155 - Empathetic Communication and Continuous Learning: Key to Successful Customer Interactions with Scalero's Will Pearson

Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started. Will Pearson, welcome to Listening with Leaders.

You are the co-founder and co-CEO of Scolero.io. Thanks for joining me today.

Thanks for having me, Doug.

So I've interviewed you on Authority Magazine, but many people probably have not read that interview. Tell me a little bit about your backstory. Let everybody know who you are and how you got to where you are today.

Yeah, absolutely. I was born in Indianapolis originally. I like to claim my Midwest roots. It's kind of a kindness and generosity and things that people say about Midwesterners. I try to convey that for sure. And after graduating college, I started a career in retail and e-commerce. I worked for a few years at Target at their headquarters in Minneapolis, and then I got the bug to get into tech and get into the startup world. So I moved to San Francisco and I joined Vivino. The wine app while I was there and worked there for 4.5-5 years during which we grew the e-commerce business there from almost nothing to a couple hundred million in top line revenue. And it was there that I accidentally learned a lot about email marketing and lifecycle marketing. And that's because as we sold wine, we found that email marketing was far and away the most effective channel to do that. And my now business co-founder Brent, he was the first marketing hire there and he was running email marketing. So we worked really closely together kind of devising strategies, looking at technologies, you know, figuring out a way to scale that business through email. And as we found success doing that at Vivino, we found that we both had a little bit of a bug to be entrepreneurs and start our own companies. So we left and we had lots of ideas on companies to start, but really the lowest barrier of entry was, was email marketing. So that's how Scalero came to be in 2019. And we We define lifecycle marketing as, as email marketing, SMS marketing, push notifications, and work with a lot of B2C type companies that have an email list. They need to nurture them. They need to focus on retention. And we offer some software and some services around that.

So you're in the kind of what I would call the opt-in warm email niche, not so much the cold email niche.

Yeah, absolutely. Yeah. Yeah. We, we tell our clients that we will optimize your existing list, but we can't necessarily, you know, add to it. We do some B2B work as well, but cold outbound is not really our specialty.

Right. And you've been, you've been, you started in 2019. So how do you manage the pandemic?

Yeah, we started at the end of 2019 as well. So We've basically only been a pandemic company. For us, I think there were actually some positives. You know, we had a few brands that had budget constraints, you know, they were in the travel space that hurt us. But otherwise, you know, as things moved more online into digital, a lot of companies found themselves realizing that they didn't have a good email marketing strategy. They didn't know how to retain all these new customers they were, they were getting. So that helped us just from a business standpoint. From a company standpoint, we originally, I was in San Francisco at the time, we had an office in San Francisco and we started to build a team in Mexico City. We really thought we'd have, you know, those two offices working really closely together. As the pandemic continued, we became a little less focused on regional placement of our team, but still try to keep some, some hubs as well. But, you know, I really envisioned a lot of traveling and going to see clients and working with our different offices. And, you know, that really took a few years to come about because of the pandemic.

Your company is mostly remote today?

Yeah, exactly. So we're in San Francisco, New York, Mexico City, and Copenhagen. Everyone's working remotely, but we do have office space, WeWork-type spaces available for those who do want to come in and or need to come in and work with others.

Now, how have you found growing an organization remotely to be?

Yeah, I mean, it's good and bad for sure. I think, you know, the good of it is just the immense amount of talent that, you know, we've been able to talk to and hire and bring in. And then also, you know, it's very quick for us to start working with our clients as well because we pretty much handle everything on Zoom. So we don't have to go to their office to set things up or anything like that. It's just, we just can just get going. And the challenges are probably, you know, pretty, pretty obvious too, right? It's, it's easy to fall into some habits of always being behind a computer screen, you know, both personally and as a team. And, you know, when we do get together as a team, from my standpoint, we collaborate better and more ideas come to life. But, you know, I don't necessarily quantify that. I don't know if that's true or it's just, you know, something that I feel. So, you know, we try to keep it balance where we do get together occasionally, but it's not really forced that much and just kind of let people be comfortable as they can.

Interesting. I mean, people, you, we read in the literature that there are a lot of companies that are forcing people to come back to work and employees are resisting. And then you hear about trying to find the right balance between being remote and coming together so people feel like they're part of a culture. And I think every company approaches it differently and some are more successful than others. It sounds like you found a balance that works for you guys.

Yeah, I think so. The, you know, having people at least close by to each other gives them the option. And I think that that option, you know, there's some extroverts that want to see people every day and some introverts who who don't ever want to see people. So, you know, you can't, you can't, in our opinion, you can't force people to do things they don't want to. And instead, we want them to try to set them up with the best tools possible to collaborate, even if it is remotely. And yeah, so far it's working pretty well.

So what is it that gets you up in the morning and gets you excited to get onto the computer and get on the Zoom and start talking with people and working your teams?

Yeah, you know, in this, in this role with this company, we talk to a lot of interesting people and I have found that my own leadership skills have enhanced quite a bit by learning from others and actually even clients who pay us for a service. I'm still learning a lot from them at times too. So, you know, I might meet with Within an hour today, even, I met with a brand new startup CEO, super eager, getting going. And that followed by a founder CEO of a $300 million company as well. So they're very different stages, but there's a lot to learn from both of them on what to do and, you know, what not to do at times. So, you know, I love meeting those types of leaders and seeing what they do well.. And, you know, trying to incorporate that into what I do, which is also what excites me of working with my team and seeing them develop and take on new projects and new skills and see that growth happen there. I, you know, I really love just developing the other people on the team and and seeing that happen.

If you, it's very interesting that you're talking to brand new CEOs and CEOs who are in major growth mode. If you think back on all these people, the CEOs and leaders that you've talked to, what do you think the number one lesson is that you've learned?

Yeah, I think as a business leader, you have a thousand things you want to do at all times, right? And the ones who seem to get it right are the ones who can take that 1,000-item list and narrow it down to 5, let's say, you know, maybe you can do 5 things in a month or a quarter or a year and then get people on board with that and be able to communicate that to others and that not the other, the other 995 things, not that they're not important, but they're not the most important. And, you know, I think those that struggle with that conversely are you know, the ones trying to do a million things at once. And ultimately, you know, nothing is really that, that successful for that reason. So I love seeing those that can prioritize and then communicate those, those priorities and get everybody on board.

It sounds like what you've learned is prioritize and then focus and then communicate.

Yeah, absolutely.

Stay focused on those top 3 or 4 or 5 things that are most important. And keep the team focused on that too. Keep the eye on the ball, right? Don't get distracted by bright shiny objects or lessons.

Absolutely.

Yeah. So when you think about this, you've been now, let's see, you've been in— this is beginning of 2024. You are, uh, what, 5 years into this now? Almost 5 years into this. What do you think it's unique about you that you bring to the table that makes, uh, Scolaro so successful?

Yeah, you know, I alluded to this a little bit early on with my kind of tongue-in-cheek reference to the Midwest, but I do take that really, really seriously of being a genuine person, being myself, being kind, thinking of others. That's something I try to convey and I, you know, I hope I do. Consistently. And I think that's helped us a lot in just not being so cutthroat all the time in business and establishing relationships and just helping out somebody one time means maybe a year later they'll be able to help you out, or maybe they'll become a business partner and there's financial incentive to that as well. So, you know, I think we've built a culture here of good people, good attitudes, and I think our clients see that and our customers see that. And, you know, we just want to be a pleasure to work with as well. And that kind of trickles down across the board where we also want to have good balance. You know, if a part of being a good person is, you know, doing, doing things for yourself and, and, you know, prioritizing the right thing. So, uh, between family and work and friends, you know, we want to make sure that all of that is, is available and, and prioritized for, for, for me and the team.

Work-life balance— I mean, this kind of flows into work-life balance, and that the whole concept of work-life balance has been a huge part of your, part of your leadership, where you felt you really think that it's critically important. Tell us more about that.

Yeah, I have a 3-year-old daughter right now that I've tried to prioritize, you know, as much as I can. And I think, you know, for anybody, whether you're running a company or not, you have a lot of things tugging at you at all times. So I do my best to lead by example. With the team that it is not about work 100% of the time. I'd be lying if I said I wasn't thinking about work almost 100% of the time, but it doesn't mean I'm in front of the computer actually doing things. You know, I think there's a healthy separation between executing and maybe brainstorming stuff later, ideas coming to you. But, you know, with a small kid, there's really no, I have to be present, right? You can't, you can't sit with a 3-year-old and be doing other things because she will call me out immediately on it, right? She'll, she'll tell me to, you know, Daddy, listen to me, Dad, you know, pay attention, let's do this. So that's, that's my focus is go all in on that when I'm with her, go all in on work when I'm working, and then, you know, try to take some time for myself too. And, and, and my team knows that, you know, around 5 o'clock most days I'm, I'm gonna be offline. At that point. And if something didn't get done by 5 o'clock, then, you know, I'm not going to sacrifice, you know, those next few hours to get that done. So I like to think that creates a nice example, you know, for the team where they can, they can see me try to create some balance in my life. And if one of the founders can do it, then anyone can.

Do you find that your team is able to do that? They're able to prioritize their life appropriately?

I hope so. You know, I don't sometimes, and when I see that they're not, or maybe I think what's common in our space of being a services company, largely services company is, you know, you want to take a day off, but then you get some, you have your clients need something from you and instead of maybe asking someone to do it for you or saying this can wait, you just do it and you don't take your day off. So we see that sometimes. And that, and try to call that out every single time. Say, hey, it's, you know, vacations are part of the, part of the game here. Take your day off. We'll figure out how to communicate to clients. Clients take vacations too. Like, it's all, it's not that serious, right? We're not, we used to always say at Target, you know, we're not, we're not saving babies here. Like, let's, let's take a step back and, and, and relax sometimes. So yeah, if we, if we see someone not able to figure out the balance, you know, we try to dig into it and figure out why and solve it.

Wow.

Good for you. I guess your organization is still small enough that you can do that, keep track of people.

Yeah, we are. Yeah, we're around 30 people. So that's, I like this size a lot. It's been a comfortable size for us where, you know, we're still really nimble and flexible, but, you know, people can take a day off and things don't fall apart.

Yeah. Fun. So this show is called Listening with Leaders, and I always like to ask the question, and I, I can sense how this is going to go: how important has listening been in your career and in your work now as a CEO, co-founder of, of Sclero?

Yeah, um, I think my listening skills were really honed in when I was at Favino, um, because I was working with people from many different cultures and countries and time zones and everything else. So you really don't have a choice but to listen intently because things are communicated quite differently than, you know, in my day-to-day. So you learn what they're trying to say, you know, what's important there. And then, you know, moving into this role at Scalero, I mean, like I said, we're mostly services business. So by definition, we need to be servicing our clients, which means we need to listen to them and understand their problems. And, you know, we're in a very niche space focused on email lifecycle marketing. So many of the problems our clients have are actually quite similar to each other, but they communicate it in very different ways. And so part of my job is to try to listen to what they're really saying, what's really the problem here, and then bring that to some of the services that we offer and kind of match the two up, right? So then we can then do what we do best because we want to streamline what we're doing. We don't need, we don't want custom solutions to everything. So how do we take one of our existing processes and align that with what they're conveying and make both sides, you know, a winner in that in that case. So yeah, I'm intently listening and trying to translate, you know, what people are telling me at all times so that we can give them the right service.

What happens? I'm sure you have this experience where you get a customer who's a little bit disgruntled. How do you, how do you, how do you guys, you and your team, deal with the disgruntled client?

Yeah, as I'm, I'm sure many listeners can relate to that. That usually is when the call is made, you know, to the founders is when things are not great, right? We don't usually get the phone call to talk about, yeah, we don't get the phone call about how amazing things are. So yeah, that's the most important listening, you know, that can be done is during those moments. And one of my techniques is to always repeat back what I'm hearing. Just to make sure there's no, yeah, there's no misinterpretation here of the situation because the situation could be something we did wrong, something we're at fault, or it could be circumstances or nothing at all. But, you know, get on that same page with the disgruntled customer and then, you know, leave there with a few steps on how it's going to be solved and kind of appease that. In the moment.

Yeah. What I teach people how to do and people like you, CEOs and founders, is to not only paraphrase, but to also listen to and reflect the emotions of your irate customer where you say, hey man, you're frustrated, you're pissed off, you don't feel like you're being heard, you don't feel like you're being supported. And the whole thing is really got you anxious. And when you reflect, when you reflect their emotions in that way, they calm down. Some neuroscience behind that that shows how this all works at a biophysiological level. And so what I teach, what I teach my students is de-escalate, then problem solve. So try not to jump into problem solving right away. Wait on the problem solving until people are calmed down, then you can invite in the problem solving. It sounds like— oh, go ahead.

Well, Branson and I often discuss kind of the what's really going on, you know, situation. And that's usually pretty telling and can humanize the person a little bit at times too. So it might be, you know, the founder, it could be the founder and business is losing traction and it's, you know, it's losing revenue and there's a lot of pressure on them, right? Or you know, somebody has a new boss and that boss is asking them a lot of questions, so therefore they're pushing us harder. You know, understanding that is often a key for us to unlock some of this.

Exactly right. Because rarely, it's probably rarely a screw-up that you guys have done, but people are pushing you because they're getting pushed from different directions with different energies. And that's when it's even more important to get them calmed down and make them feel like they've really been deeply heard. And then when they feel deeply heard, then they trust you and you can have that problem solving conversation and, and, and be really effective. So, yeah, it's good to ask the question, what's really going on here? That's, that's the right question to ask.

Yeah.

Hope, hopefully you don't have too many of those phone calls.

No, hopefully not.

But it happens, especially with new businesses. And you guys probably have a lot of clients. You know, you face these problems and the idea is how can I take this difficult conversation and transform it into something that's gonna be really positive for both the customer and, and for us. And that's learning how to do that. That, that's a huge leadership skill that a lot of people have never managed to master.

Yeah. Yeah. It's very challenging. You're, you're balancing a lot of different types of personalities, right? And, and different situations. So it takes, yeah, it takes a lot of practice. I think it has taken a lot of practice and, you know, I'm sure there's plenty of improvements to still be made. I'll have plenty more difficult conversations going forward. That's just the nature.

I mean, you never stop learning. I'm 73 years old and never stop learning, you know, stop learning, stop growing, you start dying.

Right, exactly.

I mean, you're much younger, but you— it's amazing if you keep your mind open. Growth mindset, Carol Dweck, how, how amazing your life can be.

Yeah, absolutely.

So one more question, I'll let you go. What, what's one thing, Will, about yourself that we wouldn't know about unless you revealed it to us?

Yeah, well, I am a, uh, I'm a tennis player. That may not be that revealing. I think what's interesting about it for me was tennis was kind of this blessing and curse for me growing up. So I played very seriously, and as I reflected on it and got a little older and played some in college, I realized I really didn't like tennis at all. I was playing for all the wrong reasons, and I quit, and I quit for a very long time. And then at the same time, as I think back on a lot of skills it gave me in terms of problem solving and independent thinking and some mental toughness, even though it maybe didn't feel like it at the time, I'm very grateful for the experience I did have in tennis. And I've actually started to play a little bit again, and trying to avoid the same pitfalls I had of not enjoying something you did all the time. So yeah, I'm dabbling back in. I do, I do still really like the sport and I try to take the good out of it as opposed to a lot of the bad that I was taking when I was younger.

That is a great lesson in life. Good job. Well, thank you so much. Thanks so much for joining us today. It's been a great conversation.

Yeah, I really enjoyed it. Thank you, Doug.

You're welcome, Will.

Doug Noll here. Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnull.com/podcast. If you got something out of this interview, would you Please share this episode on social media. Just do a quick screenshot with your phone and text it to a friend or post it on the socials. If you know someone that would be a great guest, tag them on the social media to let them know about the show and include the hashtag #ListeningWithLeaders. I love seeing your posts and guest suggestions. We are regularly putting out new episodes and content. To make sure you don't miss any episodes, go ahead and subscribe. Your thumbs up ratings and reviews go a long way to help promote the show and mean a lot to me and my team. Want to know more? Go to my website, DougNoll.com, or follow me on LinkedIn, Facebook, and Instagram. That's @DouglasEnoll. Thanks for listening, and we'll see you on the next show.