Scaling unconventional outbound with Sr Dir of Sales Development at Rippling

Speaker A: One piece. That is the average amount of daily volume for direct mail that someone in America receives. Now, if you compare that to cold emails, which is about 100 plus per day for the business executives that we're reaching out to, cold calling is even few. Uh, I mean, so few people even answer their phone. We have call blockers and that sort of stuff, but it's a fraction of the emails, but direct mail one to two. And the reason I share that is that oftentimes we take the path of most resistance when we're trying to get a hold of someone. We don't do the unscalable things. We do the things that you can automate with technology, right? With AI, we send email blasts, we sequence, we do all kinds of automation, rip through dialers, et cetera. And in today's episode, what we're going to talk about is how to scale unconventional methods of outbound, the unscalable stuff. But before we get to that, my name is Jason Bay, host of the Outbound Squad podcast and CEO of Outbound Squad. We're all about helping you turn complete strangers into paying customers. We've worked with some really great sales organizations like Shopify, Zoom Gong, Rippling and more. The number one thing that we help with is pipeline generation. So oftentimes that's through outbound. So how can we get our SDRs, our account executive, maybe our account managers within customer accounts to secure meetings, build pipeline, et cetera. And what's really interesting in this show is that we get to talk to some of the top leaders in SaaS. And today's guest is Ken Amar. He is the senior director of sales development at Rippling. So Rippling is a previous customer of ours. We helped them build out, um, the Outbound Motion and one of their first Outbound BDR teams, before they were all big and crazy. Like they've gotten to. They're over a billion dollars in ARR is what I saw recently. So, uh, Ken came on the show, uh, when I was actually in New York City recently in person. So I got to meet Ken in person, which has been something we've been focusing on a lot this year. With Outbound Squad, I've really been trying to elevate the brand. So hopefully you have noticed, if you're listening, that, uh, the quality of the episodes is much higher. We're getting really great guests. We're talking to a lot of our clients, like practitioners, people really doing the thing. So we talk about his time at Outreach. So just what he did as an SDR to get a 41% meeting booked rate. We talk about what he did as a manager and director of sales to Bev, uh, sales Dev rather, and the mistakes that he made. We talked about some of the custom landing pages they build for buyers at Rippling, how they do research and groundswell calls. We've talked about high value gifting. We talked about marketing events. We about talked what he thinks of the future of the SDR model. We talked about a lot of really great stuff. Ken was a really great guest. Uh, so do me a favor. Before you get to this, two things. Um, one, we have a free Outbound masterclass. It's nearly three hours of our very best stuff on Outbound. I went in a studio all day to record it. It has an interactive workbook. It's absolutely free. Go check it out. Outboundsquad.com masterclass and if you're a sales leader listening to this and you're like, you know what? I would like our team to do a little bit more of what Ken and Jason talked about today. Uh, reach out to me directly. Jason, outboundsquad.com would love to chat with you and share how we may or may not be able to help. So without further ado, let's get to the episode. So we found out, I just learned that. That you used to work with Clara.

Speaker B: Yeah.

Speaker A: Over at Outreach. So small world. I live in Seattle. You're from Seattle. We've talked a little bit back and forth on that. So it's good to jam with you in person, dude.

Speaker B: Boom. Um, I love it.

Speaker A: So what I figured would be really good to start out is. And I'm just always kind of curious, you decide to become an sdr. Where did that come from? What did your family think of you getting into sales? All of that good stuff, you know,

Speaker B: like every good sdr. I grew up wanting to get into tech sales. No, that was a bit of a lie. I was. I was actually, like, thinking about law school. And so I put myself, like, through college, like, working at Nordstrom and shoe sales, Right?

Speaker A: Yeah.

Speaker B: And I had a friend who got a job at Amazon, uh, as an sdr, like, slash, ae.

Speaker A: Okay.

Speaker B: And he said, oh, my gosh, you can, like, make so much money for this. And I was like, oh, like sales? Like, I'd never really considered it as a career path.

Speaker A: Yeah.

Speaker B: I was like, this is a great way for me to make some money, save up for law school. Right. Because at that point on the lsat, I was doing okay in the practice exams, but nowhere near enough to Get a scholarship. So I was like, I'm gonna have to pay my way through law school again. Um, so I applied to a bunch of places. You won't believe it. Uh, at Outreach, there's a recruiter named Mandy Manning who worked at the exact same Nordstrom I did in the same department maybe, like, four or five years before I did in shoe sales. So I saw her in LinkedIn, I hit her up. I was like, oh, my God. I work at Nordstrom. I'm really interested in getting into tech as an sdr. And then I applied, and the rest is history.

Speaker A: Oh, wow. Okay. So this, for you, was just a way to pay for school.

Speaker B: Exactly.

Speaker A: Okay, so did you know, like, much about what you would be doing, like, cold calling and, like, what did you think about doing that type of work? Did it make you excited? Were you a little anxious about it? Did you not really care because it was just a job?

Speaker B: Like, so I have a story I tell my reps to inspire them.

Speaker A: Right. Let's get the real.

Speaker B: Yeah, here's the real thing. So, like, cold calling conceptually, wasn't too worried about. Right. So, um, my parents had a small business, and I'd go, like, door to door to, like, businesses.

Speaker A: What did your parents do?

Speaker B: Uh, they made small leather goods and bags and wallets.

Speaker A: Okay.

Speaker B: And so I remember in a trip to New York, I went to 36 stores, tried to, like, wholesale our goods to them.

Speaker A: Oh, you like, cold called, like, door to door.

Speaker B: Door to door. Like, face to face.

Speaker A: Damn, dude. How old are you?

Speaker B: I was, like, 17 at that time. Shit. 33 out of those 36 stores told me to f off, like, in face to face, in person. And. And, like, that hurt a lot more than someone hanging out on.

Speaker A: I mean, it's like a 10% conversion rate almost. Not bad.

Speaker B: And then obviously, in Nordstrom, like, it's more of, like, an inbound. Like, people come up to you looking for shoes. Right. But still, like, sometimes, like, you could get, like, brushed off or being too pushy or whatever.

Speaker A: Yeah.

Speaker B: So, like, cold calling didn't seem, like, too difficult at first. Right. So I get the job, and I'm in onboarding. Right? Onboarding. At outreach they called boot camp.

Speaker A: Yeah.

Speaker B: And it was intense.

Speaker A: And this is, like, peak outreach. Like, they are booming.

Speaker B: Yes. Like, early days. Great product market fit.

Speaker A: Yeah.

Speaker B: Very, uh, intense sales culture. Right.

Speaker A: Yeah.

Speaker B: Bootcamp is great. And, like, you know, I, like, memorized the script, but how we do it was, like, we go one by one, like, a room of 12 people. You stand up. Oh, Shit, dude. I think I actually developed IBS from that. Like, I was so nervous. Like, I was. People could hear my stomach or. And they would just, like, reject you in the meanest ways possible. And then I was like, okay, it can't be as bad as this. So the first day off of Bootcamp, they give you accounts. What they don't tell you is that these leads or accounts have been recycled by every previous iteration of Bootcamp.

Speaker A: So they give you the worst accounts.

Speaker B: Worst accounts. I'm talking like, I had a VP of sales at a lumber company, right? Oh, dang. Yeah. He was the first connect I had. It's 11 o'.

Speaker A: Clock.

Speaker B: We make all our desks stand. And then I notice in the corner of my eyes, all the veterans are like. They start laughing. They start putting their headphones in, but they're not listening to. They're not making calls. They're listening to our calls, right? I was like, huh, that's really strange.

Speaker A: Oh, man. Dude, that's fucked up, dude.

Speaker B: And so I make, uh, my first call, no connect. Second call, no connect. Third call, I get connected with this VP of sales at this lumber and forestry company in Oregon. I'm like, hey, this is Ken from outreach. And he just goes off on this, like, 45. Second time, right? Hey, you fuckers. Call me every month. Take me off your list. Like, what do you do? Blah, blah. And he's just roasting me. And I was like, oh, my God. Cause I didn't realize that time. Like, sales leaders will pick up the phone, but they will, like, roast your sales process.

Speaker A: Yeah, totally.

Speaker B: And he made me feel, like, terrible, right? And I was like, oh, my God. Yeah. I generally was like, oh, my God. Like, I have student loans. I have to pay my rent. I have no outs. Like, what. What did I sign up for? Like, oh, my God. Am I a, uh, telemarketer? Like. And, uh, the guy across me also gets connect. Same thing. Yeah. And then, so fast forward lunch. Him and I, we get like, chicken teriyaki, which is like a well known thing in Seattle, right?

Speaker A: Yeah.

Speaker B: And we're in the lunchroom. It's like 12:55. Like, everyone's left. He's in one corner, I'm in one corner. I'm eating, like, chicken katsu, right?

Speaker A: Yeah.

Speaker B: And we're both crying, and we both can't look each other in the eyes because we're like, oh, no. We just realized, like, what we signed up for. Yeah.

Speaker A: Ah.

Speaker B: And that was like, a really interesting wake up call. Because the next day of the 12 people we had in onboarding, seven of them quit.

Speaker A: It's like Navy SEAL boot camp, dude.

Speaker B: Exactly like that, right? And I realized, okay, like, I have no ways out. Like, I gotta pay my student loans, I gotta pay my rent. Like, I gotta figure this out. And so, like, I think I probably spent, like, damn near 100 hours role playing with everyone on the team. Yeah. Uh, SCRs, top reps, bottom reps, managers, our directors.

Speaker A: So you just went around the office just bugging people, like, hey, can I practice with you?

Speaker B: Exactly.

Speaker A: Yeah.

Speaker B: And like, at a certain point, they're like, hey, Ken, they actually told me, you gotta stop role playing. Cause, like, there's no more. Like, we can.

Speaker A: There's no more to learn.

Speaker B: You gotta do.

Speaker A: Yeah, yeah.

Speaker B: And then, um. But I realized, like, really quickly, like, okay, like, this is one of those jobs where you can almost change the outcome by just practicing. It's exactly like sports. Like, you practice your free throws, you'll do better on average.

Speaker A: So you found this because you played basketball, I think you were saying, Right. So you found that sport, like, element of this that's like, oh, I can treat this like a sport. Like, there's repetition, there's like, um. With basketball, what I always thought about was the. There is a defense, right? And like, someone's guarding you, but there's all of these, like, moves that you can learn from the triple threat. There's like all of the things you can do, like when you don't have the ball, there's like, tactics and, like, tools that you can start to, like, arm yourself with. Right. And then sales. It sounds like you saw the parallel there. Exactly. This isn't just picking up the phone and randomly dialing people. Like, there are techniques involved with this. Right.

Speaker B: You know, it's interesting. Like, cold calling. I, um. So I'm in a couple men's leagues, right? I am. I can't jump very fast. I can run for days. But I'm really good at shooting. And I taught myself how to shoot by watching like, a dozen YouTube videos on how to shoot. Like, I'd never played, like, organized basketball until, like, college. Right?

Speaker A: Oh, wow.

Speaker B: But I taught myself, like I was at the rec center.

Speaker A: Yeah.

Speaker B: Probably for too long. You know, I didn't do, like, super hot in school, but I would just, like, teach myself, like, how to shoot threes, how to shoot mid range. Right. And like, cold calling is the exact same thing. I was like, if I practice, I can put in more time and energy into practicing than anyone else. And I know, uh, I can get better than anyone else.

Speaker A: So what were a couple of the things that you either were self taught or learned about cold calling? Like for example, one thing you pointed out I don't want to gloss over is the fact they had you stand up. Yeah, like, was that a mandatory thing? Like hey, everyone needs to stand up? Because that's like, I don't know how people make cold calls without standing up. Like, you're just your energy level and your confidence, you stick your chest out, you know, the whole power posing, There's a whole TED Talk on that. You know, um, what were some of the things that you learned just through observation that you were taught that you were self taught? Like what were some of the tricks of the trade around cold calling?

Speaker B: Yeah, so like a lot of the things, like, you know, like standing up, smiling when you cold call, even though we look kind of weird. Like I learned that from Sam Nelson. Right? Yeah, he had like listened to all those podcasts.

Speaker A: Was Sam your boss?

Speaker B: He was, he was my first manager.

Speaker A: Dang. Okay, so this was also during the time where he was posting all those lives on like LinkedIn and like, dude.

Speaker B: So he taught me all the like little things that can add up.

Speaker A: Right.

Speaker B: But one of the things I learned very quickly through observation, listening to people's calls was at the end of the day, it's a really simple thing. What's in it for them? Why would they take a call with you? Mhm. And if you have a good reason behind every person you reach out to or every person you call, you'll win more often than not.

Speaker A: Yeah, unpack that a little bit. So we call it reason to meet. And I know it may sound obvious to someone like yourself that's making a lot of these calls, but I don't think a lot of reps, even seasoned reps that aren't quite where they need to be on the phones, they aren't thinking about, like, why should this person meet with me? And the answer is not to get a demo of your solution. Like you can't say, I have this great thing I want to show you. Like, it's got to be more nuanced than that. It's got to be more about them than that, you know? Um, so tell me more about that. Like, what did you ultimately learn was the reason that someone should take a meeting with you?

Speaker B: Yeah. So it's like that vitamins versus painkillers analogy, right? Like you can sell, oh, we increase revenue by X, we increase pipeline by X. But that's all theoretical. Like humans by nature. Are very risk averse. Right. What is a problem they have that you can solve? Right. And at that time in outreach, it was typically like, uh, pipeline or revenue. Right. And attaching specifically to those problems. Anyone not using our tool I knew had a problem with pipeline generation.

Speaker A: Yeah.

Speaker B: Close rates or whatever you like, can imagine, essentially.

Speaker A: Yeah. So with the talk track, did they. Was there like a golden script that they gave you?

Speaker B: Oh man, I had that memorized.

Speaker A: Yeah.

Speaker B: Hey, it's Ken with outreach calling in a recording line. Did I catch you at bad time? Yes. No. Awesome. Uh, I'm reaching out because XYZ reason you have to have some kind of level of personalization.

Speaker A: Mhm.

Speaker B: And then it's really like going layered in into like what problems they might have and handling their objections. Right.

Speaker A: Yeah.

Speaker B: But one of the things I figured out really quickly was like, the script is a very good baseline. That's a framework for you to operate in. But at the end of the day, if you have something very compelling, you can more often than not just book them within like a few minutes if you have something very tactical. Right. So one of the things I used to do, I call other sales reps. Yeah. And they came in, one sales rep to another. Can you help me out?

Speaker A: Yeah.

Speaker B: Sales reps love to help other sales reps.

Speaker A: Absolutely.

Speaker B: Or if I fucked up on a cold call, I'd be, hey, I'm a brand new sales rep. And it's true, like, I've only been in SDR for a few months at that time. Right.

Speaker A: Yeah.

Speaker B: Can you give me another chance? Right.

Speaker A: Yeah.

Speaker B: Ah. And like, if you lead with empathy, people are pretty nice to you on the phones.

Speaker A: It sounds like another thing you were really good at too, is just coming through as a human, not a telemarketer. It's like you were really able to connect with a person. Um, dude, I love that. So one of the things that you talked about that was very unorthodox about your approach, which I think is really ironic, being that outreach, you're selling sequencing technology, yet you were like, you know what? For me, I'm not just gonna send more sequences and more emails. I'm actually gonna do something very different from that. Like what helped you be successful as an sdr.

Speaker B: Yeah. So like, you know, uh, success and outreach is very interesting. You have to use the process to get successful before you can come up with your own process.

Speaker A: Yeah.

Speaker B: One of the cool things about sequences that I loved was like, it would notify you if someone opened your email.

Speaker A: Yeah.

Speaker B: And then I noticed very quickly oh, if they open my email, I call them within, like, 30 seconds of them opening. Hey, just thought I'd give you your ring. They're more likely to pick up. And if they pick up, I can book them. And so, like, sequencing and emailing, like, I have never been a great copywriter. Right. Yeah. And it's like, it takes a lot of time. There's so many different.

Speaker A: I really don't like it. I would rather call people.

Speaker B: Yeah, exactly. So I realized, okay, like, I get a lot more results on the phone.

Speaker A: Yeah.

Speaker B: Like, back then I had a connect rate of 7%, which is, like, pretty average back then, right?

Speaker A: Yeah.

Speaker B: But my meeting book rate was like 41, 42%.

Speaker A: It's extremely high.

Speaker B: Almost a coin flip from all the practice I put in.

Speaker A: Yeah.

Speaker B: I was like, okay, so I could spend like eight hours a day putting, like, I don't know, 30 people into sequence. And a sequence doesn't guarantee you a response. M. Right. And I can try to let the system work for me, or I can be proactive. I can Tag my top 100 prospects, call them every single day from multiple different phone numbers, you know, obviously. Um, and get, like 3x the results of my peers. So without a dialer technology back then, I was averaging three to four hundred dials a day.

Speaker A: Yeah. Was it point and click inside of outreach?

Speaker B: Point and click disposition, the call and like, people. You know, it's funny, like, I see, like, the new dialer technologies, and I love them. Right. I think, like, it helps a lot of people, but you can do the same amount of dials in, like, at the same amount of time. Right. Like, uh, the technology helps it, but, like, I was making 300 dials the old school way, you know, in a day. In a day. Yeah.

Speaker A: What the fuck? Really?

Speaker B: Yeah.

Speaker A: So this is your whole day. You're like, this is my new strategy. I'm just gonna hit the phones all day.

Speaker B: Yes. But it comes with a bit of an asterisk.

Speaker A: Right.

Speaker B: So I realized from nine to five people are statistically more likely to pick up. Right. That is my prime time to generate revenue. Anything outside of that, I can focus on the mundane, the account research, the writing, the emails, the things that don't necessarily generate revenue but help. Right.

Speaker A: Yeah.

Speaker B: I also worked every single weekend, and I worked 12 hours a day for six months straight. You can't fake hard work. You have to put in the hard work. You can also be smart in how you generate opportunities.

Speaker A: Yeah. And you were SDR of the year because of that.

Speaker B: Yes, I was.

Speaker A: Yeah. Dude, I love that. So you stick around at outreach for a couple more years, you become a sdr, uh, manager, eventually Director of Sales. Dev, what did you learn about leadership? And I asked this because they. From what you shared prior to us hitting record here, it sounds like very similar to the first lesson I learned as a first time sales manager in that like, oh, shit, like, teaching people how to do this and managing them is a completely different ballgame than being really good at it yourself.

Speaker B: Oh, uh, yeah.

Speaker A: What were some of the lessons that you learned early on as a first time leader?

Speaker B: Yeah, so I think, like, I made every single possible mistake in leadership, like, known to mankind. Right. Like, I think the biggest one I went in for probably the wrong reasons.

Speaker A: Yeah.

Speaker B: I was like, oh, like being an SDR to grind. Like, I had this bald spot in the back of my head, you know, Like, I. Gray hair.

Speaker A: I was like, you didn't have all this thick hair.

Speaker B: I didn't have this thick. I had gray hair. I gained 20 pounds. Like, I can't keep doing this. Like, this is like really bad for my health. Right. I was like, oh, like, let me take this Mandarin role. That sounds interesting. Like, like I can motivate people. Or at least I thought I could. Right?

Speaker A: Yeah.

Speaker B: So I got in to get out of sdr. I was like, oh, like, I know how to like, coach people. Like, I'll get everyone to 200%. I'll make like a lot of money. I'll be like, super successful. Yeah. And then I get in and I get my first class, like 7 to 8 SDRs.

Speaker A: Are these all brand new SDRs?

Speaker B: Brand new. Fresh out of commerce.

Speaker A: So you're a first time manager with a completely, like, rookie team.

Speaker B: It's like the blind leading the blind, dude. Yeah.

Speaker A: That is crazy.

Speaker B: You know, it's funny. My first day of onboarding, I was given an Excel list of like, here's like the agenda items for like, boot camp.

Speaker A: Yeah.

Speaker B: Good luck.

Speaker A: So you had to run your own boot camp with them too?

Speaker B: Built everything from the ground up.

Speaker A: Oh my goodness. So this is like the wild, Wild west days in outreach where it was like you guys were just growing so fast that you didn't have time to do that stuff.

Speaker B: Exactly. And, um, I think the first lesson I learned was it's very easy for me to understand why I did things. It's very hard for me to explain to other people why to do it. And I realized we had a couple reps who were brand new to sales and didn't actually know if sales was Their end all that's.

Speaker A: I think, the hardest part about being an SDR leader. Right. Is that you have people that don't even know if they want to do that as a career.

Speaker B: It was really difficult. You can't make them want it. That was the most foreign concept to me. I want it more than anyone else. I'm willing to put in the time, the effort, energy. But some people don't. And that's all right.

Speaker A: Yeah. Uh, so you started to experience the natural bell curve that you're gonna experience on any sales team. And that there's the middle of the pack, there are underperformers, and then there's the two people on your team of eight, probably that were top performers, doing the 12 hours, reading the books, listening to the podcast, doing everything that they could. Um, what were some of the other mistakes that you made early on? So you get this brand new team. You have to onboard them. Dude, take me back to the first two or three months. What was that? Like? What were some of the stuff that you learned?

Speaker B: So I would tell everyone how to, like, so in, like, situational leadership, they talk about s1, s2, s3, s4, like, very directive, like, very low support. Uh, my training sessions were me basically just rambling at the reps. Do this exactly the way I would do it, and then they wouldn't do it the way I would do it. And then sometimes they wouldn't get results. But what bothered me the most is they'd do it in the complete opposite way and they would get results.

Speaker A: Uh, what bothered you about that?

Speaker B: My ego. Huh. I was like, oh, I'm an expert in this field. I know how to get it done. And then they'd show me a completely different way to do it, sometimes even better than mine. And that really hurt the ego, Right?

Speaker A: Oh, shit. So how did you work through that?

Speaker B: Well, I mean, like, at the end of the day, I was like, okay, like, what is the most important thing? Like, getting points up in the board, developing the talent. Right. And I think, um, it was a very, like, humbling moment. Like, so my first team of, like, those seven SDRs, I was pretty close to them, like, for two months, right? Like, yeah, I was making calls with them. I was coaching them, watching them develop, right? And then, like, we had a brand new cohort of another, like, 10 SDRs come in, and I'd, like, pass these, like, seven, like, SDRs on to, like, different teams.

Speaker A: Oh, dang. So you didn't even get to work with them for any extended period of time?

Speaker B: Yeah. So it was like a factory model in skill development, right?

Speaker A: Yeah.

Speaker B: But that was like the weirdest moment when, like, I'd like pass these SCRs off onto like, other managers.

Speaker A: Yeah.

Speaker B: And like I went on a happy hour with them and I was like, I kind of broke down a little bit. I was like, wow. Like, I actually really care about these people. Like, I care about their skill development. Like, I still am in touch with some of them. Like, they're enterprise AES. One's even the sales leader elsewhere. They're doing really well in their career now. A few of them aren't in sales anymore, but they're crushing. I think one's in hr.

Speaker A: Dang. So tell me more about. I think there is a skill and very much an art to connecting on a one to one level with the people that you lead.

Speaker B: Um, how did you.

Speaker A: How do you think about that? And what was kind of the learning curve around that? Getting to the point to where I can just let go and say, you know what? My job is to help you do better and advance your career. And some of that will be following the guidance I give you. And some of it will be just being creative and coming up with your new things. I'm not going to have an ego about that. To you being at a happy hour and being like, personally very touched, um, through the interactions that you've had with them and the relationships that you developed. Like, how do you think about that part? What did you learn about building that, like, relationship where you have like a, an actual connection with the people that, that work for you?

Speaker B: I think it was hard. Right? Like, I wasn't like, as an scr, you, you almost have to like, kind of shut off like empathy to a certain extent. I mean, like, it's the brutal truth. Right. Like, you get like, hung up on a lot on the phone, so you gotta like, learn to care less. Right.

Speaker A: Well, you know what's funny is like, what I try to tell people when I'm meeting with SDR groups and training them is like, you guys realize that this is the only job where like 80 to 90% of the time that you interact with a human, you get rejected. Think about what it would be like in any other job. HR, you show up to work and 80 to 90% of the people you interact with don't want to talk to you. And that means you're good at your job.

Speaker B: Yeah.

Speaker A: Like, there's a mental health component that I don't think people really understand about the SDR role, especially.

Speaker B: God, I still have it's.

Speaker A: Just like, oh, it's brutal, man. Sorry. Um, I didn't mean to cut you off though. So keep going.

Speaker B: Yeah. So, uh, like, developing empathy, right? Is like, it was like, very difficult. And it seems, like, interesting because, like, you think, like, oh, like, everyone can, like, learn to, like, meet people where they're at. But I really struggle with it my first year as a manager, dude.

Speaker A: Yeah.

Speaker B: And so I didn't. What I did as a first time sr. I just asked a bunch of people, hey, like, what can I do? What can I do? Right? And the beautiful thing about outreach at that time is we had some of the best sales leaders in the game, dude.

Speaker A: So many that are doing so many crazy stuff now. It's awesome.

Speaker B: Yeah. Like, we had Alex Kremer with Mark Costa glow, um, like Steve Ross. Right. And so I asked all these mentors, these sales leaders, hey, like, how do you, like, coach people? How do you develop them? Like, how do you build that empathy with them? Right. And I took a little bit from everyone and I kind of applied it, right, like, to my own teaching and philosophy. And I think one of the interesting things I heard, um, from Mark Costco was like, it's kind of similar to like, just sales in general. Mm. You're not gonna be able to coach everyone. Like, even the best, like, sales leaders or coaches are only effective 60% of the time. Um, and you've gotta tailor your coaching one to one to the individual. But then I was like, mark, how do you do that? Like, how do you actually coach an individual? He's like, well, first you understand what their motivations are. And so every one to one with a brand new sr, ask me, like, what motivates you and they'll typically give you like a BS answer. Right. So you gotta go a little layer deeper. Yeah.

Speaker A: Let's say I'm here to make money.

Speaker B: Yeah. And look, what does money mean to you? And typically, money is a way to get freedom or flexibility in the future. And why is that important to them? Maybe they didn't come from a lot of money in the past or they've got bills to pay or whatever. Really try to understand what their core motivation is and then use that to manage them. And sometimes it'll work and sometimes it won't, and that's fine too.

Speaker A: Yeah. Tell me more about the motivations piece. How did you get people to really come up with a strong. Why did you? Because I'm thinking, like, if I'm 22 or 23, maybe, I don't really even know. I Just know that I'm supposed to get a job right now. Was there any kind of mentoring that you would provide or guidance or anything like that? Because I think this is a really overlooked aspect of management. I mean, this is something like with the frontline leaders that we coach, we just ask them, like, how many of you guys know why your reps are doing it? And most of them don't raise their hand. They don't know the answers to those questions.

Speaker B: Yeah, I think, um, there was a VP of sales in Emea, Tom Cassley. Right. He's now at SEDNA doing, like, great things. And he taught me this framework called situational leadership.

Speaker A: Yeah, tell me more. You brought that up earlier. What's situational leadership?

Speaker B: So there's this bell curve, right? S4 and S3 are on left hand quadrant, S1 and S2 are on the right hand. And it's like how authoritative you are and versus how empathetic you are. Um, and the goal is you eventually progress to the state where you develop people enough that they can come up to the answers themselves and they only lean on you for strategic guidance or insight at that point. I was a very directive leader. I was like, do this, do this. And if I were to go on vacation, the team would fall apart.

Speaker A: Yeah, uh, of course.

Speaker B: And so I think the key takeaway, he told me, is you gotta put problem solving at the point of context. And I was like, what is that? He's like, told me to read this book about, um, turn the ship around, about this submarine crew, how they were the lowest in KPIs and they became the best because of this new person who came in. And anytime someone asked him for permission, he'd flip it back on them and ask them a question, well, what would you do about it? And that's such an unnatural emotion to me. But I applied that with all my reps and I asked them, hey, what would you do in this scenario? I empower you to make the best decisions because you have more context than I do. In that scenario, if you fail, I will be there to support you.

Speaker A: Yeah, yeah, it's really hard because it requires you to also slow down and have a lot of patience. And if you're thinking about, hey, I have 10 reps, let's say, and I gotta squeeze in a 30 minute one on one with every single one of them on a Monday. And it's gonna take five or ten more minutes to kind of lead them down the path to the answer versus telling them it can be really hard to do. And it's very, you know, in practice.

Speaker B: Yeah.

Speaker A: Situational, um, leadership. I love that it moves you out from being this, like, putting out fires all the time and reps asking you questions like, should I do this or this? Versus this place of freedom. Like, you're talking about as a leader where people start to be resourceful and do their own thinking and saying, hey, here's what's going on, here's what I think I should do, but I'd love a second set of eyes on it. That's a completely different management dynamic.

Speaker B: Exactly.

Speaker A: Yeah. I love that, man. Um, okay, so you said that people want different things out of their career and that what worked for me won't work for everyone. How did you think about, like, so what I said earlier today in an interview was the folks that come to Outbound squad, the senior sales leaders, when it comes to Outbound pipegen, they use words like standardization, framework, methodology, common language. And as a rep, when you hear those things, you're like, shit, okay, I'm gonna be given a script that I have to use a sequence that is mandated. There's so many teams, Ken, that don't even allow reps to customize the sequence. Like, they can't add anything to it. Like, they just have to hit send. And how did you think about with your team and sort of how now do you think about, hey, we have frameworks and guidance and like principles and approaches, but you have to make this your own. Like, how do you strike a balance between those two things?

Speaker B: Yeah, so it's interesting. I'm a third line leader now. Right. And like, I understand the need for KPIs, like, there's a bare, like, necessity or bare minimum of like, volume. You need to be successful. But I'm also like, cognizant of like, the tools in the market, the automation tools, the AI tools. And like, what we're doing now is not going to work next month, next quarter, et cetera. And so one of the things or like frameworks we've built on is this idea of like a tiger team or like a pilot team, Right?

Speaker A: Yeah.

Speaker B: The team that does the bare minimum in KPIs but spends more time doing things that everyone else is not doing. Yeah, it's like that idea, like when everyone zigs, you zag.

Speaker A: Yeah, right.

Speaker B: And I think that's really important now to be more human, to really stand out from the noise.

Speaker A: Yeah. And this has been a really big part of your success.

Speaker B: Exactly.

Speaker A: In your career. Do you have a couple of examples

Speaker B: you could share oh, man, I got some embarrassing examples. Right? Uh, so one time I was like, I was experimenting as an scr and then as a manager, like, oh, the idea of gifting. Right. Like, I really like that. So there's a store in Seattle, uh, called Archie McPhee, and they specialize in the weirdest, like, random knickknacks.

Speaker A: Okay.

Speaker B: So I got a bunch of rubber hands, and then in my, like, chicken scratch handwriting, I was like, can I get five minutes of your time? And I found, like, the address of, like, five people.

Speaker A: Yeah.

Speaker B: In a couple offices. And I mailed it in, and I got zero responses. In fact, like, I followed up with the people, and they're like, hey, like, that was really weird. Please do that again. I thought it was a great idea, like, a handful of time. But in hindsight, you know, like, a rubber hand might convey a wrong message, you know?

Speaker A: Yeah, it's really weird, dude. Um, so I love this. Like, hey, we're going to think about unconventional ways and get creative. Right? So you talked about the Tiger team. This is something that I think every org should have. Like, Google. I don't know if they still have it, but for the longest time, they were known to have this, like, 10% rule. I think it was where every employee should spend 10% of their time experimenting. Just, like, using company time to experiment and do their own thing. And they would surface a lot of really good creative product ideas. Um, I want to say that's how Gmail might have been invented. Actually, I'm pretty sure Gmail or one of those apps in the suite was invented on accident. Um, so what are some of the things? And maybe just if we kind of fast forward, how did you get involved with Rippling? And let's talk about some of the unscalable things that you guys are trying and testing and seeing some success with.

Speaker B: Yeah. So Rippling is a massive org, right? Like, 450 SDRs. Um, I met Chris Stone, my VP, at that time. Like, a mutual connection. We really got along because we both agreed fundamentally, in that quality Outbound beats, like, quantity outbound. Um, right. And so, like, one of the brain challenges we had in the last couple of quarters was this idea of this Project Alpha, right? Like, the team that tries to scale unconventional outbound.

Speaker A: Sales Team six.

Speaker B: Sales team six. Yeah. I love it. Um, and so, like, every week, we'll meet on a regular cadence and we'll analyze the experiments we run. Right? And we've come up with some, like, very interesting ideas. Right. Um, some of them are scalable. But there's also value in finding the things that aren't scalable. Right?

Speaker A: Yeah.

Speaker B: And a great example of this, like when I used to work at Vercel, we would build um, custom landing pages for prospects using our V, AH0 app generator.

Speaker A: Yeah.

Speaker B: uh, Rippling, we do the same through a vendor. The SCR will input all the information they know about the account, the ideal prospect, and it'll put together this very cool custom landing page with a customized demo. Here's what we know about your company, the areas of opportunity, and we'll send that via email. We'll send that via LinkedIn. Right. And it's a very in depth, thoughtful, like prospecting email.

Speaker A: Yeah.

Speaker B: In a different medium. And that's been really landing with our prospects.

Speaker A: Yeah. I mean if I'm a buyer and I click through and see a landing page that's been built for me that like speaks to me specifically. I know that that play has existed for a while, but I haven't seen a single company that we've worked with actually do something like that at scale. The closest thing was, and they've been very public about this, so I can share it. Shopify had a, A uh, website speed test that they would do and they conducted it like at scale and it would automate a landing page so that you could share a speed test. So like in E commerce, having a slow website means that, you know, it's literally the difference between someone buying something on Nordstrom.com versus you know, going direct and getting it on Patagonia's website, for example. Um, I've seen it done at scale there, but really not a lot of instances of that. Um, so that's a pretty cool idea. So I'm still leveraging the digital mediums. Right. Email, LinkedIn. And I'm assuming the other context that would be important is your reps sell mostly enterprise, right?

Speaker B: Exactly. Enterprise and strat level hrs. Yeah.

Speaker A: So these like you're trying to get a hold of like the busiest HR leaders at some of the largest companies in the world.

Speaker B: Exactly.

Speaker A: Yeah.

Speaker B: One thing we've done like pretty interestingly that is replicable across most industries and I think we've chatted a little bit about this is the idea of like groundswell.

Speaker A: Yeah.

Speaker B: So we have this like custom sequence where we offer like a monetary gift to a below the line prospect.

Speaker A: It's like a doordash gift card or something like that.

Speaker B: Uber Eats doordash gift card. They hop on a call with us and they're typically just like HR analysts or you know, people we don't necessarily want to book with, but who understand the frustrations of their tech stack. Right. And the SDR will run like a mini discovery call, get m all this intel and then try to multi thread up into their boss or director.

Speaker A: Yeah.

Speaker B: And we've seen a ton of success from that.

Speaker A: Yeah. So I think this is a great play because gifting, in my opinion, if you're trying to use a $50 DoorDash gift card to get a hold of a VP of HR at a Fortune 1000, that's a com that is such a poor taste in like, it's a poor use of funds in just poor taste. It's like this, this person is not going to be odd. By $50 they can afford their own lunch and they're just getting offered that a ton. Whereas the ICs and the managers, they're m so much more willing to take a meeting. And a little thing like this can definitely tip it over the edge. Um, what about that is working well? Do you have any tips on if someone else selling something different wanted to implement something like this? What kind of intel does an SDR get? And then how do they surface that up to an exec? Like what does that look like and how do you even keep track of that motion is what I'm thinking too.

Speaker B: So we've got different sequences built for the different teams testing this out. Um, so that adds a bit of a guardrail. The second thing we do is, um, we provide the reps with a script and a slide deck, very similar to an ae. And there's certain points they want to hit on, namely their tech stack when the contract renewal is and any frustrations or day to day pains with it. So the first 15 minutes is relatively pure discovery and then at the end we kind of leave it up to the rep's discretion. If they feel like they have enough rapport, they make the ask to multi thread up to their director, Chro, et cetera. It's like a 50, 50 shot. But when you compare that to an actual cold call where the connect to, uh, meeting book rate is about 10%, it's five times more effective.

Speaker A: Yeah, I mean it's, yeah, 10% if you're lucky. It's probably for most people watching, listening to this, more like 3% right now. Um, the other thing too is if you did get that chro on the phone and you knew nothing about what was going on outside of like what's publicly available, I really think you might blow an opportunity to book a meeting. Too.

Speaker B: Exactly.

Speaker A: So you have this like great insight. Do they ask about any internal projects or like names of initiatives or anything like that?

Speaker B: No, but you know, in the like, space we sell in, that's not as like, important as like a tech stack, but I could definitely see for like AI companies or like people facing that build versus buy paradigm. Yeah.

Speaker A: Dude, if there's anything related to what you sell that you can have a project name, I mean, that's a subject line of your email right there. That's, that's really killer too. Um, what about high value gifting?

Speaker B: Oh, yeah. So I, you know, I was researching this, right? There's a, like a psychological principle, like the law of reciprocity.

Speaker A: Yeah, yeah.

Speaker B: So people are more likely to be nice to you if you give them something. And that's like super intuitive, right?

Speaker A: Yeah.

Speaker B: Um, how we scale this is like, it is contingent on research and the prospect very in depth research their socials. Like if you can find their Instagram or their Facebook, so be it. Right. A great example of this. We found the Chro in Denver, right? Microbiology major in undergrad, big fan of Broadway. Um, has a favorite restaurant, like some Italian place, right. So we sent her this like very nice leather notebook with two tickets to a Broadway show. A handwritten note from us about all the context we knew about the account, their upcoming renewal with competitor X, Y, et cetera. And we mailed it to her, right? Uh, two weeks later she gets it, she opens it, she emails us back out of the blue. And that's generating a multimillion dollar opportunity for us.

Speaker A: Yeah. So if I think about the objections that someone might have to trying something like this, the first thing they might say is, oh, isn't that creepy? Knowing this kind of stuff, like, how did you, how did you guys think about, hey, I'm going to look for publicly available stuff. Some of it will be pretty personal in nature around their interests. For someone that says, hey, that's kind of creepy, isn't it? What would you say?

Speaker B: Is it like, okay, I have some thoughts on that. The people you sell into, I can guarantee you there are probably 100 other companies and 100 other esters trying to reach those same people.

Speaker A: Like through phone, email and LinkedIn.

Speaker B: Exactly. You've got to be different, you've got to stand out. And I would warrant that's not creepy. I'd actually warrant that's more thoughtful than creepy. Right.

Speaker A: Because you didn't send them a hand.

Speaker B: No, no, don't send them a hand.

Speaker A: Yeah, with fake blood on it.

Speaker B: Or anything. Or a chicken foot. Right. I had an SDR tried that once. Yeah.

Speaker A: Um, like one of the dog treat chicken foots.

Speaker B: Yeah.

Speaker A: Ah, that's a little weird.

Speaker B: That was a little weird. Yeah.

Speaker A: Um, so one other kind of tactical question. Did you find a way to send this and look up the person's like, home address or did you send it to the office?

Speaker B: So, um, gifting is a strategy we're like scaling out. Right. Typically we find it easier to just to send it to the office and put, um, them in a cadence that says, hey, we sent like a gift to your office. Right. Yeah. It can be very hit or miss finding, like, where they actually live. And some people feel like that's like crossing a boundary. Whereas the office is something that's like publicly available. Yeah.

Speaker A: I'm just curious. I go back and forth on this because the personal address, it does. Like, my instinct is to say this is a little creepy. Right. But this is also what people said about calling cell phones. M. Oh, that's such an invasion of privacy. There are reps now still entire sales orgs that have a culture around not calling cell phones because they think it's like an invasion of privacy, you know? So basically the sequence that you guys are playing around with is like, you mail something to the office. Yep. And then you'll follow up via email phone. Did you get the package that I sent you? Kind of thing.

Speaker B: Exactly.

Speaker A: And the other thing I love about this though, is that you're very transparent around what you want. It's like, here's a gift. But I'm reaching out because I think would be a good fit to help for XYZ reasons based on what I know about your company. Like, you're very forward about it.

Speaker B: Exactly. And you know, we don't get a meeting all the time. In fact, we probably get a rebuttal like, hey, we're still in contract with xyz, uh, for this long or this many quarters or this many years, but that's still really valuable intel for the next sea who works that account. Right?

Speaker A: Yeah. So, dude, I mean, even if it only worked 5 or 10% of the time, that's still a much higher clip than you're going to get through traditional digital channels. And the value, uh, like, you're doing this with like these senior buyers inside these incredibly large accounts. Like, you don't need a super high success rate for that to pay off. Um, marketing events.

Speaker B: Yes.

Speaker A: So give me your hot take on marketing events. Like, where do orgs go wrong with marketing events?

Speaker B: Oh, Man, I've seen like both ends of the spectrum where it's like, hey, like, we want the SDRs to invite people, but it's like, okay, if we get like a connect on the phone, which is rare itself. Like, why would we push for like an invite, like an event invite, when we could just book the meeting?

Speaker A: Yeah, we're doing, we're doing whatever three months from now, Right. Can I count you in? Kind of thing is. Yeah.

Speaker B: And then the other side I see, like people use events just for like late stage funnel, which makes sense. Right? Like people actively, like, involved in it. One of the happy mediums we found is we use like the event invite as a ledge to get in. Right. Primarily through email.

Speaker A: Actually.

Speaker B: Uh, one of the things we've done, for example, is, um, we rent out like suites for like popular NBA teams. Right?

Speaker A: Yeah.

Speaker B: Who is going to say no to a sweet invite to like the warriors or the Celtics, for example. Right?

Speaker A: Yeah.

Speaker B: And we find a list of all of our chros or high value execs in that region and we put them into this like email cadence. Right. There's a couple calls like baked in here and there, but the real value is like, hey, here's a personalized custom invite to you. There's only 11 seats. It's so you can network with us and other like, leaders in that space.

Speaker A: Who do you bring on your team? Do you bring your chro too?

Speaker B: We bring our sales leaders.

Speaker A: Okay.

Speaker B: So they can network with our sales leaders who can hopefully kick off that, uh, discovery cycle. Right. But the sales leaders love it too. They're like, oh, you know, like a ticket to the game. Like they'd love to go.

Speaker A: Oh, yeah. And plus, I would imagine you could with this strategy if you needed to invite a client or two also where it's like, hey, there's going to be the, uh, Chro from DocuSign and XYZ Company are going to be there. It's going to be a small event. We'll have 10 other HR leaders. It's like, it's kind of hard to say no to that.

Speaker B: Exactly. In fact, like, if you look at like the email sentiment of the Cadence, like one of our highest performing. Right. Like 70% open rate, which is like insane nowadays. Right. And like about like a, uh, 40, 41% like reply rate of which the vast majority of replies are positive or like, oh, I can't make it, but like, thank you so much for the invite, et cetera.

Speaker A: Yeah. It's like the, one of the big things that we talk About a lot is the concept around offers. And we did a really big study with gong 85 million cold emails. And the presence of an offer in the email. So something like you're talking about increases the reply rate by 28%. Asking for a meeting, like a direct ask for a meeting decreases the average reply rate by 44%. So it's like you essentially gotta trade asks for offers. Like what are you giving? Right. It could be the gift card or the, you know, whatever for the groundswell motion that we talked about. It could be an invite to uh, a uh, you know, NBA game suite, an exec dinner, a VIP dinner. Like something like the give, I think that a lot of organizations aren't really thinking about, like what tangible value am I actually giving them in return for their time?

Speaker B: Yeah, exactly.

Speaker A: What makes it worth it for them? Um, any other kind of outside of the box things that you guys are either trying or that you've done in a previous life, in a previous role that you've seen success with, that's kind of these unorthodox, unscalable things that don't involve just hammering the phones or sending out a ton of emails.

Speaker B: So when I was at Vercel, um, in the very niche world of front end web development, right, like we had all these celebrities in the space, right? Like Guillermo is like the creator of Next JS, the most popular like JavaScript framework of all time, right? And we had Malta, the guy who wrote the Google search, right? And a couple other like really well known influencers in the space. And we sold like a freaking technical product, right, that people would more likely have their DevOps team build rather than buy it from some like random startup. And you know, um, these folks tend to be very active on Twitter. They're always engaging with Jermo. And I found it really appalling one day that like they respond to Jermo on Twitter, right? Like the um, engineering lead at like Lululemon, for example.

Speaker A: Yeah.

Speaker B: And my reps have been calling and emailing that guy for like months. Yeah, I was like, how can we break through with him? Right? And we couldn't obviously take like our CEOs Twitter, but we were able to spin up email aliases for our execs and do one to one outreach on their behalf. Obviously there's some guardrails that we have to build in with like their voice and like making sure they're okay with it. But as long as we gave them like a list of the um, contacts would reach out to, I think like it was damn near like an 80% hit rate in those. Like if you get an email from someone you know who's like a well known person in that space, you are going to respond, Yes, 100%. Yeah.

Speaker A: Yes. This is something I'm surprised that more teams don't do because you can put guardrails on it and you can ghostwrite the emails. You can basically remove almost all of the work from your executive.

Speaker B: Exactly.

Speaker A: Dude, there's so much there. Um, before we switch gears, anything else that comes to mind?

Speaker B: I think those have been the pretty big ones. Yeah.

Speaker A: Ah, some good ones. Dude. Let's talk future of the SDR model because you have quite a few hot takes on this. You've been in the game now for quite a while. Where do you see the, how do you see rather the SDR model evolving? Because we were at a time where the predictable revenue era, we'll call it from 2011 to 2018 was basically, hey, let's split the sales role into three parts. Let's do hunters and farmers and let's have SDRs do basically the majority of pipegen for the account executive. And then let's have farmers account managers manage the accounts and then we have what I'm calling the sales engagement golden era. You were a part of that where it was like, hey, there's a different way to do this. Um, in order to support the predictable revenue model, you need tooling to do that. And AES, they're going to need to self source a little bit more. And then 2022 hits 2023 where the American economy at least was not booming as much anymore. Buyers are a little bit more careful. They've been burned before. They're getting started smaller. They don't have all this injection of VC and PE funding that they have to and the purchases are just being scrutinized more. And you saw a lot of SDR teams get laid off where they were looking at the numbers and they were saying, hey, this is not a profitable part of our organization. And then you saw this like really big scrutiny and trend which I'm sure you've seen in your career of hey, meetings are not as important as opportunities and pipeline generated. And what's the closed one? Revenue from the SDR team. So there's a really big narrative around like SDR model being replaced by AI, which is crazy to me. I think certain parts of what we do with outbound can be replaced, but that's like a big narrative that you see right now we have a, uh, client who I won't mention the name that dude. They're removing inbound altogether from the sales team. And when I say inbound, I don't mean demo requests, I mean anyone that is on their marketing list that is not proactively raising their hand that you would normally have SDRs call into webinar leads, case studies, like all of this kind of stuff, they're completely taking that off of the plate of the SDR team and the sales team and they're just having like AI, uh, chatbots. I'm going to call them chatbots because that's really what they are. They're not AI agents, it's just this chatbot. When the person goes to the website, there's a SDR that pops up and like interacts with them. So that I'm seeing like happening now. Um, the future I don't think is that bleak though for this team, for the SDR Org. But I'm just curious, just you being someone that's been in the game for a while, you are in the trenches right now. Like what's the future of the str. Org in your opinion?

Speaker B: Yeah, it's an interesting question. Right. Like first, like on the topic of AI, like everyone is using the same tooling to send the same generic emails.

Speaker A: Yeah.

Speaker B: And it's helping. Sure. With time savings.

Speaker A: Right.

Speaker B: But I don't think it's like a big differentiator. What I think like the org or like the, you know, the function itself is going to evolve into is more of like an ISR model.

Speaker A: Yeah.

Speaker B: And obviously if like the unit economics support this and like the deal sizes are big enough. But I genuinely think that era of like high volume generating opportunities is going to be over and it's going to be more of SCRs and SCR managers owning late stage funnel. And by late stage I mean like past what they currently do.

Speaker A: Yeah. Do you think that part of that's going to be like. So for example, let's not use rippling because you guys have like an SMB and mid market and enterprise and strat. Um, a lot of companies only sell like large enterprise deals. Do you think a part of this is Also like the ISRs, let's call them closing. Maybe the pilots, like they, they get the foot in the door with smaller project that maybe an enterprise AE doesn't have the bandwidth to work. Do you see an element of that as well or.

Speaker B: Yeah, I think there's an allocation of just like time and resources.

Speaker A: Yeah.

Speaker B: Right. Like you, uh, especially if you're selling in the enterprise, you want to land where you can, but like if it's not like a multimillion dollar deal, it's typically not worth an enterprise or strategy's time.

Speaker A: Yeah.

Speaker B: And so you come to this interesting dilemma where like you want your SDRs to generate pipeline, but you also want to get these like small at bats when you can. Right? Yeah. I genuinely think the like the function is evolving to be more like that. Yeah.

Speaker A: And it makes a lot of sense too because I'm curious your thoughts on this dude. In when you were at outreach, how quickly were the SDRs getting promoted to AE? That did well, really quick, like less than like 8, 9, 10 months.

Speaker B: Right.

Speaker A: That promotion path hardly exists for most SDR orgs right now. Yeah. Like you have to retain an SDR for sometimes a couple years. You have to keep them around and what better way to keep someone around than to like start getting them to do the things that they would do as an account executive. Right. And it's like giving them more stuff to learn, more stuff to master, more responsibility, more pay. Like all of this stuff. It's like you keep the talent in house. So many people jump at the 12 month, 18 month mark. Really. I think as the data shows, like the 18 or 17 months in, if they can't get a promotion internally, they just jump somewhere else.

Speaker B: Yeah. And they repeat it all over again, dude.

Speaker A: And you just wasted all of that time and energy and money like onboarding, managing, etc. So you see the future then the SDR owns more of the late stage funnel and it is a really interesting take. The SDR manager helping with more like discovery and that sort of stuff.

Speaker B: Yes. Okay. So like I envision a future with flatter orgs where SDRs and SDR managers are involved in like much more of the funnel. Right. Because this is a bit of a hot take. Right. But when I think about it, it's

Speaker A: a major hot take because like I'm wondering where the, where's the SDR manager going to find the time?

Speaker B: So the most important part of an SCR manager's job in my opinion, is to coach. Right. And when you have a team of five reps making 100 calls a day at an average 3% connect rate, which is like pretty strong I'd say nowadays there's not going to be enough times for them to actually actively coach. Right?

Speaker A: Yeah.

Speaker B: But if SCR managers actually took discovery calls themselves along with the SCRs, right. I think they would feel like more of a sense of ownership, more of a sense of control over their outcomes. Right. Yeah. And like, I hate to say it, but the XDR manager job is typically contingent on 5 to 10 fresh college grads making 100 calls a day to C suite executives. Right. Are they really being set up for success there?

Speaker A: Yeah, I don't think so.

Speaker B: Yeah.

Speaker A: Yeah. So where do you feel like the problem is with most orgs then? And where like the SDR manager, uh, it just seems like they can barely find time to coach.

Speaker B: I think it works good enough the way it is now.

Speaker A: Right.

Speaker B: And obviously the unit economics have to make sense for this model to be applied. But I also think part of the reason why SDR managers are so stretched so thin because at the end of the day you do have to wonder what is the value behind an SDR manager? The coaching. But if there's not enough moments to coach, you give them more reps. But then it's kind of like a chicken and egg dilemma, you know, like.

Speaker A: Yeah, um, yeah, yeah. Because you can only work with so many people at a time. Like this is a hot take that another guest shared on where they were like, oh yeah, I think with the future of AI and all this stuff, you'll see a sales model where a manager could work with 30 reps. And I'm like, I don't think so. How could you possibly have great one to one relationships with 30 people?

Speaker B: Exactly.

Speaker A: It just doesn't work out. It's too many people. Um, give me your take on just most AI tools in general. You said over promise and under deliver. What's your take on AI in the marketplace right now? And let's throw everything in there, dude. The coaching solutions, uh, the automations, the signals and triggers and all of that kind of stuff. What's your take on AI in general?

Speaker B: Uh, and I think like AI is overhyped. M. Right. Like uh, the premise of it, like you know, replicating an STR or an AE or even sales in general is not going to happen. Right. And frankly like I have been involved in sales cycles for several different AI tools.

Speaker A: Yeah.

Speaker B: And conceptually, like I understand like the value they think they can bring. Right.

Speaker A: It sounds really great in theory.

Speaker B: It sounds great.

Speaker A: Yeah.

Speaker B: You could replace inbound with like uh, an inbound AI tool.

Speaker A: Yeah.

Speaker B: Right. But it's not really AI. Right. It just like it's automation, a different form of automation. And the annoying thing is like everyone else is doing the same thing. Like two years ago signals were really hot. Now it's like commodified. Right?

Speaker A: Yeah.

Speaker B: Like automation or execution via AI.

Speaker A: Right.

Speaker B: Like that also is Getting commodified as well too. Like, AI SDRs now are just basically the next evolution of like an scp, right?

Speaker A: Yeah.

Speaker B: I don't actually think they provide tangible value yet. At least the ones I've seen so far.

Speaker A: Yeah. And when they really do provide tangible value, like let's say your best enterprise SDR right now, if AI is able to ever do, at least over email, because there's a lot of regulation around the phone, which my hot take is that this is why the phone is so important. It's the thing that AI can't do. Um, if there comes a day where an AI could be as good as one of your enterprise SDRs,

Speaker B: like, I

Speaker A: don't see that moving the needle as a whole on the efficiency, because now the floor has just been raised. And noise is noise. Like the chros that your, uh, reps are trying to get ahold of right now. Let's say that the typical one gets a hundred cold emails a week. If those are 100 A grade emails, it's still 100 emails. It's still a shit ton of noise. And like, this is where I think in your career you've talked about, hey, when everyone zigs like, how can I zag? It's like, where can I go where the attention is just, like, easier to come by. I don't think AI is going to help do that. I think it's just going to, uh. It's scaling sloppiness right now. And then it's also going to do. I think it's going to follow the same path as sequences did. Sequences were really great until everyone started

Speaker B: doing it, you know, um, one of the first SDRs I onboarded was so conceptually against the idea of sequences. Oh, yeah. So like, it was like 5pm she like, pulls me aside in front of everyone in the salesforce. She's like, ken, are we the problem? And I was like, what are you talking? She's like, you know, we put people in a sequence, but, like. Because they're not responding to us. But, like, does the purpose of a sequence defeat, like, the purpose of reaching out? And I was like, listen, Ava, like, that is really above my pay grade, but that's a very good point. Right?

Speaker A: Yeah.

Speaker B: And, you know, I think back in that conversation a lot now, I think she was right, but the market is moving in that direction and if everyone's doing it, like, uh, to your point, it's all gonna be noise.

Speaker A: Yeah. The irony is that these tools that help us better get in contact with prospects are Also, the same tools that make it harder to get ahold of prospects. It's just like what comes around, goes around with us.

Speaker B: Exactly.

Speaker A: Yeah. Um, dude, I got two, uh, rapid fire questions for you. Okay. Um, how do you prevent and deal with stress being a sales leader? Most sales leaders, reps. It's a stressful job. Like, what do you do to deal with and manage your stress?

Speaker B: Um, so I'm really into things where when I do them, I forget about work. And so CrossFit, you finish a tough workout. Right.

Speaker A: That's what we should have done while I was here. We should have got a workout in.

Speaker B: Dude, get a workout in, like, jujitsu. That's another one. Right. When you're getting choked out, like, you're not thinking about, like, your pipeline attribution. Right. Or basketball. Right. When you're playing basketball, you finally feel you can just get your mind off of work. So I think, like, anything physical for me helps me with stress.

Speaker A: We have to connect you. Do you know Armand?

Speaker B: Yes. Over in Williamsburg. Yeah, he's big. He's very good, apparently. Big jujitsu guy. Yeah.

Speaker A: You guys will have to roll.

Speaker B: Definitely.

Speaker A: Um, lastly, if you were a first time, you know, SDR or SDR leader all over again, knowing what you know now, what advice would you give yourself?

Speaker B: Oh, that's a tough question. Okay. If I was a brand new SDR necessary. I think the theme of this, like, episode has really been about, like, zagging when everyone zigs. And I still hold true to that. Right. Like, I tell my SDRs this all the time. Like, we sell in a very consolidated, like, very cramped space. It's super competitive.

Speaker A: Yeah.

Speaker B: There's probably 10 to other, like, 20 other vendors that do a similar thing to what we do. And I know for a fact our product is better. We're built differently. We have better funding, we have better execution, et cetera. But if I'm a buyer, I think all software is the same. I only care about the problems I have. So I tell my SCRs, hey, you should never pitch your problem too much. You should pitch to their problems and you should do whatever you can to stand out from the noise. I encourage them to do things that are unconventional, like text them, obviously, like if they come inbound and within certain regulations, or mail them, not a hand, but something in the mail to stand out from the noise. Right.

Speaker A: Maybe a foot or something.

Speaker B: Maybe a foot.

Speaker A: Love it. Dude. Where can people go to connect with you? Um, are you guys hiring at Rippling? Like, where can people go to check everything out.

Speaker B: Yeah, ken Amar on LinkedIn. Um, we're hiring SDRs and SDR managers. Please reach out. New York, Austin and SF.

Speaker A: Awesome. Did he have you on the show, dude?