PODCAST 122: Tips for Building a Diverse Team of High-Quality Salespeople with Wesley Ulysse

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This week on the Sales Hacker podcast, we speak with Wes Ulysse, Head of Sales, North America at Red Points, a SaaS company that’s leveraging AI and machine learning to protect brands’ online intellectual property.

Wes started his professional career as an accountant for the New York City Ballet. After four years, he didn’t like being stuck behind a desk, so he moved into SaaS. Wes started his career at Sisense, becoming head of enterprise business development and ultimately director of inside sales for North America. As of January 2019, he moved on to leading the US sales team at Red Points.

If you missed episode 121, check it out here: Lessons From Survival Mode: How to Kickstart Your Business with Matt Rizzetta

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Show Agenda and Timestamps

  1. Show Introduction [00:04]
  2. Who is Wes Ulysse and what is Red Points [1:30]
  3. Qualities that lead to success in sales [8:25]
  4. Unexpected realities of sales leadership [11:06]
  5. The biggest mistake new managers make [14:36]
  6. How to drive diversity [15:20]
  7. Sam’s Corner [29:15]

Show Introduction [00:04]

Sam Jacobs: Hey everybody, it’s Sam Jacobs. Welcome to the Sales Hacker Podcast. Today on the show we’ve got Wes Ulysse, the head of sales North America for a company called Red Points. This company is approaching the $20 million range, and our conversation is really about starting a career in a different profession. Wes actually began as an accountant, so we talk about how you move into sales and the key qualities for success both as an individual contributor and as a leader. Wes is a fantastic guy and also a great member of Revenue Collective.

Now, before we get there, we want to thank our sponsor. Our sponsor for this episode is a company called Outreach. Outreach revolutionizes customer engagement, by moving away from siloed conversations, to a streamlined and customer centric journey, leveraging the next generation of artificial intelligence. The platform allows sales reps to deliver consistent, relevant and responsible communication for each prospect every time, enabling personalization at scale previously unthinkable.

Now, without further ado, let’s listen to this interview with Wes Ulysse.

Who is Wes Ulysse and what is Red Points [1:30]

Sam Jacobs: Hey everybody, it’s Sam Jacobs. Welcome to the Sales Hacker podcast. Today on the show we’ve got Wes Ulysse and we’re going to be talking about a lot of different things, but first, let me give you his bio. Wes started his professional career as an accountant for the New York City Ballet. After four years, he didn’t like being stuck behind a desk and so he moved into SaaS and he started his career at Sisense as an SDR, promoted to manager, then to head of enterprise business development and ultimately director of inside sales for North America. As of January 2019, he’s moved on to leading the US sales team at Red Points, a SaaS company leveraging AI and machine learning to protect brands’ online intellectual property.

He also created a company called Upper Hand. The mission of that is to mentor and develop sales people of color while being a hiring resource to SaaS companies hoping to build a more diverse sales team, which we all know is an important initiative. Wes, welcome to the show.

Wes Ulysse: Thanks for having me.

Sam Jacobs: We’d like to understand a little bit about you and contextualize your expertise. You’re head of sales, North America for Red Points. What does Red Point do?

Wes Ulysse: We leverage AI and machine learning to take down counterfeits. A lot of times, we’re searching eBay, Amazon, Alibaba and it’s littered with counterfeits. And so we’re using a combination of what I mentioned before and image recognition to not only find them, but to remove them as well.

Sam Jacobs: Is this counterfeit like a fake Louis Vuitton bag or Chanel bag? Is it fake luxury? Or are there other types of counterfeits that you’re focused on?

Wes Ulysse: Yeah, you hit the nail on the head.

Sam Jacobs: How big is the company? What’s the background? How many employees?

Wes Ulysse: We’re just under 300 employees globally, three offices worldwide, one in New York, one in Barcelona, one in Salt Lake City. We’re actually just opening an office in China as well. We’re about 10 to 15 million ARR right now and still growing. Our most recent level of funding was about 38 million, which was last August. All systems go.

Sam Jacobs: I’d love to learn more about what you’re doing at Red Points, but before we get there, you mentioned, and I was reading your bio that you were originally a CPA, but what’s your background? Where are you from? Where’d you grow up? And walk us through the journey because it is pretty interesting. Love to hear it in your words, this idea that you started off as an accountant for the New York City Ballet and now you’re running a global sales team. How did that all happen? Walk us through the background.

Wes Ulysse: Love to. Originally, I’m born and raised in New York, Brooklyn specifically. Come from an immigrant background. And so my parents always said, “Look, you got to be a doctor or a lawyer or a businessman.” And they didn’t really know what a businessman was, but just someone who would just tuck in a suit and a briefcase and went to work and made a lot of money. I then went to St. John’s university, double majoring in finance and economics. And I thought to myself, I’m going to be a businessman, whatever that was. Stumbled into accounting. A friend of mine, there was a job opening and she was just like, “Hey look, I think you’re a great fit. You’re super smart, you’re great with numbers.” That was history. Did that for about four years and I was extremely unhappy. And so one day I went to Rosa Mexicano, had a couple of margaritas and never went back to work. And that was the beginning of my sales career ironically.

Sam Jacobs: How did you figure out that that finance and accounting was not for you? And what was it about those margaritas at Rosa Mexicano that led you to that decision?

Wes Ulysse: Well, we know why the margaritas hit, but more specifically, it was I did a lot of soul searching around that time. Though at the time I didn’t find anything. I just knew that it was, like you said earlier, the lack of interaction. Just project based assignment for me was just not necessarily a thing. I needed a little bit more. I needed a more dynamic environment, something changing and truth be told I needed pressure. I’m someone historically who has thrived under pressure. I perform, I’d like to think at my best under pressure. And so naturally sales are the right fit for me. Which is interesting. I never knew what sales was growing up. And I’d like to tell you a quick story about my background, but my friends would always tell me, “Look, Hey, you need to get in sales. You’re going to be awesome in sales.”

Now I had no idea what sales was. I thought to myself, wow, my friends are insulting me. They’re telling me to go sell shoes at the mall or something like that. I hadn’t been exposed to SaaS, to know what they were talking about. And so once I became exposed to SaaS, I started to realize, wow, this is my calling. This is what I enjoy doing and this is what I want to do. Which ultimately filters into the larger conversation. Which is why there is such a lack of diversity in sales in my opinion, it’s exposure. But I guess we’ll touch on that a little bit later.

Sam Jacobs: How did you develop that awareness? What did you do to find that job? And how is it a model perhaps for other folks that don’t have the same perspective or the same background to your point that don’t even know what sales is and think that sales means selling shoes in a mall? Which by the way is also an honorable profession But just not all of what sales is.

Wes Ulysse: To be honest with you, Sam, I got lucky. A good friend of mine, who is not a person of color, kept telling me, “Hey, you need to come over and interview at my company. I think you’d be a great fit.” I resisted for a little while because I was making a decent salary, but I gave it a shot. I interviewed. I tanked the interview, by the way. I remember my current mentor, Natasha Shiffrin, was a hiring manager at the time. She asked me, “Why do I think I’d be good at sales?” And I think my reply to her was, “I’m able to finesse my friends into making crazy trades in my fantasy football team.”

Sam Jacobs: Very sadly, that’s also a very gender specific example. She didn’t play fantasy football, might not really know what you’re talking about.

Wes Ulysse: What I do remember is the crazy look she gave me and thought that this kid is either a genius or a fool. Look, I ended up getting hired and I broke a couple of records from the SDR team into the sales. And so it was again, that was where it all started.

Qualities that lead to success in sales [8:25]

Sam Jacobs: What did you do to be successful when you started as an SDR? When you think about the qualities, because you’ve risen up through the ranks and you’re running a big team now, what is it that you think, because you obviously didn’t go to school for sales. What were the qualities that made you successful, particularly in your first role?

Wes Ulysse: Good question. I’m going to sound super cliche right now, but the ability to adapt. That goes into what people call, I guess, street smarts. I think it’s predominant in those who grew up in inner cities. We talk about street smarts, but we don’t actually really define it or quantify it of any sorts. But in my opinion, I think it’s the ability to observe, interpret and make a decision, an informed decision, all in a split second. And that decision is effective and productive. And so that’s essentially, what I attribute my “success” to — just being able to adapt. Not necessarily knowing the product at first. I remember, I didn’t know what the hell I was talking about. But, I kind of knew how to adapt on the phone calls. I knew how to handle objections just based on logic. And that’s just all, truth be told, street smarts.

Sam Jacobs: I think the other part of that phrase street smarts is also a more sophisticated understanding of human nature. You understand people and whether or not frankly they’re lying or telling the truth. Do you think that had something to do with your ability to handle objections potentially?

Wes Ulysse: One of my favorite books is Between the World and Me by Ta-Nehisi Coates. And he talks about a duality of mind, where, as for instance, I’ll give you an example. Growing up, I had a new bike and I would ride my bike up and down Flatbush. And I knew a group of older guys around the corner and they said, “Hey, nice bike.” In my mind, I knew exactly what that meant.

Sam Jacobs: That means give me your bike?

Wes Ulysse: No, that means, what’s going to happen is, oh, I’m going to say thank you. They’re going to ask me where I got it from. One of them is going to ask me for a ride and if I give that bike up, I’m never going to see it again. And so, as a ten-year-old, you have to process that information and then quickly find an exit route before anything happens. And so you take that muscle and you continue to exercise it, but you also continue to educate the person and expose that person to different industries and professions. And you have this experience, this unique set of skills that lends itself to sales in particular.

Unexpected realities of sales leadership [11:06]

Sam Jacobs: What surprised you about the job when you first took it on that maybe you weren’t expecting? Was it how good you are naturally at it? Or, what were the other things that came out to you?

Wes Ulysse: I think how easy the art of sales was. By no means do I think sales is easy, but I think that the difficult part in sales is not necessarily the technique. Because it’s just knowing how to take cues and respond to cues. If I say this at this time, if I hear this, then my prospect should in theory, react in a certain way, which will ultimately lead to a sale. But I think the most difficult is just the emotional and the mental toll that it takes. I don’t know many people that can make 50 phone calls and hear 50 no’s and make 50 more and maybe get one yes and make that 101st phone call with the same perceived competence that they made the first one. And so for me, that’s what surprised me, just how tiring it is.

Sam Jacobs: What did you do to overcome that? Or how do you handle that? How did you process that during the day?

Wes Ulysse: Pride. It was just pride. I couldn’t be last. I knew I was too junior to be first, but I damn sure knew I couldn’t be last. And so that fire just continued to grow and grow. And look, all credit to my dad. He’s not the most emotionally available person growing up. And so I remember getting hurt or losing a basketball game or whatever it may be. He would just look at me and say, “So what? You’re just going to just not do it again?” And for some reason as a child, that just didn’t seem like an option to me. It just sounded crazy. And so I continued to channel that in all of my challenges.

Sam Jacobs: Yeah. The pluses and the minuses of a father figure like the one you just described, but work ethic is a great thing. What was it? You started off as a BDR and then eventually if I’m not mistaken, promoted to be a manager and ultimately director of inside sales for all of North America. Which I imagine must be a pretty large team. So many people want to move from being an individual contributor to being a manager. I always ask that question, what didn’t you expect? What was surprising about being a manager? And what do you think the skills or what do you focus on in order to be great as a manager that may be subtly different from being a great individual contributor?

Wes Ulysse: Actually, I think they’re quite similar, in a sense where I firmly believe that you just got to be yourself. If you’re well informed in yourself and you’re authentic, what you believe is right, chances are, will be right. Again, I’m not sure if you were looking for a lot more elaborative of an answer, but to me, it’s pretty simple. If I feel something is right, I’m going to trust my gut, I trust my instincts. Again, my instinct is backed by some history and knowledge. And so I’m just to go ahead and take risks and do it. And so the fundamental difference between, I guess, like you mentioned being a manager and an individual contributor is the level of risk that you take, in my opinion. I think as an individual contributor, I take a lot more risk, well I took a lot more risk. As a manager, I don’t take as much risk because I know for a fact, my team depends on my sound decision making in order to help make them successful.

The biggest mistake new managers make [14:36]

Sam Jacobs: What do you think the biggest mistakes people are when they get promoted to manager?

Wes Ulysse: They think they know it all. They definitely think they know it all. Look, a lot of times you’d be surprised. As you know, in sales, the top performer is typically promoted into the manager. And a lot of times that top performer is not necessarily qualified immediately to be a manager, just because you just know how to sell doesn’t mean you know how to coach. And so I think the trap that a lot of first time managers fall into is just stepping into the position and thinking that they are the position and they know it all. It takes a very humble manager to understand that you’ll learn a lot more from your team than you will being an individual contributor and thinking that you know it all for sure.

How to drive diversity [15:20]

Sam Jacobs: Well, let’s talk about Upper Hand a little bit. You created this company, tell us about it, tell us what it does. Tell us the mission. And we can use that to have a different conversation as well. But tell us what is Upper Hand?

Wes Ulysse: Upper Hand is a combination between a fellowship and a recruiting company. And so my goal is to essentially find the other Weses that are out there. Those who have the raw skill, the natural talent, but just haven’t really been exposed to the world of SaaS. And so, I felt that it’s my job to find myself in others and not only give them the exposure, but also put them through a six-week free fellowship. Teach them the SDR role from beginning to end. I have some instructors, some known people out there within the sales community, come in and run courses out for those six weeks to prepare them for the challenges ahead. But also partner with some tech companies within the states and help place those fellows into some roles. That’s essentially what the mission is. That’s why I’m doing it. And yeah, so far, it’s just about launched. I plan on launching next week and look, I think it’s going to be an amazing thing. We need a lot more, obviously diversity but more importantly, we need to be exposed. And we need to expose others.

Sam Jacobs: When you think about driving diversity, there’s again, some people say that there’s a “pipeline problem,” which is not enough candidates of color in order to fill all of the open roles. You could agree or disagree with that statement. And then also if it’s at least partially true, you’re talking about exposure. My question is always, where does Upper Hand seek to start? Is it at the college level? Is it going to St John’s or even going to HBCUs, going to places like Howard? Or is it even earlier in high school? When do you think the education needs to happen that there are careers that extend beyond whatever’s being presented to underrepresented or underprivileged children?

Wes Ulysse: I think that needs to happen from elementary school. We just need to know our options as a people, as a community. But Upper Hand is really targeting not only the college students that are fresh out, but those who have work experience like I did, but haven’t really gotten into sales or don’t really know what SaaS is. Need some training, basic training, obviously but would like to get into sales. There’s no real starting point, but again, in terms of exposure, I think we need to expose everyone to this industry from as soon as possible, young.

Sam Jacobs: When you think about truly achieving diversity in tech sales, is this the basic idea? Just try to tell more people about it? Or is there a bigger idea that you want people to know about?

Wes Ulysse: The bigger idea is just the tech industry is evolving on a daily basis. And with anything, if you have too much of the same thing, you’re not necessarily going to be able to keep up with that type of evolution. And so I think the bigger picture here is, how can we accelerate the evolution of tech with diverse mindsets, with diverse opinions? And that’s where obviously that’s where it starts. But then that’s where I’m aiming for. And so again, it’s for me, it’s all about the exposure, on both sides, because even those who know about SaaS, who know what SaaS is, they tend to join a company and it’s not necessarily what you think it may be. All too often, what you see and what you hear during the interview process is not what you’ve actually experienced. And so when I say exposure, there is a level of authenticity that I do, I would like to see from companies as well within that process.

Sam Jacobs: When you think about the companies you’ve worked at, or heard about that have done, not just a good job on hiring for diversity, but making sure that the people that they hire feel included and that they stay and that they have some longevity. What do you think the keys are to driving that within an organization? So that if you’re joining as a new team lead, CRO, whatever the roles that you’re interviewing, that you feel like this is a place I want to work for three, four, five years. What is it that folks like me need to make sure we understand?

Wes Ulysse: Well, I’ll be honest with you, Sam. It starts from the resume screening, and it’s hard work. It’s a lot of work. For example, it’s going to require not necessarily looking for the cookie cutter salesperson. If someone looked at my resume and thought to themselves, “That’s an accountant. He has no business in sales,” they don’t know until they’ve actually met me. And so from the interview level, it’s going to require open mindedness. But more importantly, once you bring diversity candidates into your organization and into your family, it’s going to require patience and an extra level of communication. And just open mindedness in that sense, because these are people who are coming from totally different backgrounds, speaking to different types of people on a daily basis.

And so the level of communication that it’s going to require a level of patience to develop a cadence between those two people and that team is going to be major. And so again, I use myself as an example. My first two months into Sisense, I was on a plan. And I had a really candid conversation with my manager at the time. And she flat out told me, “Hey, pretty much got a couple of weeks before we have to have an unpleasant conversation.” And I just told her, “Look, just I’ll figure it out.” And when I started to have real honest conversations with those around me and really saw my team lend itself and be a lot more patient with me, that’s when I realized that that’s what it’s about. It’s communication. And if you don’t know how to communicate with those who don’t necessarily look like you, then we’re never really going to be successful.

Sam Jacobs: What do you think the keys to that are? Is it just over communication? I’m just interested in this fact that you went from being on a plan to a top performer., which frankly happens a lot. But is it that you felt too self conscious to ask for help? Is that part of it? Or was it that they weren’t communicating enough what the objectives of the job were? Or how to be successful at the job? What do you think the specific communication gaps were?

Wes Ulysse: It was a combination of all of that, actually. I had a conversation with my team lead at the time and he asked me, “Look like what’s stopping you? Why aren’t you asking me questions that I clearly see as you need help with?” And I’m saying, “Look, I don’t feel comfortable because every time I’ll ask a question, I get this type of response. And I’ll try to ask the question in a different way and I’ll get the same response.” And so there’s a roadblock there, which is why I remember when my manager told me that I’ll be on a plan and I got two weeks. I told her to leave me be and I’ll figure it out.

And then I started to become more vulnerable with my peers and I heard the same answer in different ways. And then it clicked. And then I had a conversation with my manager and said, “Hey look, this is some feedback for you. I’ve asked the same question to my peers and my colleagues in different ways and I’ve gotten these different answers and this is how I communicate.” And honestly, that worked wonders. We had that conversation. It actually got pretty deep into my background and her background. And we found some common ground. And once the line of communication was clear, it was all systems go.

Sam Jacobs: Wow. I’m really glad to hear that. And so, just making sure we get it right because there’s folks listening. If we think about first, there needs to be a focus and an emphasis on just education and exposure to communities that might not be aware of SaaS, starting as early as possible. And then it’s really about presenting sales as an option, even to people that are out of school, but in different careers. And then it’s about communication and over communication and making sure that people feel safe enough because that’s sort of what you said, but tell me if I’m wrong, safe enough to ask those questions and to be vulnerable so that you don’t feel like you have to carry the shoulder of the only person of color on the team and that pressure of making sure you succeed, but just can be another teammate that asks for help and gets it. Does that sound accurate to you? Am I missing something?

Wes Ulysse: You hit the nail on the head.

Sam Jacobs: When you think about sales in general, what’s working these days for your team when you think about outreach? When you think about being an SDR, BDR? What have you seen, particularly as COVID has happened, in terms of the effectiveness of different strategies?

Wes Ulysse: Honestly the same thing that’s been working, but just right now, it’s just magnified. Just creativity. What I tell my SDRs is, your prospect is getting messaged and called by multiple SDRs across multiple different industries. And to some extent they all sound the same. Pitch to the person and not necessarily the company and try to stand out. And so when I get SDR emails, I tend to forward them to my team on a weekly or a monthly basis. The exercise is, well, what’s the common denominator between all of these emails that I’ve sent you? And now the next exercise is how do you plan on being creative and standing out?

And so I think right now, more than ever, because of COVID, the market right now is ripe for creativity, ripe for innovation. And everyone’s kind of finding their own voice. Being at home by themselves, working, going through their frustrations by themselves. It’s not the same when you’re in the office, with your team. And so I think a lot of people are finding their voices and more than ever, I think more people are being a lot more creative with their messaging. I think that’s yielding some solid fruit.

Sam Jacobs: How’s Red Points doing through the crisis?

Wes Ulysse: Great. Look honestly, we pivoted right into industries and verticals that are doing well, during this time. Those who are focused on bolstering the eCommerce business and such. And so I’m happy to say in the last quarter, we’ve seen an increase in sales. And so we’re doing pretty well right now. We’re doing pretty well.

Sam Jacobs: Awesome. That’s great. Last question, sort of related to the fact, to Upper Hand and to everything that’s going on in the world and the country, not just around COVID, but around racial equality and racial justice, what role do you think companies have as public speakers in this moment? And do you think private companies have a responsibility to speak out in support of Black Lives Matter and other movements? Or do you think that it’s really just about individual citizens? What’s your perspective as somebody working for a company and thinking about these issues, particularly as you’re starting Upper Hand?

Wes Ulysse: I think we all have a responsibility. From the individual to the company, how that manifests is different for all of us. For instance, I’m not as outspoken when it comes to the Black Lives Matter thing or movement, Upper Hand is my way of contributing and doing my part. And so when it comes to a company, I’m okay with a company not taking a stance on social media, as long as the work is being done behind the scenes. And to be honest, that transpires in an individual as well. I’m not again, me personally, I don’t care how outspoken one is, as long as the work is being done in some form or way.

Sam Jacobs: Wes, we’re about at the end of our time together, but one of the things we like to do is sort of pay it forward at the end and share some of your inspiration, some of your mentors, you mentioned a few of them, but it’d be good to hear them again. But what are some books that you’ve read? What are some pieces of content? What are some people that have had a huge influence on you? Remind us so that we can seek them out on LinkedIn or read the book or whatever it may be.

Wes Ulysse: Look, my first SDR director, my mentor Natasha Shiffrin, she’s been instrumental in me building a career for myself. Look, as salespeople, we always talk about going back to basics and she’s literally I hear her voice when I say that. Whenever I go awry, or start messing up, back to basics. And so she again, she’s one of my mentors and she’s been instrumental. And in terms of the book, like I mentioned earlier, it’s called Between the World and Me, it’s written by Ta-Nehisi Coates. It’s incredible. It’s not only a book for people of color, but it’s a book for everyone. I’d like to think that it’s a translator in a sense. Where those who are not of the same background as myself and those that don’t look like me can get a snapshot into how I grew up and how inner city kids grew up. And so it’s a really, really, really insightful book.

Sam Jacobs: He’s an incredible writer and an incredible speaker. Hopefully some folks will check that out. Wes, if folks are listening and they want to get in touch with you, maybe they want to apply to Upper Hand. Maybe they just want you as a mentor, or maybe they just want to reach out and make a connection, what’s the best way to reach you when you think about getting contacted?

Wes Ulysse: I’ll put my personal email out there. It’s a wesleyulysse@gmail.com. Incredibly open to obviously connecting and always learning and sharing what I’ve learned throughout my journey and those who want to get in contact with me regarding Upper Hand, it’s a wes@havetheupperhand.com.

Sam’s Corner [29:15]

Sam Jacobs: Hey everybody. It’s Sam’s Corner. I really love that conversation with Wes Ulysse. The big thing that came out of that for me was, you really can come to sales from almost any kind of background provided that you have the mental composition and the fortitude necessary to commit yourself to the profession. Wes started off as an accountant for the New York City Ballet and started at the bottom. He started his career as an SDR at Sisense, ultimately was promoted and is now running a large team. And I think that that perseverance and that commitment is emblematic of people that really have a goal, set a goal and work hard to achieve it. Thought that conversation was great. And I also just really think a lot of the things that Wesley’s doing around Upper Hand, mentoring and developing sales people of color is a fantastic initiative.

There’s a lot of these different types of companies that are helping bring people of color into the technology sales profession and I’m hugely supportive of that. I think there’s an opportunity for entry level folks, but there are also an incredible number of outstanding, exceptional executives of color that we also need to be thinking about, not just bringing people in at the very bottom, but also bringing in through middle management and through the executive ranks. Regardless, I really like that conversation.

Don’t miss episode #123

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If you want to reach me, you can linkedin.com/in/samfjacobs. I’ll do my best to get back to you in a timely way.

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