Episode 385: Building Elite Sales Teams: Lessons from 1,200+ Hires

Intro

0:00:18 – (Bob Woods): Welcome to the Making Sales Social podcast featuring the top voices in sales, marketing, and business. Join Brynne Tillman, and me, Bob Woods, as we each bring you the best tips and strategies our guests teach their clients so you can leverage them for your own virtual and social selling. This episode of the Making Sales Social podcast is brought to you by Social Sales Link, the company that helps you start more trust-based conversations without being salesy through the power of LinkedIn and AI. Start your journey for free by joining our resource library. Welcome to the show.

00:01:00:00 – (Brynne Tillman): Welcome back to Making Sales Social. I’m your host, Brynne Tillman, and I’m excited to introduce you to today’s guest. Rich Rosen, the founder of Cornerstone Search, specializes in sales and leadership placement for venture and PE-backed SaaS companies and has personally placed nearly 1200 professionals throughout his career. His one-person firm has impressively ranked among the Forbes top 50 recruiting firms in America for five consecutive years, peaking at number 11, which is my lucky number out of 38,000 competitors.

00:01:35:07 – (Brynne Tillman): Rich is direct and straightforward approach has also earned him an invitation to the prestigious Pinnacle Society, where he serves on the board alongside the top 80 recruiters in the nation today. Rich will share his valuable insights on navigating the recruiting landscape and building successful teams. Rich. Welcome to the show. 

00:01:56:34 – (Rich Rosen): Hey, great to be here. Thanks for having me. 

00:01:58:09 – (Brynne Tillman): Oh my gosh. Thanks for being had. Sorry, I was not. Not yet. We’ll see how that goes. I’m so glad we started with a chuckle. That’s good. So, before we jump into your genius, we ask all of our guests one question: What does making social sales mean to you? 

00:02:24:45 – (Rich Rosen): It’s a great question. I think you know what sales are, you know making it social.

00:02:28:19 – (Rich Rosen): I just think, listen, it’s especially as a recruiter, it’s all social. It’s all about networking. You know, I mean, I like, I always tell I always find it funny when other salespeople get, like mad or jealous or angry at another rapper recruiter or whatever. That’s doing really well. Like, I always get happily jealous of them because I know I’m having a bad month.

00:02:48:26 – (Rich Rosen): You know, it’s fixable. You know, it’s so I think it takes a, sales is tough, man. Takes a village. It’s fun to have peers you can lean on, so. 

00:02:58:43 – (Brynne Tillman): Oh, I love that. So that’s great. Awesome. Well, let’s dive into kind of your expertise. With nearly 30 years in sales, recruitment for sales for SAS companies,

00:03:10:03 – (Rich Rosen): startups, SAS companies, all startups. Even crazier. 

00:03:12:96 – (Brynne Tillman): Wow. Oh my gosh. What key sales leadership traits have you consistently found to drive success in these go-to-market teams? 

00:03:24:45 – (Rich Rosen): I think from a leadership standpoint, I think the market is sorely missing a lot of leadership right now. But I feel like, you know, I look for clients that are you know, the leaders are really inspirational.

00:03:35:24 – (Rich Rosen): They empower their folks. They appreciate their team. You know, they’re not worried about, hey, did you make, you know, going to pay a rep 150 instead of $5,000 the base and then worry about whether we make ten calls today or 50 calls today. You know, they’re actually looking at the results. And what are you doing strategically? You know, yeah, you got to set up your drip campaigns and that’s fun stuff.

00:03:56:05 – (Rich Rosen): But you’re you know, if you’re not empowering your reps, you’re just going to micromanage them. Hire an SDR. It’s a waste of time. You’re going to burn them out. They’re not going to do well for you and you’re going to kind of look like a putz as a leader. You know, I think that’s fair. So, and you know, you have the reputation and chops to say that because your firm has a track record of placing high-performing sales leaders.

00:04:26:09 – (Brynne Tillman): Absolutely. What common qualities do the leaders share, particularly in that fast-paced start-up Saas environment? 

00:04:38:38 – (Rich Rosen): I mean, the good leaders, there’s a lot of bad traits for the bad leaders. The good leaders. I mean, listen, they make decisions quickl,y and they also fire quickly. You know, and it doesn’t mean you’re just a guy in a bad month, you let them go.

00:04:50:19 – (Rich Rosen): But listen, in a startup world, you can’t afford to let someone go six, seven, eight, nine, ten months before they understand your product, you know, But you’ve also, as a leader, need to have it set up for success. You’ve got to be able to have them walk in there and have a bit of a boot or a training material, you know, and steps to the process, you know, where, you know, hey, week one we’re going to do this week two, we’re going to do this and we’re by the day 30.

00:05:17:11 – (Rich Rosen): Yeah, they should be on the phones. They should be doing some kind of outbound outreach. If your product is that complex and you’re a month in, they still can’t give even a basic pitch on it. You know, you may want to reconsider that hire personally, but I think that I think so many companies bring hire these people and they don’t they just got to feed them to the wolves are like, here’s a phone, here’s the website and I’ve had it and it’s a recipe for disaster.

00:05:44:25 – (Brynne Tillman): So, you know, one of the things that I really focus on, obviously, is LinkedIn and vetting vendors and vetting, you know, what, whomever it is that I want to work with, even, you know, vetting clients. Right. Like, I’m looking on LinkedIn. The interesting thing for me is when I’m looking at, you know, a client and if they’re going to be successful in the niche that they came to me with, I’ll look at their relationships like where are they?

00:06:21:23 – (Brynne Tillman): Do you do that in recruiting? Do you when you’re looking at bringing on a successful salesperson, are you looking at their LinkedIn relationships as part of that? 

00:06:33:69 – (Rich Rosen): Yes and no. I mean, I look into it to see where it’s at. It’s more to see who they are tied to that I may not have a lot of respect for.

00:06:44:28 – (Rich Rosen): And, you know, because I’m very picky on who I work with. I don’t want to, like a lot of recruiters who will take any job that comes their way. I think it’s a waste of time. You know, just like any sales rep, they should be picky on who they’re going to spend their time focused on, you know, not go down a path that’s going to go nowhere.

00:07:01:22 – (Rich Rosen): That big busy versus productive, you know, type mentality. So if I know you are tied to, you know, Joe Blow, and I know Joe Blow treats his people like absolute garbage and he has massive turnove,r and he’s just a good old boys network kind of guy. I usually ask them like, Hey, I’m closer to so-and-so, and, you know, and then a lot of times I’ll tell them, like, you know, I say, If this is how you work, I’m probably not your guy.

00:07:30:03 – (Rich Rosen): You know, I want to work with clients and, you know, candidates that actually, you know, want to get ahead, want to do things the right way, not just run people over for a nickel. And it sounds counterproductive. But man, I’ve seen so many companies get destroyed by that kind of culture. And, you know, it’s great. It’s not usually great for me, but it’s great for some people, you know?

00:07:51:23 – (Rich Rosen): But it’s I think it’s a key it’s a valuable part of the hiring, especially when you’re building out teams. You know, you want guys that are hungry and aggressive and, you know, in theory will, you know, do whatever they’re going to do. But there’s a right way and a wrong way to do it, in my opinion.

00:08:09:12 – (Brynne Tillman): Yeah. And you know, it’s your reputation, too, right? You have a track record of these high-performing sales leaders, and the people that you’re placing do exceptionally well. They’re not happy. They’re not going to do well. 

00:08:23:43 – (Rich Rosen): Well, that’s it. And I think that’s the biggest thing. I think, you know, if you want the most out of your sales guys, you don’t have to be the screamer and yell.

00:08:29:22 – (Rich Rosen): You got to be the guy that’s compassionate and says, hey, listen, you know, you want your team to feel bad for you if they let you down like they’re disappointed, like you let your dad down kind of thing. And those are the reps that flourish and crush their numbers. And they, as a manager have lower turnover in your and you got a lower turnover.

00:08:48:15 – (Rich Rosen): Well, you’re probably going to do better. Your numbers are going to be better. You’re going to thrive in your company. You’re going to shine. And you know, if you don’t start up, your bases are going to notice that, hey, how is the whatever East region doing So much better? How is their turnover? You know, they’ve lost one guy in three years versus the West that’s had gotten, you know, new people coming in every year.

00:09:06:18 – (Rich Rosen): It’s a huge difference in your ability to earn because that first year in sales, it’s a lot of building, you know, And if you don’t have to rebuild and rehire, retrain, it’s just seems like it’s more money in the bank. So treatment, goal, retention, people overlook the importance of retention. And it sounds so basic and simple, but they do.

00:09:26:21 – (Brynne Tillman): Yeah. And I think that that’s so important. I think a challenge is matching a sales professional with the culture 100%. So what are some of the things that you do with your clients to ensure that when you are bringing them candidates that there’s likely a culture fit? 

00:09:49:07 – (Rich Rosen): Yeah, I mean, I really kind of get to know my clients. Like, I’m a big believer that my clients will treat me like they’re going to treat the people they’re hiring. So if they’re not going to give me time, they’re not going to give their reps time. And that’s a huge flag. You know, if you’re too busy to talk to me, who’s doing You’re going out to the market and trying to find that right fit for you.

00:10:09:13 – (Rich Rosen): You know, listen, there’s going to be questions we’ve got to ask, right? Discovery call, just like when you’re selling anything. And in that call, you kind of learn what this person is like, what’s what makes them tick. And I mean, I’ve had managers that I place, you know, upwards of 50, 60 plus people with and built out like the early days of Tableau or Apptio or other, you know, really super successful companies.

00:10:30:22 – (Rich Rosen): And what to your earlier question to what stands out over all those companies, it’s because the leadership actually spent time. It wasn’t like, listen, just go get me that box of Cheerios. We’ll bring that guy on, right? So, are these actually conversations that have to be had when you’re hiring? The more you know about the hiring manager and the more open hiring managers are with the candidate, the better chance you have of landing that all-star.

00:10:56:16 – (Rich Rosen): You know, if your think you’re too good because you have a fancy title, you know, you’re probably not getting the best candidates on the market or candidates that people in your space that are looking unless you got something incredible that you’re just going to pay them off with, so. 

00:11:10:38 – (Brynne Tillman): Yeah, and that’s when you’re full. Motivation is money. You’re not getting the best out of your people.

00:11:19:04 – (Rich Rosen): Ever. I mean, every sales guy or girl is motivated by money, without a doubt. It goes without saying. But if that’s your only motivation, they’re just going to leave. Once you’re competitive, get some five bucks more. You know, it’s there’s got to be some other motivator or driver. And that’s why I, without a doubt, as I said, am a leader that inspires people. I mean, I’ve had people that I got one of my favorite leaders in, say, Paris Airline who built the Enterprise team for Tableau.

00:11:48:10 – (Rich Rosen): Like, you know, Barry, he would want him to have to let people go, people would have I mean, I know these guys and they would tell me this, can’t they? They would they’d apologize to them they felt bad that they let him down. He’s that he’s they’re getting fired and they’re actually apologizing, not getting mad. You know, that’s a leader.

00:12:08:02 – (Rich Rosen): It’s amazing. That’s to me, is what you want out of your leader. Otherwise you’re just a manager, your manager, numbers manager, you know, processes. It can work, but it’s not nearly as fun. 

00:12:23:12 – (Brynne Tillman): What are some of the things that you when you’re pre interviewing these candidates? Right. Are you deciding which client this candidate will best fit? And you know, you’re playing that.

00:12:36:04 – (Brynne Tillman): What are one or two questions that you ask them? That’s not a typical question that helps you to figure out where they’re going to fit best. 

00:12:47:32 – (Rich Rosen): It’s more just a conversation. You know, I’m very laid back. You know, this year everyone has the same question. Say you had to do what you know what you make had to do.

00:12:58:19 – (Rich Rosen): But ever but it’s you know, I try to go into the depth of how they because most of my clients want hunters you know plays a lot of become managers, too, but a lot of account executives and a lot of sales leaders. And, you know, it’s really if it’s a sales year, I always want to ask about retention because again, like I said earlier, if you’ve got people that stay with you, that’s a telling stat that most I find most CEOs don’t even ask about in interviews, but think about how much money that can save you and how much energy it saves a company again.

00:13:27:19 – (Rich Rosen): So I like to go into about the retention, how they retain people, you know, and then obviously how they built their teams and what’s the strategies are for growth that they’ve used and how flexible they are. And on reps, it’s you know, it’s really tell me about like, you know, how you got in to your deals and you know, if they start with well I got an invalid they’re probably not the biggest owner you know so it’s their answers are way more important than the question.

00:13:53:28 – (Rich Rosen): Sometimes it’s the old age, you know, adage of, hey, it’s worth the questions. They ask me, are they’re showing curiosity. You know, the they they have, you know, intellectual interest in anything. Do they stay on top of podcasts? You know, I it’s I’m willing to bet 90% of reps do listen to podcasts or read a book, which is a little scary sometimes. You know? 

00:14:18:26 – (Brynne Tillman): Yeah, I do. I ask that often. What are the podcasts you listen to? What was the last podcast you listened to? Yeah, I think that’s really important. Yeah. So I love that you’re asking that. I think that’s awesome, too. I want to go back just for a moment. So I’m a startup SaaS company couple of years in, just got Series, A, and they’re telling me I need to build my sales team and I’ve got two sales reps, right?

00:14:50:18 – (Brynne Tillman): And I’m the sales leader. So what is that process like? I call you and what do we do? 

00:14:59:63 – (Rich Rosen): So I love it. So, you know, they’ll call me. It’s always my favorite. So we do a whole deep dive discovery is, you know, that I can do it in 15 minutes, I can do it over in 3 hours.

00:15:10:29 – (Rich Rosen): I have an unlimited amount of questions. That’s the more information I have, the better. You know, once I understand what you guys are doing, what the right person looks like and, you know, and kind of get to the why was the company founded in the first place? Why, you know, do we think we need this person? You know, a lot of companies are like, hey, we need to have, you know, someone from our domain and like, if it’s a startup, it’s in theory, it sounds great.

00:15:37:09 – (Rich Rosen): It’d be great to have someone that is sold, you know, whatever DevOps software, but if they’ve sold, you know, other stuff into engineering or, you know, a tangible solution to DevOps or whatever or ERP and they’ve sold business intelligence or something, you know, some tangential solution, I personally, I listen, if you get a guy or girl that is a killer hunter and prospector and they have the, the drive that you want and that startup mentality, awesome.

00:16:06:04 – (Rich Rosen): But reality is you really just need the startup mentality and the drive. So I always try to figure out, really, are you open to the best athlete or is that better athlete? Have to have domain expertise. And I don’t know. I’m willing to bet my house that, you know, a good driven sales rep can figure out any product, but a good product rep who only knows X is fine.

00:16:34:12 – (Rich Rosen): But if things get bumpy and they can’t sell their current clients because you’re selling a competitive solution now that you just left, you’re back to hunting. And they may not really like to hunt, but they know their product really well. So it’s got value. But how much? Not as much as you probably might. 

00:16:49:08 – (Brynne Tillman): I’m listening to you. My head goes to Moneyball. Right. It’s about the right people in the right spot. They don’t have to be the best at that, but they have to be the best of what you need to get that done so well. 

00:17:03:26 – (Rich Rosen): And I think just having a solid sales process is so important. And most of these reps don’t have it, or they’re reliant on inbound leads, marketing qualified leads, you know, or anything.

00:17:16:27 – (Rich Rosen): But they don’t want to do the pipeline generation. And if you’re a hunter, sorry, you got to do their enterprise reps, you know, don’t tell me you don’t have time, you know, at least throughout the week to make a certain amount of calls or do a certain amount of things, because I know hundreds of thousands of enterprise reps and I can tell you they play a lot of golf and, you know, and yeah, you could be doing business on the golf course, but not, not at scale.

00:17:44:07 – (Rich Rosen): Yeah, exactly. So there’s always time to get things done. You want to get it done, and no one wants to do is the problem. So yeah. 

00:17:52:83 – (Brynne Tillman): Yeah. You know, and that’s one of the reasons I love to look at their network, like who are they already connected to and what are their relationships? Because likely they’re okay reaching out to those folks.

00:18:03:15 – (Brynne Tillman): Exactly right. So if they already have a strong network, there’s a good chance they’ll get some. 

00:18:09:47 – (Rich Rosen): Yeah, they can get some calls. But the problem I always find where people are looking at networks as a main focus, it’s great. We all have a network. I’ve got 30,000 1st level connections on LinkedIn. Unfortunately, I cannot promise you not all 30,000 people are getting back to me.

00:18:25:28 – (Rich Rosen): I wish they would if you’re watching, you know, but the end of the day is, you know, I’ll ask candidates especially. I’m like, who are the five people you can have a beer with tomorrow? All right. And most of them struggle, you know. Wow. But, ask it start asking. You’ll be surprised. Yeah, they have a huge network, but how many are getting back to them, right?

00:18:47:25 – (Rich Rosen): That you know, and just because that you have the network in, you know, financial services. Well, maybe they don’t need what you just what you’re selling now; maybe they just bought a competitor’s product a year ago. So the network is it’s good. It’s a great starter for 30, 60 days. But after that, then what? You know, now you’re back to hunting and pipeline generation.

00:19:09:11 – (Brynne Tillman): So our second degrees, who can they introduce you to? Of course that that’s the stats my world right Lik,e that’s where I play. How do you how do you earn the right to get the conversation even when they’re not interested?

00:19:23:59 – (Rich Rosen): That’s the million dollar one. Exactly. But you know, to do it from an interview standpoint, it’s, I mean, there’s no it’s so hard to judge on that.

00:19:32:13 – (Rich Rosen): I mean, it’s only it’s because sales guys talk, right. That’s what they do. So. That’s right. What you want to hear. But I just think hiring based on a network is it can be done limiting it is it gives you a false sense of security. 

00:19:48:82 – (Brynne Tillman): Interesting. You know, that’s good to hear because I stress that a lot.

00:19:52:10 – (Brynne Tillman): So I guess there needs to be about, I think there needs to be a balance in everything we do. You can never have one string to the business. 

00:20:01:10 – (Rich Rosen): There’s no perfect process in hiring, you know, and you’re hiring salespeople. I mean, they should have some knowledge, you know, network. And you know, when they have a knowledge of your domain, then listen, there’s no question that’s the benefit.

00:20:12:15 – (Rich Rosen): But, you know, again, I sell across all of software and I’m selling, you know, ERPs, you know, in the morning and AI develops in the afternoon that have nothing to do with each other other than good salespeople can sell either, you know. So it’s, and they have and they do, you know, I’ve got a lot of a lot of like reps that I know that have done the $2 million W twos multiple times.

00:20:38:13 – (Rich Rosen): They won’t sell the same solution twice, at least not twice in a row. You know, if they spend four years at company A, they’re not going to be competitive for the next four years. 

00:20:47:43 – (Brynne Tillman): Well, they probably can’t reach out to those folks for the same exact. However, if there’s a new product that those people can use. Yeah, exactly.

00:20:56:27 – (Rich Rosen): But that’s why I’m selling you BRP today. And I closed 2 million. I did a $2 million W2, and now I’m selling whatever, you know, some C solution. Well, yeah. I can’t go back to those people, can I? I don’t. Yeah, I don’t, I maybe I know that domain, but I don’t know that C X products set. Right.

00:21:14:09 – (Rich Rosen): So in that case, it can work out great, assuming they need the solutions, you know. 

00:21:19:93 – (Brynne Tillman): Right. Absolutely. It’s great. This is great. So the last question I’m going to ask you is really the second to last question is what question did I not ask you that I should have? 

00:21:30:64 – (Rich Rosen): Always a great question. I know you have asked some really good questions.

00:21:34:04 – (Rich Rosen): I think let’s say that is a good question. What question should you ask? I think, you know, just I don’t really know. Did I? I don’t know if I could answer that.

00:21:47:81- (Brynne Tillman): If I were to be leading into this, it would be essentially what is the mindset of a company that’s moving from CEO led sales teams into something like, yeah, we bring a founder-led to a leadership sell, you know, sell I guess.

00:22:11:06 – (Rich Rosen): Yeah, I mean I think listen, leading, you know bringing on your first found, you know, your first real leader after getting it a founder you know it’s really got to be a culture fit. You know, culture is king. You know, you’ve got to you know, and this the founder has to be willing to let go. And that’s as a candidate; that’s the biggest thing you got to judge is this person really going to trust me and how are they going to trust me?

00:22:33:29 – (Rich Rosen): And then, you know, and you got to test you know, I would be talking to the VCs if I’m the candidate, I’m talking to the VC about this. The leader I want to talk to people maybe he’s worked with in the past, too, even because, listen, does this guy really want to let go? And we all know a lot of these founders about, yeah, they’re micromanaging their baby for sure.

00:22:54:18 – (Rich Rosen): It’s like you always want to understand, does the CEO who sold, maybe sold this product to friends and family, do they, you know, does he understand that? Listen, selling your own baby is different than someone else coming, just learning it and starting to sell it. It’s a different mindset. You’re saying you’re selling to a personal friend or network or even someone whose vision is too far different to the.

00:23:22:25 – (Rich Rosen): Do they truly understand, you know, the difference in those sales processes? You know, that’s if I’m a candidate coming in, that’s what I have. Crowe: Coming into that first, you know, VP sales, those are the questions I want to get answered. So 

00:23:36:74 – (Brynne Tillman): That’s great. It really is fantastic. Well, thank you, Rich. Please, if we have listeners out there saying either I’m looking for a new sales opportunity or we are looking for sales leadership, how do people get in touch with you?

00:23:50:28 – (Rich Rosen): Yeah. The best way you can follow me on LinkedIn is through Rich at Corners RichRose Cornerstone Search. That’s the best way to follow me on LinkedIn and I try to get back to everyone, but my numbers there are too. So if we can help you guys, you know, fill some roles at ease reps, do everything. Go do everything. Go to market for startups serving well.

00:24:13:28 – (Brynne Tillman): Thank you so much. I think you brought a lot of value to our listeners, and I really appreciate your insights. 

00:24:19:84 – (Rich Rosen): Excellent. Thank you so much for having me. It’s great.

00:24:13:28 – (Brynne Tillman): Oh, so much fun, and so for all of you folks out there, when you are out and about, don’t forget to make your sales social.

Outro:

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