SPOTLIGHT: How Rick Smolen Built Confidence Leading Outside of Sales | with Rick Smolen, CRO @ ShipHero

0:06Sam Jacobs: Welcome to Topline, 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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1:08Now back to the show.

1:13Sam Jacobs: Hey, everybody. It's Topline Spotlight, a Topline Spotlight in your face. It's that weekly show, you know, Topline Spotlight, you know about it. We spotlight a leading 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.

1:53Sam Jacobs: 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 Topline Spotlight. Sam, it is great to be here. I listen to Topline 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. 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.

2:33Sam Jacobs: Really interesting company. Yeah, 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. ShipHero started with a focus in the e-commerce world. So anything that's direct to consumer and trying to make that whole process more efficient and easier, which everybody enjoys. Obviously that got accelerated through COVID when everybody started buying everything online. During that time, not only did ShipHero provide a warehouse management system to help companies be able to ship things faster to the consumer.

3:12They went into fulfillment as well. So today, we offer fulfillment services through a brand called LVK, but our primary business that I focus on is around our WMS technology to help both brands that ship directly to consumers and Omnichannel and 3PL companies that do that on behalf of brands, get goods to the customer, faster, cheaper, easier, more reliable, less errors.

3:36Sam Jacobs: That's and so roughly how big is the company from age? How old is the company? You know rough revenue range you don't have to tell us anything confidential but I mean the company's been around for more than a decade it was a bootstrapped business for a really long time as the venture money started to flow into tech you almost took capital solely as like an existential thing because the competition was getting so much capital at the time Shapiro does have one outside investor in Riverwood Capital, which I'm sort of a part of, which is how I got to know Aaron and the Shapiro team. So the company's taken a decent amount of money, but only from one growth equity investor and has no plans to raise money in the near term, operating with the Sam Jacobs model of profitable efficient growth.

4:24Let's go. And we're about$100 million business today.

4:28Sam Jacobs: That's fantastic. And then last thing before we dive in, we're going to dive in, Richard. A fun fact for the folks in the audience, Rick lives in my old building in, well, it's his building. It's really more his building than it is my old building. Let's be fair. I've only lived there a couple of years, but Rick does live there. It's 10.

4:49Now people know how to find me.

4:52Sam Jacobs: You've been hiding out. Prepare to be disappointed. That's your motto. That's when you walk in the door. It's the little thing on your desk. Keep expectations low. That's a secret to success in life. I could not agree more. All right. Before Ship Hero, you've had a really – I'm not just blowing smoke. You've had a long and illustrious career. Give us some of the highlights because you've been doing this for 26 years, if I'm not mistaken. Yeah. I mean, I sort of started a career in finance, ended up in software, ended up on the finance side of software, then ended up in sales. I grew up at a company called Intralinks from sort of 2004 to 2012.

5:35That was a fascinating business to be able to be a part of and grow up within tech sales, individual contributor, manager, living internationally, running North America businesses. This was all before the word SaaS existed. You know, this was just sort of tech that was happening. And so I was so fortunate to be part of a growing business and be able to have accelerated advancement into different roles. So that was a total thrill. be able to spend 12 and a half years at one company was very fortunate. I was able to make the leap from there to very much into the SaaS world. I led sales at Greenhouse Software for three years.

6:10I, through that experience, got to have all the types of experiences of a high growth, high ambition, you know, horizontal SaaS business. I then joined, I almost started a company on my own, joined sort of force management as a facilitator, teaching the sort of customer engagement methodology that we had applied at the prior two companies. I did head of sales at, SVP of sales at Lupio for almost three years, which was a sort of copy and paste of the size, scale, and growth rate of greenhouse. That was a really fortunate experience, and we had some success along the way there. And then I sort of fell into a vertical SaaS play in the last year and a half.

6:51I did a go-to-market assessment on behalf of Riverwood of Ship Hero, and I found some dimensions that were just terrific for a go-to-market leader. One, incredible differentiated tech. No real peer competitor that was anywhere close. All the other businesses, there was a one and a two that were fighting in a knife fight all of the time. Here we had differentiated tech. And then I had the backing of the board on day one. It's not often that the board sort of brings you into an organization and you have their full support. And then the founders and OGs of the organization are very product oriented and focused.

7:22So I didn't see a lot of like conflict as it relates to how we should do things on the go to market side. So I've made the leap from a head of sales background into a CRO role where now my reward is you get to own all the challenges across the entire customer lifecycle from marketing to sales to partnerships to customer success to support to rev ops all the way through. And so new sets of challenges and learnings along the way.

7:49Sam Jacobs: What do you think is the biggest difference? What surprised you about the move from SVP, VP to CRO? When you see people earlier in their careers and you're coaching them or mentoring them, what do you think the biggest unexpected piece of the job is that maybe they're least prepared for? Well, all right. So I'll just say broadly, the thing that I think emerging leaders are the least prepared for is letting go. Like one of the reasons that they've become a leader is because they are really good at doing the things. And now they've been advanced in their career and they have to hire other people to do the things.

8:26And so the support for folks on your team is the first thing. Like how do you empower them to actually do it and avoid them being reliant upon you? But then additionally, a lot of the top people in an organization that get promoted are also good at getting things done. And so the easier thing for them to do is just do it themselves. But to be successful in a scaling org, especially as headcount grows and processes need to be solidified and sort of followed, it's a tough leap to then have to. It's actually harder for the individual to document a process or to train others on how to do the thing correctly.

9:08It's easier for them to just do it. And so what you'll often see is they'll continue acting in what made them successful, which is just like doing all of the work, going above and beyond all the time. And then you'll see them potentially burn out. And so the thing that I see is how do you help someone along the way see that, like, hey, you are a massive talent and it probably is easier for you to do the thing yourself. But for us to succeed long term, that's actually not your job anymore. And so how are we going to set up others within your span of control, whether it be sort of horizontally in another function or your team to be able to do that and you be able to provide coaching along the way?

9:47So I find, you know, so if we take that to changing my level of responsibility from just sort of focused on sales to being focused on the entire lifecycle of the customer, I don't feel the pressure that I have to have all the answers. Like, 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.

10:35And 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.

10:47Sam Jacobs: Tell me why I'm mistaken in my fear. My fear is that when I hear you, that, hey, 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 is it, am I mistaken in how I characterize it? No, I think it's a great point.

11:26I 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 like, whoa, like 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.

11:58And 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.

12:38Like, I don't feel like I need to have all of the answers up front, nor does 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 like, well, what is 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 like hands off, like that's not my responsibility because that's not my background.

13:18So you're right. Like 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 will actually be able to execute.

13:33Sam Jacobs: I think that takes, I 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 pleaser. I have 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?

14:08Yeah, 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 like written down what my personal values are, what I'm all about. You know, you tend to, with your direct reports, interact with them fairly frequently. You can kind of tell pretty quick if there's 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.

14:32Sam Jacobs: Even before that, you're from Philly. It's like you're never not direct. I 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 I feel like the folks that are in my organization know that what I actually care about is our collective success. That is the North Star of 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. them. So I'm maniacally focused on the prize, which is achieving our goals.

15:12And 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 that those interactions that we talked about. But if those table stakes aren't there and people are unclear of what my motives are, then yeah, like, and I've experienced this in the past, Sam, like not everyone loves me because, you know, that, that, those dimensions weren't in place.

15:39Sam Jacobs: So what, so, you know, when we're thinking about assembling this leadership team, what other lessons have you learned over the years? One of them is probably recruiting, you know, and talk, talk to us about your methodology for building the team. And like you said, and then entrusting them with success. And the last piece, I know it's like, oh, there's a lot in there. Sometimes that's what people say. Because it's like a mixture of like three questions plus a few observations. But the point is like your tolerance for failure. Because I think some part of like development is I'm going to let them do their thing.

16:14Sam Jacobs: Their thing is not always going to work out. So how do we talk about the learning process? Yeah, no, it's a good one. Look, we're all human. So like I have 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 a 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.

16:54But I don't try to, again, use any of those failures as an excuse for achieving the wider goal. We just need to sort of 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 like changing it. I always felt that Sam, I'll share like, you know, you and I have both been in unfortunate circumstances in our careers.

17:31And what I mean by that is we've been asked to leave organizations. It's fine. It's fine. It happens. Like we've learned from it.

17:37Sam Jacobs: That's a good idea. Who would like you to leave? Can I stay? You cannot stay. You cannot stay. So we've been in a situation where our employment was ended without our like saying the matter, which was a surprise and a learning experience. And so it poses the question of like, okay, 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.

18:13And 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. But it really 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.

18:52And we all should, as leaders, 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?

19:29And 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. What are the ways we're going to win despite whatever those obstacles are?

20:02And 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.

20:43And 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 rearview 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, 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.

21:09Sam Jacobs: Did 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 came up? No, I mean, again, I would say 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.

21:51but 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.

22:25Sam Jacobs: Rick, this has been great. 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 so 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 what's a great book you've read give us something to read well 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 because it is just like it's the layups and free throws of like how to run a productive life um so i'm a big fan nobody's read i haven't read it um i'm a big fan it's so habits give me give me i mean i'll tell you just like, like one tactic that I learned from there.

23:12That'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 and not urgent 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.

23:46There'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. I mean, I'm not, listen, who am I to say?

24:17Sam Jacobs: Maybe this is the best 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? I'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.

24:55I'm very easy to find it 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?

25:10Sam Jacobs: Let's go, baby. All right, this has been Top Light 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.

25:37Sam Jacobs: Thanks for listening to Topline. 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 Topline 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 learn more about membership at joinpavilion.com forward slash membership. Thanks again for listening.