The Blueprint to Stacking Your Calendar and Closing Deals with Cold Outreach

What up prompt jockeys. We have a very special guest today, one of my best friends, someone who went to high school with Andrew Holman. Welcome, brother. Thanks for having me, Joe. So Andrew has been in the startup game for a while and been slinging Sass ever since we graduated college. And he is a wizard when it comes to cold outreach, getting meetings booked on the calendar. So he's here to impart some wisdom on us share his experiences, and teach us how to make sure our calendars are always full. Yeah,

I think that's, that's really what it's all about, man. You can never have enough top of funnel, both in terms of quality and quantity. Yeah, a little a little bit more about how I wound up here. I, much like most people had no idea what I wanted to do after college, he graduated with a degree in marketing and was just like, what, what can you do with that? And got my first job working at Prudential over in Rockefeller Center, and, you know, was dealing with marketing and sales direct to consumer, trying to push annuities, life insurance, auto insurance, like the whole nine, it was the most fucking boring thing you could possibly imagine. Every single person in the office was a older white male, no diversity. No women, only women that worked. There were secretaries. And I just knew that that was like a very demotivating environment. So I started to talk to more people and saw that there was a high demand and SAS sales jobs. So I really knew nothing about it started interviewing and places and landed my first company company called cerros. Back in 2017. I was I think their fourth ever SDR hire internally, they had outsourced lead gen for a while and then began to bring it on internally as the company position to scale was an individual contributor there for a little over two years, then I was fortunate enough to get to manage my own team. So I started managing a team of anywhere between eight to 12 people, we received a Series Series B funding, we went through one of those scaling motions of just like get asses and seats, the team continued to grow, we were fortunate enough, throughout COVID-19, to have a product that was in really high demand. So luckily, we weren't really that impacted. We actually raised the Series C 100 million round during, in July 2020. And then soon, soon thereafter, I was promoted to a director level role where I oversaw the entire operation. domestically in North America, we had a, I had a counterpart who oversaw things in the UK. And I was also tasked with forming a completely new function, which we we dubbed our junior account executive function, it was sort of an in between between being an SDR and an AE. And they were responsible for full sales cycle, prospecting, discovery, everything all up until the negotiation, but more geared towards net retention. So with our current clients, focusing on cross sell, and upsell. So it was there for about a little over six years. And now I've spent the last six months at a completely different type of company in HR technology company called Nya, again, based here in New York, where I've had a team of anywhere between six to eight people focusing on top of funnel, very, very different motion. But yeah, it's just something I've always been passionate about, and always, you know, just sort of wakes me up in the morning,

dude, so something that I think is very unique to you is that, like you said, you are passionate about this stuff. And you have embraced the SDR role, obviously, you're in a managerial position now. But embracing that role, and being passionate about it, I think is what has led to your success. And it's something that I also saw Google, like the top reps at Google were the ones that worked at Yelp, they worked at home advisor they worked at Indeed, and they didn't dread the cold calling every day they embraced it, and they got really fucking good at it. And it led to them being like the top killer AES out there. And you've done something similar where you took the job seriously and made it your own. And I've seen some of the the outreach that you've done. And it's it's very impressive, you approach it differently. So talk to me about your your philosophy a bit and how you approach these things.

Yeah, yeah. So I think I think it obviously depends on on what you're trying to accomplish. Right? If you're a one man band, just trying to, you know, set up a high volume of appointments for a highly transactional type sale. It's definitely different than if you're going to Be at a you know, mid sized company focusing on you know, penetrating enterprise mid market type businesses, businesses that are doing 500 mil a billion in revenue right there there will always be the aspect of like the set it and forget it the spray and pray for I guess for the purposes of here I'll talk more like commercially and what my experience what I've seen to be successful and what I've seen to be unsuccessful, the spray and pray the set it and forget it, motion is dying, it's dying very, very quickly, especially if you want to be considered a legitimate operation. Right? Like, there's nothing I always all of my philosophy all of my like motions always stem back to just putting myself in the seat of the person I'm trying to get to answer my email my phone call? What would what would optimize like their day? What would optimize their experience with me? Again, a complete stranger, who for all they know I'm some robot created out in India or something? What would it look like if I'm trying to get the entire finance departments attention, and all of them receive the exact same word for word email in their inbox? 30 seconds apart. And they're all sitting in the same office, right? spam, spam, spam, unsubscribe, unsubscribe, unsubscribe. Right like that? Is I believe that that's not a in a I believe it's an effective way of getting the right people on the line, right? Because there's always going to be the argument of, do we care about quality? Or do we care about quantity? And I think it's about blending the two together? Again, it really depends on Hey, are we selling a$500? More transactional software? Or are we selling a software that's, you know, the average order value is between 56 figures, seven figures, right? It's gonna it's gonna depend what I use spray and pray set it and forget it to do is to sort of funnel out the week, right? I like to analogize a lot of things in in the day, in the day to day, and what I would equate, you know, setting a, let's just say I'm gonna send out 500 emails today on instantly or SalesLoft, or outreach or whatever it may be HubSpot, what I want to do, then at the end of that day, or the first thing the next morning, is look at what I got. And let's just say, you know, out of 500, you got a 10%, open rates, you got 50 people open it. And you don't necessarily have to take a next step there, right? Let's let the sequences do their job, which in my mind is not booked the appointments. But it's tell it's to tell me, who I'm more likely to actually have a conversation with, and thus, more likely to book set appointments. So then maybe that was on Monday, maybe then on Wednesday, they get round number two, and of those 50 people and other 25 open for the second time. So what I've done there is I've verified a few things. A, they're approachable via email, which is big, right? Like, I have a legitimate chance of getting their attention over email. That's big, that saves me a shit ton of time, with all the bounces with all the spam traps out there. That's a really big learning, and B, now I can dive into those 25 people that now should be somewhat familiar with me. And I can really say okay, of those 25, who is worth my time, based on my ideal customer. If I'm trying to get the finance or accounting manager at an organization of 500 people and their finance team is 10 People did the person, right? Was it just an analyst that opened the email twice? Or was it a manager? If it was the manager, guess what I'm doing. I'm taking him out him or her out of that sequence. And now I am putting them to the side and I'm saying you are you've won the jackpot, you have now won my attention for the remainder of my outreach. And I'm going in and I'm getting in the trenches, and I'm beginning to do research on the person I'm beginning to do research on the company. Obviously, this is a very, very it's a very, very manual process. And there's a bunch of tools out there that can help you along with with so to speak, personalized email writing, but I've always found it to be the most effective to pick something or multiple things that you know, really, really well and utilize that. For example, Joe and I are big sports guys. If I'm trying to get the attention of the finance manager and I see that they're in Massachusetts, or I see that they went to a big name College, I'm referencing the Patriots or I'm referencing LSU or FSU in the subject line. I'm right maybe one or two sentences, and I'm saying, Hey, I'm gonna go out on a limb here, seeing that you're over in Boston, and say that you're a Patriots fan. As a self loathing Jets fan, I gotta say, it looks like it's gonna be a long year for the both of us. And then I'm going directly into a value prop, CTA, and I'm ending it there. And it takes me no longer than 90 seconds to write that email, so that I can write 2025 3050 of them. I'm a big proponent of the thought process of 100 highly personalized, crafted emails a week is much more effective if it is just as effective if not more effective, than 2000 Canned generic emails again, because you always need to be keeping in the back of your mind, who is it that you want to get on the phone? Are you happy with getting a finance analyst on the phone? Who has no buying power? Who's three rungs below a decision maker? Or is it worth your while to actually go more towards the top? It's always a conversation about opportunity costs. But I guess enclosing, personalization is key. And this is just with regard to email, right? Obviously, if someone's opened a couple emails, first, I'm calling them first. First and foremost is the first thing I'm doing. Because I want to get my answers quick, this is a game of opportunity cost. It's saying, if I'm going to make an ad, if I'm going to spend an hour, from noon to one making dials, that's an hour that I don't get back during that day, researching client researching prospects, writing emails, doing admin work, whatever it may be. And so you really have to have an intrinsic, very, very deep down appreciation and understanding for your ideal customers, because that should always just be dictating where, where your motions go throughout the day.

That's really fucking smart. I wish that I spoke to you about this, when I was still a BDR, I was a horrible fucking BDR when I worked at Google, I was really bad. And then when I got a EA roles later on, I would do spray and pray. And I would hope that my BDR has brought me leads or that things came in inbound. And obviously, it never worked out that way. I think that regardless of whether you're starting your own company, or you're an AE, or you're an S, like, top of funnel is the most important and the most, the most challenging aspect of, of jobs. Yeah. And it's something that everyone always wants to automate and get off their plates. But if you're really, really good at it, and really pay attention to it, that's how you build pipeline. That's how you build businesses. Yeah, the. So I like the idea of you go through the opens and you see who your who your potential warm interest is there. What are your thoughts on like, the length of the initial email because what you're doing it sounds like they might be a little bit longer. But you can kind of ignored the conventional wisdom that says longer is bad in this case, because the personalization makes up for it. Is that Is that accurate?

Yeah, I would say overall, it's accurate. But brevity is important, like being concise. Because what I'm what I essentially, here's what I'm offering to them, by taking five minutes of my time to research them as an individual, right? Gong did a really, really good webinar a couple years ago about personalization at scale. And what you want to think about is the nine to five, what the person cares about during the hours of nine to five. And if you can find out anything about their five to nine, what they care about after work, you're golden, right? So if I say, all right, Joe, he's an entrepreneur, he's a self starter, he's probably always looking for ways to increase efficiencies, save money, and I have a product that does that. That's great. And I also find out by doing some snooping, right by doing some true hunting, that He's an avid softball fan, guess what I'm doing? I'm googling something about softball. And I'm throwing that in the subject line. What I'm doing by that by saying, Hey, Joe, I've just invested some time in you, is I'm hopefully asking for you to give me the time of your day to just read what I have to say. So in that sense, right? I mean, it's pretty logical, right? And of course, this is like, what percentage of of the time does this work? I couldn't tell you that because there's always going to be the people that have a strict no email reading policy from vendors I don't recognize or whatever it is, right. However, I like just logically speaking, Intuit intuitively speaking, like, that's what I'm doing by that. I'm saying, Joe, please just read what I have to say. And guess what? Also, like, if you're reading it, and I see that you're coming back to it multiple times. I'm gonna do it. Again. It's a war of attrition, right? It doesn't work. On the first touch, second touch all the time. You have to If you have to also pick people that you're going to be able to have ammunition for to write three, four or five personalized emails over the course of two weeks. But that's not to say that you shouldn't always have brevity in the back of your mind, in my mind, it's like, I care about the subject line a lot. Because that's the first thing that's going to get someone's attention, right? If you're looking at if you're looking at email on the phone, you have subject line, and then you maybe have the first line, if you're looking at email on your, on your computer, you have a little bit more of the first line showing. So it's like, you know, for the softball reference, it's like, you know, Jenny Finch is my idol. And Joe is like, what the hell? I don't know, because I know nothing about softball. And in the first sentence of saying, Hey, Joe, saw on LinkedIn, or saw on Twitter, or whatever it is, like, you can't cross that line of like, what's thoughtful versus what's creepy? And in my mind, if I'm, if I'm referencing something that is publicly available, that's not creepy, right? If I'm referencing your family, or something like that, of course, that's fucking creepy, right? But, but I'm getting right into it. Hey, Joe. So you're an avid softball fan. or So you're an avid

What's the subject line? In that case?

I google like, you know, best softball bat, or, you know, best softball tournament, or just anything, like play a lot of play a lot of softball this summer, right? Like, ask a question, something that is just going to be different than what everything else you're seeing. And so again, that's it's the first step to get your attention and hopefully read what I have to say, first one or two sentences is about you. And I'm not really talking about myself at all, or the product. And I'm using the word I as least as possible. Hey, Joe. So you're an avid softball player. You know, we got some, so So you're an avid softball player, and that you're, you're down in Florida, you must have had some great weather this year, hit any homeruns. Right, something corny, but also like, it's never a bad idea to sort of fluff the person up. People love to be the center of attention. And then it doesn't really matter. I'm just going directly in second paragraph two sentences about what my product does and why other people buy it. And in third sentences, like CTA, it can be as short is that. And it's difficult because some products have a more complicated value, prop and multiple, multiple value propositions. But again, it then goes back to under having a deep understanding of that purse of your persona, right? Yeah, like when I was at service, we were selling to marketers. And the content marketing persona has a lot different. has a much different day to day and cares about much different things, although they all lead up to the same goals than a product marketer. And I needed to know those differences inside and out. Because if I'm talking to a content marketer about things that a product marketer cares about, I'm losing all credibility right away.

And then, so talk to me about the, let's say you want to do the cold call. Right? Let's say they they open you send your personal, they open it again. Yo, now you want to go to the cold call. Yeah. What are you going to open up? Like, how long is it going to be? How many of those can you bang through in in an hour? Because I think a lot of this manual stuff in people's heads, even myself included, I'm like, Now that takes too much fucking time. But with what you're saying there, you can you can standardize that second and third paragraph and personalize the first one. You're going through those in like an hour. Yeah, the cold call. Talk to me about that. Yeah,

I mean, no to your point, like if you're just reaching out to CFOs, and the value prop doesn't change your copy and pasting the second and third paragraph so you can bang out a lot. And also like, what I tell reps when, when they're like telling me all this, this is too burdensome, it takes too long. I'm like, yeah, it takes too long today. The goal in sales with all of these different crafts, whether it's email, writing, cold calling, filling out admin shit in your CRM, is to get incrementally better over time. That's why you do call practices, right? You listen to bad calls that people made, and you provide actionable feedback, so that next week, they come they come back, feeling a lot more confident, hopefully, right? But obviously, if you don't have the desire, the coach ability, right, they call it like, a lot of places called will will skill and Hill, right. Do you have the will? Do you have the skills? Do you have any any sort of like natural ability, and are you able to climb the hill? Right? And if you're lacking in certain areas, then you know, I don't know, I really don't know if you're going to be successful. That's why you know, a lot of these jobs look for self motivated self starters entrepreneurial, because you are an entrepreneur, even if you're a BDR. at Salesforce, you are an entrepreneur in the sense that you have a territory it's not getting bigger and it's hopefully not getting smaller, and you have to extract the most amount of value out of that territory as possible. Much like an entrepreneur, right. But going back to the cold call, I'll give you an example. So I was covering for a rep of mine. Over the summer, their territory was like the upper Midwest. So like Ohio, Minnesota, Wisconsin, right place in the country that I've never fucking been to. And I honestly don't plan on ever going to. And I was going through these people's LinkedIn ads was identifying the right people that I wanted to enter into, like a personalized sequence. Thus, like write a personalized email, and then follow up with a call, either next day or same day, if I saw they opened up and just be imaginative. Like, this is where the beauty of it comes into play. Because it's only cumbersome if you can't think outside the box. Right? And every single person I don't care who you are, is able to think outside the box. Like we all played with fucking toys in our childhood, hopefully, and had some sort of imagination. So I would go I went to this woman's LinkedIn, she was bare, enough of her job title, her history, where she went to college and that she lived somewhere in Minnesota, but it had the exact city in Minnesota. I'm like, Alright, fuck it. i This is someone I really, really want to talk with. She was like an instrumental person in that territory. I googled the town in Minnesota, followed by restaurants. I picked one restaurant. I said, Have you ever been to GE is that BS? Right? Hopefully, hopefully, like, okay, that's, that's right. Like if you were to throw in an obscure restaurant in Forest Hills in New York, where I grew up, like, that would get my attention. She opened it. She didn't answer. And I followed up with a call, like, 20 minutes later, and I said, Hey, this is I was pretending to be someone else. But whatever. I said, Hey, this is Andrew calling from nya. How you doing? Yeah, I'm the guy and I dove right into it. I am the guy that that shot you over an email about this episode before how you doing right like I am. I'm establishing right away, that I'm the guy that's like, really putting in some effort here. And she was taken aback. She was like, oh, you know, nice. Thanks for the call. What What can I do for you? And you know, to sort of like disband any of the awkwardness. I was like, Yeah, you know, honestly, like I, I hope that didn't come off weird. It's just that if I'm trying to get someone's attention, I like to put in some thought and some research, I hope you don't mind. Right. And again, the self deprecation angle, like a lot of salespeople use it, some people don't. Because at the end of the day, I'm just doing my job. But I wanted to give her the proper context. And then she was like, oh, no, actually, that's sort of thoughtful. Boom, my right like my, I'm in, I'm gonna have a conversation with her. Because the thing about cold calling is that no matter who you are, when you see an unknown number, like calling your phone, your guard goes way up, because you're expecting it to be someone trying to sell you something over in China or whatever. Someone trying to pitch you something that you don't need. Someone trying to bother you. Somebody interrupting. Yeah, maybe they're going to try and steal your identity, whatever it is. However, I think as humans, we have a natural curiosity to say, Oh, let me answer this, right. Maybe it's maybe it's my friend, or maybe I have been expecting a call. Or maybe, maybe it's a lawyer calling to tell me that I had a great aunt over in Virginia I never knew about and died and she left me a million dollars, right? Like, whatever we have.

Last night, maybe this is Brian Cashman. Maybe this is Brian Cashman. He saw me play softball.

Yeah, yeah. Right. You have that natural curiosity, but the guard is up. And I want to do everything in my power within those first 1530 seconds to get that guard as low as possible. And some people you're just never going to be able to because again, they have a policy or that's just who they are. They woke up on the wrong side of the bed. They're getting divorced, whatever it may be. I like to do like a little like, Hey, this is Andrew like a little laughter in my voice because tone tone is everything. There's a big difference between saying like, Hey, this is Andrew versus Hey, this is Andrew, how you doing today? You know like that, that right there could kill any sort of conversation. The great thing about personalizing emails out like any sort of outreach, LinkedIn, it becomes your phone script. Right? Like all I did, was referenced the email. That's not the reason why I'm calling by the way, right. So it goes something like this. Hey, it's Andrew calling from nya. How you doing? Yeah, sorry. I was wanting to send you an email about Giuseppe before Yeah, I always like to do some research on on folks. When I'm trying to get their attention. I think it's the least I can do. To please does look delicious. But anyways, sorry to call you out of the blue. The reason for my call is and I go into right like why are you going to find value in not hanging up on me even Right? Like, I can't expect that, or they're not obligated to give me any more of their time than they've already given me. And I want to establish credibility, I want to establish, you know, that I'm being thoughtful. And then I want to get right into it, right? There's a lot of schools of thought on it. A lot of people will say, hey, it's Andrew, this is a cold call, right? And they, they get the awkwardness out of the way. And I've seen that work. Some people say, hey, it's Andrew, do you mind if I borrow 27 seconds of your time they pick an obscure number, because the person is not expecting it? And they just say sure, right? However you want to do it, that's up to you. But yeah, it's it's about establishing some some level of credibility. And then I am very, very quick to delivering value, right? Because I can't ask, I can't ask for time. I can't ask for a meeting. If I haven't delivered any sort of value. The person if they do say, yes, they're not going to show up.

Yeah, I've seen. So I've seen the and I've used it before, to where you, you try as hard as you can to pretend it's not a cold call, or you pretend you're not a sales guy. Like I had a guy at Google I used to work with and on the phone, he would say like, this is not a sales call. I am not a salesperson. And it was a sales call. And then, like one of the managers overheard, and he was like, No, I take the opposite approach. And I let them know like, I am a salesperson, this is a sales call, and I'm going to sell you something right now. And I think that just attacking it head on the sort of way that you do. Well, you get the awkwardness out of the way, but they know what's good. Like they know you're a salesperson. And if you're upfront about it, they may respect it and give you the actual time, especially if you took the research like you like you typically do.

Yeah, there. On that note, I mean, I think there's there's the interesting concept of the diverse our, which is very really that that struggle, diverse are being your identity versus your role in sales, where it's like, my role is an SDR or an A, or a VP of sales is not my identity. It's not who I am. And as long as you're like not selling something that's, you know, goes against any of your moral beliefs you should buy into your role, it's only going to help you. But if you're like embarrassed, or, you know, like, you tiptoe around that, that's what gives salespeople the bad reputation, right? Obviously, there's many things that give people a bad reputation, because people are trying to sell snake oil out there. But you want to be your own individual person and hopefully go against the grain when it comes to that I would Yeah, I would always, I would always buy into it.

There like there is no way around this stuff if you if you're an SDR, if your goal is to be an AE, if your goal is to be an entrepreneur, you have to get good at this at some point. And if you're not, and you're still successful, you will only be more successful if you get good at this top of funnel the ability it's a superpower. If you're able to call people email people out of the blue and convert them into paying customers, you have a superpower that is extremely desirable. And you essentially have a money printer at that point. Yes, I think a lot of people try to outsource or automate as much of this as possible when in reality if you just got really good at it, and I'm not saying I've actually done this, because I made the mistake in the past, I just wished the way my SDR my ad rolls. But no matter what it always comes back, like you always get into these positions where you have to do cold outreach. And that's the one thing holding back your business, holding back your career success. So it's very, very important to actually apply these concepts and take it seriously. You it's it's

I find it fascinating because from a top of funnel perspective, like if you look at the like what you're able to actually do and what it leads to, you literally create something out of nothing, you create a dang customer out of a name in your in your CRM, right out of a target account. When I when I talk to like new reps, right, because I most of my most of the reps that I've had to onboard and like literally this is their first time ever picking up the phone. I phrase it to him like this, like cold calling is not fun for most people. And we talked about like the psychology behind it. And really, it stems back to the caveman, right? Like not to get too deep. But it stems back to like these intrinsic fears that are ingrained in all human beings. Because when we were cavemen if you were not accepted by the group, you died, you had no food, you had no shelter. This is this is very, very similar, right? You're afraid of being told no, you're afraid of the uncertain. And once you're able to just like understand that, hey, and hopefully you're you're in an environment where this sort of conversation is encouraged where it's like, if you fuck up on a cold call. I'm not going to raise my hand to you. I'm not gonna slap your wrist, I'm not going to yell at you, I'm going to commend you, right? This is the only way to get better, especially this. But it's also a skill that like you're saying, Joe, it's invaluable. If you have any sort of aspirations at all, because it's going to teach you a lot of things, it's going to teach you critical thought. Because script a no script, I'm a huge, huge fan of being like your script is the first 20 seconds and then it's improv. Because no matter how well how good of a script I provide it, you're always going to have to go off it when you least expect it, or right away, right. So it's going to teach you how to think more critically on the spot, which, which is a great great, just like intellectual game to play. It's also going to teach you how to read is also going to teach you your EQ levels, how to read people, right? Because you can't see their face, you don't know what sort of, right like communication is, is a lot of like visual cues, we can only go based off of how they sound, their tone. So if I start up here, and omitted in their remaining down here, I probably want to go a little bit lower. Because people feel more comfortable around those that you're that are the mirror mirroring Exactly. That tone Mirroring is like, you know, it's used across all enterprise sales, structures and methodologies. And yeah, I mean, it's gonna teach you public speaking skills. It's a it's an invaluable skill. It really, really is. And obviously, it fucking helps you grow hair on your chest. Yes, like,

the first time we got for that container business. The like the mod better website that I have. I cold called Belmont dude, I cold called Belmont, just out of the blue. And like the feeling that I had when they said like, yeah, like, send me a quote, like, we do actually need this stuff. Like you feel like you conquered the world. Like, like you said before you just turn something that didn't previously exist into something into a sale with with just your words. And it's a very empowering feeling. But that didn't make the next call any easier. I still, I still want to procrastinate, I still don't want to do it. Even though I've seen it work. My brain still tells me not just send a few emails, or just take the easy way out, just automate a bunch of shit. But the the success comes from that uncomfortability. And if you're able to push, push, the more you can push through that uncomfortability the more successful you'll be in any of this shit.

The beauty about the phones too, is like, you know, I'll have someone on my team come up to me and be like, your phones phones are dry today. I'll be like, great. law of averages will say tomorrow, they're going to be on fucking fire. So you know what you should do? You should make more calls tomorrow. Beauty about it is like you're having a shit day. Maybe you got told no, from a deal that was you know, you know, moving along in the pipeline. You can't buy a conversation with someone over email, LinkedIn, and the phones. And it's like 430 And you're like, the day's wrapping up, I have the choice to log off early and fucking have a beer and start making dinner or say, You know what, I'm going to put an extra half hour in a call today. Because literally a two minute call could change your entire perspective on the day on the week on the month can be the difference between missing quota and hitting it. That's the beauty of it. It's also the curse, right because there are also going to be those days in those weeks where you're like mind numbing all I hear a dial tones gatekeepers people telling me to fuck off. And and I think going back to like what you were saying Joe is like, it is really really satisfying to know that you were able to fight in the weight class of like a C suite person, bring them down on a call, book an appointment, haven't haven't become a customer. But then you're like, fuck, like, how do I keep doing this? And my advice would always be like, You got to you got to have some sort of discipline and create a routine for yourself. So like,

I think you have a good routine. I think that's actually it all goes back to what you said earlier if you structure it so that it's it's you don't have to cold call everyone you could do your cadences, you send out the cadences whoever opens it, maybe whoever opens it three times that so you start off with that. So you start doing the code and then it also in your head you're like well they opened my email so they might be somewhat interested and it makes you a little less scared because you may feel you might be more confident because you think they're interested to begin with and they might not be but that confidence you could you could ride that momentum a bit. Ya

know, 100% and again, right like it's for anyone for anyone who's like struggling or like this is this is a pretty lame plug but honestly, the fanatical prospecting by Jeb Blount is the best book I've ever read on sales. He talks about the three things that you control your actions, your reactions in your mind. So and it's strictly mindset, it's like, you just gotta get up, get your coffee, have a fucking banana or an apple. So I'm gonna give you some energy, walk around the room, make your dials right. And just do it every day. And don't let a small sample size ie today, being slow on the phones dictate what you're going to do tomorrow, consistency in this game is the hardest thing to come by. And if you are inconsistent with your inputs, you're going to be inconsistent with your outputs. And you have to have to understand and sign up for the mantra that the work you put in today does not pay off tomorrow. It like simply put, like the shit I'm doing today as a rep is going to feed my it's going to put food on my plate next month. And if I slack, right now i Hey, I might end the month well, but I'm going to be struggling next month, I'm going to be behind, I'm gonna have to work late, I'm going to be more anxious. If you are just fucking consistent everyday you show up to work like that is the biggest thing.

So what you've seen a lot of good reps, a lot of bad reps in your day, what do the most successful reps do that differentiates them from the ones that are bad? And again, I'm because I'm not in a corporate setting anymore. But this is very valuable info for me because I need to get good at top of funnel. So I think it's applicable, regardless of where you are. As long as you're in a position that you're trying to generate revenue. Yeah, I want to know what the best of the best are doing. Even if they're a kid fresh out of college. That's an SDR. Like, there's stuff I could learn from him. Like what are the best ones?

Yeah, so my best read that I have right now. And she is doing on the month right now she's doubling the second best rap like she is leagues ahead. And you know, obviously, what you want to do is you want to extract what she's doing and scale it out. But that's just not the case. Like that's not, you're never going to be able to do that. Because working in sales is such a wide range of personalities, skills, strengths, weaknesses, and

it's just habit like there is skill involved. Some kids like I've seen, they have a magic touch. They're very, very good. Like there's all these. There's a you can copy exactly what they're doing word for word, and they just have it. But they have a gift. Yeah. There's, there's things that you can learn.

And alternatively, like what she's doing to be successful here may not make her successful if she were doing it another job. But she's mastered how to do it here, right. And what she does is she's very, very detail oriented. She holds herself to a strict routine that always incorporates finding new leads, no matter how manual or how long it takes. She's always constantly thinking about next week and next month, right? And she's very, very good with her process. She's very good with her time. She doesn't waste time. She rarely has to pick up the phone. She does this all through email. Now if you go back to Sarah's my best, my best two reps, when will that come to mind at Sarah's we're fucking sharks on the phones. One of them we had a dialer, you know, so obviously not everyone has access to one of those things that that dials, you know, either multiple numbers at once or just goes down a list. But she would do like three hours of dialing a day and book three meetings. And she would she never like I think it was like nine months straight. She was at the top of the leaderboard, she was so valuable to that company, that we were paying her close to double the salary of an average rep just to retain her as an SDR because we knew she didn't have it. She didn't have like the like the like the skills necessary to be a closer, but we didn't want her to leave. We were like you are way too valuable. You are sourcing the same amount of pipeline pipeline that three reps are doing. Right. And it was just because she was a shark on the phone. My next best rep was fearless. She would cold call CMOS at Fortune 500 companies at eight o'clock in the morning. She came from a world she was a she was a gorgeous girl. She was a model. And she was a recruiter. And that she was essentially just like constantly in cutthroat worlds where people were putting you down, insulting you, right telling you you're too fat or yada, yada. And then as a recruiter, it's essentially like sales. But again, people treat you more like shit, arguably. And you're a lot less, you're a lot more disposable because someone may be talking to seven recruiters at once right? She was fearless. She would cold call whoever it was at eight o'clock in the morning, at whenever at 6pm at night, just so long as it gives her an opportunity to get to get her in front of people. Right? Those are like the intangibles, right? Those are the things that people do without being explicitly told. They just know that it's going to put them in a better position. I would say like the explicit skills that like you can also teach to be really good organization. Organizations like a quarter of this job. You wake up every day If you have your urgent tasks, for sure important, what is an urgent task in sales, something that is going to lead to pipeline, or something that is going to lead to a deal, or expediting a deal moving a deal along, that is the shit I have to make sure I get done today. What's important, it's like your overhead no matter how much you're selling, or how much you're, you're doing, you still have to do it, you still have to prospect you have to set it and forget, you have to make your dials right. But the urgent dials are the ones who their their nurture dials, or their follow ups or their you know, you got disconnected or whatever it is organizing that so that you understand every single day, what do I have to get done today? To have a productive day? I'd say you have to, you have to have some sort of creativity, if you really want to master top of funnel, because again, the ones who are just like Nah, I'm just gonna set and forget 2000 contacts, and it's going to be a numbers game for me. That's great. You might do well. But again, that is not transferable. That might work in one business, and it's not going to work at the next. And then you have to have some competitive nature to you. You have to like it, you have to have it bother you. Where if Joe and I are on the same team, like Yeah, we fucking love each other. But I also want to kill Joe, I want to be able to say I'm top dog. I don't want Joe to be me, because then Joe can hold it over, hold it over me and I have to buy him beers next time I'm out, right? You have to have some sort of like, competitive nature, hopefully coupled with like aspirations, right? Like, I want to be competitive. I also want to be a team player. But I know that if I'm competitive and I grit my teeth through this all it's going to elicit opportunities for me like I've seen, I'll give you a prime example. I hired a girl at saris in the midst of COVID 20 and she started in June 2020. I will never forget, she was fucking fantastic. She was a great SDR she was an SDR for about a year. Then she joined our program of like in between SDR and a, she did that for about six months. She grit her teeth, she was sourcing all of her own deals trying to close some of them she didn't close any, she still got promoted a because they wanted to invest in her. She's she's been in a at Sarah's for a year and a half. Now she just got a job at Google as an AE, she probably doubled her ote in the course of two years, and is now and is 26 years old. You know, 25 that that is the thing. Because if you want to get those jobs at Google, and because I remember, right, it's like, oh,

I'm working at it because I entered that indeed. And it feels very boiler room at those companies. There's it's a big sales pit. And I'm sure it's different with remote now, but you're like, damn, I could have I could have just gone straight from high school and worked here. Like what was the point of even going to school, and it's very easy to get down on yourself. But the ones who do take it seriously and are fearless. Like you said, Google Facebook, they want those types of killers that cut their teeth in the small Startup Grind, and succeed there and then they'll recruit afterwards. And if being an entrepreneur is your goal, again, this all makes you a good like entrepreneurs are good at sales.

So if you're unless you're a dev, like a god, like Dev, or whatever you're gonna have to sales is gonna be your role at your startup. So you got to get good at this stuff. And if you are a good SDR good at, it'll lead to being essentially a good entrepreneur at the end of the day. Yeah, but But what you can't do is get comfortable behind the computer and say, right, because again, like I know, people, back when I was an IC, like 85% of my pipeline came from email, just because I got so good at the process. And I really understood the market and the product inside out. So I never I rarely had to pick up the phone. But that is bad, especially if you're if you want to behave like more entrepreneurial minded, because you're gonna have to fucking talk to people, like face to face over the phone, you're gonna have to deal with difficult questions. Right? Like one of the, again, another like great mantra for people getting starting out is like, get comfortable with the uncomfortable. Like it is very corny, but it is very, very true. The more uncomfortable positions you put yourself in, the less uncomfortable it'll be the next time it pops up, and it's going to pop up. It's like it's not like it comes back

and comes back to me like they avoided as an SDR seven years ago are still popping up today. You know what I mean? It's like you have to, at some point, you're gonna have to break through that and it's not you're gonna have to keep breaking through like, Yo, I don't know if you've seen the show about we work we crashed. And whatever you think about that guy, Adam Newman, bro, he was the most insane salesperson that there was he had zero fear. He built a billion dollar net worth. He couldn't code he couldn't design nothing. He was just pure A salesman and he will not take no for an answer. Yeah. Yeah. I mean, they say

like a lot of like sales. You know, like a lot of people I've seen on my team we're having, like, good months will be like, Yeah, you know, I'm just getting I'm getting lucky. And there's definitely a component that we can't control to all this right. Like, how do I know that the only reason this guy answered my email was because he was he sat down to take a shit. And he just so happened to check his phone that the moment it came through, right, like, I don't know, I can't control that. But the more preparation, I do, the luck, the luckier I tend to be right like that. I will, I will live I will live in standby that for forever.

100%. So what about the when marketing comes into play, let's say you get in touch with someone. They're like, hey, Andrew, this sounds pretty cool. But I'm not ready right now. Because what I noticed in a lot of my ad roles was that when it came to outbound, outbound, I would get in touch, and then they would essentially, come back to me a few months later and be ready to buy. A lot of the a lot of the actual deal flow was coming inbound, but outbound was good for getting people's attention. And then a few months later, they may reach back out. So how do you keep that relationship with them and keep them aware of your product? If they're not in the bank position at this moment? Yeah,

I think it all starts with like, I, whenever someone tells me something that like the disposition is not necessarily positive, although like I would I would consider that a positive disposition. Like interest timing, right, would be the disposition you see on one of those sales engagement tools. I want to know why. Right, like, just out of curiosity, just so I can take something back to the team. Why is now a difficult time? Because the the answer is run the gamut. Oh, I'm about to go on maternity leave. We're having layoffs. We're heads down. Because we're trying to get a new product out the door. I just need to understand why. Because again, I as a rep i It's all about opportunity costs. And if you think about like the marketing sales funnel in its totality, you're having that initial conversation with someone and let's just say they're at the very top and they're just it's pure, pure play awareness. And they're like, Yeah, timings not right. Because, you know, like, if Oram was cold calling me or you know, one of these like dialer companies, I'd say, Yeah, it's pretty bad timing, right? We're going through a lot of shifts. Also, like I don't have that big of a team to necessitate a product like this, because I know it's expensive, very, very legitimate excuse, right to not meet, because I literally just don't have a need for your product. So if I'm the Oram, rep, I'm jotting that down, I'm jotting that note down, I'm saying, fuck this company, I'm not spending any time with them. Because they don't, they literally will never be in a position to buy my product. It's important to understand that versus someone who's saying like, yeah, reach back out in a couple of months, we just have a lot of things going on. Right? Then I'm, again, it goes back to the organization play, regardless of what marketing is doing, right? Because I think whether you're an entrepreneur or you're working at a midsize company, your marketing resources are always gonna be very, very limited. And they're always going to be jumping around from campaign initiative. Right? So I want to make sure that like that lead that I found in August, is going to pay dividends in November. So what am I doing? I'm fucking utilizing the tools that the company gives me to make that happen in your CRM, right? Or I'm just jotting it down. I'm putting a calendar invite up for my own calendar on November 3, saying follow up with Joe. Right. It's about being organized. As a manager, there's the one thing that really, really rubs me the wrong way, is when we have things fall through the cracks. And the easiest way for things to fall through the cracks is just by purely being disorganized.

Yeah, bro, you would have hated me. If I worked for you. I would have been fired real quick. With a nightmare. What about the when it comes to actually hiring reps, right? Because I think this is something that one day I'm going to need to get a lot better at. How do you go about the hiring process? Like how do you know when you got a good one, sort of in the in the interview room? Because I think that even when I've been hiring contractors throughout the years, I've been way too overly optimistic. And based on their credentials, or what they say I'm like, alright, this person is gonna be a superstar and next thing you know, they fall off real quick. So how do you manage like bringing on good people and then setting them up for success? Have they actually get shit done? Yeah.

I mean, it's tough, right? Like they're I remember like the first couple of interviews I did. Everyone else who, who had interviewed them all had dissenting opinions than me, simply just because I had the rose colored glasses on There's definitely like the experience portion of it where you eventually hear things that you're just like, that's a red flag. Alright, I'll give them one strike. Like when someone says, like, you know, what's, what's your biggest weakness, I take on too much. Oh, so you're actually fucking complimenting yourself by telling me that that's, that's like, I hate that shit. Obviously, people, different people look for different things, depending on the company. But I'd like to get a sense of A, is this person remotely intelligent? Like are they going to be able to pick up the complex subject matter that I'm going to have to teach them? Give me an intelligent person, any day over a dumb person who's just like, I'm gonna get on the fucking phones, right? Because the intelligent person will be able to understand the market, understand the value prop, understand the product, hopefully be a little bit more curious. And then they're going to forge their own path on how to get the job done the best way as long as I'm there for support. So I really care about getting that intelligence, right? I'll ask them, like, What did you study in school? What was the hardest class you took? What do you think of calculus, right? Like, shit that they're not expecting? That I just want to get a sense of like, did like, Are you smart. And then the second level is accountability, right? Like, am I going to be able to fucking trust this person, and that's the hardest thing to interview for. Because these roles, right, you're interviewing a lot of green employees, or people who are trying to switch jobs, and they think it's gonna be cool, they're gonna work for a tech company, they're gonna get fucking lunch, I'm gonna have dogs in the office, or whatever it is, you get a lot of freedom in this job, especially in remote world. And I just have to know, when my bag is turning, you're going to be getting shit done. And I don't want to find out in month three, that it was all a facade. So I will ask them like pointed questions like, tell me a time in your life, when someone was, like needed you or was relying on you could be professional, could be academic, could be personal, whatever it is. But tell me how you react to that. Tell me? Tell me what you did. Right? It could be fucking anything. My mom needed me to walk the dog for a week while I was away, and I had to drive over, you know, like, whatever it is, I just want to know, like, I'm going to bring a certain level of accountability at the table, are you going to match it? Are you going to get to at least give me the effort? Because if not, you're not going to make it and I'm not going to invest the time in you. Definitely. And as it as it pertains to like longer term, you got to think about it in terms of, of three things, I think are really important. You have your autonomy, you have your mastery, and that is supported by your purpose, right? So the first three, six months? It's about building the autonomy with the rep. Right? Do they feel comfortable using our technology? Do they feel comfortable writing emails, making calls on their own knowing that they're going to get consistent feedback from me? Right? Are they essentially able to do the job to a high degree by themselves? When they're only coming to me? Right? And and obviously, my my job is to pick out early indicators that are going to prove otherwise. Or if they're really picking up on it, keep them fucking challenge, then you work on the mastery, where they ask you a question, you don't give them the answer. You say, What is your answer? And then depending on their answer, you sort of like, guide them to the answer, right, but you, you make it so that they have to figure out everything on their fucking own. And you become redundant. Like that is the goal with any rep is for the manager to become redundant. A so they feel more empowered, be so that you can spend time with other people that need it. And see it's about or not see. But the third component is like, instilling like purpose and making sure that they don't forget about it, right. Like, what is your purpose here? My purpose is to book meetings. No, your purpose is to make sure that the lights don't go off, right? Like you are a very, very important person to this company. Even if you're low on the totem pole, you've arguably been tasked with the hardest job in the entire company.

Right? Don't forget, from a from a business, it is the hardest. I think so. Yeah.

And like, don't forget that. And then Don't also forget about your like the wider purpose, which is not I want to like try and see if this is for me. And if this is a career that I'm going to excel at, and be able to make a lot of money, take on more responsibility, so on and so forth.

That's good advice. That's good feedback. What about the I've seen some reps do it really well, like I've seen Gong's reps do social selling really well, where they build up their own little personal brand on LinkedIn. And I've seen others do it really bad where they're just reposting marketing collateral, it's very bland. How much time would you put in as a rep, trying to build up that sort of Persona versus the more tried and true methods of campaigns, personalized emails, cold calls? How would you balance that out? Or would you even put effort into it?

I think it depends, right? Like I've seen some of those Gong posts that have like 10,000 was in likes, right?

And it's a really it's like a it's like an SDR. Yeah.

But it's like to me it's like is gone like, like is this like all an act internally we're like Gong is like promoting this post like they're putting money behind it just right. Like it's a it's a plug. Like it's an actual campaign. They're just getting someone on the team to make a post, I'm sure. Yeah, cuz it's like, Yo, like, just because you're a fucking a gong does not mean you're fucking Einstein, right? Like that product probably sells itself and I guarantee you it's getting much and it's getting a lot lot harder to sell it. Because the that industry is getting really, really saturated, and they're super expensive. But anyway, I think it depends on your market. If the people you're trying to get the attention of spend a lot of time on LinkedIn like salespeople do, because salespeople are fucking always constantly looking for, I don't know, some some like, you know, words of advice from a sales leader and Gary Vee or whatever, looking for another job,

right? Like you want to, you see a blog post and it's like the 10 subject lines that work? Yeah, percent of the Yeah, like fucking copy these.

This one trick changed my discovery process, right? It's like, Oh, great. Like, that's actually very valuable to me. So it's no, it's no surprise that people like fucking Gong and these other you know, these other revenue related tools get a lot of attention on LinkedIn. I rarely see, like, in a, at an accounting software, get the same sort of recognition, or maybe my algorithms different I don't know. Very true. I think it's important to maintain like a human approach on on social, right. Like, I've seen some posts from people who are just like, hey, like they're posting about how, what their what their workout regimen is. And, like, that's cool. I, I think it really depends on on who you're like who you are to, like, there's also no point in being like a phony. Like, if you're an outwardly facing, like extrovert, like, for sure. Like it can't hurt. Because at the end of the day, this is all about like the subconscious, right. Like, you just want people to fucking remember Joe to Rico, you want them to remember your name and your company. So that hey, like, who knows, maybe a business problem does arise? And they're like, oh, yeah, I remember that guy on LinkedIn. You know, let me Google that. That firm, or that company? Oh, wow. This is actually really

aggressively. If your rep reaches out. Let's say you're the CEO of a startup. And you post a lot on link, your rep reaches out, the person might be like, oh, yeah, I've actually heard of you guys. I know, I see your CEO, like, posting pictures of his dog on LinkedIn, or whatever it is, like, then there's at least a, you know, it's some sort of a warm intro there.

It also has to do with the brand, I think, to some brands are like, they probably don't appreciate a salesperson being so like blase on LinkedIn, because of their reputation. You know, most of these startups and entrepreneurs like they can give a shit because all they do all they want is eyeballs, right? They just want clicks. But yeah, like if I was a rep at like Philips, like I don't know, or like, yeah, like Baker Hughes, like, social selling is probably really something that I don't invest in, because my I'm gearing towards, like older people who probably don't spend that much time on LinkedIn or probably might not even have one, I don't know. But yes, as far as it pertains to like the tech tech industry, it's important to have some sort of presence, I think, and send your connections. And what I've been seeing, you know, being very successful recently is sending voice notes. Once you connect with people, you can send voice notes through the mobile app on LinkedIn. And it's a very, very human way of just being like, hey, I want to put a voice to the name. How are you doing? Here's what I got. Are you interested in learning more otherwise told me to fuck off? You know?

them? Uh, yeah, a lot of a lot of good advice in here. Man. I appreciate you coming on and helping the prom jockeys out. There's I think, like we said, regardless of where you're at, the information here is applicable. And if you're trying to drive revenue, whatever the role is, you could take something out of this. So again, man, appreciate your time. Thank you for coming on. Of course, closing any like, what's your favorite favorite interview question?

I like asking what was the hardest class you took in college? That's like your go that's like your favorite one. Or, or what's your biggest fear? And people will usually say like, rejection, and I'll say really more than dying. Like to see just to see what they say. Because like, if you asked me what my biggest fear is, I'd be like my parents dying or me. Right? Like, if you're gonna tell me that your biggest fear is, you know, rejection, I'd be like, I call you out on it. And I challenge you and I'd see how you react. But yeah,

I have a very dude. My old job the kid used to ask if you You were the starting shooting guard for your college team. Would you rather hit the buzzer beater at home or on the road? That was his go to.

That's a good one. I thought it was going to be would you rather make the final shot or make the assist on the final shot? But that that's a good one. That is good. What was he looking for? Like what I like I'd probably say on the road, honestly.

I'm sure he's looking for on the road, but I guess you could justify it either way. But I'm sure he wanted on the road. That's a good one. I might use that. Give a shot. All right. Yeah. Thank you, brother. Appreciate your time. All right, brother.

I'll talk with you soon. Peace out