The Sales Engagement Podcast
The Sales Engagement Podcast

Episode · 11 months ago

An Alternative Leadership Style That Embraces Difference


You have a big problem if your VP of Sales is the best salesperson in the company. Their job is actually to help make their teams better than they ever were.

Today, we hear from Wesley Ulysse, Vice President of Sales, North America at Red Points, about an alternative leadership style driven by open-mindedness, patience, inclusivity, vulnerability, and dynamism.

Join us as we discuss:

- Why patience can be the biggest leadership challenge

- The reason your VP of Sales shouldn’t be the top seller

- How an open-minded manager interviews and hires

- The most important quality a manager can have is…?

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, Spotify, or our website.

Welcome to the sales engagement podcast. This podcast is brought you by outreach, the leading sales engagement platform, and they just launched outreach on outreach, the place to learn how outreach well does outreach? Learn how the team follows up with every lead in record time after virtual events and turns them into revenue. You can also see how outreach runs account based plays, manages reps and so much more using their own sales engagement platform. Everything is backed by data pulled from outreach processes and customer base. When you're done, you'll be able to do it as good as they do. Head to outreach Doo on outreach to see what they have going on. Now let's get into today's episode. Welcome everyone to the sales of engagement at podcast. This is your host, Caitlyn Kelly, senior manager of sales development at outreach as well as cofounder of STRs anonymous. For today's episode, I am so excited to be taking a deeper dive into alternative sales leadership styles, and there's no better gas to have on than West e Lee's, who is vp of sales in North America at Red Points West. I'M gonna toss it over to you to introduce yourself and tell us a little bit about what you're doing over at red points. Yeah, thanks, obviously I'm really excited to be my name is West, I see, vp of sales at red points. Yeah, my task is really just to scale the US business. Right. I managed the New York and Salt Lake City office sales divisions is in particular. And Yeah, look, I think you know, as many startups in the tech world, we're here just to scale and he reached that Unicorn status. And so at a very, very high level, I'll keep it simple and and and that's where what I'm responsible for. Okay, amazing, brevity is key, and so looks like you're looking at it dry revenue for the US teams essentially amazing. So kind of West, when we look at you know, red points is a Spanish...

...hued company and you're running the US sales team, and so kind of the first things that come to mine is, okay, global initiatives. Cultures are going to be different, and I can kind of speak from my experience coming from Seattle, Washington, now over in the MEA region. But I'd love to understand in your opinion, what has been the biggest challenge and really leading a diverse culture. Yeah, I mean I think for me in particular, the biggest challenge has been my patients. Like look, leading a diverse, you know, culture, it requires a high level of open mindedness and patients. I'm a contrarian by nature and I'm a very impatient person, and so, especially when hiring, when you're not astready hiring, you know, the proverbial salesperson, right, it requires a lot of patients because you're essentially, you know, looking at a piece of a puzzle and when you start to tire, you know, a build a team, looking at, you know, another piece that is not necessary from the same box, right, but you got to figure out on how to make that fit and how to make it mess and how to make it Mesh well, and so that can take a lot of time. But at the same time I think my openmindedness has allowed me to really excel it and really do well, I guess really, you know, tackle that in a most efficient way. Yeah, I think there's something to be said about, you know, having the diverse backgrounds that you can bring into different sales at orgs and different strengths that people can really lean into and kind of I'm filled a culture that is quite quite amazing to be a part of. When you kind of look at like your sales team and what kind of is there any people with non traditional cult or not quote non traditional backgrounds that they kind of transition into a sales role that you've been able to kind of identify that you're that you see kind of some trends in. Yeah, I mean we have a we have a couple of team members that are not necessary, you know, from the non too old aditional sales background, including myself. Right like, when I first out of my career, I was actual an account for the nuke city ballet for about four years. I mean I was really good at it, I didn't enjoy it.

I was actually pretty miserable to point where one day I literally went to lunch, I had a few drinks and I actually never went back and I was essentially my introduction to sales. But again, right like, I always thought of myself as I didn't never thought I thought I was an accountant. Right, I'm coming from an immigrant, an immigrant background. My parents always told me I have to be, you know, a doctor or lawyer or a businessman, right, but they didn't know what you know what is a businessman, right, and so I thought two makes of hey, I just go ahead and get into accounting them. But again, right, like that's not necessarily someone that the profile of one that you know just jumps into sales right away and one would hire. And so we'd like to keep an open minded I read Rod read points for sure. Yeah, I I love that you mentioned that. You know, you would you went you were an accountant. I think a lot of people, and I have an entraditional background as well, in the transition into it. But when you're kind of figuring out what you want to do, I think there's a lot of education into the type of career that you can have with in sales. But if you think about almost every industry, there's a sales vision that's driving the industry on the back end. So there is loads of opportunity there and I think that's a different conversation that we can get into. What I love to know is how have you really been able to create an inclusive environment, especially within a global company? How are you guys kind of keeping that flow of communication, especially when all its hybrid, a lot of it is going to be remote? Yeah, I mean that's important. Right, open dialog, right, and impact. I mean here it all the time. People need to be heard, but but I mean people need to feel as if they can express themselves, express their concerns. But, more importantly, when they do that, they need to see the impact of that. Right, not only in how, in what you do and your follow up in terms of your actions, but, you know, especially in a high velocity startup like people want to see their impact. Like revenue is not enough anymore, right, like we assess leaders, help everyone. You know, you're the sales people, you're driving the company with your revenue. Yeah, that's true, but I find that...

...revenue is not enough anymore. Right. You need to listen to your people, hear you people, but, more importantly, put into practice, you know, their suggestions, their input, so that they actually see that they're building a business along with you. Write in, just not drawing, and they're not a resource in the sense. And so I think you know that's paramount when it comes to, you know, building a diverse team and inclusive environment, especially in a global company. Yeah, I love that you're kind of talking about, you know, showing what that impact is. Do you have any specific examples where you've been able to kind of bring, because bring different teams that you're overseeing together to kind of show you, hey, you know, whence on sales team does this, the other one benefits from it. From well, how can we kind of leverage this type of partnership? Yeah, I mean in the past, I remember. This is a big kind of intuitive, but I remember asking the account of executives to literally just for quarter of the demos and I had the STR team listen to all the demos and just from literally just these are Seis who have never been any kind of executives. I think four out of seven of them were not even, you know, in sales before they got into the St r role, and I just asked for their input, right like how does this demo feel to you, like what is it tone, you know, and these are obviously unjaded eyes, right under a year, so to say, and so they I got a lot of really good feedback and then, you know, I went back to the count executive team and fibbed a little bit and tell them that I had, you know, an outside, you know person listen to these demos and this is how they felt listening to it. So you should change your tone here. You should change your post approach there, and they did it. Well, number of them did it. They found some good success and then I let him know that, Hey, those are actually dsdr suggestions, and so we created a really good, you know, working relationship between Sdr a team and a mutual respect in a sense. Yeah, that is so good there, because you know, it's important to be like a different view, from a different set of Lens, but especially coming from like an str standpoint. Who is it living that life of the AE? They're not going to be repeating the same thing. You're looking for the same thing...

...that the a nextra might point out. So love that you guys are doing that. Previously, when we had talked, we talked a little bit about leadership styles and how you like to leave from the front with your team, and we talked a little bit about having more of an alternative style. Can you tell us a little bit more about that? Yeah, I mean, look, all too often, especially in sales, right like these tend to put their egos first, right and feel as if they should either, you know, have all the answers or, you know, maybe they're the best sales person in the come beany and in reality, I believe that, you know, if THREEPA sales is the best sales for president the company, that's a problem, right, because my job is supposed to be, you know, helping those you know get better, better than I ever was, and sense help build careers. And so I truly believe there's so much power in legitimately asking your team for advice. Right perspective is a must if you're going to succeed in sales, because that's that's the job at its core, right, understanding different, you know, approaches, different perspectives, and so, you know, all my alternative leadership style is literally leaning on my team, you know, from SDR to ae to, you know, whatever position in the company, right to to you know, help me, I guess, identify my blind spots in a way, right, there's so much power in saying hey, like, I don't know the answer to this question right, and I'll give you an example. Right there a few times where we many tend to come to me and ask me, Hey, what's you know? What would you do in a situation? How would you respond to this prospect? I'll give them my two cents, of course, because they asked right, and that's, you know, what I'm supposed to do, but I always want to know, you know, what were you thinking? Right, you know, how would you have replied? And you'd be surprised how many times that person's approach is better than mine, right, or better than someone else's suggestion. And so try to really empower, you know, my team to trust their gut and their instincts and, you know, be confident in their approaches. Yeah, one of my things, one of the things I learned early on. It is that kind of similar to what you're saying there.

But you don't always have to have the answer and one of the best things you can do is actually not provide the answer, but give them the opportunity the like. One of the Times that what you'll hear us do often over here is if somebody comes to us with like hey, you know, can you help me with this, or what do you think about this? All, actually put it back on them and I'll be like hey, you know, I love that you're bringing this up. Why don't we come up with three different solutions? Let me know what's fun, is your favorite, and then we can talk it through. Right, like you just said, nine times out of ten they're going to bring back something that you want to have thought of. That solves it probably better than what you probably would have like told them to do. Yeah, and that's actually something I struggle with, to be honest with you. Is I mean when to just tell them hind no, look, do it my way. Yeah, right, so it's something I'm still working on. Yeah, I think that is it kind of takes you back to like situational leadership and it is easier to just tell them and it's quicker, but if we just pause and it's like, Oh, let's like work it through, it allows things that grow and then they can actually become experts in different areas as well. Yeah, so kind of we talked a little bit about. You know, you have a day diverse background, coming from accounting and also in the ballet industry, which I love. Thinking back on your different types of career progressions, what events are rolls have really helped shape your leadership style today? You that that's a that's a tough one, but I actually, you know, it's pretty easy. So, now that I think of it, I think I remember my first months as an str right, I was somewhat new to SASS was new to sales at the time, but I was failing right, I was failing and I and I could not understand why or what I was doing wrong. And I would know do like mock demos and pitches and stuff like that, and it'd be great. But the men I get on the phone, my mind just went blank and I remember in my oneon won, my manager at the time, she basically, you know, had that conversation with me like look, quest you know, kind of have two weeks to kind of give it together...

...or else, you know, we're going to have another conversation right, and that's not going to be so pretty. And and you know, she asked me again, like a good manager, you know, what do I need to succeed? You know, she'll do any she was super competed to them to my success. And I literally told her like look, honestly, just leave me alone, I'll figure it out. And I was lucky enough to have, you know, an open minded in a really good manager at the time to allow me to do that right, because I think it's time. I might have been twenty nine or thirty. My teammates were about like five to six years younger than I was. I had had a career. I had sold a business at the time, so I had no significant experience and I just think I was in my head. But it really takes a good manager and open minded manager to look at someone and think to themselves, right, this person is not like. It is not should be categorized, you know, based on his or characteristics. Right, this not the mold, and she had to take a step back and kind of let me figure myself out and manage me the way that I needed to be managed, not necessarily you know, my teammates, and so I think that really probably sparked, I would say birth, like, I guess, the idea of my management style, which is essentially like everyone is different. Right now, it sounds Super Cliche, but like we still tend to categorize people. Oh, this is this type of person, that is that type of person, but in reality the same person can, you know, show different tendencies and characteristics based on different types of pressure, that there's pressure situations they're put in, and so I like to remain dynamic, I tremain almond open minded, but also let people figure it out and beat themselves, but be themselves in the role right, not necessarily follow a formula, I would have the case maybe, and so I think that might have really really shaped my my management style. I love the I think like one of the things that, like style, flex seemed so huge and I think a lot of people sometimes, especially in sales, can get caught up with just the number and presenting a formula and like this is how to do it. Just repeat this for Pete this, repeat this. But everyone is different and people learn different and they have different...

...strengths, and so if you can help them understand like where their strings are, what they can lean into to dry their successes, and that's like a super powerful thing, especially from a leadership standpoint. Yeah, no, pretty for sure. And into that effect. You know, an example of that it is there times where, like I get, you know, messages from like strs and can executives, you know, my inbox. And again, going back to the formula that you know, we talked about, it all kind of feels and looks the same, right, and so there are a lot of times where, like these are good emails, right by standard, right, not the problem to me by standard. So I'll share these emails, you know, with my st as, my can executives and all that. Another look, this is a great email, it's well structured, but it's all more of the same, right. So, take the theme on making your own. How can you stand out right, and and again it's more so deviating from the Norman trying to make this yours. Yeah, I know that it's fantastic. So kind of talking a little bit more and deviating from the norm. How would you kind of say say that your style compares more so to a traditional leadership style? If somebody was looking to really implement this kind of more sits like style, flax scene type of mentality, as are looking to scale and bring up a team, what would be some things that you would recommend that they do to kind of almost get themselves out of the way so they're not stopping the growth? Yeah, I mean first and foremost, I mean I think this is a hot topic, right, but I think vulnerability, right like that from me, is probably the most important you know quality of manager can have, and I think that's something that's lacking in traditional, you know management. But vulnerability in a sense of overcommunicating, right, letting people know that you know, yes, you do appreciate their effort. Yes, things aren't perfect. Yes, sometimes it sucks right, it's and letting them know. You know, I often let my team know my, you know, struggles and my challenges in my role, right, so they understand when my decisions are coming from. The understand, you know, the bigger picture in a sense. Yeah, and aside from that,...

I mean obviously curiosity and human in humility, right, like you can't be ashamed to just one ask the question that you are meant to know, like meant to know, right, but you should always, always be asking those questions, especially as a sale leader. Sale leader one to make everyone feel included, because they should be. I'm into so you can grow, right, I am. I'm on my own journey as well, right, just at a different stage. Yeah, I know, I love that. So creating like the inclusive environment and then yet being vulnerable. I think that's something that a lot of people, and especially myself, struggle with because it's like how do you express that vulnerability? And it kind of takes me under the next thing around creating a space where it's actually okay to fail. So if you're being vulnerable and you're talking about your failures and kind of how you overcome them, that allows your team to have the space to fail. And know that it is okay because they're going to grow from him. Yeah, I'll tell you a quick funny like it's instant. Like in my sales interviews I tend to you know, like everyone in sales, and maybe everyone everyone's a rock star. Right. Everyone wants to talk about out you know how much revenue day a g they generated. I often don't even touch that, right. I often want to know more so about, you know, one's failures, you know what they're working on. I want to get to know someone for who they really are, because I feel like if you're not failing in your role, or if you haven't failed and you're not really doing your best, and so I tend to throw interview he's for a loop when I just tell them like look, I don't want to know what you've done, I want to know what you haven't done and and how you're trying to do that and do it better. Yeah, that's a great question. They're fantastic, but would you say you're like kin of some of the biggest challenges that you're going to have to overcome, especially in a hybrid work environment? I think I mean honestly, I think my struggles are pretty common I think hiring right now from me is a really, really big struggle. But more important that gets getting down to more of like a qualitative measure. I think team spirit, right, is something that is is more difficult to, you know,...

...grow and maintain, especially in a hybrid environment. We're not necessarily in the office full time. We tend to go with maybe one two days a week. Sometimes, you know, we don't going to the office at all, you know, for a couple of weeks. And so going back to like, you know, the team spirit aspect of this whole thing, I often ask myself like is it necessary, right, and this is something I'm actually working to my my own mind, especially in sales, right, because in reality sales is is a money driven profession. Right, and I notice is going to sound super contrarian, but I mean as an ae or as I as n str like you're on a team, but you don't get paid for, you know, what your team does. You get paid for what you do, right, but I dude, I do believe in togetherness as human beings and I do think that we're much, much better together, and so finding that balance right on how to accommodate, you know, the work life balance and the quality of life with allowing everyone to, you know, work from home and come in. You know, we're really come in, but still fostering that team spirit and togetherness is still somewhat of a challenge, but I think we got it. I think we we're doing pretty well with it. Good. Do you have any examples of ways that you guys have been able to make sure that, you know, the teams are talking? You's mentioned you guys have in New York office. You know, Salt Lake City office. So what are some of the things that you guys are doing to keep kind of that communication and Camaradi yes, I think I mean so. In reality, again, it goes back to just me leveraging my team's perspective, and so I'm always asking them for advice, always asking for their opinion, for their perspective, and so I actually know who's better at what right and so when I get a question, I'll say, Hey, go talk to this person. You know, you should actually talk to that person. Oh, he or she is definitely the expert. Right, I couldn't help you as much as they can. And so we create this this this web of like just information that's always, always transferring, and so when a new hire comes in, like on boarding is really an inclusive thing, like they talked to everyone on a team. Like, in a weird way, I...

...think I talked to that person the least out of everyone else, and so it's a really, really special thing. Yeah, that's that is awesome that you guys are able to still do that and kind of keep that communication going. So what's thank you so much for training to me your insights in your leadership style kind of how you transition from a non traditional background into a sales later that you are today. If anyone was looking to connect with you and wanted to chat about career progression or how you are going to take red points seeing over in status, where would be the best place for them to reach out to? Linkedin, obviously, can find me Linkedin by name Wesley Wesley. Last thing, you lease you, llys se, and that's my email address as well. Less see you leas at GMAILCOM. All right, fantastic. Well, you heard it here first, and thank you everyone for coming today. This was another episode of the sales engagement podcast. To help this get in front of more eyes and ears, please leave us a shining five star review. Join US at sales engagementcom for new episodes resources in the book on sales engagement. To get the most out of your sales engagement strategy, make sure to check out outreach. That ioh, the leading sales engagement platform. See you on the next episode.

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