Steve Shallenberger: Welcome to all of our Becoming Your Best podcast listeners, wherever you may be in the world! This is your host, Steve Shallenberger, and we have a great guest, very interesting, on the show today. He has a terrific background – businessman, musician, public speaker, he has built dozens of web and mobile products, his product portfolio ranges from language learning products for the US Military to the most popular free CRM product in the world. Welcome, Christopher O’Donnell!

Christopher O’Donnell: Thanks for having me, Steve, I’m very excited to be here!

Steve Shallenberger: We’re going to have some fun today! Before we get started, I’d like to tell you a little bit more about Christopher. He serves as a Senior Vice President of Product at HubSpot, which he led from startup to a successful publicly-traded company, he is a passionate individual about leading and supporting teams, really, to build anything, from developing tech products, creating rock & roll records, which we are going to hear more about in just a moment. Christopher is a frequent guest lecturer at MIT Sloan School of Management, and major global corporations, speaking on topics like leadership and team building to audiences of over 10,000. Outside of his day job, Christopher spends his time as a songwriter, and a guitarist for his band, The Providers, with whom he has recorded dozens of albums across a variety of genres. So, this is going to be fun today. So, Christopher, tell us about your background, where were you raised and what were the things that led you to get to where you are today? We’d love to hear about your background!

Christopher O’Donnell: Sure thing, Steve, yeah. So, I had sort of an interesting, meandering kind of career path and background. I’ve lived in New England my whole life though I was born in San Francisco, we moved within a month out to the East Coast, so I’ve lived out here my whole life within a couple of hours of Boston in one direction or another through college and everything. And the two things I was drawn to more than anything else from a very early age were technology and music and even before I was old enough to get involved in technology, I was the kid in the basement with the glue gun trying to glue balls of wood together and build airplanes and sort of build stuff, go-karts and everything else. So that’s my DNA as a builder and a maker and that sort of led me at this point, 38 years old, building and leading teams, that’s sort of the product that I work on, although we also obviously have products that we build ourselves.

Christopher O’Donnell: And so, along the way there, I went to school for actually, literally, computers and music. I got my undergrad degree in Rhode Island from Brown University in music, but specifically, the major was computers and music, which felt like, maybe a little bit of liberal arts vacation at the time. It was really fun and really challenging and I got to learn important language and I played a lot of music and did a lot of coding and all this kind of stuff. I didn’t quite know how that was going to translate into a career and here, a couple of decades later, it actually has, and those are the things I spend my time doing. I’ve been living in the Boston Cambridge area, working on technology products for the last 10-15 years and I’m really loving it. Outside of that, I’m in a band called, The Providers, we record a lot of music, always writing music and recording music, publishing that, people can learn about that at theproviders.com, and beyond that, I’m a husband and a father and a family guy – I think that kind of comes first through all this.

Steve Shallenberger: It sure does! Well, that’s great! Good priority. So, you mean you actually go out and do gigs with your band? Tell us about that.

Christopher O’Donnell: Yeah. Well, it’s funny because we’re really in an old school Steely Dan studio band. That’s how we spend our time, it’s the songwriting and production and the creative process of building the recordings. And we don’t actually play a lot, which is interesting, I think at some point we will cross that bridge. It’s this funny atmosphere where, it’s almost like 1974, being in a big recording studio, with grumpy opinionated session musicians coming in to play their parts and trying to get the whole thing to sit just right and get that magic moment that you’re looking for that you can keep forever as a recording. In a lot of ways, it’s very similar to what I do at work.

Steve Shallenberger: That’s great! And you enjoy it, and it works?

Christopher O’Donnell: I love it! I mean, I love making things and I love storytelling. In product management, my day job, there’s a ton of storytelling involved in modern leadership of creative individuals. It’s really about story, it’s really about context and I think the best vehicle possible, at least for me, in my own human experience, to hear a story and experience a story and all of the associated emotions, is really through song. And that’s kind of, on a personal level, the goal I will keep reaching for, the great American rock song.

Steve Shallenberger: I love it! Oh, that’s good. Tell us about HubSpot. How did you become involved with HubSpot? Tell us about the adventure of HubSpot and what’s happening today with it?

Christopher O’Donnell: Yeah, HubSpot is just a fascinating enterprise and community and ecosystem. The company was started, perhaps 14 years ago, by a couple of fellows, Brian Halligan and Dharmesh Shah, who are still leading the company today, who met at MIT Sloan and had this insight that was just really remarkable and really brilliant, which was that the way that people shop and buy has fundamentally changed, forever. And for small business, on a limited budget with limited resources, it was going to be really hard for people to pivot and stay in business. In the ’80s and the ’90s and the early aughts, you could still put Yellow Pages ads out, you could go to trade shows, you could knock on doors, you could do these kinds of things and generate business. In the modern world of today and even up 10 years ago, where do we go to research products? Well, we go to the search engines, we go to our friends for referrals, is a totally different power dynamic that puts the buyer in control.

Christopher O’Donnell: Alright, so where’s the business opportunity in that? Build software tools, build a unified all-in-one platform, so that a business of really any size can adopt these best practices, can have a website, can have an email marketing list, can have a CRM, can have customer engagement tools, all in one place; and that’s what they asked me to come help build, when I joined the company, about eight, nine years ago. My time here has been entirely on the product side, though I find it fascinating to watch the other functions grow, I find it fascinating to learn about sales, and service, and finance, and marketing, and all these wonderful folks that I get to work with. My time has been in the product side, working with engineering, working with design and trying to be very customer driven and understand what the market is looking for from us and translate that into a product that really delivers and delights on that promise.

Christopher O’Donnell: And where we are today, we’re a publicly-traded company, market cap over $7 billion, at this time, so we’re a small-cap company, we’ve been in the public market for a few years and that’s been really fascinating for me to see, from the inside, I joined around employee 200-230, something like that, and now we’re over 3000 employees, we have eight offices around the world, from Cambridge to Dublin, to Tokyo, you name it! So it’s just fascinating to see all of these departments, the green shoots of all these ideas, turn into a really growing, thriving company and customer ecosystem, that largely gathers around our annual event, that we call Inbound, which is in Boston in September, people can check inbound.com. We have great speakers, we have Michelle Obama come to speak, Serena Williams, we’ve had some really amazing people come and help lead our community. It’s just a fascinating movement, even more than a product or an enterprise.

Steve Shallenberger: I bet that’s been amazing and gratifying to see where it’s at today because it’s not easy to do that, is it?

Christopher O’Donnell: I’ve really largely grown up here, but I can’t imagine this is typical and is certainly very humbling, very, very humbling.

Steve Shallenberger: That’s great! Good going! And so, we’re talking about music and talking about business and growing business enterprise. What are the similarities, Christopher, between creating a rock&roll album, and developing a successful tech product?

Christopher O’Donnell: It’s a great question! And a lot of people find this to be an interesting topic, I’ve learned over the years. It’s a question I get in a lot of Q&A’s. You know, you wake up in the morning and your goal is to build something that you can’t quite describe, that is going to require a lot of creative contributors, who probably are way better than you, in their particular discipline than you are, and it’s your job to get everybody in the room and build a vision and execute on that vision and to get the absolute best out of each of these people, across all of these disciplines, and to build something that without you there, as the producer, people wouldn’t do anything. And so, that’s the same challenge, whether you’re going into the studio to record a song, make a record or walking into a high-tech company to build something from scratch, that people are going to love and share with friends and pay for, and be very happy with, it starts at the same place – what’s the need, what’s the vision, and how do you let people project their own talents into that vision?

Christopher O’Donnell: In the case of a song, the drummer understands, “Oh, okay, I see the tempo, I see the feel, I see the sounds, I see points of reference from records that we’re discussing here, I have an idea of where we’re headed with this. How about this? How about I try this? How about I try this?” And then, on the tech side, an engineer coming in and saying, “Oh, okay, so they’re going to need something, oh this is going to be a mobile app. Okay, that makes a lot of sense. Let’s talk about it, how is it going to feel? Here are the right technologies for that; here’s the right way for us to think about building and deploying that.” You know, all of these things, where you walk in, and you’re not walking in with all the answers, you’re not walking in, as the producer, and say, “Okay, here are your drumsticks, here is every note you need no play, now go play.” And you’re not walking over to the engineer with 500 page Word document, saying, “Go code. Essentially, I’ve written the code for you in a Word document, now go pound it out on the keyboard.” It doesn’t work that way.

Steve Shallenberger: Yeah, right!

Christopher O’Donnell: Engineers and designers and also engineers on the music side, by the way, there’s a deep level of science and physics and engineering that happens in both of these things, whether it’s acoustic or whether it’s 1s and 0s and the nature of the Internet and fiber connections and all the rest of that, it’s very, very similar. What you want to do, is you want to build an amazing creative team, that pushes back on the vision, understands the vision, then gets very excited about it and brings ideas to the table that you could’ve never suggested to them. And then, have the culture and the sort of the safety between those creative people across disciplines to try things and share ideas and go a little bit down this road, go a little bit down that road, show things to customers, get feedback and iterate. When I think about modern leadership and how people want to work, and particularly, how people just do their best, most fulfilling work, that’s really the goal. And I think that if you adopt that mindset, I think you can make anything, whether you’re trying to make a rocket or you’re trying to make a dining room table, you’re trying to make a jazz record, I think that these are all… All of these challenges – interdisciplinary, creative, innovation challenges – benefit from this type of leadership mindset.

Steve Shallenberger: Oh, great answer! I loved it! And, you know, this is an exciting time, and one of the things that Christopher just mentioned was, you’re not walking into the room with all the answers. If there’s anything that describes today’s world, that’s it!

Christopher O’Donnell: Oh, my goodness! Man, I mean, in the minute you think you have it figured out, even if you did have it figured out, as a leader, even if you did have all the answers, give it 24 hours and the answers are going to change, just with the rate of innovation and the way the world is changing. People talk about impostor syndrome and feeling like you’re not qualified to be doing your job these days, and I just don’t think anybody is qualified. Hopefully, neurosurgeons are qualified to do their job, but when it comes to information work, I mean, we’re all really just trying to understand how to ride the wave and how to bring our best and become our best, as that best in that target, in those goal posters, are constantly moving, absolutely!

Steve Shallenberger: Yeah, totally! We love that kind of language, Christopher! Words like, your best, becoming your best, bringing the best out in people, I mean, that’s what brings excitement to life right there, into organizations, and we are in a great time. I mean, last week we all celebrated 50 years of man walking on the moon for the first time and just think about what Christopher just talked about, what creates this excellence, what creates a great outcome. Well, it all starts with a vision. Think about the vision that Kennedy articulated, about that, “We will send a man to the moon and bring him back safely within the decade.” It just changed everything, that’s leadership. We were at Machu Picchu about a year and a half ago. Same principles. I mean, it’s vision, you’ve got to organize it, they didn’t have all the answers, got to figure out how to do it, set up a plan, and I like the science of engineering, you’ve got to apply some tools here, and bring it all together to get that great outcome. So, just thinking about this whole thing that we’re talking about, from your experience, Christopher, what are the key elements to building sustainable high-performance creative teams?

Christopher O’Donnell: Well, I think you just, really, touched on some of the best ones and that’s a great intro to a great question. Setting a vision and a challenge and giving people the autonomy and the space within that challenge to do their best work, is absolutely the foundation. John F. Kennedy didn’t know how to make a spacesuit, and people, as I understand it, across the nation, people said, “This is preposterous, how are we going to do this?” And it’s exciting, too. And then, people started to say, “Well, you know, as a materials engineer, I guess we need a way to have fabrics that stick to each other, we need to do this, or we need a different kind of wiring, or we need our computers to have this much memory or whatever else it may be.” And who ended up making the spacesuits, as I understand it, I may have this wrong, but as I understand it, the spacesuit material was made by Playtex because they just had the best fabric science, or whatever you call it, materials engineers for that kind of problem.

Christopher O’Donnell: And so, I think that’s really the starting point and that starts in recruiting. That starts in how you talk to the mission of your team with your parents, with your family, with your kids. What is the mission, the sense of urgency, the opportunity, and is it just pouring out of you? And from an interview and saying, “Look, this is what we’re trying to go and do”, and getting people excited and getting people like JFK did, getting people to say, “Boy, I see where I fit.” There’s this idea of diversity and inclusivity and now being expanded to diversity, inclusivity, and belonging. And I think the idea of belonging is so critical to doing high-performance creative work because you have to feel like you belong there, you have to feel as though your ideas are valuable. You have to feel as though you have the support of the people around you, that people are going to listen, that you’re able to listen, and that you’re not always looking over your shoulder. And so that’s kind of the next piece.

Christopher O’Donnell: The first piece is really about vision and energy, and then autonomy within that, and saying, “Look, you’re going to come here, you’re going to be a part of this team, and people are going to listen to you.” If you are a session musician and you come in, you say, “Boy, I just really think that we could rearrange the tune this way.” Well, okay, this is an environment where you can say that and making that very clear to people. And what happens is better and better people want to become part of that team, the more you live up to that promise. It’s this idea of, what’s the opposite of a micromanager? A macro manager! It’s like, how do you become a macro manager, where it’s very clear to people on the team, here’s your box; within your box, you can try stuff, within your box you can fail, within your box, you can really move and try things and not fear any kind of consequences, really. And that box may be very small and it probably ought to be very small at first, and then grow over time.

Christopher O’Donnell: And so then, the third piece there is attracting great people, bringing the best out of those people and then showing the world that. I mean, we pull people in, all the time, “Come walk around, come have a coffee, come sit with a team, see how we work, and think about whether it’s for you.” And what people end up finding is they do want to come and be a part of it, and the main reason is, it’s not me, it’s not even the mission necessarily, it’s the pears. And so, you can snowball in this direction. You know, they say, A players hire A players, B players hire C players. Well, okay, maybe that’s true, I don’t know, but what I do know is that when I can hire somebody who is significantly better than me, they hire people who are better than them. And now you’re cooking! And developing people through their career and bringing out the best, that’s how you start to scale, that’s how you start to really do this, beyond two or three people working together at a little startup, around a little team and start to get to a point where we have hundreds and hundreds of people working on this product. And they still feel totally invested in solving customer problems.

Christopher O’Donnell: And we have a culture where customer problems and solving hard problems is the most prized and rewarded thing you can do, and we give you all the tools to do it. So that’s a big investment and within a larger enterprise it can be a really scary one, where, as a leader and a manager, boy, prepare yourself to walk in the meetings and say, “We don’t have the answer yet.” Prepare to say, “We didn’t make a deadline.” Prepare to take the blame and then go back to your team and get them super excited. But that team is going to win. Small, lean, autonomous teams that have a very strategic mindset can connect the dots all the way between the macro opportunity of the business and the challenges that face today, down to the work that they are doing every minute and every hour. Let them connect those dots, help them connect those dots, and don’t just give them work orders because you’ll never connect the dots as well and as completely as they will in their own imagination, if you give them the chance.

Steve Shallenberger: Yeah, great advice! I mean, these are the principles that we’ve also seen, we were just talking about Becoming your Best, the 12 Principles of Highly Successful Leaders before we started our show today and this has been a long 40 years of research on what outstanding, high-performers do over and over again and this is what Christopher is talking about today, these are the things, this is not rocket science but it’s not easy to do. I mean, leadership is creating this vision that’s exciting! I’m so glad you brought this up and once you have that, then it is getting the people around you that can buy into that and create this environment where they can thrive. I love what you’re describing! And to take responsibility for the outcome, and you make the adjustments, and you build high trust so that you can solve problems and make it fun! Way to go! That’s good stuff! I was just thinking, I read a quote yesterday, Christopher, because one of the grand things of leadership is this ability to say, “Hold it!” Set the direction, the vision, and sometimes we’re actually can be limited by that or trust forward with it. Here’s the quote: “Without leaps of imagination, or dreaming, we lose the excitement of possibilities. Dreaming, after all, is a form of planning.” – Gloria Steinman. And I love it! That’s just part of what we do every day and you don’t get too big for it, it’s about changing the world and solving problems and finding joy in your work, so that was so fun! Way to go, Christopher, well done!

Christopher O’Donnell: I’ll tell you. This may seem off-topic, but I really don’t think it is. I was putting my son to bed the other night, he’s six, and he asked me a question. He and his sister, they’re four and six, and they’re wildly into imaginative play – from the minute they get up, they want to be ninjas or princesses or lizards or whatever it is, it’s totally real to them and it’s this amazing thing! And as a grown-up, you get wrapped up in it and have a ton of fun with them. But sometimes, grown-ups don’t want to do that. We’re trying to have a grown-up conversation, we’re having a dinner party or whatever it is. So, my son asked me, he says, “Why don’t grown-ups like playing as much as we do?” It was a brilliant question, right? And I said to him, I should’ve just said to myself but I just told them honestly, I said, “Well, you know, as you grow up, you lose your imagination.” And I saw the look on his face. This was the scariest thing that I could possibly tell him. I mean, when he found out that animals and humans pass away, he sort of said, “Boy, that’s sad, but that kind of makes sense.” This didn’t make sense!

Steve Shallenberger: Wow! I love it, yeah!

Christopher O’Donnell: The idea that, as he at his next birthday, this world that he creates for himself is going to be less vivid, and that by the time he’s my age, that world won’t exist at all, this was the greatest possible loss that I could explain to him. And I had to walk it back a little bit. And walking it back with him, I really sort of traversed what was important to me in leadership and working with creative people, which is, “Okay, what are all of the things that we have to do as grown-ups, to not lose our imagination?” Why don’t we speak up? Why don’t we suggest these things? Why don’t we play these games, why don’t we do this stuff? Because we’re scared and what are we scared of? Well, we’re scared of how we’re going to look. Okay, great, so if you pull all those threads and then you go back to your team and you go back to walking in the building Monday morning and you start looking for them. And you start looking for the reward system, you start looking for things you can do, that will get you in trouble for using your imagination.

Christopher O’Donnell: Google calls it psychological safety. They did this huge Project Aristotle on the factors that lead to creative, innovative teams. And psychological safety is sort of a hierarchy, that’s the foundation. What I love about HubSpot is, we’d be halfway through some huge Executive Presentation and somebody would raise their hand and say, “I didn’t understand that last part.” From the CEO to me, to somebody on my team, if we don’t understand an acronym or we’re lost in the conversation, we’ll ask a friend or we’ll stop the conversation and say, “Boy, this seems really important! Could somebody explain this to me?” And it creates this teaching hospital kind of environment where it’s like, “Oh, yeah, great!” Hop up at the whiteboard and explain this. I had one-on-ones with my boss, who used to be a public company CFO, and I’ll say to him one-on-one, “Hey, I don’t actually understand the difference between bookings and billings in this context” and he’ll go, “Oh, okay, let me explain it to you!” And he’ll grab a whiteboard and he’ll explain it to me.

Christopher O’Donnell: And when you show people that, and as a leader you have to do that, you can’t expect your team to do that, you have to actually be the one raising your hand stopping the meeting, saying, “I didn’t get that!” And so, it really starts at the top, but it creates an environment where people can kind of say, “Here’s where I feel comfortable, here’s where I am not comfortable” and from there, the daydreaming starts to happen, because it becomes cool to daydream, it becomes cool to ask questions and be curious, and that link between curiosity and dreaming, from there, once that’s happening, getting it down into project plans and decisions that need to be made, it’s not actually the hard part. The hard part is getting people to speak up and say, “Boy, maybe we’re thinking about this totally the wrong way. Hear me out on this” And then, boom! And then have the room to kind of sit and listen and react. That I think is really what we’re after here, and I find it amazing that my son picked up on it so quickly and really, in many ways showed it to me.

Steve Shallenberger: That’s a great story, and a breath of fresh air, so fun! What’s his name?

Christopher O’Donnell: His name is Caleb.

Steve Shallenberger: Oh, that’s great! What a fun story! And, how important it is that this is one of the things we create within our organizations, that kind of feeling. I mean, man, we’ve got to totally push back on that, we’ve got to give air to our creativity, to our imagination and it’s so magical of what it can do for all of us. Good! Well, I’m just always shocked by how fast time goes, and we’re at the end of our show today. This has been fun, Christopher! Now, any final tips that you might be able to leave with our listeners that you think would be helpful in their success?

Christopher O’Donnell: Well, I’ll put a plug in to come work with us.

Steve Shallenberger: There we go! I love it!

Christopher O’Donnell: We have hundreds of open roles, hubspot.com/jobs, put the impostor’s syndrome aside that we all have, and go raise your hand on there. We’re leaning more into remote work, we have eight offices around the world, there are tons of opportunities across all of our departments – sales, product, you name it! Come talk to us and have a conversation about joining the team. We’d love to have that conversation! Beyond that, try to get enough sleep, hug your kids tight, what can I say, I’m not the wisest person in terms of advice but I’m learning every day and I’m trying to have fun doing it.

Steve Shallenberger: Alright, that’s pretty good advice! Get sleep and hug each other and be kind to people and have fun, so good going! How can people find out about what you’re doing?

Christopher O’Donnell: In addition to hubspot.com/jobs, check out the band, theproviders.com, we are releasing music consistently. It’s sort of this modern format where we’re going to be releasing music on an ongoing basis and telling the story around our creative process. It’s going to be a ton of fun! People can go to theproviders.com and pop their email address in and be a part of that story with us, we’d love that!

Steve Shallenberger: Great! Well, thank you so much, Christopher for being part of this show today, it’s been a lot of fun, it’s been great take-home value, it’s been inspirational, a lot of creative ideas and encouraging. So, thank you so much! It’s been a thrill to have you!

Christopher O’Donnell: My pleasure! And Steve, thank you very much for opening your doors here. I hope to have another conversation with you in the future!

Steve Shallenberger: You bet! For all of our listeners, you’re a big part of this magical feeling of touching everybody that you do, to have the chance to lift with the type of things we’ve been talking about. You’re amazing, it’s an honor to be able to associate with you and have you with us today, we know your time is valuable. And you lift us, as much as maybe you might get something out of this, that’s helpful to you. So we wish you the best today, and every day. This is Steve Shallenberger, with Becoming Your Best, wishing you a great day!

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