EPISODE 382: Sales Management Expert Wesleyne Greer Offers Three Ways Sales Managers Can Become Leaders

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[EDITOR’S NOTE: This is a replay of the Women in Sales Webinar sponsored by the Institute for Excellence in Sales on June 19, 2021. It featured sales management expert Wesleyne Greer and was hosted by IES Women in Sales Program Director Gina Stracuzzi,]

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WESLEYNE’S TIP FOR EMERGING SALES LEADERS: “Manage up. When you’re trying to grow your career to get to the next step, when you’re trying to show your boss that you are the right person for this job, they need to know that you’re a strategic thinker, so stop being so much of a tactical manager and start being a strategic manager by managing up.”


Gina Stracuzzi: Wonderful. Wesleyne is going to be talking to us about helping sales managers who maybe are underperforming or struggling a bit to rise up to where they need to be. If maybe you’re a sales manager or you have sales managers that could use a little bit of help, this is a discussion for you. Wesleyne, why don’t you start us off with telling us a little bit about yourself and how you got to where you’re doing what you’re doing?

Wesleyne Greer: I always start with I’m a chemist by trade, and I spent many years in the petrochemical industry. I was always that curious chemists who was like, “There’s no one in the lab. Let me go walk around and talk to the salespeople.” Every time they would come back from being in the field, I was asking them questions about the customers they saw and why we were doing this and all of that.

I got into a sales role and I tell people, when I got into sales I finally figured out what I wanted to be when I grew up, because I loved everything about it. Because of my love and my passion, I read every book, went to every webinar, I did everything I could because I wanted to be good. That desire to really be good helped propel my career, because I made a very fast ascent from individual contributor to international sales manager.

The difference was when I became an international sales manager, all of that great training and all of those books and things that I had to become a good salesperson, they were nonexistent when I became a sales manager [laughs]. It was like, okay, go figure it out on your own. It was like drinking from a firehose.

I really figured out how to develop as a leader, as well as help my team hit quota every single month. A few years ago, I started my own company, Transformed Sales, and that’s really what we focus on. Building the leader up to build strong teams.

Gina Stracuzzi: That is awesome. What do you usually help people with the most when you go into their companies? What do you see are the biggest challenges they face? Are those the same biggest challenges that you encountered in your sales career?

Wesleyne Greer: The biggest challenge that I see is I call it being in the weeds. As sales managers, we’re always in the weeds, and we always find ourselves wanting to still close sales instead of manage our team strategically. That’s one of the biggest things, and that’s typically the first thing that we work on.

I help the sales managers, the leaders to realize that in order to grow their revenue, their region, their company, that they have to stop being so focused on every single deal that’s closing and think about the company, their team holistically.

Gina Stracuzzi: I would think that working directly with sales managers is a different beast than working with salespeople, because the sales manager is getting pressure from both sides. What do you find is the biggest roadblock for them in maybe even getting out of their own way, or letting that stress move away from them and figuring out a plan?

Wesleyne Greer: I love to say that sales managers are different, and they just love when I say that because they’re like, “Yes! We are different.” Because unlike a traditional manager, you have to worry about revenue, you have to worry about people that are not working in the office with you. Many times you have outside salespeople. Then you also have to worry about the illustrious managing up.

When you have all of those balls that you’re juggling, a lot of times sales managers, they focus on the one. They focus on, okay, I have to make my boss happy. Everything I do makes my boss happy and by making my boss happy, I’m making my team miserable. Or I’m only focused on what my team needs to succeed and I’m not thinking about the company.

Again, you have to step a couple levels out and take that view of, okay, this is actually what I need to focus on. I have to think about all of these things, and really putting in that plan of all of the different areas that you need to focus on.

Gina Stracuzzi: That makes a lot of sense. Let’s back up a little bit to you, and the biggest challenges that you faced in your career and how that led you to where you are today.

Wesleyne Greer: Within my career, there were two big challenges that I would say that I faced. One, me being a woman and one, me being a person of color. I’ll give you both experiences. The first one was when my now seven-year-old, I was pregnant with him. I was the first outside salesperson to ever get pregnant at this company, and this was in 2013.

This was not 1980 [laughs], just 2013. Because of that, they didn’t have any policies. Essentially when I went to HR and I said, “Hey, I’m pregnant. This is what’s happening.” They’re like, “Okay, great. Yes, congratulations. While you’re out on leave, you won’t get any commission for any orders that come in whether you’ve worked on them or not.”

I was like, “What? Okay, let’s back up a little bit.” My son was born in May and I was like, “You’re telling me I should not work for the next five months. I should just sit here and do nothing, because no matter what I do, if something comes in while I’m gone then I’m not going to get paid for it.” I had a long sales cycle.

This wasn’t a quick sale, this was a complex sale. Three to 18 months, so something that I worked on a year ago could just come in while I was gone. I really had to fight to get that policy changed. I was able to get them to understand how important it was for them if they wanted to attract and retain, because it’s not enough just to attract, you have to retain women.

You have to build an environment where they are actually able to say, yes, I can do this. I can have a family, I can still be a good salesperson. The policy was changed, or I should say was instituted and it was that, hey, if something comes in in your territory and you’re out on leave, you still get credit for it because you’ve still worked it, or you’re still going to have to work when you come back.

I am so proud because that year in 2014, I was number two in sales for the company. I tell people I was number one, because I was gone for six weeks. If I had back the time, I was number one in sales [laughs].

Gina Stracuzzi: I love it.

Wesleyne Greer: That was one challenge, and I think that because I had to stand up for myself and I really had to find my voice, that was the first time that I ever felt like, okay, I’m different. I always was like, “Okay, I’m a salesperson. I can go out there and as long as I can do what I need to do, fight, present, do good to discovery meetings, I’m okay.” But that was the first time I was like, “Okay, I’m different.”

Then another experience that I had was it was a Sunday night, and I was at a conference. Again, any salesperson, your weekends are valuable because you’re always on the road. I was at this conference, and we were in a group talking and there was a professor at a university here in Texas. I’ll just say that.

He looked at me and he said, “Back in those days, you wouldn’t have been allowed on campus. I don’t know if it’s because you’re a woman or because you’re black, but you wouldn’t have been allowed on campus.” I was like, “Huh? Seriously?” I was so taken aback, I didn’t even know what to say or how to react. Literally, I just excused myself from the conversation and I was like, “Yeah, I’m done. I’m going home to my family.”

The next day, I confronted him and I said, “Sir, one, you should be ashamed of yourself, because you have students in your class that look like me. For you to physically say that, that means that you have preconceived notions about them. Two, there was absolutely no reason for you to add that to your story. Your story still would have been perfectly fine.” I caught him all the way off guard, and I felt good because I stood up for myself.

Literally the next day, somebody reached out to me on LinkedIn and they said, “Hey, last night I saw you and I love the way that you handled that situation. I want to interview you for a job.” Again, all of these things that we deal with and it’s not what you do in the moment, it’s how you take the experience and grow from it. Those are the two things that I would say, within my career that have really helped me realize or strengthen who I am.

Gina Stracuzzi: That’s awesome, and good for you that you called him out on it. You went home and collected yourself, because if you’re anything like me, sometimes when I speak in the moment I say all the wrong things for the right reasons. By just taking a deep breath, I might have been better off.

Building on that, let’s talk a little bit about what you see in your clients, women sales managers particularly, that you think is both maybe let’s say a strength and something that trips them up a little bit because of situational preconceived notions, or outdated policies, whatever the case might be. How do you see women sales managers in different situations than men?

Wesleyne Greer: I really think it’s our passion. We’re so passionate about so many things, and that passion helps when you are out there and you’re in front of a customer and you’re trying to convince them that hey, this is the product you need. This is why you should buy from me. It also helps when you’re advocating for your sales people, like if there’s a policy or if there’s something that’s happening, you’re their internal advocate.

That passion hurts when sometimes you get so passionate about something and you have laser vision, and you don’t realize how that passion is affecting other things. You bark up this tree or you go down this train, and you forget everything else that’s around you. Again, like when I was talking about getting out of the weeds, the passion and the weeds collide. You’re so laser focused on something that a lot of times, everything else around you goes by the wayside.

Gina Stracuzzi: Okay, we have two questions. The first one is from Aya. She says, “I work for a niche startup and I am the company’s first sales manager. The biggest struggle for us is to prove ourselves to clients and in the industry. Which areas should we or should I be focusing on in this case? More on revenue or my team, or setting a strategy?”

Wesleyne Greer: Congratulations on your position as a first sales manager. Can you see my screen? I feel like this is just teed up for exactly what I have showing. I call this my three Ps. It’s people, process and profits. It doesn’t matter where you are in your journey, if you’re a brand-new sales manager or if you’ve been there for a long time. People are your number one asset.

People are internal and external so when we think about our team internally, we think about all of the players that we touch. All of our inside salespeople, outside salespeople, as well as the operations people that are fulfilling the orders. The finance people that we have to satisfy to ensure that we have the right terms.

All of those people, you have to ensure all of those players are working well. Then when you think about the external people, the players, it’s like who are our customers? Who is the ideal person that we should be speaking to? Let’s make sure that we’re focusing 100% of our time on the ideal buyer, the ideal person.

Once you have all of those pieces of people, then you move into your process. Once you have the right players on the team, it’s okay, now I know that this is the strong team that I need to succeed, but they need to know how to do their job. They need to know if we get an incoming web lead, what’s the first thing that they do? Do they pick up the phone and call them? Do they send them a LinkedIn message?

Then now we’re at a discovery meeting, so what are the questions I ask in a discovery meeting? How do I know that this person is qualified? That’s all about your sales process. Once you have the right people on the team, you build an actionable sales process, then the profits are going to come naturally. Really, profit is not something that I focus on.

As a sales coach, sales manager it’s like, “What? How do you not think about it?” I don’t, because have the right people on the bus, focus on the right people that are outside the bus. Build the process, and you’re going to win deals more times than you’re going to lose them.

Gina Stracuzzi: Great answer and great question. Thank you. Daniella would like to know, she starts with outstanding character, integrity. Pausing and collecting your thoughts and keeping the emotion from the moment out is always the best way to handle being blindsided by comments such as the one your professor made. No question, but just kudos. You’re absolutely right, Daniella.

Wesleyne Greer: Thank you, Daniella. Again, a lot of times women, we get dinged in a corporate realm for wearing our emotions on our sleeve, or being too quick to react, or all of these other things and preconceived notions that people put on us. But at the end of the day, I feel that we’re cultured to be the way that we want to be.

So because I had been in so many high pressure situations, because I had shown up to a customer that I’ve sold like a six-figure instrument to and he’s looking at me like, “You’re a woman? I thought this whole time I was emailing a man.” Those experiences teach you how to deal with the future experiences. Again, it helped me in my career because I know when to speak, and I know when not to speak.

When I was that international sales manager in the board meeting, and the only woman in the room in a board meeting and they were saying things that were absolutely ridiculous, I could just close my eyes, roll them internally, compose myself and then say what I wanted to say. Thank you.

Gina Stracuzzi: I love that roll them internally [laughs]. I have gotten better at that as I’ve gotten older, and it’s like when you and I were talking offline. The knowledge that we have now just wasn’t there 20 years ago. You were just left to hope it goes well, and a lot of times it didn’t go well. Companies lost really good people because of it, so it’s been a journey and we’re not done yet, but we’re certainly making progress.

Strong women leaders like yourself really make it possible, I think for other women to see themselves and to know it’s possible. To know that you can fit a pregnancy in there and still be a phenomenal salesperson. It’s what you allow yourself to think. You can come up with a solution like you did, as long as you’re really committed to what you’re doing.

Wesleyne Greer: I think that one thing is again, as women sometimes we feel that we don’t want to ask the questions, or maybe we don’t want to do something. I was very committed, and I know that I’m probably all over the world telling people this. I was very committed to ensuring that I nursed my son for a full 12 months. What did that mean?

That meant that I was going to see customers, I was doing demos. I was doing all of that stuff, and I would have my little black bag and I would ask my customer, I would say, “Where’s your Mothers’ Room?” Sometimes they would turn beet red and be like, “Oh, my goodness, I know what she’s talking about and I think I’ve seen that, but I don’t really know where it is. Do you want to go to the bathroom?”

“No, do you eat in the bathroom? No, I’m not making my baby’s food in the bathroom.” Again, it’s standing up for yourself and knowing that sometimes you’re going to ruffle feathers, but it’s okay because at the end of the day, your customers don’t have to be your friends. They need to respect you.

Your internal team players, yes, you do want to have a relationship with them, but at the end of the day you have to stand up for yourself. When you go to your manager and you ask your manager for something, or you ask a colleague, or somebody who’s in the same realm as you, stand up for yourself. Ask for what you need, and be firm if you know that this is going to help yourself or your team.

Gina Stracuzzi: That’s right. If somebody doesn’t respect you, that’s their problem, not yours. That is great advice. Daniella now has a question. I love this, Daniella. “How are you managing your team in these virtual times? Are you looking forward to in-person events? How do you network and connect and start those conversations with prospects while we’re still in the virtual world?” Great questions.

Wesleyne Greer: I love that. The first one is in the virtual world. I’ve always been a remote sales manager, so I’ve never actually been in the office with my sales team. This realm is actually no different, because I always had to find ways for us to connect virtually. For instance, when we would get on our team calls, the first 5, 10 minutes we would just have a lecture to blow the steam off.

Something happened internally, this person annoyed you, let’s just clear the air. Then everybody felt like we’re at the same space, and now let’s get to what we need to get to. Really I think that for me, it’s very natural to manage a team this way. I would say, I have this – maybe it’s not right, but I’m a chemist so I think about things like this.

I have these four quadrants that I use and literally I put my people in the quadrants. It is an effort versus revenue thing. The people who have high effort and high revenue, I just check on them every now and then. Offer my support, see if they need me but they’re doing what they need to succeed and they’re hitting their numbers so they’re good.

The people who have high effort but low revenue, they’re doing something, but it’s probably not the right things. That means we need to have more one-on-one coaching. I need to go into the CRM and physically see what they’re doing. Those low revenue, low effort people, it’s always, can I level them up or do I need to put them on an improvement plan so that I can get somebody who actually wants to be in here?

Really when I have my people plotted like that, that’s how I focus my time when I’m coaching with them. In terms of customers in the virtual realm, again, when I had my very first sales job, it was this ridiculous territory of I’m in Texas, and I covered all the way up to like the Dakotas. I wasn’t flying there all the time, so even that virtual selling 15 years ago was what I was doing.

Again, it was all about bringing the customers’ value. There was no Zoom there, there was no Teams, there was none of that. It was, “Hey, we’re about to do this webinar, or hey we have this white paper, can we get on a call? Let me talk you through it. Do you have something? Is there something you want see?” Really just being a resource to those clients, and I love getting out and talking to clients.

As you can see, I like to talk. Now that the world is opening up and I can do that, I make a very concerted effort. What I tell my team is you shouldn’t just go to a spot or a place just to see one person. That’s absolutely ridiculous. You need to have a full schedule, so really push them to look outside the box. If they have a hot prospect, who else around that area can they go call on while they’re there?

Who else may they be able to get an introduction to? Can they just stop and do a cold call? Is there an existing customer that hasn’t bought anything in 12 or 18 months? Really make them have a plan before they get out there, and they start calling on customers again in person. I think I answered all your questions. I’m not sure.

Gina Stracuzzi: I think you did. Something you said really leads me to another question, and this is something that we hear a lot too. As you mentioned, retention of good employees is so critical to success. It’s one of the tenets that IES is built on, is helping employers hire, retain, motivate and elevate top talent.

Let’s talk a little bit about what happens when you have some of those low-upper, low output, or even high effort and low output, and maybe they’re just not in the right job. What do you do when you find yourself in those situations?

Wesleyne Greer: The first thing you do is you stop and you ask yourself, have I done everything that I can to help this person succeed? If you cannot say yes, then you’re the problem. What I like to say is people don’t come ready made, they have to be developed. As their manager, or as I like my clients to call themselves, as their sales coach, it’s your job to understand the areas that they need help with.

Again, when you are going into the CRM or you’re sitting on a sales call with them, you should be writing notes. You should be saying, “Okay, this was really great. They did this but no, they didn’t ask this question. Why did they jump and pop open a presentation in the first call?” You have to really hone in and figure out what that individual needs to succeed, because that person doesn’t need the same thing as the next person.

The ones who you focus on are the high effort low-revenue, because they want to be good, they want to be excellent. They just need a little tweak here or a little tweak there. Once you’re able to tweak here or there, you’re able to really go exponential. When I work with clients and we focus on just that quadrant of sales people, they see so much growth.

They double their close rates just because they’re focusing there. Those people that have low effort, low-revenue, probably 75% or 80% of the time they have something going on personally. It’s your job as a sales manager to figure out what is happening in that person’s life that is causing them to not exert any effort, and to not care. That’s a salesperson that doesn’t care, and most salespeople care. They want to make money.

Peel back the onion, it’s not always about hitting numbers and revenue. Sometimes it’s about I’m going through a divorce, my child is sick. It’s about understanding what else. That person is a human being, so what does that human being need to succeed?

Gina Stracuzzi: That’s good advice. I was thinking about the seven mistakes you have written about, the seven mistakes that sales managers make. I would think that that is probably right up there at the top of not finding out what it is they need to succeed.

Wesleyne Greer: Absolutely. One of the biggest mistakes that sales managers make is having – I guess there are a couple mistakes. One is thinking that everybody is the same. That’s one of the biggest mistakes. Another mistake is thinking that what you did to be successful is going to work for everybody on your team.

Another mistake is not remembering that salespeople are people too. We like to make money and we like to drive revenue, and we like to negotiate and do all of those things, but we’re human beings. As a human being, we have feelings, we have personal things going on. I had somebody who I was working with recently, and this person was in the President’s Club for the last three years.

Last year and this year, had like 30% or 40% of budget. I have a client go and just take the employee out to play golf. He likes to play golf, and what he found out was he was experiencing some medical challenges. Not just him personally, but also his mom was sick, he had a child that was sick. That was weighing on him, so he couldn’t be fully focused at work.

What the manager did was they came up with a plan. He asked him, “How can I best support you?” Because at the end of the day you’re the coach. I need to support my people. That is the single most important thing for you to be as a sales manager. It is to be an advocate for everyone on your team. That is your job.

Gina Stracuzzi: Absolutely. It has never been more critical than it was over the last 15 months. I would tell people too that when they were asking, what advice do most women sales leaders have for how companies can help their employees? I’m like, you can’t just say you’re here. Say, “What do you need? What can I do for you?”

If you say, “Just let me know if you need something.” They’re not going to tell you, so you have to get them that open. That is amazing advice. Let’s talk about some of the biggest things that you like to tell your clients as sales managers that they can do to help themselves and their people outside of asking, what do you need to be supported?

Wesleyne Greer: One thing that is very important for a sales leader to realize is that your team is a reflection of you. If your team is failing, you’re failing. If your team is winning, you’re winning. When your boss comes to you and says, “Okay, you guys didn’t hit quota.” You don’t say, “Well, Mary didn’t hit quota and Sam didn’t hit quota but these people did, so we’re doing okay.” No, you say that as a leader, I failed.

Other than really helping each and every person on your team set personal goals, it is important to ensure that you are actively coaching them. What does active coaching mean? Active coaching means not random acts of coaching, not you lost five deals or you didn’t hit your quota this month. It is we have a time on the calendar, and we are working through the areas that I’ve identified as your leader that you need help with.

Whether that’s prospecting, whether that’s conducting effective discovery meetings, that’s your job as a leader. Do ride-alongs. You can still do a ride-along in a virtual environment. Just hop on a Zoom call with them, or hop on the conference call. Your job, you should not be the boss. Please don’t be the boss. Please don’t talk. You can even introduce yourself as the intern, diminish yourself.

You need your salesperson to be elevated, and your job is to just sit back and take notes. You can actually give them feedback on, you did these things really well, but these three things are what we’re going to work on. Then the next call that you do with them, the next ride along you can see how they’ve improved and they feel like okay, my boss, my manager is in my corner. They want me to succeed, not because I have to hit this $5 million target. They want me to succeed because they care about me as a person.

Gina Stracuzzi: One of the things that we like to do when we close out the webcast and podcast is to ask our guests to give the listeners one piece of advice they can put into action today to start improving their situation. In your case a sales manager, or their team’s outlook.

Wesleyne Greer: I would say the one piece of advice that I would give is to manage up. I recently spoke to someone and they have this growth goal, in 24 months they need to grow a company by 5X. They’re adding so many people to the team, but only 10% of the people they’re adding are salespeople.

I said, I need you to go to your boss and say, “Does it make sense that 10% of the company is generating 100% of the revenue? Does that even make sense to you?” That is what’s called managing up. That is helping your boss know I’m thinking about this strategically. I’m not just thinking about each order that comes in, I’m thinking about the company and what is best for the company.

You manage up by letting your boss know that I understand the vision, but I don’t have the resources I need to succeed. If you want us to grow 5X in this amount of time, this is what I need. Don’t just think about your team and get in the weeds of the numbers and the quotas, and the phone calls, and all of those little things. Let your boss know what you’re actually doing to help your team succeed.

At the end of the day when you’re trying to grow your career to get to the next step, when you’re trying to show your boss that I am the right person for this job, that’s what they need to know. They need to know that you’re a strategic thinker, so stop being so much of a tactical manager and start being a strategic manager by managing up.

Gina Stracuzzi: Phenomenal advice. I really have enjoyed this conversation. I’ve learned a lot about being a sales manager, and what it really means to be a good one. Thank you so very much for your time, and I hope you’ll come back and see us and we can hit another topic. I have to ask before we go, what is that “take it” behind you?

Wesleyne Greer: It says take it easy, because we’re high-strung. Salespeople are always high-strung, so take it easy.

Gina Stracuzzi: Thank you again, Wesleyne, and thank you everyone who participated. We will see you next week.

Transcribed by Mariana Badillo

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