Dustin Crawford: How to Motivate Reps and Decode Buyer Behavior

All right, I never thought I'd say this, but I don't take notes on my sales calls anymore. And it's not because I'm getting lazy. It's because I'm using Otter.ai to take them for me. Otter.ai lets me invite an AI note taker into all my sales calls, which not only transcribes them for me, but summarizes them, pulls out sales specific insights and syncs everything to my CRM. Oh, and it has an incredible AI chat feature that allows me to ask it any question I have about any meeting. Even if my note taker wasn't in the meeting, I can simply upload any recorded conversation to Otter. The amount of time it personally saves me is absolutely ridiculous. And that's not even scratching the surface of what it can do for teams.

So I'm super excited to be partnering with them to give you an exclusive offer to get Otter.ai for sales today for free. Go to otter.ai, that's O-T-T-E-R dot A-I forward slash JBSales to get your free offer and start saving time and selling more effectively today. I would always, as a younger rep, be like, what do they think of me? Did I say the right thing? We're so much in our head. As soon as you kind of break away from that, you will start to like work differently. Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us.

Now today's conversation is with Dustin Crawford. Now he's the VP of sales over at Otter.ai. And for those of you who have been following me for a while, you should know that Otter is a sponsor of mine, but that's not actually why I had him on the podcast. He's got a really interesting background and I love his leadership philosophy. He focuses a lot on psychology of sales and really tapping into what motivates individual reps. And that's really where we took this conversation. We started, I mean, Otter is a call recording intelligence platform that has a lot more to it. And it's one of my favorite tools. And you can ask questions to the data, right? So you can record the call and then ask questions to it.

And so we started with that about asking questions and how that, no matter where you go in sales or how experienced you are, asking better questions is something we all need to get better at. And with Otter or any tool or any customer, quite frankly, the better question you ask, the better answers you get. So how do you teach people how to ask better questions? That's the first thing that we dove into. And then we got into his approach about being, from a psychology standpoint, optimistic versus pessimistic sales reps and the superpowers of both of them and how and why you need to pay attention to that, which I thought was really, really interesting. Then we got into one of my topics, which is sophisticated versus unsophisticated buyers and getting the hell out of the way when you need to.

How do you drive urgency or how do you as a sales rep push and get out of your own head? I mean, a lot of us think that, oh my God, I can't bother the client. And nine times out of 10, the client actually wants you to bother them because they got a million other things going on and you need to be the one that pushes. So we talked a little bit about that and then leadership and specifically transparency when it comes to that and how transparent should you be as a leader to make sure that people instill confidence, but you don't lie if you don't know what the hell you're doing. So we went in a lot of different directions on this one and I thought it was a really, really rich conversation about leadership, about psychology, about sales and evolution and everything else.

So I hope you enjoy the conversation as much as I did. Let's make it happen. All right, Dustin, welcome to the Make It Happen podcast, my friend. How are you doing today? Good, man. Thanks for having me. I appreciate it. Yeah, this is, we were just talking, I'm actually looking forward to this conversation even more than I was before I prepped for it because all the conversation we had right before. I should hit record right, like as soon as people pop on because half the time, like the conversation that happens before we hit record is like, oh shit. It's always before or afterwards. That's where the good content comes from. Totally. There's actually, you know, the guy, so, you know, a niche, right?

That I work with. So he's now tapped into Jerry Maguire, like the guy who, right? That's great. And, and I guess when he does a podcast, you don't even know it, but he records you from the minute you walk into the, into the building. So there's cameras on you the entire time and you don't know it. And, and then, and afterwards, so you just think you're recording his, but he's recording you the entire time. And he's like, that's where the rich shit comes from. So, uh, but I think, I think the harder questions, right? You ask harder questions and you dive deep or that's just like sales. Yeah. As soon as you're done with the call, that's when the magic happens. Cause then you're, you're, you're kind of guards are down.

You can ask the harder questions. What happened? Like, what should we do? And that's where the strategy comes into play. Exactly. So let's try to get into some of that. Cause you, I mean, you got, look, um, you're two, I mean, now as the VP of sales over at Otter, but sling, DocuSign, Intercom, Basia, like you've had a pretty cool, uh, especially with all these acquisitions to background, but let's back up a little bit more. Um, uh, origin story. So where'd you come from, uh, family, uh, parents, like where'd you get that, that itch for sales and, and, you know, DNA stuff here. So talk, talk us through growing up and where you kind of caught your flair. Yeah. I come from a very small town in Michigan called Pygmy.

Um, yeah, very much blue collar, uh, same about parents work day in, day out when they come home and they, you know, work on the house. It's just a constant mentality of work, work, work to, to try to make it. So that's where they work at. That comes from sales is something that was interesting. How I just fell backwards into it. I remember my, my brother was in boy Scouts and he had to sell candy and I would be the one to take the candy and go run and go sell it to, to people. And my mom always told me about my first hustle that I had, I actually was on a bus and because I'm from a small town, I would go to a school and then I had to transfer a bus from there to another school. So in that transfer, there were like pencils, uh, and they were like holograms, like of sports.

And so I would buy those and then I would take them and I would go sell them at the school that I was in. And I would come home with like a lunch pail with money. And my mom would be like, what are you doing? Right. And I'm like seven, eight years old and she didn't know where I was getting this money from. So it was just, that's how selling started for me was doing these little hustles. And I fell kind of backwards into it where I wanted and thought I wanted to get into print. And so I did an internship for like spinning by magazine out in New York city. And, and I had a mentor at that time who worked at Warner media. He goes, get out of print, go, you know, this is obviously day, day says he's like, get in, get into the internet world.

And he's like, just, just get there and you'll be just fine. Cause it's just going to rapidly grow. And that's exactly what I did. I, you know, I, I, I found myself at career builder when we were fighting against newspapers and just worked my way up. And that's a place where if you're 99% to quota, you're on the chopping block because they did a extensive training for like months on end before you even got on a call. And every time I got promoted, you would go into another training course of like how you sell to that next level. So they did a great job with training and enablement. And I think that that's where, you know, I really, um, appreciate all the time and effort that they put into their, to their employees to be successful.

And I think that if you notice a lot of people that stuck around with career builder, you will see their success, you know, leaders over at, uh, at Slack, uh, Upwork, uh, Mural. Um, so you will see a lot of those folks because they just were trained earlier in their career. And then, you know, obviously I, I, I've been writing those coattails and I've been very lucky at intercom docu-sign and then came over at, um, Otter about four years ago now and key is relationships, especially out here in the Bay. Uh, I was actually, uh, before I started at intercom, I was on a solo trip to, in, in Bali and I met someone on the plane and going on to completely different trips and just in passing and they reached out to me one day and go, you're on the short list for, for Otter.

And because of that relationship landed me at Otter and it was a long, long, long process, but, um, it was like six months. And so when I was starting that interviewing process, we were in the second single digit million. So when I joined, you know, I was like 34th employee about, and I just saw the opportunity just kind of using, um, you know, some of the other tools that are out there for call recording and just saw it opened it up, not just for sales, but it opened up for, for everybody and everyone needs it. And I know it, um, you know, just from even school, for example, like I was, I got the tape recorder cause I'd forget everything and I needed something to remind me like, what, what did the professor say?

So I saw the huge opportunity. Um, and so, you know, I just saw it and during the pandemic, next thing you know, we, we hit a hundred million this year and, you know, it's been a great ride. So, you know, long story, but that's how I love it where I've been. I love it. Let me ask you on the honor. Were you, cause AI really didn't hit the, the consumer market, if you will, until like early 2023. Right. So you were there four years, right? So it's 20, so 2020 ish, give or take, right? Were you, was Otter AI native or was Otter a call recording? Uh, like was it, was the focal point call recording and then you added AI to it? Or did you start with AI to differentiate yourself from the, all the other players in the space?

Yeah. Great question. So a lot of people don't realize that the live transcription was the game changer for us. So live transcription, cause the AI in real time was changing and adapting and being the highest level on the market. And that's where we had a partnership early on with zoom and we powered their live transcription because they, they went out to every organization that was out there and they compared us. And so we have the highest level and a lot of companies don't have live transcription. They have like post transcription. And so for us, like that was the AI piece. And then we transcribed over a billion meetings, which then helped us create our own like LLM model, like that everyone now knows is like, you know, the chat, like, you know, open AI chat, chat, QPT type of search.

So we built our own now, you know, transcript is just one thing that we do, but no one is going to want to go back and re-listen to your call or look at the transcript. They just want the information at your fingertips. And now you can just, you know, ask it. And I, and I love it. Cause I'm like, I literally forget a lot of stuff. Cause I'm in so many meetings and I literally just the other day, I was asking it, you know, why we win, why we lose or what languages. Cause my team's like, what languages they're like, we just hired another individual from an engineer team. Like what languages are being requested? I'm like, I don't know. I'm not asking my sales reps to put it in your Salesforce. So I just do a quick search over all of our calls.

And I'm like, that's the power is like the knowledge that we're accumulating. And that's kind of what, and how we started in the first place was just recalling information, you know, just from the actual call that you have, but now it's much more. And now we're starting to add additional layers of knowledge into the system versus just calls now email. Cause at the end of the day, why you win, why you lose is an email or call, not necessarily Salesforce. So, you know, we'll, we'll pull those things. So it's quite interesting. No, it's, I mean, that's what I mean. I use it all the time too. And when I started the function at like, again, asking the questions to the AI is just, it was like, Holy shit.

Okay. Cause I'm on with you. Like my memory is absolute dog shit. I mean, we could like, we'll literally have this conversation an hour later. You'll be like, dude, what are we, I'm like, I have no fucking idea. Like I, like I'm, I've had 700 conversations. My brain doesn't work that way, but having that at your fingertips to be able to just ask it, whatever question the question is, is do you know the right questions to ask? And that, that is where I'm curious kind of how you teach people. Cause it's just like AI, right? If you give it the right prompts, if you give it the right stuff, you'll get gold out of it. But if you give it shitty prompts, if you give it, if you ask shitty questions and it's kind of like asking questions, customers too.

So how do you like, what's your approach to let's back up. What's your approach to asking questions, right? Forget about AI for a second here. Like, you know, when it comes to discovery and you're coaching your teams and, and those types of things, how do you approach asking better questions? Because I think no matter how good you get in sales, you could always figure out how to ask better questions. So what's your approach to that? So that's a good question. I would say there's like two different parts. One as a leader, I get asked a thousand questions, you know, from my senior leadership, uh, on down and I've got to recall that information, whether it's my call or others calls. So that's where I use search because again, I'm not going to, am I going to go ask my rep or am I just going to ask Otter?

Like that's literally how the chain of command now works. And that has been really freeing for me. Um, and now I have to rely on getting that information to, to other folks that need that information. Now, if it's a sales rep, I think that's where, you know, looking at it from like a different lens. What is it that we're trying to, to accomplish? Um, and a lot of times people don't know what to ask. And I think that that's the reason why we're creating, um, you know, we have, I told you, we started with live, live transcription. We're taking that live transcription and now actually having a live coach. So taking the data from all of your calls and all of your data set to give you in bubble up, like what questions should you ask?

So you don't even no longer need to like prompt, you know, the chat. It will hopefully give you the answers that you're looking for. And, or we have a new, um, a sales assistant agent that if it hears something that it knows it will bubble up that information for you. So this agent will be coming to like the chat, uh, either afterwards or, you know, in real time, giving that information that, that you're looking for. And you, sometimes you don't even know, uh, especially for sales reps, they miss a lot of the questions that are being asked because they're so focused on the process, process, process. What question am I going to ask that's in my Rolodex versus going off of maybe what the customer is asking or prospects about asking and feeding off of what they're, what they're giving you.

Hey, real quick, we're talking about how time kills all deals. And this is absolutely true. That's why in our scorecards for our negotiation training on the JV sales membership, we talk about a give is more time to make a decision and it's a heavy one. So if you want to understand the implications of time and how they impact deals and learn how to address it, join the membership today. Take the driving to close course and the objective negotiations. Now back to the show. Curiosity. I'm going back to EQ over IQ all day at this point because AI has taken over the eye, the IQ in spades. Like it's already smarter than all of us. Um, frighteningly so quite frankly, but the, the, so it's the EQ piece and I, I'd look at agility, business acumen and, and curiosity as the superpowers moving forward.

Right. And, you know, I've had this podcast. I've probably asked a hundred people the question of like, can you, can you teach curiosity or is it ingrained? Is it, is it nature or nurture? And I think the general consensus is genuine curiosity is, is more nature than nurture. Um, but you can kind of maybe guide people's towards curiosity. So how do you, you know, I just, as a leader in general, get, get kids to be curious, get people to give a shit about the questions to your point of like, just instead of just thinking about the next question and what do I like and not active listening. So like, how do you instill the curiosity factor, the give a shit factor, the don't just ask the question to ask it, but ask it to understand and be curious about it.

How do you, as a leader, even if you didn't have honor, right? Like, what would you do to, to coach that? I love this because I've always tried to train people about being generally curious and it doesn't work coaching or say it doesn't. So I came up with being an optimist or pessimist. And I think this is where it really resonated with people. And I go, listen, you know, there's a, and let me pause real quick. Um, and I kind of start off with, do you like winning arguments and like being right with your spouse or your significant other? And the answer is always like, yes. I'm like, so think about it from like, first of all, that lens now create these optimistic or pessimistic mindset. Cause if you're a pessimist, I love pessimists.

I'm a pessimist. Cause I want to ask hard questions and I'm going to prove that you're not going to move forward or not. So you're going to ask the harder questions and you want to prove yourself you're, you're right or wrong. Cause if you're, if you're wrong, you're actually still right because that deal is still going to move forward. You know, but if you want to prove yourself that you are, you're right and it's not going to move forward, then it's, it's a good feeling that it's not going to move forward, but you're asking these harder questions. You're going to dive deeper into the layers to ensure that either you're right or wrong. Um, but at the other side, you're still winning. And then when you're an optimist, I think this is where you, you know, you have to make sure that you were well aware that you're an optimist, because if you're an optimist, then you're going to say, Oh, great.

Like you're going with the flow. You're not asking those harder questions. So you need to pause. So the first piece is like recognizing which one you are, when you will know that you're more of like an optimist. That means that you've got to dive deeper into the questions. Like that needs to be very buttoned up and in real time, what I, how my reps do is write down questions, ask the questions. Cause a lot of times, because you're a pessimist or you're optimist, you're hoping that all because let's just say if they're inbound deal and they're telling you, I love Otter, I love what you guys are doing. Does it mean that they're going to buy? You have to ask the harder questions. And sometimes like, because you're an optimist, you connected, you, you literally connected with someone on a personal level.

And you're like, we've got a good connection. Everything's going to go well. And so you're not really going to challenge. And so you need to come up with questions. And the best thing for, for optimists to do is write things down in real time. So it forces them to ask those questions because at the end of the day, like no one cares and you're not going to be buddy, buddy with this person after you sell, because they don't really care about you and you shouldn't care about them. It's you should treat every deals transactional and take away that emotion from the deals and you'll find yourself in a better place. And that's where I think, you know, a lot of reps, uh, within my team, it's started to find a lot more success because they're kind of getting away from the, how do I ask?

What do I ask? You have to just generally challenge them because in your mind, you're, you're having this moment where I don't believe them. I don't trust them. And that's where I, the, the, the, the pessimistic mindset comes from, uh, where some of the reps, but when you're a pessimist, you're also disqualifying deals much faster because in your head you already, so you already disqualified them in your head because you're not sometimes asking the questions. You're already assuming in your head that they're going to close until you're asking a question. So you've got to be mindful of that when you're a pessimist. So, but don't, so a couple of things on that. Don't you have to kind of adjust to the scenario?

Aren't some dynamics of, of the people you talk to? Well, right. So I walk in on a certain situation and I'm optimistic, but then at a certain point I turned pessimistic because something, something I heard versus walking in a bit like, okay, this is a shitty lead. It's pessimistic. I'm going to disqualify it. But all of a sudden, halfway through, they say something. I'm like, holy shit, like this is actually a huge opportunity. So how's, I mean, I know there's an experience arc there as, as just, you got to learn how to do it. But I guess with, with the, with the younger reps, helping them understand those conversation, the kind of light bulb goes off. Okay. You know, I'm an optimist. I'm a pessimist.

How do you guide them to, to adjust that during the conversation when certain things arise, certain triggers or whatever it might be? What I say is when you are asking these questions and they're coming back with answers to these questions, you know, that you got a fish on the line and you want to keep. Asking and digging deeper because you're, you're like, wow, this is going well. And I think what a lot of times is deals could go much faster than, than what you believe it can do because you have a mindset of, this is how a process should go. And a lot of times if you push and you ask the right questions and you continuously move the line, you'd be amazed at like how many people actually know the answers to the questions that you have.

And so you just need to ask them. So if you have a fish on the hook, you constantly ask them, you know, the harder questions. What I always say is like, do you have the two yeses? Like not just one person's going to say yes to this. And I say, who's going to design and who's like from us, like who's the department head that's really like spearheading this. And if you get those, if you know who those people are and you're able to get those two people in line, like you should feel good. Now it's like, well, where's the, where's the budget coming from now? If they have an answer for this or you feel good about it, you're like you, now you continuously go down the line of all the questions. And now you have this light bulb moment where you went from a pessimist to now an optimist of the deal, but you proved yourself because these are the questions.

So kind of taking a step back. The reason why I want people to think about it that way is because this is exactly what leaders do behind closed doors. We just got to say after the deal or after the call, we are challenging reps with the same mindset of a being of a pessimist. Like I don't believe any of my reps. They have to prove to me that a deal is going to move forward. So if I can teach a rep to have the same mentality, then they can show up, especially in our pipeline reviews differently. And they go, I've challenged, I did this, I did this. And this is where we're at with the deal. Now we're having stronger conversations. Love it. You said something also that I think some people might have an issue with, which I'm curious to unpack this a little bit.

It says you treat every deal as transactional, right? We're moving. So my thing here is I think we've, I think COVID forced a transactional relationship between buyer and seller. Whereas before we at least had the semblance of relationships, right? We could go out with people, you know, there was a lot more face-to-face like dinners and all, and now we're sitting behind a, you know, a screen. And quite frankly, all those soft things that we used to do as sales reps to quote unquote develop rapport that the client hated, but ultimately worked, right? Like, cause if I was in your office, like physically in your office, it was really hard to just kick me out, right? Like get the fuck out, whatever, leave me alone.

Whereas Zoom, it's like, dude, I got 30 minutes. And at the end of that 30 minutes, sorry, it is what it is. So my fear is that we've actually gone too transactional with, and there's no relationship left. There's no depth left. So could you clarify that for me? Cause I don't, I want to, yeah. Cause I think what I mean by transactional is you got to treat it in the transactional way of like move fast, move fast within the job, move the deal along as fast as you can. And don't forget, like it is a transactional deal because after the deal is closed, if you are an AE, you're done with that. It goes to a CSF. So there's a difference between, you know, a net new rep versus someone who's going to hold that and build that relationship and build upon that.

So where I'm trying to get these, these net new reps trying to close deals, it's like, as soon as you're done, like you're, you're moved on unless you hold things, then that's a whole different story. And then you want to cultivate that relationship and build upon that because it is a working relationship. But at the end of the day, I say it's transactional because this is just one thing that they're focused on. You know, this is just one technology. I'm sure that they have a bunch of things that they have going on, whether it's internally or externally. So, you know, they will move just as fast as you, you kind of, I guess, outline. And I think that a lot of people don't do that. And I want to make sure that people are starting to like push and ask for the deal.

I think what people say, uh, we got to go through a trial. Like, do you, why? I don't think you actually do need to go through a trial and, and that's why I'm trying to get like a mindset of transactional. And I'm glad that you said it because I think there's relationships, especially for enterprise deals. You want to cultivate relationships. There's a lot that you've got to do, you know, um, especially cultivating that relationship to go to the CSM side. But, um, at the end of the day, these, these reps, they don't want to close deals. They think that there's a, you know, much larger process when I'm like, did you even ask like, or even think of strategize, how do you overcome this trial? Like, for example, there's one that wants to do a trial because they want to see an integration.

And I go, do they, or do they believe in their mind because they don't know what the next step is that they believe the trial is tried to test that out. Cause did you even ask them, what do we need to do to, to button this up before the end of the month? And by the way, we've done this integration with someone else. Here's a screenshot of what it looks like. Like, and they're like, no, I didn't do any of that. I'm like, well, there you go. You're, so you're not even asking for the deal. You're not even trying to close the deal as fast as you possibly can. So that's where I mean, he's like, we got to just have that mentality. Well, I don't think we've lost that, you know, a lot of the, the hard questions, right.

And, and it's awkward. And I, but I tell reps again, you know, I think you do a good job of relating to personal stuff that people can relate to. It's like, if you've ever had to make a big decision on something, right? Like nobody wants to go through the process of evaluating three vendors, doing this, like doing this. Nobody wants to do that. If somebody came to me with like the perfect fucking solution and said, look, dude, this solves all your problems. It fits in your budget. It's exactly what you need. I'd be like, thank God. I don't have to go through three months of trial bullshit here. That's exactly what I want. And I've always been kind of a very quick decision maker myself. Like as soon as I see something that I want, I'm like, yeah, I'm actually the one put it.

And it's funny that you bring it up because a lot of the times when I buy something, I'm literally pushing the rep to get like, no, like, like just, I know, I don't want to now go talk to your SD. I don't want to like, just give me the fucking contract and let me sign it and let's move forward. Cause I got to get this done. And they're like, well, I got to next week. I got to set you up with my, no, here's my credit card. Give it to me. And because actually I ended up purchasing, purchasing a tool because the sales rep just took forever because they want to go through the process. And I'm like, no, you've got to fish on the hook. Like I'm ready to move forward because we didn't move fast. Like I went with another vendor and I tried to teach my reps the same thing.

And I'm like, listen, you got to know when people are willing to move fast. Like I am willing to move fast. Don't slow things down. Yeah. Uh, again, it goes back to, do I have all the answers that you're looking for? What do we need to do to get the deal done and find and be strategic on like how you're willing to get the deal done? Cause it's going to take some type of, um, strategic planning. And that's why I loop folks in. It's like, what are we going to do? Like, how are we going to approach this? How are we going to win the deal? Uh, yeah, I've kind of nailed that down and, and I don't, again, I think it's experience, but I think there's some pretty quick things you can do to, to figure it out.

Right. Cause I look at sophisticated versus unsophisticated buyers. Yeah. There's, there's sophisticated buyers like you and I, when we want something like, it's like, fuck it. I've already done my homework. I'm that guy who's already 60% of the way through the sales process. By the time you get me, don't get my, like get in for sophisticated buyers. You got to literally get out of their way. The more friction you put into the sales process. And unfortunately right now there's so many options that if you put friction into, the sales process and, and if I don't like absolutely want your solution specifically, I'm going to go find somebody else. Right. It's almost like the same thing with me. I don't know about you on websites.

If I go to a website and I, and I can't see a video of not a promo video, not a marketing video, but literally a video that shows me how the product actually works. I actually move on. Cause I'm like, I need to, I need to see how this would work and, and whatever. And, and if I don't, and if I, cause if I'm comfortable with that, I'm in man. Like, okay, cool. Let's have this conversation. But I don't want to get on a phone call so that a rep can show that to me. So on the flip side, there's the unsophisticated buyer that is like, Hey, I'm just looking into this. My boss told me to look in blah, blah, blah. Those are the ones you need to take a step back, walk them through the process, help them make that decision.

But that's hard for a 22, 23, 24 year old kid to figure out right up front. Well, a lot of people are tasked with it. Right. And I think that this goes back to urgency. I think the biggest piece, uh, in my mind with any rep these days is, is run with urgency. I, I struggle with this, with, with my team. I think there's a preconceived notion that I'm bugging them or like it's coming across as just salesy. And I go, I can tell you sure as shit that they are going to appreciate it. So we actually, we did this. We did this test. I was like, everybody, we have a, we have a, basically like a three day report and a seven day report. And I want no one to be on that. That means that everyone needs to be touched every two to three days or every seven days.

And we also have 21 days. I was like, I want to be able to see you guys touching these things aggressively. And I go, and then after a month, I want to be able to ask this entire room, how many people got yelled at? And so we, no one raised their hand. I go, okay, give me feedback of how, in what I'm doing. What happened? Majority of the team goes, I was actually thanked for being on top of this. And I go, this is my point. You guys have this preconceived notion that if you, if you email someone back to back, don't forget, you earned the right, especially if they came in about, you earned the right to go hunting within that organization to be as aggressive because they came to you. And we have, as leaders, we're in back-to-back meetings.

Like I'm interested in tools right now, but I don't have the mental capacity to sometimes take that on. I'm like, I'm going to put it on the back burner. So if I'm a rep is like constantly getting on me and being like, hey, let's, let's get to the next step. Like, what do we need to do to progress this deal? Like, like, is there something I could do? Is there something that we'd like, we could do internally or jump on a call? Can we schedule something? Like keep it moving forward because otherwise it could die at any point in time. We always hear, uh, time kills deals and it could not be more of the truth because we all have so much stuff going on. We're trying to do more with less than there's a bunch of tools that, like you said, out there doing the same thing.

So if we come across or someone internally tells me about another tool, I'm probably going to take precedent of that one versus the one that, you know what? I probably wanted in the first place. So there's, there's so much of that. And we, we just need to learn to be more aggressive as sales reps, even though it, and, but you can do it. It's polite. We call it polite, polite persistence. Like there's a way there's an art to it. Be a fricking human being. Yeah. Well, and I think the, the part on that, right. I mean, you're spot on like time kills all deals. It's like that to me, I go, I do this give, get scorecard. And one of the biggest gives on the scorecard is more time to make a decision.

Right. And, and so, cause the longer the interaction, like everybody knows that the closer we get to closing this deal out, the faster the interactions go, right. We're going back and forth on terms, on contract, on all this stuff and on scheduling and all the, the longer the space goes between interactions, the less likely it is to close. And so, you know, if you're not urgent, they're not going to be urgent. And if they're urgent, they probably don't need you quite frankly. Like, like your, the sales rep is not needed in an urgent situation for them because they are ready. Give me some answers. Here's my credit card. Let's go. But if it's a evaluation process, to your point, priorities come up all the time.

And so I get pulled in 85 different directions and unless it's on fire right now, I'm probably not going to be paying attention to it. And so if you don't professionally, you know, you know, professional persistence, I call it. Right. But I think that the mind shift that I try to get reps is, is, is it, is it because of you or is it because of them? Yes. That's the key is because some kid asked me once like, John, how hard can you push? Like, say it comes the end of the month, end of the quarter, end of the year, right? Like how hard can you push to get a deal done? And my answer to him was it's, it's in direct proportion to how much it's in your best interest versus their best interest. Yep.

If it's in their best interest, fucking push as hard as you want and like literally go over their head, stuff it down their throat because it's in their best interest. Yep. And it's not just because they're going to miss out on the discount. Okay. Like that's not their best interest, but, um, but, uh, but if it's in your best interest, right, because you've got to close out in a month, then you're a douchebag, then you're just a douchebag sales rep and you should feel douchey following up 17 times in a week. Yeah, exactly. And I think that that's where you always have to put it back on them. And I think that's the reason why like, you know, I was actually working with a rep today because we were kind of going back and forth and I noticed in the email, it was, it was like the used car salesman approach of, you know, why you need this.

I'm like, no, you need to tell them like what you're doing to help them. Like, honestly, it's all you need to do is have a spin of like what you're doing to help them and what they are wanting and needing. Like you just avoided everything that they're, they're asking for. And you just kind of went down like your direct path of like, how do I close this deal faster without addressing anything? I'm like, there's a way to be able to approach this by making it about them. And like, you're going to bat for them. Like you're going to try to get them the best deal or you tell them this is what you need. Right. It's, you have to prescribe like what you believe is best. Cause a lot of, cause we have a pro business in enterprise.

We only sell for us a business in enterprise. And it's more of a lot of, most customers need the enterprise, but if they see the price of business that they will kind of like go here and it's like, well, no enterprise is what you need. Like based off of what you told me, if it's price that is bogging you down, let's figure it out, like, I'm happy to go to bat for you. Like, I don't even care about price. Like I care about the right solution for you. If you take that approach, then they're like, oh wow, this person is like really going to like help me. And they're going to know that I'm going to find success. And then we're going to get the right package. Again, like they're tasked with this.

They don't know the ins and outs half of the time. And they haven't maybe purchased before. So those are things you need to hire now. So, and I think what we're talking about, a lot of it comes with just experience, right? To, to say the wrong thing, do the, you know, have somebody react to a certain way and adjust to it. But, and, but it is a lot about just getting out of your own way. And you talk a lot about psychology and, you know, you're big into tapping into, you know, individual coaching with individual reps, helping them find their why, which I want to get to in a second. But when kind of, for you personally, did it dawn on you that the psychology was actually one of the more important parts of sales than the process, the tips, the, you know, all that, the tech, like, when did kind of, you were like, wait a minute, I can put all this process together.

I can put all, but if I can't tap into the psychology of the reps and the customer and that type of stuff, none of it matters. I think when you kind of, you know, mature a little bit more in sales, because sales is very difficult. And if you're not winning, you're not succeeding, it's very difficult mentally. And I'll touch on that here in a little bit. When you, when you start to realize that you're comfortable and secure in, in anything you do, but more, more sales. And you realize that there's a lot of things that are in your control and are out of your control. And you can kind of put things past you. If things go well, as long as that you put in the effort and all that, but if things go well, then, then you're, you're, you're going to do well.

But if you're, don't do well, like it's not just, it's not you. It doesn't mean that you're a bad sales rep. The faster you can get away from that, psychologically, it frees you. That means that like when you do, and when you're getting there, because I would always, as a younger rep, you're like, what do they think of me? Uh, did I say the right thing? You like, we're so much in our head. It's not even funny. And as soon as, as soon as you kind of break away from that and you realize those other things that I mentioned of, you know, it could be your territory. It could be, um, you know, the product's not mature enough. Like there's so many different elements outside of just you being a sales rep.

And if you're good or not, it frees you to ask the hard questions. It's okay to like lose deals. So it's just more freeing. And I think once you free yourself from that, you will start to like work differently. You will ask harder questions. You will, you will work harder. Uh, you will try to get the right people on the call. Um, so, so what's the difference between that and having excuses though? Right. Because let's use the territory as an example. I've had reps who use their shitty territory as an excuse and, and, and I'll use just my self as an example, right? When I got into Xerox, there were, uh, I got, I was put in a territory that had like five reps in three years. They had burned it to the ground.

There was no relationships. And, and I got this handed this bag of shit territory. Right. And my mentality is cool. Let's figure this shit out. Like I'm going to like, all right, cool. And I turned it into one of the best territories in the region, blah, blah, blah. Right. So, so where do you, from a psychology standpoint, I feel like so many reps use certain things as excuses as opposed to saying, fuck it, I'm figuring this thing out. Like, I'm like, and okay, it sucks. I lost, but whatever, but it's not the territory's fault. I just got to work better. So where's that balance of, I got to work harder and I got to be better versus it's really not me. Cause it is the circumstance. It is the company.

It is the territory. So how do you do that? Cause I'm, my fear right now is everybody's looking for an excuse. Oh, and so if they hear this, they're going to say, oh, well, yeah, my, it isn't my fault. Like, you know, my territory, the product isn't perfect and my territory does suck. So it, I I'm okay. Like this isn't Mr. Rogers. We're all, you know, special here. This is like, you got to fucking put in the work. So how do you balance that? I think that the reason why I say that it goes back to identifying what is going on, right? Is it your territory? Is it something else? Cause there's something to probably figure out. Okay. Is it my territory? But now go into the layer deeper. What about my territory is, is the issue when you kind of dive deeper and then you want to look at some of the things that you can obviously work with your, your, your internal team, you might find it to be more around blue collar in your territory.

And there's probably a certain vertical, there's certain things. And so you, you have to just start to figure out these little pieces that what's working, what's not working to that goes into your favor and you have to work differently, but you have to identify, you know, what, what is not working? How do I overcome this? Because I think people do come with excuses all day long. Like I hear, I hear all the time. They're like, oh, we've got too many meetings. That's the reason why I couldn't email. Like I, there's just always an excuse. It's like, okay, well let's take away the excuses and let's figure out like how we're going to be successful. Like, you know, if, if it's a, you know, if you're selling enterprise and you're a product not enterprise and you have a, you know, a crappy territory that that's, it's probably not going to go well.

Right. I've been in that situation where it's like I was, you know, for, for me, one of the first tech startups that I was out here, you know, we were going up against Salesforce and I had to find, you know, I was leading an outbound team and I'm like, okay, like, how do you do this? And so I was finding needles and needles and haystacks and, but I was doing them, setting up meetings. Like we were, we're getting these large enterprise customers because we wanted to be enterprise, not that commercial. And we were getting the meetings. But when I started to realize like we were having the meetings. So that's the first step, but if they weren't going well and they weren't closing, there's the issue that it's, it's the product.

Right. So that's the reason why I always want to make sure that like people are looking at it holistically versus just being very narrow. But, um, and I think what role does leadership have to play in that as far as being effectively open and honest about that. Right. Cause I think so many leaders pretend like, oh, you know, we did this all fair. Everybody's got their territory. We mapped it out perfectly, which they never do, you know, our product. Yes, it has its warts, but you know, it's good enough to sell. So versus, Hey, look, it is what it is. Like we're, we're building as we're growing. There's going to be some gaps and look, I'm yet used to shitty. So I guess where is, where is it on leadership?

And I, and from your perspective specifically, how honest can you slash should you be in that regard? That's a good topic. It's a really good topic. And the reason why is because a lot of leaders aren't transparent. And I know, and I've been, most of them are, most of them are. And like it, and that's the reason why you hire, they hire quick and then they, they fire quick. And then next thing you know, that, that, that leader's gone. Yeah. I'm a hundred percent transparent with my team. You know, we, we test things out and I'm like, listen, it may or may not go well, but we're going to, we're going to fight hard and we're going to put in all our effort to see if this works. But if it doesn't, I'm going to have to work with you, you know, on the compensation side or the commission side, you know, like, you know, in quota, like we're going to have to work together, but I have to be open and transparent or else no one's going to like working here.

And, you know, I have a very low churn within my team because I think that I'm very open and transparent and I keep hiring more and more people. And when we, when that usually happens, people are disgruntled. People feel like they can't, you know, make it. And I'm like, okay, we're going to keep doing these things and we're going to keep iterating and trying to improve each one of your, like the deal cycles. And that way we can do this, you know, and then if we're, you know, if you talk about like territories, like, okay, let's look at the data. Like, should you have two reps or versus one person in that territory versus like two people in like California, you know, the, on the West coast, like there's, there's so many different elements.

And I think it's a lot on the leadership to really understand their business in like what's working, what's not working. And, and I think a lot of leaders don't look at data. And honestly, a lot of leaders out here in the Bay, they were a sales rep and they got into leadership by chance. And they didn't actually do the work and due diligence of, you know, working them themselves up. Like I started as an SDR manager because I wanted to understand the ins and outs of outbound. I wanted to do, understand the ins and outs of inbound. I wanted to understand like how it all worked. Right. And so for me, data really drove all the decisions. And I think a lot of leaders, you know, they haven't been either successful selling themselves or they haven't been really a successful like leader.

Um, and they just wind themselves in this position and so they don't know how to push internally and say, Hey, senior leadership, like five months at having to hire this many people, like there's like, there's a lot of risk here. And so we need to make sure that we keep a good culture and we're not going to let people go. So we're going to be responsible as we grow. And I think that's on the leader to like, have that upfront conversation. If you don't have leaders, then I wouldn't work for that company, honestly. Yeah. And that's kind of what I struggle with a little bit with like leading in uncertain times. Right. Cause if you tell me anybody, if anybody can look at me right now and tell me like pretends to tell me in six months, they know what the fuck's going to happen.

Right. I'm like, you're full of shit, but I can't even see what next week for crying out loud. What's going to happen at this point. So I guess, you know, I used to, when I took my, when I took the bachelor training of this boss was, you know, anyway, he was like a hardcore dude and, and he showed this movie with a Matthew McConaughey and he was like, it was a perfect example of what not to do as a leader. Right. And it was, it was the U-571, right. Where he was on the submarine and, and, and all shit, like the captain gets killed and he's the next in command and all his people are looking at him and they like, what do we do and he goes, I have no idea. Like, I, I, I don't have any idea. And, and my old boss was like, that's just the worst thing you could possibly do.

You instill no confidence and dah, dah, dah, dah, dah. And I'm like, yeah, well, what's he going to do? Lie? Like, what's he going to do? Sit there and say, yep, no, I got to plan. Everybody follow me. So I guess what's the, like in now, let's, let's look at like, cause you were there. Well, we, did you join Otter after COVID or before? During. Yeah. During. So after it, after it happened, after like the holy shit March. Right. Yeah. So, so that was a time, I guess you kind of came in a weird spot, but like 2023, let's use that. Yep. I mean, that was, that was fucked up like that. There was some shit like Silicon Valley bank. See you later. Everything came to a stop in the tech world. And there was a lot of like, oh my God.

What's going to happen. And so when your team looked at you and said, what do we do boss? You can't tell me with a straight face. You had any idea what the fuck was going to happen. Like, like what, like how you were going to get out of it. You never know. Right. Right. So I guess, how do you balance that? How do you balance the comp? Like, look, we'll, we're going to figure this out together versus I, the, the, wait a minute, my boss doesn't know. So, cause I, and I guess I'm asking, cause I failed at this horribly when that happened, literally when 2023 happened, I was like, okay, cool. And I went boom and I mapped out all this plan and I came to my reps. I was like, no, we can do this. We can do this.

We got this. Right. But it was so obviously burning to the ground that I was like, you know, I was trying to force the optimism. And I think a lot of them got scared because I was so like, we can do this, but I was so hardcore about, we could do this. That I think they were like, holy shit, this is all scary. And you're just adding fear to this. So first, you know, call I got from a recruiter, I'm going out of here. Right. Cause this is, this is too much shit. So I guess where, how do you balance that? I think first, I think a lot of leaders don't lead from the front first and foremost. And I've had those leaders. And I think that's the reason why when there was a light bulb moment of, I can do this role because I seen all the leaders just go into a locked door and they're so basically like untuned from what was going on from the rest of the org.

They saw it from their ivory tower, if you will. And they don't know what was going on, why you win, why you lose, what was going on with the deals and you know, what are the products functionalities that are like being requested the most? Like they're just so out of touch. And so I'm always in the weeds with them like day in and day out. I'm on calls. I love it. It's like the thing I love to do. And like, they know that I'm in the trenches with them. So they know that we are in this together first and foremost. And I believe in radical candor. It's like, if we're going to go through bumpy times, I'm going to tell you, I'm going to tell you that we're in bumpy times and like, but you know what, we're going to figure it out and I'm going to try to take care of you and we're going to try to get through that time.

And obviously I talked to my senior leadership during these times. It's like, because we did have these conversations behind closed doors at the end of the day. Like we thought the macroeconomic climate was going to decrease. And so we were like, okay, if we, cause we were growing and we're, I was hiring a lot of people and I go, there could be repercussions. If this happens, I need to know that if I do this and the macroeconomic climate does decrease, we will still be able to take care of our people. Whether we lower their quota or we do X, Y, Y, Z, have a game plan in the back of my mind of what we're going to do. But I needed to have that upfront conversation because that, and it's what I do with my CEO.

And he, he agreed that if we do this, if we start hiring aggressively and something happens, we were aligned and I wanted to make sure with my team and tell them, I didn't tell them everything. I just go, we will take care of you. Like we will figure this out. Like I've got confirmation internally. If things happen and things slow down, that we're going to be in the right place at the right time, uh, when things turn around and, and we will take care of you. So I think it's just having that transparency. I think that earns trust and people want to stay with you even in tough times. Yeah. I think that the tough part is, is like, you know, I've, cause I've done that and I've made, unfortunately made those promises and had the buy-in from senior leadership.

And then all of a sudden senior leadership rips the carpet out from under. And now you're, now you're the asshole because you're the one who delivered it. And you gave them the confidence. Like my old company, Basho, like the, my, my seat, my VP of sales, like it was obvious, like it was, it was 2007. So another crash. Right. And it was pretty obvious that it was not going well. And my VP of sales went to the CEO and said, look, like I'm keeping my team here. Like we're in this, but I need your confidence that this is going to happen. It goes like, yeah, yeah, absolutely. No problem. We're definitely going to do this. And then literally last little week later, he fires all of us on the spot.

And we were like, what the fuck? So I think it goes back to trust and transparency and those types of things. But really having, to your point, like, you know, being in the shit with everybody so that they see you and trust you that you're, you're in it with them. Right. The ivory tower management style is just the absolute worst you could possibly approach. It's terrible. And you, you see a lot of that. And I think that comes from like the insecurity of people in that role, because again, it goes back to why are that, why are they doing that? Uh, and so I just see it, you know, that come from larger companies and they're not familiar with what they do. And there's, they're scared that people are going to find out, you know, it's like, we're all faking until we make it.

It's just like, it's like the, I don't know. I've seen the meme on, on Instagram these days. It's like, you know, when you realize that when you're adult that like when you're a kid, you think that all the adults figured everything out and they all know what they're talking about. And then when you get there, you're like, wait a minute, nobody knows what they're talking about. Nobody's figured this out. I tell that. I literally tell that to my team all the time. I'm like, well, first of all, we're all in a complaint, Phil. I work for you just as much as you work for me. So you guys are all well aware. And I go, do you think I have all the answers? You're, you're dead wrong. So the reason why we're all in a complaint, Phil, is because I still learn from you guys.

You teach me things. And I think, you know, it was, it was great. Cause someone was teaching me like the other day of what they're doing differently with trials. And I'm like, I love it. Like they were, they were treating trials completely different than I ever thought. And I'm like, see, I'm learning things from you guys just as much as you guys learned from me. And I'm like, that's the atmosphere. There's no ivory tower here. We're all, we're all equal. Speaking of which, let's, let's finish up on this. Like, so let's stay on leadership. I guess for you, what was, what was one of your bigger mistakes when it came to leadership? Like something, cause I got a laundry list of them that I fucked up on, but is it, what's the one that kind of sticks out to you where you were like, eh, I should have done that different or, or I will never do that again because I, the way I approached it was, it just didn't, it just didn't land.

I think the biggest aha moment for me was knowing, knowing how I am and there's like color codes and this was a, I really recommend people doing this identifying like who you are as an individual. Like I was like a red, right? I'm like fire red. I'm like, go, go, go. And then you identify the people that you're dealing with and how, how fire reds deal with like, let's just say like a blue and a blue is more reserved and they're not necessarily like outgoing. They're not going to like fight, uh, you have to work with them differently and you've got to treat people and you've got to like, you know, work with them because I can fight, I, you know, I can push on a fire red, but if I put a shot up on a blue, they're going to take it very personal and they're not going to like that.

Not to say that like, there's anything wrong with blue. It's just like, you've got to approach them completely differently. And so I was approaching leadership as treating everybody equal, you know, just the way I wanted to be treated, you know, and being like hands-on. And so the big a-ho moment was like, I've got to treat things differently. Um, but also, you know, another learning is you got to know the ins and outs of your product. Like, I think that was like another big thing is, you know, you get into leadership and you don't know the ins and outs of every little thing. And I think that that I, and selling as a leader is probably like the biggest thing that you could be doing. And I, and I think that people get into leadership and you, you, you don't have it that lens, uh, of what the reps are going through and that goes leaning from the front.

And I think that that is something that I always want to instill here is get on some calls. Like, let's go through it together and let's learn how to sell. Cause you're going to have a different perspective and you're going to coach differently once you come on board, but you have to know the ins and outs of how to sell the product. And I think that's like where I think a lot of leaders, leaders fail personally. Yeah. And I think that's why I look for organizations that are sales led, not engineering led, quite frankly, or at least have really strong sales leadership that get it. Cause I, I always cringe when I have, when I hear engineer, you know, founders without strong sales leadership because on, and I, and I've worked my entire life with engineers.

I was, you know, I started an IT services company. I was 50 engineers. I was the only sales guy. I know how to speak the language and, and I get it, but they almost always look at sales as, as kind of a necessary evil, right. And that the product is the best. And these days, I'm sorry, your product tomorrow, it's not going to be the best because it's just moving. So it's not about how you, it's not about what you sell, it's how you sell. And if you can't really lead from the front on that, on, on sales, like, how do you, how do we drive this? So I can understand the market and I can understand what people are saying out there. You know, I haven't, let's put it this way. I haven't seen too many companies fail because the product market fit or the product wasn't good enough or any of that.

I've seen a shitload fail. Cause I can't sell it. Honestly, it's everybody should be future selling, especially in our world. And I think that if you're not iterating, iterating, iterating, I mean, I can't tell you how many times we've iterated our pitch and who we are. And I think that that's where, uh, my team has done a great job because we constantly are testing new top tracks of like what's working, what's not working. Um, and that's why I like people, especially leaders getting on calls because they're going to have a different perspective and different view. And like, I just hired another, another rep and he's got more of like an analytics background and I, and I, and I love it because he's coming with a different mindset of like talk tracks of like how we can talk about this from like a different level, a higher level.

And now again, we are, we are changing the way we're speaking about Otter at a different level. And I think people are starting to see who we are, you know, a much greater scale than just like a transcription and recording tool. It's like that future vision of like what we're becoming and being able to like really put that on paper because marketing is not going to do it. You know, engineering in the senior leadership, they're not going to do it. It's on, it's on us. It's on us to like, well, they'll do it. They won't deliver it though. And so they won't know how it lands. That's my thing. Like my background in marketing, I love marketing, a healthy respect for them. But the problem is, is they come up with whatever they come up with and they never see the reaction to it when it's delivered.

We are the ones that see the reaction to it. We watch the facial people, like, you know, people go, huh? Like, or like watch them zone out or get ghosted. All like, we're the ones who have to deal with that last mile. Yeah. And I think that's why the, the, the, the crime of it is that, you know, that sales and marketing divide is that there's, there's regardless of the divide, the feedback loop just isn't there. And the sales of your frontline, like talk about data, talk about insights into the marketplace. Oh yeah. If you want insights into your marketplace, tap into your sales org and, and have them gather additional information outside of your stupid band qualification shit. You know what I mean?

Like, come on. That's what we do is we test it out and then we're like, okay, well, this is really working. Like, that's the reason why we all work together. We try to have the very similar talk track and then we slowly iterate pieces here and there just if it works, if it doesn't work, then we, we, we, we try to adjust. But then we take that information back to our senior leadership and this, we take it back to marketing and we're like, now this is what works. Let's, let's run with it. Love it. Awesome. Dustin. Well, we could keep having this conversation forever still. Let's say questions that I was going to dive into. I'm like, ah, you know what? This is way more interesting conversations.

I get nerd out stuff all day, every day. Absolutely. Right. Well, look, um, you know, for everybody who's listening, you probably already know that, you know, Otter and I have got a real good relationship. I love, you know, I, I told Anish when we first started working together from a sponsorship standpoint, especially when I went off on my own that I will not, uh, you know, partner with anybody who a, I don't use their shit or, or believe in their leadership and, and can't speak authentically to it. And I will tell you, you know, honestly, Otter has been one of the, the tools, uh, the platforms, the solutions, however you want to position it, that is made a actual difference in, in what I'm doing.

And isn't just one of those things that I have. And I kind of try out every once in a while, cause I got to do a post about it. Like I actively use it on a regular basis. And for going back to what we were talking about memory wise, I have such a shitty memory that, that Otter has been a godsend for so many reasons. So I appreciate what you guys are doing. I appreciate the relationship. Well, I appreciate you having me. And I, and I want to maybe share this with people because I think this is an interesting story. Yeah. You interviewed us just as much as we interviewed you to see if this is a good fit. Yeah. And what people don't know is, you know, it was a lengthy process. I had a, we had a showcase what we do and the workflow, if it works with your process, if it didn't, you're like, I'm not, I'm not going to go through with it.

So, you know, and I, and I appreciate that. And that's why I knew I was like, this is, this is the right guy. Right. And so it was a mutual fit at the end of the day. I mean, we, we've turned down people and, you know, but no one's ever like interviewed us to say, is this the right fit for me? And you told us your workflow. We walked through what your workflow. I remember distinctly, you know, cause we had a whole group of people in the, in the conversation. And so we were all walking you through how it works. So yeah, I can contest that, you know, just making sure that everyone knows it's not just money with you. Well, and I think, I mean, and on that. I don't know though. I think it's important for sales reps to hear that in general.

First of all, like interviews, like obviously when you're interviewing for a job, you better be interviewing them just as much as they're interviewing you, even though you need the job. Leadership actually appreciates that. Like when I, when somebody's interviewing me after I'm like, Ooh, all right, this kid's interested. So you're going to go to the top of the list, but it's the same thing with customers. I tell people all the time, like if you're a pain in the ass during the sales process, you're going to be a pain in the ass as a fucking customer. So I want nothing to do with you. So, so as much as I need, I want your business and all that other fun stuff. If, if this is square peg round hole, or if this is, you know, just doesn't feel right or values are off.

Like it's just, it's not going to work. I mean, even though, yeah, you might be able to sign that contract and never see that person again. It's not going to get your customer company to a hundred million. It's not, that's, those aren't the type of customers that are going to get you there. So I implore sales reps to, to your point, optimistic, pessimistic, be both and be a pessimist at certain point to disqualify. Exactly. Yeah. Right. Until they, until they prove you, you know, that's a good fit. And then it's like, cause you know, everyone has, has that gut feeling. And that's why I'm always trying to get people to go, man, that feels right. And whether you're optimist or pessimist is like, if, when you get there, you know, you're in the groove and you're like, this is, this is a good deal.

This is like, I feel good about this. So just trust your, your internal instincts. Totally. Awesome. Dustin. We'll tell people where they can find out more information about you, about Otter and all the fun stuff that you're doing over there. Yeah. Otter.ai. Um, yeah. If you want to connect on LinkedIn, I like to chat about all things sales. Uh, I just did a talk at university of South Carolina and also snowflake. So I, I enjoy the conversation. I want to make sure that people are well-educated in this space. And, you know, understand like the mental health of sales because it's, it is grueling. And I think that it's extremely important for people to, you know, know and understand that it is a grind and to take care of themselves physically as well.

You know, I think it's really important. And I wake up every single day, work out, get, get yourself right before you get into the mental grind of sales. And I think that if you start your day that way, um, and just know that it, you know, there's things that are in your control and there's things out of your control, but put in your work. Yeah, man. I think the, the, and I wish, I wish experience wasn't the best teacher. I, I know. You know what I mean? Like, cause there's, cause look, I'm, you know, I'm about to, I'll be 50 this year. Right. And it's just like, you know, when my daughter is 14, it's like, I want to instill all these mistakes that I've made in my life and just get so that I'm, please don't make all the mistakes that I've made and all this stuff.

But you just can't, you just gotta, sometimes there's a certain point of stuff that they just have to figure it out on themselves. They just have to fail hard. And, and then, cause that quite frankly, I found that failing hard is the best teacher. And that's why the last thing that I do just to give you, because I've been kicked in my teeth so often in sales, I, I still, I kick other reps in the teeth, but somewhat respectfully. And so you, I do this and this, anytime a sales rep comes on a call with me, like trying to sell me something, we have one question before we get started and I'll say, Hey, before we get started here, just tell me what you know about me, but business. So we can kind of skip that shit.

And if they, all they really have to do, by the way, is say, Oh, I know you do some sales training and I know you work with companies like this, as long as you can say that conversation continues. But if the conversation goes, uh, or, uh, well, I'd really like to hear from you, blah, blah, blah. Or you see them kind of grab the, the, you know, type in jbarrows.com. And I literally say, when you ask for somebody's time, make sure you respect it. This conversation's over. And I hang up the phone less than five minutes in. And it's like, and it's a very abrupt, like you wasted my time. I'm going to take it back, learn from this. Right. And, and everybody thinks I'm an asshole, but that is the only way that I learned to prepare.

You know what I mean? Like, I remember walking into a meeting and a CEO was like, all right, tell me what you know about the business. And I was like, Oh, and I felt that. And I was like, Oh my God, I feel like an asshole. And he literally kicked me out of his office. He's like, you, you, you, you asked for my time. You don't do any prep. I was like, Ooh, okay. So anyways, I'm going to, we can go all day long. I, I do a similar approach during interviews. If I know that they, if, if it starts to like hint that they haven't done the research about me or the company, I'll, it's not a vain thing. I go, what do you know about me? Like, and I just want to know if they had done their homework, they don't know anything about me.

They're like, I think you went to like somewhere like in Michigan for school. Like, no man. Like I went to Eastern, like, you know, it's like, come on, do a little bit of due diligence. It's that's the part that I don't understand because it is, especially now it is so easy. To do prep and get insights, like literally one prompt on a GPT. I was going to say, I was, I do that all day long. I mean, I, I've literally created my own GPTs to prep for podcasts, to prep for meetings, to write social, and I've created it all. And all I need to do is go like, I'm meeting with Dustin. He works at Audera and it, here's everything I need to know about him. Here's some questions you can ask him. Here's how your stuff aligns with what he's trying to accomplish.

I'm like, and it takes five seconds. It's unreal right now. There's zero, it's kind of like when Uber, it's like when Uber came out, there's zero, like if you get caught for drunk driving right now, you're a, you're just a straight up asshole. I thought about that too, because everyone in LA always was getting caught with DUIs. I'm like, you're, what are you doing? You're like, I'm in one of the first markets that they're in. Like, come on. Right. What's wrong with you? Like $30, like the most expensive Uber ride I've ever taken in my entire life is not as expensive as going to jail and paying for an OU offer. Exactly. And then, you know, putting a ding on your, in your background, like, come on.

Yeah. So anyways, all right. Let me keep going. All right. Thanks so much for coming on. I really appreciate it. And everybody, I hope you enjoy the conversation as much as I did. Like I always say at the end of all these podcasts, go out there and make somebody smile today. Cause no matter how bad your day is going or how bad you think it went, if you make somebody smile, you know, you had a good day in the world and there's a lot more of that right now. Thank you all very much. And I will see you on the other side. Hey everyone. I hope you enjoyed that conversation as much as I did with your support and our incredible guests. We're one of the top sales podcasts out there right now. And I can't thank you enough now to keep the momentum going.

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