Luke Arno: Building Grit, Passion, and Real Revenue Teams

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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 am terrified about what that means for unemployment rates and all that other stuff, because if you're not on this train trying to figure this shit out, or if you're not finding your way to work your ass off to get up to the next level, then you're going to wake up one day and be irrelevant. 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 Luke Arno. He is the CRO at Transcend. But before Transcend, Luke was a global VP of sales at Twilio segment and a VP of sales at Box, two roles where he solidified his track record for growing ARR at global companies. Overall, he's a powerhouse revenue leader with a data-driven, customer-focused, and innovative centric mindsets. And look, he's a coach at heart. And we really got into this one for the difference between coaching, leadership, mentoring, and everything. And what are the characteristics of great coaches versus great leaders? And how passion, drive, and grit are some of the characteristics you have to hire for because you can't build? And so how do you identify those in the hiring process, especially in today's world where AI is presenting everybody as perfect fit for your organization using their resume builders?

And one of the things he looks for is just a positive energy, quite frankly, and an optimistic. Because you look, in sales, you have to be optimistic here to be in this profession. You know, shit, startups, you have to be optimistic or almost delusionally or else, why would you do it? And really what his passion is, is talking about how enablement is the most overlooked growth lever in organizations right now and how too many of them look at it very reactively. And so we talked about how to make it proactive and be part of the strategy and the balance of sales fundamentals with all this tech that's happening out there, which is what I'm trying to struggle figuring out even what the fundamentals are anymore.

And he brings up something about this sales-free buying experience, which is an interesting topic I think we should pay more attention to, and how I think we've actually scienced out sales a little bit too much and how we have to get back to the art form. So if you like sales, if you're trying to figure out which way is up right now and where to focus, you're going to like this one. So hopefully you enjoy it as much as I did. Let's make it happen. Luke Arno, welcome to the Make It Happen Monday podcast, my friend. How are you doing? I'm great, John. Thanks. Happy to be here. Yeah. As we were just talking right before this, I was trying to figure out like, when did we first connect? And when you said Salesforce, because I thought it was Box, but you're right.

I think it was early days of Salesforce where both of us were just getting started. Early days, man. Early days. It's been a fun journey, man. It's been crazy. And it's getting even crazier now. And I'm loving your perspective on a lot of the stuff as I was prepping for this. I'm really interested in your perspective on enablement and coaching and where this is all going. But before we get there, I always love to ask the origin story, my friend. So parents growing up, you know, all that fun stuff. Like, where did your influences, your real influences come from? The ones that we don't look at on LinkedIn. Talk us through that growing up and where you got your sales, you know, bug to you and all that fun stuff.

Yeah. I'm going to actually start where I'm at now because I think it's a good signal for the journey that I've been on. So firstly, I'm a father of two beautiful young girls, centerpiece of my life, husband of 17 years to a New Englander, actually known her for 20. Red Sox fan, came West Coast, took me to a game for a first date, sold right there. There you go. And then I like to think of myself as a coach at heart. And I lead the revenue organization over at Transcend. Like, where this all started, I, you know, if I go back without sharing too much of the nitty gritty, although if you want to go, you can. I always love the nitty gritty, man. I got into, I got into this profession, I'd say a bit out of necessity, out of survival, a bit out of, you know, it felt like a good path for me.

But when I came, when I came out of college, I was at UC Santa Barbara, I wasn't on the path to go sell enterprise software. This was early 2000s.com crash just happened. I was, I was knee deep in athletic coaching, fitness, kinesiology, all this stuff. I wanted to go spend time where there's fresh cut grass and chalk on a field. And so I started pursuing paths to coach and find myself back into secondary school. And, uh, but like, you know, as, as we all do, I went through adversity at a pretty young age. You know, I was the oldest sibling to a single mom growing up. And, uh, and then I lost my mom at a pretty young age and I had a younger sister, 10 years younger and like the real world hit me.

I had to go find a way to make money, to go provide, to go be a dad or an older brother that served as a guardian. And, uh, so I found myself in banking pretty quickly after that. So 2003 to 2008, I was in the banking world and, uh, we all know what happened in 08. And so come 08, I I'm sitting here, same, same responsibilities, probably more, uh, as, as you think about, you know, what we were talking about right before this, like the burn and, um, and the world crashed around me. So I had to go reinvent myself in 2008. And, uh, as I'm watching my savings dwindle down, I'm going around the, the, the block. I'm asking for referrals. I'm doing everything I can to network into what I believe to be a good path was stability.

I just came out of a world with no stability. And I, I knocked on the door. I got actually introduced into salesforce.com and, um, I went in for an interview process and lo and behold, I actually didn't get the job. Um, and I sat on waiting back to hear this for probably two months and I kept following up and they said, we're just wait, wait, wait, patient care. And then two and a half, three months later, as I'm just burning, burning, burning, they finally said, nah, um, your background didn't, didn't fit the criteria for what we're looking for. And I, uh, I took that one personally and, uh, I went and fought for another opportunity. And I, um, I asked for a meeting with their, their leadership team.

And I said, give me an opportunity to show myself and, and action. And so this was kind of cool because these people and like Salesforce in 08 is still a really tight knit community in 2025. Like most of the core connects I've developed in my network were Salesforce in the two years I was there and I left, but the two unions for crying out loud, like there's reunions for original Salesforce people. They all go and hang out and like all those, right. And you're invited to all of them. I mean, you're part of that crew. So, um, so I, I got, you know, I was in front of Tony Rodoni and I was in front of Amy Gorman and Carla, and I'm sitting there presenting the tip of the iceberg slide on how we're going to go beat Microsoft, right.

And, uh, or, or Siebel. And, um, and they're like, where did this kid learn this? And, and, uh, like I had to survive. I had to find a way to go make it happen. And so I did, and I got in, I got the job and, you know, I, two years in a row, I went to club and that's where you make a ton of really powerful connections and, uh, and anyway, so the rest is, I actually, I left, I left Salesforce and then my journey started beyond and beyond and beyond, but, uh, that that's where it all, you know, it came from. And now I'm a father and I'm a provider and, you know, I love, I love being the rock of my family because I, I didn't have that growing up as much. So, uh, I wake up with a smile on my face every day.

I get to do this, man. Love it, man. Being a girl dad too is awesome. It gives you. Yeah. Yeah. Yeah. Same here. Like, uh, you know, I obviously, you know, I'm sure boys are great too. Right. But, uh, but, uh, if there's one happiness, you know, if you ask for happiness, being a girl, that is just like when she gets put in your arms the first time, it's like, Jesus Christ, like nothing else matters. So that's the best thing in the world. Let me ask you, let's back up a little bit on coaching. Cause you're super passionate about it. Was there a coach in your, um, early days that had an impression on you that, that, that got you to be passionate about it? Like what, what got the coaching bug for you?

Um, there was, there was actually, um, I think where it started for me, uh, when I was a high school, I was a freshman, I was a sophomore in high school and I'm going out playing football. All my buddies are playing football and, you know, I'm kind of the run of the group. You know, he's all, these guys playing lineman, the linebacker and I'm, you know, the receiver on the side. And it started to get real about that age. And, and, you know, I'm, I'm looking around, I'm like, do I really want to do this? And I, you know, I said, you know what, I think I'm going to, I think I'm going to pull out and go play baseball. And, uh, the head coach, Biff Barnes called me that weekend and he's, he gave me the spiel.

He's just like, Hey, I'm going to support you, whatever you want to do. But if you come out, I'm going to make sure you grow and learn something, no matter where you are on the field. And it turned out that was a really impactful moment for me. And, uh, what it unlocked for me on a football field was, uh, a male figure investing in me and my development at that time, single mom as I connect the dots here. And, uh, but I was, I was the Z receiver flanker running plays and every time. So I had to know the offense really well and communicate it to our quarterback. And I got to understand the operating mechanism of the game far more deeply than anybody else. And I just programmed that. And then as I came out of college, I went back in and I coached high school football for two years.

And, uh, and, and there was a direct correlation between those two things. And then I got to go replay back. And then as I moved into this profession, I found a ton of joy and gratification and being able to program people with the core fundamentals of everything they do, whether it's picking up a phone to call somebody or preparing for a meeting or, you know, going out and I coach my girls softball teams now. So it's all the same stuff, man. It's just like focusing on that part of it to help people better at just basics. Hey, I hope you're enjoying the conversation so far. I want to take a quick minute to share with you what I'm working on these days with my new JB sales membership. It includes live monthly training delivered by me on my two signature courses, which are filling the funnel and driving a close that cover all aspects of the sales process.

It also includes monthly workshops that I'll be running on specific sales skills and different tech skills like ChatGPT and how to leverage AI throughout the entire sales process. Finally, the membership gives you access to my entire online catalog with every course and every tip I've ever done. And as an exclusive offer to my podcast listeners, if you go to jbarrows.com, click on the individual membership link and use coupon code podcast at checkout, you'll get 25% off. Now let's get back to the conversation. Is there one trait you look for in like on your sales teams of all the teams you've managed at this point, you know, there's the inherent issue with most organizations just promote their best sales reps to be managers.

And that's usually the worst thing that you can do, right? Because the best sales reps are usually the artists. They're just innately able to do certain things and it's hard for them to teach, right? The structure and the behind it. And then there's other people that are really good at the structure and that type of thing and, you know, and maybe average sellers, but they might be great managers. So is there one characteristic you look for as you get a group of, you know, young sales professionals out there that you start to identify like, Ooh, this one has the characteristic to be a manager and a leader. Is there one that you look for specifically? I don't think I've ever pared it down to the one specific thing.

Typically it's a few things that come together that give you a strong signal. If I were to pare it down, it's drive. It's who is showing up every day to get better and hit the number, self-improve, help their peers and all that's just tied to grit, hustle, drive. So yeah, I think that's to me, like that's the one. And I do, do you have anything to use to like test for that in an interview, right? Cause it's hard to, you know, somebody could tell you how great they are and how driven they are, but how do you test for drive passion? Cause I thought that was what, what shifted my mentality was I was, I remember as my first company, we were like, you know, five people, 10 people, whatever. And we got the 50 and like, they just didn't have the drive.

And I remember Jack Welsh literally, um, I worked for him for a couple of months getting his online MBA program, but this was way before that. And this is when Jack was kind of my, at that time, my business idol. I loved winning the whole book and everything else. And I went to a seminar that he had done and he does just Q and A's, right? So when you go to the seminar, you stand up and you ask the mic in front of a house and he just answers, right? So it was like a couple thousand people in Boston. And I, and I stood up and I asked the, what I now know is a dumb question, which is, Hey Jack, you talk a lot about passion and all this fun stuff. Uh, you know, like we're, you know, we're 50 people now, right?

When we were 10 people, everybody's passionate, 20 people, everybody's passionate, but that 51st person that we're hiring just doesn't seem to have the driver passion. And I asked the dumb question, which was how do you instill your passion on somebody else? And, you know, he looked at, basically told me I was an idiot in front of a couple thousand people and said, you can't, you can't teach passion. You have to hire it. That's why it's so important. So how do you flush out passion, drive grit in an interview? Yeah. Um, I love the question. Uh, you know, there's, there's some behavioral questions you can ask about just tough things they've, people have gone through, what motivates you. Um, what I, I typically try and hone in on, uh, are three things in an interview process.

Uh, the first is, um, probably less relevant to the drive, but just, I need a, I need a good baseline on the transferable skills you bring over. So, you know, how would you summarize the last four to five years of your career? What have you, what have you overcame? How have you, uh, maintained success through adversity? Those types of things. And that gives you a good signal on where they've been. Uh, I think the counter to that is help me understand where you want to go over the next few years, what you want to accomplish. If people weren't dialed into the goals they have specifically, I think there's a big red flag there. Um, and I love to ask people what gives you your greatest sense of positive energy?

Where, what is like, what surrounding do you have or environment are you operating in to be at your absolute best? And, uh, typically people will open up pretty quickly. If you ask the inverse, you know, what inspires negative energy? Uh, you can flag some, some cues there too, right? Like, oh, if my, you know, my manager or the, I don't get the territory, I don't get this. And so, um, those are, those are key things that I flag in a one-on-one interview when I am at the table with reps. And I typically try and interview every rep coming in our business at some point during the process. Uh, you know, the, the number one thing I can learn from my experience is when you have to, then you're going to.

And if, if, if people haven't gone through that, uh, it's, it's an unknown. So do your best to find that experience within them. When did they have to go get it and how do they do it and how to make them feel? Yeah. It's funny you bring that up because, you know, I, as, as sick and twisted as this might sounds, you know, what happened to me in 2023 going from 6 million to zero and that whole thing, like it actually taught me a lot. You know what I mean? Like I can figure it out. I've, I've, I've always had to figure it out mentality. That's where make it happen actually comes from. But that one specifically, cause it was so bad. And I, I went to literally zero into your point, you know, watching bank account go like this and I'm got a family, I got a house and all this other stuff.

And I remember sitting, looking out my window being like, and my wife was like, are you okay? I'm like, and I was way quieter than usual. And I'm just like, I think so. I'm like, I just, I gotta, I gotta think about this for a minute here. Cause I, cause I'm in a spot now where I can't just keep moving forward. Like I usually do. I need to think, I need to really think this thing through and figure out how to get, get on the other side of it. And then I started moving again and I was like, all right, cool. And so if that shit can happen, like whatever's coming up next, I don't give a shit. So, and I think that's a question. Do you think that grit is, I think I only answered this, but do you, if somebody doesn't have any adversity or like real adversity in their life, how do they develop grit?

I, I, I, I don't know if I can answer that question. I don't think so either. It's, uh, I think it's what Angela Duckworth tries to do in her testing and her books. I think it's what every, you know, leader tries to, to make sense of, um, use the word privileged, uh, in, you know, some of your podcasts and I, I think we all can get to a state of privilege, but you know, what is the journey to get there and, and, uh, do people face, I think most people just typically face adversity. It just is, it, it appears differently in scenarios. So, um, well, it's all relative to, right? Like, I mean, your adversity versus my, I mean, I, I talk about adversity. It's like, yeah, I'm not living in Ukraine, you know?

Yeah. I mean, exactly. Exactly. Yeah. All right. Let's talk a little bit about, um, sales. So you kind of ended that story with Salesforce, but then you went to a startup, right? What made that? Cause that is a, I mean, talk about different, right? Like huge corporate. Cause I did the same thing. I went to Xerox and I was like, great. And then I went to thrive networks, a four person company, self-funded figure it the fuck out. And for me, it was like, I was a breath of fresh air. Cause I'm like, oh my God. Like I actually matter now. Like what I do definitively impacts this business in every way, shape and form. So why did you take the risk? Quite frankly, of leaving Salesforce and going to a startup.

And what was that like for you? What was that decision process? So the startup I went to was a series, a funded startup first round capital, put the investment in and they had built a platform to connect buyers and sellers in private markets. So MNA transactions, private equity groups, investment banks in that industry, very much from the outside. I had always found very interesting. I came from the banking world and I wanted, I wanted a seat at that table. Um, and I was like, that could be cool. The, um, but the, the real answer here is I was, I was dumb. I was ignorant. Like I just, I didn't have a mentor in the enterprise software. So I, I fought my way in out of necessity, out of survival.

I was there. I punched the clock. Uh, I shouldn't say punch the clock. I punched the number. And yet my earnings were about half as much as I was making in the previous years. And I still had these, uh, these responsibilities. And I was like, I got to do better. I'm going to do better. I'm going to, I'm going to go find a company that's going to pay me more, bet on me and, and I'll go take the risk. And, uh, if, if my career ended in that moment, I'd say that was the worst decision of my life, but luckily it didn't. And, uh, and I, I found a path out of it. And, um, and I learned a lot during that year. Um, I learned how to go be valuable as an employee, but I also learned when you are not setting up the chessboard to, to give yourself a chance to win, you're going to set yourself up to lose.

And the company was headquartered in New York. I was in SF. They wanted me out there at least one, if not two weeks, a month. Um, I just talked about my wife and like, we were getting off in our, in our, our journey. And, uh, and it was really early days for this company. And I wasn't hitting the OTE I saw on paper when I took the job, even though I was at 150% of my OTE at Salesforce. I, so I saw a net drive. So, um, I took the, the, the risk because I didn't know that it was a risk. And, uh, and how old were you just out of curiosity? How old were you at that point? So, um, because I restarted my career at Salesforce, I was 28 when I started at Salesforce. I left when I was 30. Okay. So, uh, you know, I, I'm a late, like I hire these kids right out of college and they're like, when am I getting promoted?

When am I moving to the next door? And I'm like, let me tell you about that staircase there. And if you step every single step up that staircase, you're going to a lot further than thinking about how you take that elevator up. Yeah. Cause I, I didn't start to really get going until I was in my early thirties and that was post that startup. I think there's something to that, man, as being almost forced through the grinds. Right. And I, I, I still feel genuinely, you know, lucky, however you want to pay it that I, that I grew up without tech, but I, that I grew up with the, you got to fucking figure this shit out and not be entitled. And maybe it's the East coaster in me where my dad's always like, you earn it, earn it, earn it.

Like put your head down, I can earn it, you know, that type of stuff. But, you know, it gives you just so much more perspective. I tell these kids all the time. I'm like, your career is 40, 50 years. Like, and, and actually the stat that I, because I'm doing a lot of research right now on the SDR BDR role and how I think it's, you know, needs to be reshaped completely. Um, and one of the interesting things that bridge group came up with a report that if, if an SDR stays in their, in their role for like over, I think it's 16 months, if they get promoted in less than 10, the failure rate is 55%. Interesting. If they stay for, I think it's 13 or 14 months or more, the failure rate's 5%. So stay an extra year, figure out the craft, perfect it, and then move to the next.

But this is just the impatience level right now is so brutal. I don't know how to deal with it. It is. It is. Um, yeah, the last few years, I think have changed things a bit, right? As companies have reset and tightened up, people are, I think a little more patient to understand, like, you gotta make sure you're picking the right company. You're not going to go through rifts. There's going to be opportunity in the future. But yeah, the, the 18 to 21 era was like, it was crazy. Yeah. Let's talk about enablement. You have a seemingly, uh, special place in your heart for it as it relates to, right? And I think you and I both, right? You, you talk about it being the most overlooked growth lever in sales.

Um, why do you say that? First of all, that, that enablement is the most overlooked growth thing in sales? Uh, I, I, I, as you know, coach at heart, um, everyone was in, and still in, in the nature of, of what we do, you have to move fast. You have to grow quickly. You have to find ways to go capture market share. So everyone's just always moving so darn fast. And in this sprint every quarter or every month or every year, it's really easy to overlook the fundamental development of the people who are responsible for engaging our customers, having the meaningful conversation, um, trying to understand if there's pain and, uh, negative consequences and, and value. And can we be the platform to do that?

How do you build, you know, advocates and champions along the way? So, uh, and I've seen it firsthand. You pretend to coach and train people and then hold them accountable to the number. But I saw the other side of that, which is when the markets all of a sudden crashed and I'm looking at a team around me who I'll be at, they're all great. We've hired great reps, but they lack some of the fundamental skills around how to uncover where there is true pain in a company that's associated to our platform and the value we provide. I scratched my head and I said, where did I go wrong? Like, what did I miss on this journey where we were growing a hundred percent year over year, where I can't even ask a rep to connect the dots between the pain and the value in the, in the, the required capabilities to achieve that value.

And so it was a big, just reset moment. How do we go back to first principles? And, um, anyway, so I, uh, I think that's why now, as we look at the world is slowed down from a, uh, like a hiring perspective. Maybe we'll get back to this for certain companies and certain verticals certainly are, are spreading there. I'm at a company where we get to intentionally invest in development of our people to improve productivity per rep before we go, uh, unleash the, the spend envelope for, for sales reps. And, um, with my capacity, my first hire here was head of an implement field sales strategy. Um, if I were to measure anything against my success, clearly it's the number, but it's my ability to make every single person on my team believe they can go punch 150% of the number in any given year because they have a hundred percent control of their success.

What I love about the industry we're in, and you put whatever product or company name on the front as a sales professional, you are, and you hear this adage a lot, but you are the CEO of a company of your territory, which is your little company with one exception. Like you didn't build the product. You don't have to market the product. You don't have to support the product post sale. You don't have to, there's a lot of things you don't have to do. In fact, everyone helps support you go be the CEO of a growth business. And what you have to do is take ownership of the things that are within your competency framework. And that's be really effective at your job. And, um, I just think there's a lot you can do to help still coach people up on the fundamentals in that part of the world.

So, um, I love to work with people on enablement because of that. And I think you can unlock a lot of value there. Why do you think most organizations still look at, it's still treat enablement as a reactive position. So what I've seen time and time again is, you know, uh, VPS sales usually is the loudest voice, right? And this quarter pipelines done, you know, sucks. And so they go yelling at enablement saying, Hey, we need, we need prospecting training. Go, go, go get us some prospecting training. Right. And then enablement runs around like chickens with their heads cut off, trying to figure out programs, calling me, calling whoever else. And then all of a sudden the next quarter, the VP is like, yeah, I don't give a shit about that.

And yeah, we got to close. Like we missed our forecast. We got to close. So go, go, go find that. And they run around to do it. Like, how do you get out of that loop? Because it is, what I found with enablement, it's very similar to, um, HR in a lot of ways where it's, it's, you know, sales, marketing, CRO, that type of stuff. And then you have the CHRO really okay, but rarely at the strategic level. And there's no C level for enablement. So inevitably it's like, okay, do what I tell you to do. And they're not a strategic part of your organization. So how do you, if you're one of those orgs that is one of the like, okay, enablement, they kind of treat it more like training than anything else.

How do you get the seat of the table or how should you be looking at it differently and why? Uh, well, if you were to associate it to a metric, the most, the two most important metrics you can look at are the inputs and outputs, um, on the output side of sales productivity. So baseline your rep productivity today and, uh, and set a high watermark for where it needs to be. If you don't hire another rep to grow against the metric you have. So what do you have to do on a per rep basis to get there? And then second to that, the input here is conversion rate. If pipeline were to stay flat, which it's really hard to go generate pipeline. If you haven't noticed, it's incredibly noisy with every other tool that, you know, our reps think they have to use to go get attention.

Uh, so if pipeline stays flat and in fact the source or the integrity of the pipeline degrades over time because it's, it's just, it's not coming inbound, it's up. Uh, how do you convert more? And, um, so I think if you were to give enablement or field sales strategy teams, hard metrics to improve upon, they certainly can earn their seat at the table because they're more directly tied to revenue. You take a little bit of responsibility off the marketing organization and generate more pipeline. In fact, if you told me I can't give you more than $10 million worth of pipeline in any given year, but I need you to go from, you know, 5 million in revenue to 10 million. That means I, my, my conversion rate has to go from 50% to a hundred percent.

So if I can't do anything else, I have to improve how I engage my customers and convert or influence them to purchase. And that is where we, we can see enablement teams coming in and make a dramatic impact. And so how much does that balance with the tools, right? Because this, that's the, the right now in the world of AI, it's, you know, I don't necessarily I'm bought into the, I mean, yeah, the average and the crappy reps that can replace them, but I'm more bought into like, let's enable and empower the existing reps with the AI tool. So we don't necessarily have to hire as much, right. As opposed to laying people off, let's, let's get that 50 to a hundred with some tech. But I feel like tech has gotten in the way for the most part, uh, over the course of the 10 years, you know, grow at all costs, interest rates where there were, and we've over-processed, we've, we've taught way more on the tech and the process than we have fundamentals.

So what's your philosophy or approach to how to leverage technology the right way? So it, it amplifies the human experience and doesn't automate it. Um, so if we think about the, like the intersection of where reps and AI meet specifically to preparing for customer engagement or enabling them on the fundamentals or the, the, the message, the command we should have of our message, uh, there's a few intersections. I think the deep research tools are great. Um, and in fact, I, our head of enablement ran pretty good enablement strategy in session and deployment of how to use the different deep research tools. So we have, uh, a technology called Glean inside of our company. And we also use Gemini, um, reps are using, you know, pick your favorite, uh, generative tool, but nonetheless, we've built frameworks around how to think about using those tools to, uh, accelerate the preparation time before you get new in the account.

And then what tools can you use to parse out the key contacts to build org charts? And then what tools can you use to automate some of that prospecting, but still have high integrity in the corporate messaging? I think, um, those are the easiest, like low hanging fruit, uh, uh, technology, um, advancements we're using today to help augment that enablement. I, I fundamentally believe where you win and lose deals though, if we're talking about improving conversion rate, which impacts productivity, it is in this moment though, right? So a lot of that stuff is designed to try and get the attention of your buyer or your prospective buyer. Like we live in this really noisy world, but, and, and you and Jeff taught me this one, the old AIDA model.

It's like, if you can't capture someone's attention, that is one of the hardest parts of this funnel. If you can't get their attention, you don't have an opportunity. And so, but it, when you get their attention, you have to be incredibly well prepared to be audible ready and have a active listening engagement and be, uh, wired with the right like psychology to, to go in and have a discussion about current state pain, not trying qualify and pitch and go. So you have to do all the heavy work up front around point of view and, and thesis based approach to prospecting. And you can use all those tools to automate that, but you still need to enable, or at least make sure you're hiring and then continue to challenge and develop reps to be really strong in that first call engagement.

And that's, that's where I think a lot of these deals can be influences. It's, it's first call engagement. It's winning that call, winning that stage and, uh, and progressing from there. So, so help me with something I'm struggling with here because going back to like AI and skills and fundamentals, right? Here's where I'm struggling. I've been talking about this for the past six months. And finally, some of the heads of the AI are starting to say the same thing, which is the entry level positions in almost every role are now going to get done better with AI than sales reps and in, in front or, or, or lawyers or doc, you know what I mean? Like what, like pick a, pick a lawyer, right? Lawyer goes to school, they get their, you know, they go to the bar and then the first five, 10 years, just case precedent bullshit, sifting through stuff, whatever.

And now, Hey, chat GPT, go find me the three cases that are most relevant to me. So like when you and I were growing up in sales, we, we had to go through the grunt work and the bullshit and the, you know, the hand to hand combat stuff and all that stuff to, to allow us now to have this type of conversation, right? In a sales call where it's not feel like I'm qualifying you. It's, it's a genuine conversation. I'm curious about your thing. I'm bringing in knowledge from different experiences, whatever. Right. So I, like for me, AI is a godsend because it takes, it takes away all the shit work that I don't want to do. And it gives me the ability to have this conversation, but where, I guess the question I'm, I'm, I'm struggling with right now is where do the fundamentals come from anymore?

But actually even more importantly, you're curious is what are the fundamentals anymore? Yeah, it's a great point. Would we be able to have the same level conversation today, John, if we grew up in this era 20 years ago? And, and I, I don't, I don't know. Um, it's funny, you know, having, um, nieces and nephews who are in high school right now, this, this same conversation is happening around using AI for coursework and curriculum. And it's like, you know, parents challenge the fact that you're not developing the active learning muscle and, um, and it's, it's the same concept here. Uh, so what are the fundamentals? Is it, is it shortcut to the output or is it the learning that comes along? And then now you have awareness that you can shortcut all that.

Um, I, uh, I'm not going to overlook the fact that I think there is value in the learning process. So we intentionally invest in our BDR team to teach them a lot of the framework stuff. You and I know what really well, so how to build a point of view, how I, I embrace using these research tools, but you still have to use long form written, um, distillation or, or synthesis and summarization into documents we've provided for preparation. Um, so we teach that we try and hold reps accountable to it, uh, accountability as far as, as, as their motivation to do it. Um, and, and it shows up, I, a lot of times it shows up in the work. Some of the things we actively do with enablement are role play. So a lot of improv role play stuff.

All of our certifications are, uh, we record them, um, but we'll, we manually grade them in, in real life. So in our quarterly, uh, get togethers for QBRs and enablement, we actively certify people on, on command of the message and the content. And, um, and those are dynamic conversations. So we'll play the part of a buyer or a seller and we'll do our best to try and stump people because it is all like, if you've just read the output from Gemini or Chachi PT, chances are I'm going to find the corner and get around you. Um, but if you've done the work at, at typically you'll show when I think that's the, that's the difference, right? And I just worry that too many of us are looking, you know, we want to get promoted after a year.

We want to do this. Like we're looking for the easy button as fast as we can get it. And we're not willing to kind of go that layer deep. And, you know, I keep saying we've gone from an, uh, a search engine to an answer engine, you know, like with Google, you know, whether you agree that, you know, we can all say Google fed us whatever it felt like feeding us. Right. But at least there was a perception of choice and I could kind of look through it. Oh, there's my truth. Right. Where now it's an answer engine. It's like, and inherently it can't be true. It can't be accurate all the time because it's pulling off the internet for crying out loud. But so many reps, I feel are just going to take whatever that is, cut and paste it into an email, into a call or, and the fear here is like, even a, say we got the most AI powered everything and tells me exactly what you care about Luke and all that other stuff.

And I make a cold call and you pick up the phone and I say something like, holy shit. And you get like, wow, like, yeah, as a matter of fact, you nailed it. I want to have this conversation. Now, if you can't go layer deep to three, like I'm done, you know what I mean? So I like, I just, I don't know. I mean, I, I try to balance, like not thinking like, oh, I'm this old man, you know, back in my day and this is how it's done. But I'm also worried, quite frankly, for our kids and the, and the act of learning, active listening, learning, critical thinking, those types of things. Right. So I don't know how we saw that problem, but I think AI could be a superpower for it if used the right way. Right.

Cause business, my business acumen is going through the roof with, with AI. Cause now I can sift through annual reports, 10 Ks and like seconds and get distilled information about them. So I don't have to read through the whole stupid thing. Like it's fantastic, but I worry for the kid who's just going to be like, yeah, write me an email to Luke and make sure it's awesome. And then send it to you. Yep. Yep. Agree. Agree. Well, your bot will send it to my bot. The bots will, you know, we'll move on. So let's, um, well, look, going from this, cause there's something else you said in one of your, I don't know if it was one of your interviews or not, but you know, your approach to sales, you know, trusted advisor, but you said something that stuck out to me, which is a sales free buying experience.

Yeah. Talk to me a little bit about what that means to you. I appreciate you, your reference in that. That was, that was actually a really fun podcast I did with Ian Faison. Yeah. And that's what it was. You know, the, the way we like to show up and you would talk about attention, right. And, um, we talk about trying to get people to, um, to lean in and want to have a conversation with us. And when they do, um, you know, the last thing you want to do is go blow it up by acting like you're trying to shove product. So there's that, I think the genesis of that statement though, in the conversation with Ian was, um, when we, we do quite a bit of our ICP is large enterprise strats. So it's, um, there's almost a limitless amount of problems we can try and go anchor to solve with, with companies.

And you have to be really calculated on who you're reaching out to and prepared to, to have that conversation. And you have to make sure you understand the world, uh, you know, your prospective customers living in before you can pretend to, to be valuable in their world. So, um, but when this is all on full display when we sponsor events and we, um, we do a tremendous, tremendous amount of field marketing through our event sponsorships or, uh, dinners or whatever maybe, and we extend our sales team to go be the, the engagement layer there. And Ian had asked, and similar to this, I probably where you're coming from, um, how do you create a sales free environment with buyers and sales reps, right?

If, if a sales reps coming and they're thinking one thing in their mind, and it's starts with the D and ends with an R like, like, how are you going to hold them back? And, um, and I, uh, uniquely to our platform, uh, we're a data privacy platform. So just intrinsically, we are motivated to go help solve problems bigger than just, you know, reps trying to find the quickest path to dollars. Um, and we hire people specifically to this persona. Uh, I also seek to send people who are not related to the accounts where there are events happening. Actually, I don't do this reps just naturally are doing this or say, we have a dinner in New York in two weeks. And I'd say like 80% of the attendees are going are not, uh, under the account of the rep who's putting it on.

And, and like, that's just cool stuff. So, um, so that's one thing too. So showing up prepared and just having thoughtful discussions about the current state of the industry and you and John, uh, I mean, Jeff taught this and this is largely just, you know, part of how I operate, but the perfect meeting concept, right? It's like you show up ready to have a conversation about just industry trends macro, like, and how that may influence an impact company. And then if given the opportunity or coming into org and then maybe projects like, and if you can just really put yourself in the position to be thoughtful, genuinely curious about industry and, uh, macro trends as the impact company, uh, typically you put the guard down and change the paradigm pretty darn quickly on, uh, a seller free engagement.

Yeah. It's like, I, I feel like we want, we, you know, Jeff actually, um, reminded me of this a little bit when we did, I don't know if you, um, following what I did with the Glenn Gary, Glenn Ross event where I brought everybody. I did. I did. Yeah. So it was super fun. But afterwards, what was interesting was, and Jeff is the greatest sales professional I've ever met in my life. There's not even a close second, by the way. Right. Um, and, and I, and for all the right reasons, like all the right, not like the douchey reasons. And, uh, and it was funny because the Willie Loma, like the, no, not Willie Loma, the guy who was the Al Pacino character, right. Um, in Glenn Gary, Glenn Ross, it was, um, Kieran Culkin.

And we started talking about that character and all he's in a dirt bag. And he's like, you know, all this other stuff. But Jeff had such a different perspective on it. He's like, I don't see why he was a dirt bag. And cause that guy he was sitting next to in the, you know, in the, in, in, in, he's like, he wasn't convincing him of shit. That guy, he was leading that guy down a path. He was just not getting in his way. Right. So he's like, it's not my job to stop you on the, on whatever road it is because it's an unethical thing to do. That's your problem. Not mine. He's like, I just, I meet you where you are. And it was funny because the, like at first, like almost every other person in the room, all sales influencers are like, we're like, what, what the fuck?

But then as he started explaining it, you saw him start to lean in and start to, and what it struck me was Jeff's an artist. Like in every sense of the word, he's an artist when it comes to sales, he knows how to read people. He knows how to ask the right question, you know, Wednesday. And I just feel like we've lost that. And, and, and that's coming from a scientist here. Like I, I always position myself, Jeff's the artist. I'm the scientist. I break it down and give a structure so everybody else can do it. Right. And I say that sales should be more of a science than an art, but I, I don't know. I feel like we've actually gone too far on that realm. And we've tried to over science sales and the art is lost.

And, and really when it comes to the art, it goes back to being a problem solver, not a fucking sales rep. So any ideas on how to get back to that, that art of sales? I love that. Um, and I think you're right. You know, and the science of it shows up in so many different ways. All of it just tied to metrics and, you know, all that, everything in there. It's in the world has changed. So how do we get back to the art side of it? How do we get back to the core ethos of what we're trying to do, which is become trusted advisors, help solve problems, work with people to, to bring them closer, to see how we can create value in their organization. Um, there, the generation that's in seat doing this today, uh, who, who have been doing this for a decade plus, I think are still really well-equipped to go do this well.

And they do it. And those are the diamonds in the rough. Those are the A players out there. Every company is trying to hire myself included. Okay. We're hiring if you're out there listening, but for the generation who has come up before the, or after then, and, you know, really just stepping back and, and trying to understand how to over-prepare for any part of the discussion and where it may go and then go with the flow and be genuinely present and curious and active. Like Jeff benefits from having taught this, let alone doing it for so long. And it's just imprinted in his mind. Like he, he sees the signals so far in advance and he's really good at it. And if we all aspire to be, you know, 50% of where he's at, we'll be fine.

Uh, but I, I don't even think you need to be, I think that you just need to understand like directionally correct. Like how do you, how to prepare for a first call? Like, how am I going to train my mind to go into this conversation, set an agenda. So I am intentional about what you care to cover. Uh, I check the clock, make sure we all have a mutual agreed upon exit time. We're, uh, you know, we're finding the, the right like altitude. Is it product demo or is it just like those things, John are, are still overlooked today by, by, you know, it's like, and who's responsible for, for helping our sellers. Come up to speed there. Um, not only like there's a single person, I, I put a lot of pressure on my enablement team to help, uh, myself, my frontline managers for last mile enablement.

Um, but I think you're right. Like, and this is where it shows up in the conversion metrics. If we're, if we're closing 10% of the deals coming in the pipeline, whose fault is that? Is that marketing for delivering an underqualified pipeline? The BDRs for qualifying underqualified by it or, uh, the reps for not approaching first call engagement, moving it through the pipeline law. Uh, yeah. And it's shared, but I think it's a lot of the, you know, the, the sales team. And it's also, you had to talk about those diamonds in the rough and the A players. It's also, I think that what I've known, what I know is, is that the A players take it upon themselves. So they, they don't wait for enablement.

They don't wait for the training. They don't wait for the tech. I mean, it's all out there to go get, you know, there's, there's the growth mindset and the limiting mindset, right? And so many people are stuck in this limiting. Well, I don't have the tools. I don't have the territory. I don't have this. It's like, what the fuck? Like go into chat GPT and just start asking some questions for crying out loud. Like it's that easy these days. You don't even have to try anymore for crying out loud. Literally. I hooked my microphone up to chat GPT and I'm like, I don't know what I'm trying to figure out here, but I'm going to throw up all over you for the next 15 minutes. And I need you to tell me what to do.

And it fucking tells me what to do. So I don't know. I know. I know. Yeah. But I, I mean, I, I have faith we're, uh, we're naturally course correcting in the moment right now. And I see it like, like I mentioned earlier, people are not raising their hand to get, get promoted every 10, six months now. They're not, they're just like, part of this though, is in the expectation you set up from doing your business, right? It's like, we're going to go do this thing and I'm going to love you. Uh, every second you're here and after like we were making this commitment, but gosh, I'm going to hold you accountable to the way we're going to do it. We're going to do it the right way. And I think people really enjoy that tough love leadership style.

And, uh, and that's, and I think there's, there's a good crop of leaders who are emerging all over tech right now to do that. And the bad ones are finding their way out or the ones that are just, maybe not, they're not bad, but just the ones who haven't gone through the adversity, the losses and found a way to win. They're, they're realizing they have to go retool as well. And I think everyone's trying to find ways to get better now. Yeah. I think I, you know, I hope so. Right. Cause I, cause I, I have a lot of optimism for the reps who are willing to go get it. Like who are willing to put in the work, who have the grit and are willing to go get it. I am extremely pessimistic about the rest.

Like, I, I, I think the rest who are not, who are just the B players who are just kind of trying to skate by and do enough. Like I am, I am terrified about what that means for unemployment rates and all that other stuff, because it's, it's so obvious now that this shit is, is so good compared to us that it's like, if you're not on this train trying to figure this shit out, or if you're not finding your way to work your ass off to get up to the next level, then you're going to wake up one day and be a relevant faster than I've ever seen. So yeah. Yep. Yep. Yep. So for those of you out there who are listening, be the ones, be the top 20% cause there's a shitload of opportunity out there waiting for you.

And hopefully the majority of my audience is in that, in that point, cause I've been hearing me preach about it for the past, you know, fucking 20 years here. So, uh, look, we could keep talking here, but let's talk a little bit about what you said you're hiring. Where can people find out more information about what you're doing, what the team's doing? Cause you, I noticed you're doing some really cool shit, working with some really cool clients. So yeah. Yeah. You bet. Company is transcend.io, uh, find us on LinkedIn website. You can find me LinkedIn, Luke Arno. Uh, so we're, we operate at the intersection of data privacy and, and customer data. And, uh, I spent four years at Twilio segment where we were on the customer data side, collecting a bunch of customer data to power, uh, uh, marketing outcomes.

And we're in a very similar position at transcend where we're helping companies who have collected a bunch of customer data now apply the proper governance, compliance controls, consent, so they can go power that customer data against AI initiatives, marketing initiatives, product initiatives. It seemingly is just a really challenging problem for companies right now because data lives everywhere. And so it's a really cool company. It's a really cool opportunity. It's an early market and, uh, we're, we're the, uh, we're the darling in it. And there's, there's a lot of great things happening. So you can find us there if, if you want to learn more, uh, we got a great team and it's just really cool founder story.

And, um, and, and that's, that's a fun one. So anyway, love it. Awesome. So Luke, thanks so much for coming on, man. I appreciate it. And hopefully, uh, we can, uh, reconnect here sometime soon here. And if there's, uh, anybody out there listening, definitely check them out, check out the company. There's all, I mean, if you're looking for, you know, your next move and you're one of those A players is willing to put in the work, uh, it'll be fun. Appreciate you, John. Thanks, man. All right. Hopefully you enjoyed the conversation as much as I did. And 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 and the world needs a lot more of that right now.

So thank you all very much. And I'll 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. It would mean the world to me. If you could go and leave a five-star review on your favorite podcast platform and share some of your favorite episodes with your network. Also, I am super excited to be launching my new newsletter where I'll be sharing everything I know and everything I'm learning along the way while I'm out there selling every day just like you. Go to jbarrows.com slash newsletter to sign up today.

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