practices or things I do, a lot of it to me is being unapologetically open about needing to learn. And it's amazing how you attract people. When you reach out to someone, you're like, hey, I'm looking for a mentor. They're like, okay, why? But when you're on LinkedIn and you're in your intros to your speeches and you're like, here's some things I'm learning about. Here are things that I'm excited about or interested, the amount of people that will come to you and be like, I can help or I want to talk to you about that. So that's a big approach that I've taken, is just being really open. And the last piece too, I would say from a networking perspective is just not being afraid that it doesn't have to be very formal. Like, I think initially in my career I was like, oh, it has to be like a relationship and we have to have like a quarterly meeting and we have to take notes. Like, absolutely not. I went to a coffee shop in December with my really good friend Jenny, who also works at a tech company, also runs customer success, and we just had like a 45 minute brainstorm about how scaled CS works. Like, she is a mentor. She's one of my very close friends and a mentor. Like, it doesn't have to be this formal, like, shake hand relationship and we forget that a lot and we don't lean into some of those relationships. Brian Childs is another incredible mentor to me and my friend. It doesn't have to be one or the other. And don't hold yourself like away from those people. Like, you can learn from friends, you can learn from your family as well as like more formal, like coaches and mentors.

I love this so much because it's like this growth mindset, this holistic mindset. But then when you said like friends, like networking and being human and friends and like, it just kind of cannot be what we have historically always tried to put it in the box that it has been. So that's amazing. Listen, Courtney, you've done a ton of things. I got a couple more questions and we're out of here. But you've done a ton of things. I want you to boil down one thing, like, what has been the most rewarding aspect of your career so far?

Having an impact on other people's lives. Like, I know that's cheesy and it might be like, I don't know. I think about that a lot of. There are some amazing things I've done, don't get me wrong. Presenting at Inbound, being able to create new strategies for HubSpot that have changed the way we go to market. Awesome. I love that stuff. That's checklist stuff. That stuff, you know, that ends up on a LinkedIn, et cetera. Looking at someone and knowing that you had an impact and hopefully a positive one. Right. We do have impact. That's not always positive, but like a positive impact on someone else's life. There has been no greater gift, I think, in my career than when people have left the Academy team and been like, I couldn't have done this without you. And I'm like, well, you definitely could have. Like, you are. You've got this. But that gift of knowing you're able to do something that inspires them, gives them joy, grows their career, and also supports them. Something that I love about being a formal people leader is bringing that philosophy of, you have to care about the full person. You have to care about what's going on outside of work, to care about what's going on inside of work. If you don't have that context, it's going to be really hard to be a people leader. It's going to be hard to look at them and give them feedback. If you don't know what's going on, you don't know the way they communicate. You don't know what their dog's name is. Like, all of those things matter, particularly in a hybrid, remote world. It was a lot easier when we were in person. But in a hybrid, remote world, having that impact, there is someone sitting at a computer who you might be the only person they talk to that day. If they're single, if they're alone in their house, be that person that reaches out and provides that support. Because, gosh, it gives you a lot. It touches my heart. And that's. It's been a beautiful gift.

Yeah, I love that. People leader. And again, you're kind of bumping in that holistic understanding of life and the fact that we are in a completely different world from workspace right now. So what advice would you give other women who might want to choose this career path, by the way? Like, what. What would you say to them?

The first thing I would say is, like, do it. I've been at HubSpot 10 years now. You couldn't have told me 10 years ago this is where I'd be? And it all came down to taking that, like, leap of faith. And the first thing I would say is, like, do it. I've been at HubSpot 10 years now. You couldn't have told me 10 years ago this is where I'd be. And it all came down to taking that, like, leap of faith and trying something out, being scared, doing it anyways. It's such a myth. That like you ever get over being scared? You don't? I still get scared when I talk to my team. I love them so much. I care about them, I work with them every day and I still get nervous sometimes when I talk to them. You just do it anyways. So that's the first thing that I would say. The second is I think there's a misconception in the HubSpot ecosystem and in a lot of ecosystems that there's just like one way to be a thought leader or just one way to be a subject matter expert. There's a lot of different ways to be an expert in the tech space, in the software space, in the customer ed space. And your experience that you have today, I guarantee you it applies. Like if you want to get into the marketing space, if you want to get in the sales space, but you've only worked in some other sector, the skills you've learned and what you've experienced will apply. You just need someone to help you kind of like translate it and like get it out of you. So talk to someone in the space, like ask them good questions, listen and start to create your story. There are so many people who can help you craft that story. But don't be afraid that making any sort of transition leap or being like, I don't have any experience at all. I came from an environmental nonprofit. I joined HubSpot having very limited tech experience. But what I learned and how I'd worked with people, it all applied. And that's just something to keep yourself honest about of. Don't limit yourself just based off of maybe what your resume says.

Yeah, don't be afraid. Start creating your story. Come on. Just like that just needs to be it. Every day wake up and say that to yourself. Don't be afraid. Today's the day to create my story. Speaking of creating stories, Courtney Sembler, what are your long term goals?

My long term goals? Well, it probably doesn't surprise you, but at the beginning of every year I host a board meeting for myself where we talk about Courtney's goals and all the things that she wants to do. I have a lot of long term goals. I have some short term, medium, long term. I do really want to be a leader of a company someday. Being on the C suite, being a CEO, I have that ambition. If I on the way to that can be a chief learning officer, then I would really feel as if I've accomplished the things that I want in life, in my professional life. I also have, you know, to the point of work life Integration. I want to be a mom. I have amazing nieces that they give me a heart attack, but they also bring so much joy to my life and I want to be able to experience that firsthand. And you know those two things, I share them because they will contrast at some point. And working with my partner to figure out how those dreams all come to life, you have to talk about them in the same sentence. You can't just be like, I want to be a CEO and expect the other stuff to figure it out. And, and I'd say like my biggest long term goal is really continuing to put customer education at the center of scaling businesses strategies. We still haven't quite round the circle. It can sometimes be an afterthought or a point solution, but getting it embedded into every business's core strategy of how they go to market, how they talk to their customers. I'm excited for the day. That, that just feels like a part of the conversation. Just like sales and marketing and customer success are.

Yeah, it's so important and so needed. All right, Courtney, I've got two more questions for you and then we'll get you back to your regularly scheduled days. So what's a surprising or little known fact about you that people might not expect?

One fact about me that I think some people might know is in 2017, I read 200 books in one year. And I did it to change the way I spent micro time. So I was getting really frustrated that like when I waited for the bus or I waited for a friend at a bar, I just scrolled on my phone or like just stared like at the ceiling, like didn't. I wasn't using that time to do anything or to better myself. And so I set out in 2017, I was like, you know what, Warren Buffett says that you should read like, you know, some, something like a hundred plus pages every day to, you know, it's compound to interest is his point. Like if you read every day, you'll grow more than if you only read on the weekends or, or whatnot. And so in 2017, I was like, I'm going to read 200 books. Would I ever do it again? Absolutely not. It was very hard. I loved it though. And it, it did, it changed the way I spent micro time and it helped me, I think, grow as a professional and in my personal life. So that's it. That's maybe a surprising fact. Not everybody would know about me. I know some people know, but yeah.

Yeah, 200 bucks, that's crazy. But it's also very cool. Very cool. So, last question. Other than after this, I'm going to ask if people want to connect with you, where do you want to send them? But last question is. Finish this sentence. For me, success to me means blank.

Success to me means that when I wake up in the morning, I feel joy.