Episode 21 Edited
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[00:00:00] Richard Ellis: Hiring the right sales talent is one of the biggest challenges for business leaders. 52% of sales leaders say recruiting and hiring strong salespeople is very difficult, and for good reason only 16% of new sales hires are considered long-term successes. The consequences of a bad hire are costly.
[00:00:19] Richard Ellis: Replacing an underperforming salesperson can cost upwards of $115,000. But when you get it right, a strong sales team doesn't just hit quota. It builds lasting customer relationships that can drive 2.3 times higher revenue for a company.
[00:00:40] Richard Ellis: Welcome to some goodness where we engage seasoned business leaders and experts to share practical guidance and tips to help new and future seed level leaders maximize their impact. My guest today is David Wolf, an executive recruiter with over 24 years of experience helping technology and software companies build high performing sales and support teams [00:01:00] across the nation as an executive recruiter, att.
[00:01:04] Richard Ellis: David has worked with senior executives to identify and attract top sales talent consistently exceeding client expectations. His deep understanding of what makes a great sales hire and where companies often go wrong makes him the perfect person to help us navigate today's conversation. David, welcome to the show.
[00:01:22] Richard Ellis: Thanks, Richard. Thanks for having
[00:01:23] David Wolf: me.
[00:01:24] Richard Ellis: Yeah, so we've worked together for the past year or so. I know you've worked with some of my mentors and leaders and sponsors over the years, and I'd love to just spend some time digging into everything about building a great sales team. If that sounds good to you. I.
[00:01:39] David Wolf: Oh, I love it. 'cause that's what I do for a living.
[00:01:41] Richard Ellis: Yeah, absolutely. And so we're looking forward to just gleaning some insight from you and sharing with perspective and current leaders out there that have to build their own sales teams. And one of the things you mentioned to me is it's not easy, right?
[00:01:54] Richard Ellis: Building a great sales team is hard. And so when you think about hiring top sales talent and [00:02:00] the difficulty of that, why is it today difficult to get that right?
[00:02:03] David Wolf: Well, things are more complicated today, especially now with the remote employees. You don't have that togetherness. You don't have the kickoff meeting in person.
[00:02:11] David Wolf: You don't have quarterly get togethers. Remote learning's, very difficult, especially for young salespeople, and I know a lot of them that are 32, 33 years old, they get hired. They never go visit corporate headquarters. They're reading documents and it takes them three or four times longer to get what they're supposed to get while they have a quota that's ticking on.
[00:02:31] David Wolf: So the thing to do is to start with the end in mind, like as usual. Yeah. Start with what do you want to have accomplished? What are your goals as a company, and how does that break down to the individual contributors? Okay. And once you understand that, then you can start building the job description. From that.
[00:02:46] David Wolf: You have to understand the culture, the products. Are we new? Are we existent? Are we a mid-enterprise company? Are we already there And we just growing? I mean, these are all criteria that you wanna understand so that when you start looking at potential candidates, [00:03:00] you know what you're looking for. And especially in today's world, we don't have the ground that we had years ago of training people and they finally came out of Xerox or IBM or ca even.
[00:03:10] David Wolf: That have honed these guys, they spend their first five or six years basically as a trainee. Mm-hmm. Inhouse. And then they leave to go to more exciting opportunities. So now we're getting people without that kind of a background, and we have to teach them while they're producing. Right. And they need more handholding, they need a better relationship with the hiring manager and the sales managers.
[00:03:31] David Wolf: And oftentimes the VP of sales of Say, for North America is remote from the actual recruiting process. I mean, he talks to his managers, he talks to the talent acquisition team, or typically a lot of young people who are just doing word searches on resumes. Right? And as you know, in the marketplace today, when you see a job description posted on LinkedIn, there's a hundred applicants.
[00:03:51] David Wolf: I know they don't go through a hundred applicants. You know, after 220 they're going, oh, I'm just gonna settle for the shiniest star right now. And they give up because they [00:04:00] don't really know what they're looking for and it's probably very frustrating for them.
[00:04:03] Richard Ellis: Right. Well you mentioned just kind of the new world that we live in, and I do see across the clients we serve that there's not always a robust.
[00:04:11] Richard Ellis: Full onboarding program with a two to four week bootcamp, like the old days of IBM and Xerox, et cetera. And so because you don't have that to lean on to bring just anybody in, I think that probably requires that you look for some specific traits in a salesperson that's gonna be. More Okay with some murkiness in that onboarding process and maybe just kind of having the personality that fits well with jumping in the fire before you know everything.
[00:04:42] Richard Ellis: Right. And so tell me a little bit about what are some of those characteristics you look for in a top seller today that can jump in without having all of the ducks in a row in terms of an onboarding process.
[00:04:54] David Wolf: When I look at profiles on LinkedIn, let's face it, everybody's on LinkedIn in our industry, right?
[00:04:59] David Wolf: Our most industries, [00:05:00] I look at the top presentation that they make, the picture they put on there, their comments. I then go down to the bottom. To see their educational background, their activities, sports-wise, I like athletes. I like people who've competed. I like people who like to win and who know how to get up after you've lost a game.
[00:05:16] David Wolf: Like in March Madness yesterday, Texas lost a buzzer beater and you get up and do it again. So resilience is the number one issue. Resilience. Resilience. Resilience. And I want people who feel good about what they're doing. I want people who feel a pride in my product, pride in my associates, a pride in the company I represent.
[00:05:34] David Wolf: And then I want somebody who's a good listener because you just can't call a customer up and start pitching in features and functions, right? You're gonna tune 'em out. Customers wanna feel loved, they wanna feel understood. They want you to know that this is important to them and their associates. And then their customers.
[00:05:51] David Wolf: And then their customer's. Customers spreading the goodness just doesn't stop. 'cause we're really entrepreneurs working for a company. Hopefully for a long time, no one wants to [00:06:00] join the company to leave in two or three years, right? That's not in anybody's plan. It's not always the salesperson. Sometimes they've dropped the product, sometimes the CEO changes and they want their team in from another vendor, right?
[00:06:12] David Wolf: So you have to be, you have to be really flexible, and again, that word resilient is not a better word out there. Maybe grit. Yep. Yep. I love grit. Yep. And last but not least, you have to love what you do. Mm. You have to love being a salesperson or being a pre-sales person, or being a solutions consultant and embrace it.
[00:06:28] David Wolf: Non-stop learning every day you wanna get better and more skilled at what you do. I wanted to ask you about two
[00:06:33] Richard Ellis: things. So one was that continuous learning mindset, right? But I wanna pause on that because you mentioned a word entrepreneur. One of the things that you know, you and I have talked about is, especially if you're hiring an account executive role.
[00:06:48] Richard Ellis: Where they're not only doing the hunting, but also the farming. Right. And we've talked about finding those people that really look at that as their business, right? They're building a book of business. They're not just a sales rep, [00:07:00] right? They're not just, you know, a tech vendor going to try to sell the latest software.
[00:07:05] Richard Ellis: But they're really looking at it as like I own, whether it's a list of named accounts or a region or a territory, that's my business. And you want that entrepreneur mindset of, I'm gonna go build this business. Is there anything that you've found when you're kind of looking at profiles and talking to people to understand their experience or background?
[00:07:25] Richard Ellis: That just kind of gives you that insight that, okay, they've got the right mindset here.
[00:07:29] David Wolf: I think it's a combination of the profile. I often will look down, as I said, at the bottom of the profile first. Then I look at where did they go to work first and how long did they stay there. I like to see people in their first company stay there more than a handful of years.
[00:07:43] David Wolf: It's not three years and now, but I'd like to see people who've spent eight or 10 years with their original vendor because we know life's not perfect. There's bumps, there's hills, there's valleys, and they've lived through them, and now they're a seasoned veteran. They don't tip over very easily because every day is a surprise.
[00:07:58] David Wolf: It's like the gotcha moment and you go, [00:08:00] okay, I can still go for it. I got the rest of the day to make this thing work. So a great attitude. I. With resilience and really caring for your customers, and don't go to work for somebody you don't believe in. Don't go to work for a product just to, you don't wanna chase a comp plan.
[00:08:14] David Wolf: The money will chase you if you're doing what you really love to do.
[00:08:17] Richard Ellis: That's great. That's awesome. Some of your phrases are just so great. You know, they don't tip over easy, right? I mean, that's something that we can look for and test for in the interviewing process. So the other thing that you mentioned is this idea of really finding those team members that have the growth mindset that are hungry for knowledge and learning and improving.
[00:08:37] Richard Ellis: I mean, I've trained sales teams large and small, and from people that have 30 years. Tenure to fresh, and it's every now and then you just kind of get these teams where they're sitting back, they're like, okay, I've seen all the trainings and the methodology, you know, there's nothing new for me to learn.
[00:08:53] Richard Ellis: Right. And it just kind of surprises me when they don't look at all the opportunities as. Is there something I can take away [00:09:00] from this? Let me at least give it a chance. But that growth mindset I think is just so key and something that I recognize in those sellers that are successful. Tell me a little bit more about some of the best hires that you've found and how they kind of demonstrated growth mindset.
[00:09:15] David Wolf: They're always interested in the new day. I mean, they're always interested in learning something more. Us who like to be the best are lifelong learners. You know, they start off the morning doing the right things, putting themselves in the right mood, and when you put yourself in the right mood in the morning to start the day off, you know, don't go to your feeds right away.
[00:09:30] David Wolf: Don't go to social media, turn off the news, have your cup of coffee, and just settle into who you are. Then give your best that day and play some music or feel good and then your day can't go wrong even when it seems to tip over. 'cause we don't tip with it. Mm. And again, the resilience, lifelong learner, love your work.
[00:09:48] David Wolf: And then it's not work. It's a game, but it's a serious game and it matters. But when you're playing a game, it doesn't matter if you don't win the game that day because the next day the game starts over again. The board is set up, the chess pieces are [00:10:00] there and you're moving them along. And the best thing to do is to build a good pipeline.
[00:10:04] David Wolf: Of multiple opportunities so you don't live and die on one deal. The more opportunities you have in your pipeline, the less pressure you have to do the wrong thing and you don't wanna do the wrong thing. I like that. That's a key to a very successful sales career.
[00:10:18] Richard Ellis: Yeah, and just having that intentionality to do that, right, versus chasing the latest big deal that comes along and then you're letting your activity and the rest of your pipeline fall away.
[00:10:28] Richard Ellis: And then if you lose that big whale. And now you're screwed. Right? And so one of the principles we'll teach for building healthy pipelines is, you know, yes, of course you want it, the right quantity and the right quality, but you need to have balance, right? Balance across small, medium, and big deals, right?
[00:10:43] Richard Ellis: Well cause the Nibble Bike gulch approach. Oh, I like that. Nibble Bike Gulch. That's another one. All right. Gonna have to write that one down. The other thing that, as I've gotten to know your kind of process for finding the right talent for a company is you dig in deep with your clients and [00:11:00] really understand, not just, oh, okay.
[00:11:01] Richard Ellis: Yes, I've hired consultants or solution consultants before, or account execs before. I know what you're gonna need. Right. Because you're a software company, you go way deeper than that, right? It's what type of software, it's what problems they're solving. What industries do they solve, right? And so you get in deep.
[00:11:17] Richard Ellis: And one of the things about getting deep is you also have shared with me that you learn about the culture of the company. And so tell me a little bit about if you've got a new sales leader. Needs to build out a sales team. What do they need to be thinking about in terms of kind of that culture fit and maybe the nuances in that type of business or in that industry that they can look for to get this right?
[00:11:40] David Wolf: I think they have to figure out where they're at. I mean, a new leader comes to a new company. What's my install base look like? How old is the company? What release am I on? What are the issues? You know, look at the customer satisfaction numbers. Are they where they're supposed to be? 'cause you can build a great sales team, but if you don't have a great customer success team.
[00:11:57] David Wolf: To make sure that once the deal is [00:12:00] closed, that their hands are held to install this and to use it. And so the adoption rate is high, and then everybody's happy. The last thing you want is have somebody buy your product and it sits on a shelf How they use one module amongst the 37 things it does do. So customer success is tied hand in hand with the salesperson, and it's the sales leader's job to be the cultural leader for the team, to be the player coach because they don't work for the VP of sales.
[00:12:26] David Wolf: The VP of sales works for a sales team. I like it. Once he adopts that attitude that they're not afraid to call 'em and tell 'em I lost a deal. We want an authentic relationship between the VP of sales and the sales team so that they can win and lose together.
[00:12:39] Richard Ellis: That's great and I love just flipping it on its head.
[00:12:42] Richard Ellis: Hey, you're in service of your sales team. You're not just guiding and directing, right? Yes, you have to do that, but you also have to serve them well. Tell me a little bit about when you think about building out 5, 10, 20 person sales team. 'cause I know you've done it over and over again. What just worked really [00:13:00] well in doing that most efficiently and effectively.
[00:13:03] Richard Ellis: Are there any kind of common tips or just practical guidance, others out there that are listening can take away to say, okay, we're gonna be able to do this in half the time because of some of these tips that David shared?
[00:13:14] David Wolf: It takes market knowledge. So I'm a student of the market. I track. Thousands of software companies.
[00:13:20] David Wolf: I have a database on LinkedIn. It's over 5 million people I get on LinkedIn in the morning 'cause it's the great place to be. And I scroll through all of the postings for the day and I do searches and I'm generally inquisitive about where the market's moving. Like right now, AI's a big deal. AI's a great customer support application for anybody who's already got an application.
[00:13:39] David Wolf: So everybody's out there pitching the AI piece to their tool, but there's gotta be something amid special about this company. That resonates with me. And then I can communicate that feeling to the potential candidates. And then by knowing what the marketplace is going like Company A used to be hot, but now it's a cybersecurity company on the way down.
[00:13:58] David Wolf: The only way they're staying alive is [00:14:00] by giving away the new signups. But the customers don't know that they're actually paying a 40% margin on maintenance fees. So every three years they bought the software over. And again, even if they thought they got it for free. And that's taking place now in a lot of the older cybersecurity companies that can't keep up with the times and the new guys are eating their lunch.
[00:14:20] David Wolf: The problem with the new guys is that they're fighting that zero cost from the established vendors. So you gotta know that that battle's going on and you gotta know how to use your partnerships to communicate with your customers, so you have more than one voice talking to the customer. I mean, every company, no matter what industry is now a technology company, pharmaceutical companies, banks, automation runs everything.
[00:14:41] David Wolf: Right. It's complicated.
[00:14:43] Richard Ellis: That's good. I like it. For years we've said, Hey, everybody in the company's a salesperson to some degree in these days. Yeah. Every type of company is a technology company in some way. Right. And just to have that awareness can give you some insights into how you can align better to their needs, really surface their [00:15:00] challenges that you can solve.
[00:15:01] Richard Ellis: I think that's great. I know that many organizations will hire somebody to help them in their headhunting or their recruiting like yourself. They've got HR departments that might have recruiters internally that they'll leverage. But my question for you is for the particular hiring manager or that sales VP that's building out a team, what role should they play in the recruiting process and is there some that get it right and some that get it wrong?
[00:15:29] David Wolf: That's true in everything. Some sales managers are great sales managers, but lousy recruiters and it's because they're busy. I mean, they're working 50, 60, 70 hour weeks running the quarterly chase, right? Yep. I was talking to a company the other day and they said, we don't count our lifetime here in years, we counted in quarters, and I've been here for 48 quarters 'cause we only have 90 day windows.
[00:15:51] David Wolf: That's the downside to this. So the good news is you're on the enterprise sales team. The bad news is you're on the enterprise sales team [00:16:00] because look at this. The enterprise sales team, they don't close in 12 months anymore, right? So for the first quarter, you're setting things up. The second quarter you're sort of digging in.
[00:16:08] David Wolf: Now you're racing to that quarter where they, you know, buy stuff. And then when you get into December, if you're not on the buying list, you're out. And then that means your deal pushes into year two, which means are you gonna keep your job because you're working on a four or $5 million deal and your boss is looking at you going, you know, you're at 20%.
[00:16:26] David Wolf: Not knowing that you're gonna commit at 300% year two if he lets you live, you know? And that's the challenge. I mean, sales cycles do not fall in line with everybody's desires on the management team. They get very, I talked to a person yesterday on a board of directors, was on his call for a review and he said, I could feel the tension.
[00:16:48] David Wolf: Yes. 'cause they're pressure on them from the investors, you know, and they're trying to drip it down into me and they shouldn't give me tension. They should give me support.
[00:16:55] Richard Ellis: That's interesting. Yeah. Well, and one thing that comes to mind just mentioning that [00:17:00] is we were talking about, you really have to understand not only the role, but the culture and the fit and how they're gonna sell.
[00:17:06] Richard Ellis: It's very different hiring people that it's in a small PE led company that's got a board that's very involved where, you know, these. Sellers are gonna be in front of the board. The board members are gonna be on some of their customer calls. That takes a level of, you know, executive presence and resilience to bring up that word from earlier versus maybe some others which just would kind of cave under that pressure or tension.
[00:17:30] David Wolf: Yeah. I rather throw the word grit in there too. 'cause you, you know, it takes that to stand in front of your board of directors or your executive team. You know that you're doing all the right things, but the thing's not closing this quarter. And I know a person in Chicago who is the number one sales rep in the company this year, but last year he thought every time he was gonna talk to his immediate manager, he was gonna get a pink slip.
[00:17:51] David Wolf: Oh, wow. And, and he, the day he closed the deal, he still thought he was gonna get fired. Now they're holding him up on stage going, you know, do like he does.
[00:17:59] Richard Ellis: [00:18:00] Right. Yeah. You gotta stick with it and power through. As we think about wrapping up here, I wanna just kind of give you an opportunity. Is there one big thing that we wanna share with the listeners out there in terms of keep focused on this as you're gonna build your sales team going forward?
[00:18:15] David Wolf: Communicate with your executive search team. Communicate. Don't be afraid to interview somebody that doesn't match because job descriptions are living organisms. You have this perfect job description and you meet candidate A and you go, wait, I didn't think about that. He is got something I like. You add that to the job description, which may change the candidate profile.
[00:18:35] David Wolf: So interviewing some not so good candidates is a good way to find yourself to the best candidate.
[00:18:41] Richard Ellis: Yeah,
[00:18:41] David Wolf: but that's great.
[00:18:42] Richard Ellis: Love that. Thank you for that. And the other practical tips that we covered today, I gave you a heads up, and I'm sure you know this from listening to some of our other episodes, but when we wrap up, I always like to say, okay, separate from our conversation today, totally.
[00:18:57] Richard Ellis: Something that that's not related to billing a [00:19:00] sales team here. What is some goodness that you've appreciated recently in your life, whether it be your business life or your personal life that you wouldn't mind sharing?
[00:19:08] David Wolf: Well, the goodness is that I've got a lot of friends and I've been playing pickleball, so I even have many more friends.
[00:19:14] David Wolf: In fact, I live in a community of a thousand homes and I knew maybe a hundred people and well, now I know 500 people. Wow. 'cause we're all out there. We're having fun. You're meeting people from different walks of life, different age groups, from teenagers to senior citizens and it's really brought our community together and I really enjoy that camaraderie.
[00:19:35] Richard Ellis: Yeah, that is really good. That's fun. Well, thank you again for your time today, David, and being here, and I appreciate all you do for us. As far as you know, helping us build our own sales team, but certainly thanks for your insights to share to our listeners out there.
[00:19:50] David Wolf: Thank you very much.
[00:19:54] Speaker 3: Some goodness is a creation of revenue innovations. Visit [00:20:00] [email protected] and subscribe to our newsletter.
