Speaker 1Welcome to Top Line, the podcast for the best founders, operators, and investors in B2B tech. Every week, AJ Bruno, Asad Zaman, and me, Sam Jacobs, will break down what's important for you to know to be the most well-informed professionals in the market.
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Speaker 1Hey, everybody. It's Top Line Spotlight, a Top Line Spotlight in your face. It's that weekly show. You know Top Line Spotlight. You know about it. We spotlight a leading company. We go to market executive in the world, somebody that's immersed in the world of B2B technology, leading teams, building companies, and we ask about a challenge that they've encountered over the last 18 months and what they did about it. We're looking for real-life, practical leadership lessons, and today I'm solo. I don't have any of my co-hosts. They're off gallivanting. They're gallivanters, but I do have a good friend of mine that is our guest, and his name is Richard Smolin, a.k.a. Rick Smolin. Rick is the. CRO of a company called Ship Hero, and Rick and I have known each other for about 15 years now. Rick, welcome to Top Line Spotlight.
Speaker 3Sam, it is great to be here. I listen to Top Line all the time, so I feel like I've been pulled through the audio waves onto the show only to not find AJ and the other hosts there. It's a little disappointing, but we'll make do, just the two of us. I'll try to bring enough energy for all three of you. Oh, my Lord.
Speaker 1You have enough energy. You have enough energy for five people. All right. You're the chief revenue officer of Ship Hero. Tell us what Ship Hero does before we dive in. Really interesting company.
Speaker 3Yeah. Ship Hero is a great company. I like to predominantly think about how companies can be excellent at getting goods to the consumer. It's a really hard thing. Ship Hero started with a focus in the e-commerce world, so anything that's direct to consumer and trying to make that whole process more accessible. I think it's a really hard thing. have to have all the answers. I don't have a robust B2B marketing background. I'm not the partnerships guy. I don't run the support team historically and have pre-determined ideas of what that should look like. So I don't feel the burden of having to have all the answers. I now have to rely solely upon having the right leadership team in place and empowering them to prioritize the things they need to do, supporting them both from a challenging directly, but also sort of supporting and advocating for what needs to get done in the interest of the business. And so my role is less about hands-on doing things and more about ensuring that the harmony of all those departments is in place as we try to collectively achieve whatever the goal is.
Speaker 1Tell me why I'm mistaken in my fear. My fear is that when I hear you that, hey, I don't know. I don't know that much about B2B marketing. I don't have to. I've hired somebody that's great. But I always worry that the people that report to us need to feel like they're learning something from us or that we're teaching something often about their discipline. If there's a marketing person that wants to be CMO, I would imagine they might be concerned that they're reporting to the CRO who has a sales background. How do you deal with that tension? Or am I mistaken in how I characterize it?
Speaker 3No, I think it's a great point. I probably made that mistake when I first sort of joined the organization. There was a marketing leader in place. And I was like, oh, great. This person already has all the answers. All I need to do is let them do their thing. And then I'll do mine and make sure that we're staying in alignment along the way. I think I realized-- I don't know how long in-- that, whoa, what you said is more of the case than what I did. And so the word that comes to mind for me as you share that is just curiosity, just like we look for a sales contributor that has high levels of curiosity, because they need to understand the customer problem. And by better understanding the customer problem, they should be able to put together a solution that helps solves it and win. And that's a key aspect of what winning looks like in sales today. As a leader, I think that curiosity carries over significantly. So today, I'm not just taking for granted that I have the right leader in there to do, let's say, marketing. I'm bringing tons of curiosity about what they're doing, what the priorities are, and what are the downstream implications of that. I want to be able to see enough of the path to success to feel like we are on the right journey. Again, that's not a change of what I said earlier. I don't feel like I need to have all of the answers up front, nor do the ideas need to be my ideas. But I do feel the responsibility of being a thought partner and helping to see beyond the task list and seeing around, well, what does success look like? What are the things we're doing to get there, and then can I see that path? If we do those things well, will we achieve what the actual goal is? And if I am doing my job really well, I'm a great thought partner, a sounding board, someone that can challenge and say, well, I'm not really sure about this, but what about that? And not just be hands off, like that's not my responsibility because that's not my background. So you're right. I have a deep level of responsibility to be good at thinking through all of the issues while still prioritizing that I have the talent that I'll actually be able to execute.
Speaker 1I love the word curiosity, and I generally agree with you. And I think it also takes a certain level of both humility and confidence because, again, I'm sort of a people please drive this fear of this need for approval. And so I would be worried that maybe they think I'm micromanaging them by asking all these questions, and maybe they think I'm an idiot and I don't know what I'm talking about. And so you have to, like you said, you come with humility and curiosity. I don't know if you have a reaction to that, but I would still be afraid that they'd be like, why is this guy bothering me?
Speaker 3Yeah, look, I try to set the stage for what our working relationship is going to look like from the get go. I mean, I've got written down what my personal values are, what I'm all about. You tend to, with your direct reports, interact with them fairly frequently. You can kind of tell pretty quick if they're like chemistry is going to be there. I feel like I'm a New Yorker for over 20 years. Like I'm so direct that it's like you'll stop.
Speaker 1Even before that, you're from Philly. It's never not direct.
Speaker 3I got a bad hand in the course of like a poker face. But yeah, I mean, I think I just try to be consistent in how I am. And, you know, I feel like the folks that are in my organization know that like what I actually care about is our collective success. That's the only that is the North Star of everybody. Everything that I'm trying to do. I have a high bar, I have high standards, I expect us to win. I don't really care about the macro reasons that we could lose. Like yeah, those are just obstacles that we have to overcome. So I'm maniacally focused on the prize, which is achieving our goals. And if we can get past that point as the table stakes of what our interactions are going to be, then we can thrive in the battle of ideas and in those interactions that we talked about. If those table stakes aren't there and people are unclear of what my motives are, then yeah, and I've experienced this in the past, Sam, not everyone loves me because those dimensions weren't in place.
Speaker 1So when we're thinking about assembling this leadership team, what other lessons have you learned over the years? One of them is probably recruiting. And talk to us about your methodology for building the team, and like you said, and trusting them with success. And the last piece, I know it's like there's a lot in there, sometimes that's what people say, because it's like a mixture of three questions plus a few observations. But the point is your tolerance for failure, because I think some part of development is I'm going to let them do their thing. Their thing is not always going to work out. So how do we talk about the learning process?
Speaker 3Yeah, no, it's a good one. Look, we're all human. There's no illusions about my capabilities. I feel like I'm nowhere near the finish line of being the leader that would achieve its potential of what that leadership could be. So I still feel like almost 20 years into a career, I'm in the early innings of that growth and that continued improvement. So I'm totally accepting of failure, especially in a world where we have to be more agile than ever. We have to experiment with things like AI. We need to be thinking differently and doing things differently all the time, and not all of that is going to work. We don't try to, again, use any of those failures as an excuse for achieving the wider goal. We just need to have more agility in the way that we approach things. As it relates to how do we all interact and succeed together in an environment where people might need more help or might not get something right, again, that just goes back to communication. It goes back to prioritization. It goes back to recognizing if something isn't in place that it should be and changing it. I always felt that, Sam, I'll share it like, you know, you and I have both been in unfortunate circumstances in our careers, and what I mean by that is we've been asked to leave organizations. It's fine. It's fine. It happens.
Speaker 1We've learned from it. That's a good idea. They would like you to leave. Can I stay? You cannot stay.
Speaker 3You cannot stay. So we've been in a situation where our employment was ended without our say in the matter, which was a surprise and a learning experience, and so it poses the question of like, okay, what is the criteria? What is the criteria in which you should evaluate leadership? What is the reason that you should determine whether somebody should keep their role or not, especially in a senior leadership position? And I think the answer that I've come out to is there's so many factors that determine the success of a business. Performance of the business is only one of them, and frankly, as a revenue leader, as a sales leader, you aren't the key reason why the company has performed or not. You are a contributor to it. It is not something that should be ignored, of course. Nobody isn't the lens of which you should determine whether or not you're succeeding. The lens that you should determine whether or not you're succeeding is all about what is your plan from this moment right now, based on the landscape that we have and everything that's going on, what is your plan moving forward? Is it thoughtful? Is it based on the realities? Is it put us in the best position to succeed on a go-forward basis, regardless of what's recently occurred? And we all should, as leaders, be. Be accountable to that in the moment. I see so many examples, especially, you know, we do CRO school with Pavilion, and we're talking to emerging leaders, and they're dealing with a dynamic with their CEO and the board, and that communication cycle and expectations and goal setting. And how do they navigate when there's a big top-down number to build the bottoms-up plan to navigate that right? How do they go about doing that well? What is the communication like? What if they're being sort of forced into a number? They're not super comfortable with, but do they just sort of take it on the chin and then do the best they can? And my feedback has always been, and this is maybe the biggest learning is, there are so many environmental circumstances and so many of those political dimensions that are going to exist. The only thing you should be holding yourself accountable to is based on the reality of right now, do you have a good plan for what we're going to do next, for the next quarter, for the next two quarters? What is that plan? Is it tangible? Is it creative? Is it dealing with realities but making the most of them, do not become a wet blanket, don't figure out the reason something isn't going to work? we're going to win despite whatever those obstacles are. And if you have a good plan and it's well supported and you've got good collaboration with your partners, right, cross-functionally, then you should feel great. And if someone else taps you on the shoulder and says, time to go, you can hold your head high because you were operating within the landscape. And maybe sometimes you're the baby with the bathwater that goes out based on environmental factors that are outside your control. So I think for me, I try to put that same dimension into everything that we do as a go-to-market organization. All I want for each of the leaders within there is to have the best plan that they can come up with that we'll work on together and feel really good that we're doing the best work possible. And then, you know, if we can get to that place, like not everything's going to work, right? Something might not be a success, but we can then, that's in the rear view mirror. And now we have the same exact dimension because now we have a new present and a new plan. And so that's the sort of cycle of life that I'm trying to live for myself based on some of maybe those hard experiences and then use as a tool to help the leadership team.
Speaker 1Did you feel like, so last comment, because we're almost at time, but did you feel like you didn't have a plan when you got
Speaker 3No, I mean, I, again, like I would say like I never left an organization and felt like a failure. Like I thought, like, look, sometimes being, when you are in a high empowered role, there is a lot of pressure on you. You have to embrace that and be very comfortable with it and understand that like things are going to happen that are outside your control. There are certainly things that I can learn from, from, you know, either mistakes that I've made or being tapped on the shoulder and say bye. But did I like feel like, um, did I like my vision of myself or my, like, um, change? Like, no, I still felt pretty good. It's just like, you know, one of the biggest thing I learned, Sam is like when you do, even as an executive work in an organization, like it's not all about you. It isn't. And so sometimes things are going to happen and maybe it was 20% your fault, but you're going to take it on the chin. Like that's life. Like you'll have to just learn from it, move on, try to be better in the future. So that's, that's just the way I think about it. I love it.
Speaker 1Rick, this has been great. Uh, before we go, let's pay it forward. You're a big reader. We've had some great Rick and I are good friends. People just said, it's very clear. We're quite good friends. And we do our CNJs. We do our chat and jogs when we're in the same city. And we talk about one of the things we talk about is books. Uh, what's, what is it? What's a great book you've read? Give us something to read.
Speaker 3Well, the, the, the book, like it's so, you know, it's been said over and over again, but I don't think that many people actually read it. Like seven habits of highly effective people is a book I read once a year. Cause it is just, it's a book that I've read once a year. And I think that it's just like, it's the layups and free throws of like how to run a productive life. Um, so I'm, I'm a big fan. Nobody's read it. I haven't read it. Um, I'm a big fan. It's so habits.
Speaker 1Give me, give me a couple.
Speaker 3I mean, I'll tell you just like, like one tactic that I learned from there. That's incredible. And it's basically, there's a two by two that talks about things that are either urgent or important. And then you can do on that, that two by two and like what actually moves the needle and drive success. It's things that are important, but not urgent. Guess how often things that are important, but not urgent. And then you can do on that, that two by two and get done rarely. Why? Because they're not urgent. And so you actually have to go make time in your busy little life to go do those important things. And what if you just once a week sat down and said, what for this week, if I did this, it would actually be meaningful, but there's no compelling event. There's no like deadline on Friday. It's just the stuff that isn't going to happen unless I go make it happen. So what are two or three things that like, if I did that, it would be more impactful than just getting through my emails as an example. Now, am I going to schedule the time to go do that? Because if I don't, it ain't happening. That alone, just that habit and that exercise has been, I'll call it impact altering for me. And that's just one little tactic within that book.
Speaker 1I mean, I'm not, listen, who am I to say, maybe this is the best top line spotlight ever. Maybe it is. I don't know, but I'm somebody, I am the host. This was great. Rick, if folks want to reach out to you and engage with you, first of all, what class do you teach at CRO school in Pavilion? And then what's another way to contact you?
Speaker 3I've been teaching the scaling section of the CRO school at Pavilion. I've loved the opportunity to be able to do that and engage with an audience that has the aspirations to make bigger impacts within go to market. It has been so fun. So thank you, Sam, for the opportunity to do that. If folks want to get in touch with me, the best way is just to look me up on LinkedIn. I'm very easy to find there. As a member of Pavilion, I'm also just always trying to see how I can be helpful and how we can continue to learn from each other. We have very hard jobs and we can't do it ourselves. So let's do it together. Isn't that the idea for the business, Sam?
Speaker 1Let's go, baby. All right. This has been top line spotlight. Rick, thank you so much. It was actually, not actually, it was great. You're great. Surprisingly, it was okay. You said one interesting thing, which was a surprise. Over 26 minutes. No, seriously, thanks for being here. It was great seeing you. Thank you, Sam. Thanks for listening to Top Line. New episodes come out every Sunday. If you like what you heard today, subscribe so you never miss an episode, leave a five-star review and share it with your friends. Don't forget to join our Top Line Slack channel to connect with us and discuss the topics we cover with other listeners. Click the link in the show notes. Lastly, if you're interested in joining Pavilion, you can subscribe to our YouTube channel. We have a lot of great content. You can learn more about membership at joinpavilion.com forward slash membership. Thanks again for listening.
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