19. Josh Shirley ~ Sandler Powered by Coffman Group
Episode Notes
Key moments from this episode
Josh Shirley joins Tailwind for a practical conversation about building sales teams that treat business development as a core revenue engine: why BDR and SDR roles should not be treated like junior varsity sales work, how hunting and closing require different skills, why strong prospectors need a real path to growth, how closing-only cultures can stall when the market gets quiet, and why leaders should reward controllable prospecting behavior before the meeting ever gets booked.
Takeaways
- BDR and SDR work should be treated as a critical revenue function, not junior varsity sales work.
- Hunting, closing, management, and customer success require different skills and should not be treated as one ladder by default.
- Companies lose strong prospectors when the only way to grow income or status is to leave the business development role.
- A hunting culture gives teams more controllable momentum than a culture that only celebrates closed deals.
- Leaders should reward the prospecting behaviors that create opportunities, not only the meetings or deals that follow.
Key Moments
- 0:36
Sales Tales and learning from misses
Josh introduces his sales coaching work, his Sales Tales podcast, and why laughing at sales mistakes can make lessons easier to hear.
- 8:31
Dividing sales roles as teams scale
The conversation moves into how growing teams separate hunting, closing, and client success responsibilities as they reach scale.
- 9:58
BDRs are not junior varsity
Josh explains why treating business development as lower-status work creates culture problems and overlooks one of the hardest sales jobs.
- 12:58
Losing strong prospectors to the wrong ladder
Josh describes how companies lose great BDRs when the only path to income or recognition is leaving the role for management or AE work.
- 17:35
Choosing a hunting culture
Josh contrasts a closing culture with a hunting culture and explains why controllable prospecting behavior matters when the market gets quiet.
- 23:04
Rewarding prospecting behavior
Josh closes by encouraging leaders to make prospecting behavior rewarding before the booked meeting or closed deal arrives.
Transcript
0:03 All right. Well, we've got another episode of Tailwind. Today, we're joined by Josh Shirley. Josh, tell us a little bit more about yourself. This is Josh.
0:10 Um I I feel like that was redundant just starting off with with you just said my name and I'm just like I'll try and say
0:19 it different. I don't know what I'm doing there.
0:22 It's like when you go in a circle and everyone's like, Austin, introduce yourself. Go, well, my name's Austin. I feel like it's the exact same thing.
0:28 It's natural. Yes. Yes. I don't know, man. Maybe it's the podcast nerves. I Yes. I have a podcast. It's called Sales
0:36 Tales. Um what I do professionally as I work with and coach, develop uh sales
0:43 leaders and and sales people. Um do coaching, mentoring.
0:49 I'm a Sandler guy. So use the Sandler methodology to deliver those things. I I love selling. I think um
0:58 helping somebody get better at that helps them get better in other places in their life, right? Like yeah,
1:05 it's really sales is is very parallel to a person's self-development.
1:11 And you know, when I got into this business, I saw an opportunity to really uh really do that and help people and
1:19 change their lives. And I've been rewarded with with that ever since.
1:24 Um, I in my background, I'm a stand-up comic, so I um I have an appreciation for, you know, performance art and and
1:32 things like that. And I feel like what I'm passionate about is, you know, I I think laughter is a
1:41 genuine uh response. Like you can't fake it. And and if you fake it, you know you're faking it. Everyone does and you can't for long.
1:50 So, I think if you can take the message you want to deliver to somebody to help them get better, help them grow, and you
1:59 can put it inside that loop and they're laughing, it confirms that they're listening as well. Nice. I like that.
2:07 So, uh, yeah, podcast called Sales Tales. You can find it on any, you know, uh, podcast outlet, whatever you found this podcast on. Don't stop listening to
2:15 this podcast. I want you to keep listening to this podcast, but you're probably a qualified listener for for my
2:22 show as well. Sales tales is really um we bring a guest on sometimes and if you
2:29 want to hear the best salespeople in the world talk about the time they ate it and did a terrible job selling, um it's
2:37 full of stories about how a sale didn't quite go their way. So it's more of a sales fail but then we talk about okay
2:45 well what have you have done differently and try and unpack the lesson from there. So I think AEES uh BDRs uh sales leaders
2:55 managers all the way down will find some solace in listening to a story about
3:02 okay other people do that too and then uh some takeaways that you can totally steal rewrite as your own and tell your team about.
3:10 Nice. I like that a lot. Um I love just being able to like commiserate in, you know, what happens when you make a mistake during the sales process because
3:18 we're all making them and it doesn't feel great, but to be able to then recognize that, hey, even this worldass salesperson made the same mistake that I did. Dang. All right. I feel good. Like
3:27 I get together with my founder once a day and we laugh about the mistakes that we make because we're going to expect to make them more even though we're reducing them. It's like we're never going to be perfect.
3:36 Yeah, man. the it's I I once uh had a guy fake his own death just so he didn't have to talk to me on the phone. I was
3:45 making cold calls when I got into this business like really early on.
3:49 Now I should have caught it because the receptionist is one of the few times I ever called got a receptionist and had
3:57 to like you know do a gate house getound a little bit and you know I I don't lie but I but I play it cool.
4:05 Yeah.
4:06 Just Okay. I don't suppose Zach Pike's floating around the office today, is he?
4:10 Uh, can I ask who's calling? Like, she asked me who I was first. Yeah.
4:15 And that's when I should have known that this was all just a bunch of crap, right? So, I call. She answers, "Don't
4:23 suppose Zach's floating around the office today. Who can I say is calling?" Said, "Tell him Josh Shirley's holding." And she says, "Okay." And I got to tell
4:32 you, Austin, like 99 times out of a hundred when I get to that moment, they come back and go and and they either
4:40 give me the voicemail or they send me through to the person. I was ready to go. I thought I had it nailed and she comes back and tells me that he died in a boat explosion.
4:51 And I believed it. And if that was just a cold call, that'd be the end of the story. But um it was not. It was a referral.
5:01 So, I had to call the first guy back and tell him what hap cuz I didn't, you
5:09 know, I didn't I guess he I he couldn't have known that the guy was dead. I had to tell him a I didn't want him to send him out and
5:17 introduce him to anybody else. And then and then b, you know, I mean, it's terribly tragic and I wanted to make
5:24 sure that he knew. Um, so I call him and you know, uh, he answers the phone. I'm
5:31 like, "Hey, Mark, I called Zack Pike." And he goes, "Oh, yeah. How's that son of a bitch?" Yeah.
5:38 I said, "Not good. He's dead." And, um, you know, two text messages later, that
5:45 guy thinks I'm a complete jackass. Never sent me uh another referral. It was It was
5:52 pretty bad. So, I've messed up. I've made all the mistakes, man.
5:57 I mean, I it doesn't feel like that much of a mistake. I feel like, you know, how are you supposed to know that was supposed to be a joke? I bet that guy says that to every time he doesn't he
6:06 doesn't know the name. He's like, I think it wasn't the guy. It was It was the uh receptionist. She apparently made it up.
6:14 Oh, really?
6:15 Because when he called him back, he's like, "No, I I just told her to like get rid of him." And she like goes, "Oh, yeah. Crack crack and like I'm gonna I'm
6:24 gonna get this guy like just nailed me, man. So kudos to her. Good job, Beatatric.
6:29 You gotta have some fun every once in a while, right? Like can't always be serious. So was that the start of your standup career right there? You're like,
6:37 "Oh, I gota I got my big joke ready to go." No, I have a background in I spent several years in New York City as an
6:44 actor. I did um uh plays. Uh I did uh commercials, had a commercial agent
6:51 there, was was on some commercials and that was that was an exciting time before I had a mortgage and and all of that and and during that time I was able
7:00 to weave in a corporate life, right? So I had a sales training career where I worked in a marketing team kind of enabling the sales team with different
7:08 tools and so um I had a sales career uh prior to that and then after that as
7:15 well um I developed uh I built a software company up a software sales team up um I live in Kansas City now and
7:24 uh from 2013 to 2020 uh I suppose I was uh work my way up to
7:33 being uh the basically the chief revenue officer of that of that company. We called it something else but so everybody understands the
7:41 responsibility. It was basically doing that built got us from a team of 11 to a
7:48 team of 60 and we were uh no you know it was all bootstrap stuff no big infusion of cash
7:56 uh and we did it all with Sandler all all with selling and uh it was all very organic. So um you I leverage a lot of
8:04 that experience when I go in and talk to leaders if you know if I haven't done that before they can see it.
8:10 Yeah. Um, so when you're building that team, now that's a big from 11 to 60, you know, this is really a lot of explosive growth. Like what are some of
8:18 the big takeaways that you think some people miss on when they're trying to put together a highly effective team um that you'd recommend? Hey, these are things to watch out for. Here's some
8:26 things that you should be doing in order to have success while, you know, have achieving that growth.
8:31 Good question. Um uh at some point when you start reaching scale, you start to realize that I need
8:39 to u there needs to be a division of labor here.
8:44 Like I I have some people who like hunting and going out and finding the next thing and I I have some people who
8:50 like to roost and work with accounts a little bit more closely. And so what typically develops out of that is an
8:57 acquisition team that goes directly after people um to uh as as if we're tip
9:05 of the spear to expose our product service to people that we don't know.
9:10 Right? So that's a SDR BDR type role uh in today's landscape.
9:16 And then I've got kind of a a closing team. I I would I would call like a group of account executives who wait for
9:23 that to happen and then they get a lead or they field inbound leads and you my more experienced sales team kind of sits towards the back end of that pipeline
9:32 and gets things across the finish line and then there's typically a third diversification where I've got it an implementation slashclient
9:42 success team as well. Uh I've worked on all three components of of that and your
9:49 question was where do people go wrong sometimes or or what's a misstep and one thing I would say I see a lot is
9:58 this sense that my u tip of spear BDR SDR group is junior varsity.
10:09 Mhm.
10:10 Like for the rest of the company, right? I think that's um that's a culture miss and I think a lot of people make that error.
10:20 Yeah. What are what are the reasons that you think people assign it as the JV team and then what do you think are the unintended consequences of treating it as a JB team?
10:30 Well, I I think it's it's work nobody wants to do, right? So, um I I don't care who you
10:37 are, no one likes cold calling, cold outreach. No one really likes doing it.
10:44 But whether it's fortunately or unfortunately, there's a lot of people who are really good at it.
10:50 And so I think it's natural to say, "Okay, you got to earn your stripes. I don't know how you're going to work out here. I'm going to give you this job."
10:58 But an unintended consequence is, well, that's actually the hardest job in sales.
11:04 Now, it might take more nuance, more business acumen, and more familiarity with my product to, you know, show a
11:11 demo, show a product, and naturally weave the customer conversation back and forth across features and benefits
11:18 toward need, right? Like, I think that's nuanced, and I'm not stepping on that by any means when I say that we often
11:27 overlook an even harder responsibility, which is to meet Austin for the first time. Mhm.
11:34 no prior knowledge at all and go from completely unaware to some form of
11:41 interest. It takes a real um it takes a lot of rejection. Uh the best sales uh development business
11:50 development reps out there will book two or three meetings and making a hundred calls. And you know, you've got to be
11:58 okay with yourself. you have to do work on yourself in order to throw yourself at that all the time. And so unfortunately
12:06 um we don't put the care and attention into that as much and a lot of people kind of wash out. So, um, one unintended
12:14 consequence is you like, um, you know, we we don't
12:21 tend to keep the best people on the team because we, uh, we're constantly looking at that team and going, "Well, we need
12:30 another one. Somebody left or washed out. They didn't make it." Yeah.
12:35 And it's because we're not it's because we have a culture um at our madeup company that we're talking about right
12:42 now. I see this a lot like the culture is closing. The culture is results. The culture is not behavior and
12:52 um hunting, right? If we have a hunting culture, then I'm totally okay with a great BDR
13:00 who goes out and can make $250,000 a year. And what I what I mean by JV is
13:07 there's no path to that at most most places. Yeah.
13:11 Because we consider this job to be up to a certain experience level or threshold.
13:17 And so we put a ceiling on it. And what happens is you have an awesome uh BDR
13:23 and his or her only means to achieve the income and personal goals that they have for themselves is to not be on the team anymore.
13:34 And and so unintentionally I create bad situations and one of those is I take my best person and I promote them to a manager.
13:44 Right? So, you know that managers um just like any other position, they need training to be managers. They need
13:52 training to be leaders. Just because I'm awesome at something does not give me the right to teach, train, coach,
13:59 mentor, supervise others. That is that's an entirely different set of skills.
14:04 Most companies have absolutely no uh plan for how I can develop that person. So simultaneously
14:13 I've taken away my best person off the floor in selling in acquiring these
14:20 meetings, acquiring the filling the funnel and added a terrible leader and you know
14:29 u so so that's one disservice that that gets done uh unintentionally. I don't think people
14:36 are intentionally doing this. Um and second you know it if if our culture is
14:43 closing then you like in and that same BDR wants to make more money wants to advance in the company then they the
14:52 second route they take is to become an AE um that's the most common one right so different role in the company so now
15:00 I'm on the closing team I'm an account executive and I might not transition
15:07 well to that I think that's a different set of skills. I I think um people who are really really good AEES aren't
15:14 necessarily the best business developers and so uh you can simultaneously remove
15:21 your best SDR and give yourself a bad AE in exchange. That's just not a good exchange.
15:29 Yeah. I mean it it's so funny to like to think about it from that perspective. I actually have noticed in my own career
15:36 sometimes the people who are the worst operators are the best managers.
15:40 Sometimes people who are the best operators are the worst managers. I mean that's not to say that that is always how the story goes but there is just
15:47 this established like culture like a perception for some reason in the business community that well if you're good at doing this the next step up is
15:56 to be a leader. the next step up is to do this and it doesn't take into consideration the differences between those two those two three four five different things that are going into the
16:04 different roles. Um and you know like knowing that and experiencing that myself never occurred to me that people
16:12 treat you know SDRs BDRs as a JV team but then you say that and I'm like they do they always do that and it seems so
16:19 kind of backwards. So when you get caught in that trap or maybe not the trap but maybe you find yourself in the situation where your team has like do
16:28 you have like specific prescriptive ideas on how people can start breaking themselves out of it or is this a onetoone like how do you would start
16:36 navigating that as a sales leader is seeing that situation well I think there's two obstacles technical and conceptual
16:44 um technically uh I think we can learn to uh involve those people in
16:53 uh you know a program with within the SDR team or within the the business development team to be able to achieve
17:02 their goals without having to leave the team.
17:06 And but I think the reason that doesn't happen as often as we'd like is
17:15 my own perception of that. It's never people don't typically think of it that way. And I think what people typically
17:24 believe is that that's a lower level job and therefore the pay and benefits of that are lower level. So I think to
17:34 answer your question, you have to overcome that. I I think you have to start thinking about your culture. Well, if my culture is a closing culture and
17:42 we're not closing right now, everybody's miserable.
17:46 Yeah. So there there's you you can choose a culture. You you can choose a closing culture. You can choose a hunting culture when it comes to your uh
17:55 client-f facing sales team. A close is not under my control.
18:01 And so uh I can't get you to do anything. Right? And if if if we got quiet on the show right now and you said, "Josh, go close a deal." I'd be a
18:10 little scared, right? Like I can't I can't make that happen. But if you said, "Okay, Josh will give you two minutes.
18:17 Go ask for a referral." Oh, uh, yeah, I could do that in two minutes. Yeah.
18:24 So, a hunting culture is active. It's something that people can actually go do. So, eventually the well's going to
18:32 run dry. It's going to be slow or that time of year or we didn't go to the right trade show or the competitor entered the market. something's going to
18:39 happen that is going to require me to go to my AEES and say, "You guys need to get on
18:46 the phone and start pro prospecting." And I think the danger of not thinking it through could leave you with a bunch of people who say, "Well, that's I
18:55 graduated from that." Yeah, that's see that's not me. Those other people do that. And now you got a who
19:04 are trying to look busy because they are the closers, right? But if I flip that around and go, our best paid people, not
19:12 our only best paid people, but like we got some really good people here and they go hunting, they go out and find
19:20 new business for me to close. How do I get everybody behaving like them? And if
19:27 you make that the standard, uh, I think you have some AES who are really excited to go out and to to flex
19:35 that muscle again when when the company needs them to.
19:39 Yeah. And I I work with a company who's had to go through this kind of a transition and and they've really taken that to heart and began to focus
19:48 on well this is a hunting company and before you join us I want you to know that like we go out and and we hunt. We're not we're not jerks.
20:00 We're not overly aggressive. We don't hard sell. Um we're listeners. We want to find the right people. uh we meet
20:08 with people when the timing is right and if we call enough of them and have enough conversations, we're going to
20:15 find our next client. Right? If I have that kind of a mentality, I think that's the conceptual barrier
20:22 that we can break through is to choose another goal for my culture. And then I
20:29 think you can find that things start to align there and those technical barriers start to open up. And it's not so weird now
20:37 for me to pay a BDR who makes cold calls and can make 40 calls and book two meetings.
20:46 Pay that guy. Well, yeah. That that gal well.
20:52 Well, I mean, you can't close if you don't have any opportunities created.
20:55 And if you have somebody who's creating all these wonderful opportunities or even higher value opportunities, right, that how does that devalue their role
21:02 just because they're the spirit, the tip of the spear? So, so it seems like what you're saying is, you know, culturally you're bringing up to the same standard.
21:11 Even within like the pay structure, you're starting to bring up the same standard. But you can't just bump the pay and then hope the culture follows.
21:19 It's a you have to focus on the culture and then you can restructure underneath.
21:24 or does it matter? I mean, is there a certain formula with this one?
21:28 Well, I think if you structure your compensation plan correctly and you don't put limits on it,
21:36 um, and it makes financial sense, then money is essentially under the control of the BDR.
21:44 Um, you want to work 80 hours a week, uh, and instead of booking two or three meetings a week, you book nine.
21:52 And those nine meetings are of value. Um they're sales accepted. Yeah.
21:57 Um right. Like if I'm contributing more, I should be paid more. And I think that takes care of itself.
22:06 Yeah, that makes a lot of sense. All right. I mean this was a great topic to think about and especially like you know
22:14 as a somebody who's a founder who is you know both BDR AEM customer service just
22:21 everything in one and you know seeing the future where you know hoping to be more than or not everything in one but you know a piece of it you know I love
22:30 having this idea of keeping in mind that traditional structures should be questioned on how do I have my sales
22:37 team operating and looking at and saying, "How do I keep these BDRs, this tip of my spear, elevated throughout the entire process instead of falling into,
22:45 you know, what I'm seeing elsewhere and have to dig myself back out." So, that'll be fun to keep track of. Um, you know, we did get to time, so I want to
22:54 respect your calendar, uh, or sorry, your, you know, schedule. Um, any parting final thoughts to kind of like, you know, drive the whole thing home for
23:02 those who are listening in during this, uh, conversation?
23:04 Yeah, the main thing I'd say is prospecting can be its own reward. Yeah.
23:10 Yeah. And it feels really good when you get a a book meeting. Feels good. It does. Yeah. It's good for everybody. Good good behavior should be rewarded.
23:19 And uh you know we we have a gong or you know a bell we can ring and I I think that's important. But if we can take
23:27 whatever you know the rewards are and we can scale those down so that people see benefits from doing the behaviors and
23:35 and and trying right if if we consider a meeting to be a result but the attempt to get the meeting the behavior
23:43 I think rewarding those behaviors is is a a big lesson learned for me Josh really appreciate you that was
23:52 super eye opening for me uh everyone should go listen to tail sales or wait. Sales Tales. Sales Tales. Yeah.
23:58 I'm sorry. You know, I think I was thinking of DuctTales and I didn't want to mess that up and so I went the opposite direction.
24:04 What a great theme song DuctTales had, though. I know what you're talking about.
24:08 You guys might have to re uh redo your opening theme song and make it kind of DuctTales. Yeah. Won't get in any trouble for that.
24:15 Yeah. All right, Josh. Appreciate you, man. Austin, good times.