Transcript

Chris Orlob: My job is not to make you smarter. If you take this course or this training and you walk away, and you have more information crammed into your brain, but your behavior didn't change, you failed, and I've failed. My job is not to make you smarter. It is to change your behavior in such a way that shows up on sales calls and gets you more performance. It just so happens that that whole process starts with me giving you information. Your job as a manager is to get leverage. It's to get things done through other people, and the best way to do that is to improve their skills so you can get more done through the people that you have in your purview.

Ted Blosser: Hi, I'm Ted Blosser, CEO, and Co-founder of WorkRamp, where we're redefining the corporate learning space with the world's first all-in-one learning cloud for employee and customer learning. Welcome to the Learn podcast, where we learn from the biggest leaders in SaaS and hear what makes them successful. Hope you enjoy the show. Hey, what's happening? Everybody? Excited to have you all back today. We have a great guest, Chris Orlob, ceo@pcl.io, and formerly of Gong. Thanks so much for joining us, Chris.

Chris Orlob: Ted, what's a going on?

Ted Blosser: Not much. It's a nice Thursday here as we're recording almost end of week here, dog days of summer, but excited and when I saw this on the calendar, I was excited to chat with you. I was saying you're like a celebrity where I see your content everywhere, but never had a chance to actually meet you, so thanks for coming on.

Chris Orlob: Yeah, I'm excited. Let's do it.

Ted Blosser: Let's, okay, let's get kicked off. Love an elevator pitch on yourself so the audience gets some context on you and then we'll jump into some of the core line of questioning here.

Chris Orlob: Yeah, so right now I run a business called pclub.io, which is an online course business where we work with the top sales practitioners in B2B sales tech to create online courses so you can steal the playbooks of some of the most successful sales practitioners in the world. I think probably the thing that I'm best known for is I spent a little under six years helping grow a company called Gong from less than $200,000 in annual revenue. When I joined all the way, well past $200 million by the time I left before that, I kind of mixed bag of being an entrepreneur again, being a sales leader, and eventually joined Gong in a product marketing capacity. And a bunch of years later, here I am,

Ted Blosser: We'll talk about this later, hopefully we get time about the transition from product marketing into sales. But the thing I had to ask you is what was the motivation going from Gong to starting your own thing where you're educating sales professionals? What was that? If you could give us a quick background on that move,

Chris Orlob: That's going to be a long story. I think there's several pieces of context. The first piece is the question, what motivated me to move from Gong to start my own company is actually the backwards question. The right question is, I was an entrepreneur before Gong and I eventually joined Gong. And so the right question, if you know me well, which this is the first time we're meeting, is why did you stay at Gong for so long when you weren't an entrepreneur there? And one of the reasons for that is I started a business called Convers, which intended to be Gong. This was back in 2015. This was before Gong was on the scene. And, after about 18 months of trying to run that company and struggling, and frankly we failed, gong came on the scene maybe a quarter or two before we closed up shop and I shut down the business and I desperately wanted to continue building the category of what at the time we referred to as Conversation Intelligence.

So I joined Gong and after I stayed there for as long as I did, because it fulfilled a lot of the needs, I had to be an entrepreneur even though I wasn't right, there was so much building to be done. We were creating a new category. I changed jobs several times there, so I was I always building something. But there came a point, and I won't go into too much detail here, but this time last year, right? We're recording this July, 2023. In June, 2022, I took my old team to President's Club. I wasn't managing that team anymore. I moved on to a different job record-breaking number of President's Club

Ted Blosser: But they let you go. That's still great

Chris Orlob: And most beautiful place in the world, right? Punta to Mexico, gorgeous ocean, 80-degree weather. You'd think I'd be about as relaxed as a person can be. But one of the nights I was there at midnight, I was rushed to the hospital to a Mexican hospital thinking I was having a heart attack. Now, what turned out to be after 20 hours of testing and me being in this hospital, and frankly it's funny to say this,

Ted Blosser: You're so young, that's crazy.

Chris Orlob: I thought that was my last day on earth. I legitimately thought I was having a heart attack and I was going to die and that this was, it turns out it was just an incredible panic attack. And so my boss who at the time was Kelly Wright, right? She's president of Gong. 

Ted Blosser: We had her at one of our conferences recently.

Chris Orlob: Yeah, an amazing leader. And she and I had already been talking about a sabbatical. So this happens and she goes, go take six weeks off. So July of last year I started taking six weeks off and during that 45-day period, I had a severe panic attack probably for 40 out of 45 of those days to the point where I'm starting to develop and think I was developing panic disorder. A lot of people don't know that about me because I'm pretty calm and collected at least on the surface. But I thought I was dying. I thought something was wrong. My wife is in Redwood City, the Kaiser over there.

To Kaiser a bunch of times because I thought I was having a stroke or something crazy like that. And what ended up happening is I took a new job earlier that year as head of multi-product thinking it was right for my career. And I spent six months or so doing that job convincing myself to like it and I hated it. And so I was like a boiling tea kettle that finally just exploded. And so there was this point, and I remember having this, and this is a little dramatic because honestly, I think it's funny that I thought I was going to die that night. It's so dumb to think about. But I remember being in Mexico and I was like, you know what? I've already been thinking about co-founding another business. If this ends up to being a fluke and I'm not about to die, which I wasn't, then I'm going to go be an entrepreneur.

And so that ended up being the case I took. Well, Amit, the CEO of Gong, he's a mentor of mine and still is to this day. We went to breakfast in San Francisco around this time last year and I told him I was leaving. He was one of the first people to know, and I made a couple of declarations to him. I said, number one, Gong will be the last company I ever work for as a W2 employee. I'm going to be a serial entrepreneur from here on out. That's what I love doing. And then number two, I used to think I wanted to be a CRO, a chief revenue officer. I don't anymore. I want to hire and fire.

I was mostly kidding, but I was trying to make that point. So that's the long kind of backstory that motivated me to go be an entrepreneur. Again, the reason I chose pcl.io, which is exactly what I explained, it was like an online course platform for sales is one of the things I became very well known for at Gong was giving really good sales trainings to people. I would train my own team and then other teams would hear about it and they would ask me to go deliver the same training and to the point where my nickname became professor or people started referring to me that way. And I've always had a passion, frankly. I've always had a passion more so for learning than for teaching, but I also have a passion for teaching and I figured that I can create a scalable company. I didn't want to be an individual contributor sales trainer or anything like that. I wanted to create a big company because I want to make a big impact on the world. And so that's what led to P Club and we've been fortunate enough thanks to our customers to grow pretty fast so far.

Ted Blosser: Wow, I did not expect such a great story, Chris. That is amazing story. 

Chris Orlob: Wild ride.

Ted Blosser: But I love how you came to that conclusion and really stuck with your guns and said, Hey, this is what I want to do. I mean, people, you're at such a great company, that must've been a hard thing to leave, but your heart knew what it wanted and it was physically telling you what it wanted and you decided on it, which is great. Well, that's why I want to have you on as a guest. You have this unique perspective of essentially the intersection of learning professor or lab and really the sales profession. And if you think about the sales profession, most of us, and I used to be in sales at Box, almost had a similar background as yourself where you're kind of selling on the job, you're going after the next deal, you're not really taking the time to learn. So what I want to do is walk through three, I call 'em kind of personas of sales, basically salespeople who have the opportunity to learn. So I'll talk through the rep and then the manager and then the enabler. But let's start with the rep. Give us your viewpoint of what do you think the responsibility is today for reps to take learning in their own hands? I'll kind of start with a very open-ended question there, and then we'll move into the management layer. I mean,

Chris Orlob: A hundred percent of the responsibility should be on the reps. Now that's not to give managers enablement off the hook because it's more like a 300% pie, right? A hundred percent on the rep, a hundred percent and a hundred percent. The most successful reps I've ever met or obsessed with building their skills, they're obsessed with learning. In fact, I often have friends that I grew up with in college and my high school years who compared to them, I hate to say it this way, but I've achieved significantly more in my career. And I've gone back home to Utah to visit with some of them. And they asked me, they're like, sometimes they call me lucky, which is always funny to me. But they asked me, how did you make this happen? And I said, well, when I was about 21 years old, I started waking up at 6:00 AM every day, and I would read for 45 minutes before I got to work.

And I did that every day. And when I was done with work and I got home before I was married and had kids and stuff, I would go on websites and take courses and learn stuff. And I repeated that every day for however long it was 12 years, and then I woke up to this life. So it's like this long consistent journey of just compounding skills. There's no greater piece of advice I could give somebody, aside from having clear goals that you're shooting for to be successful in life, which is just to overinvest in building your own skills.

If any rep came up to me, which I don't think they would admit this on the outside, but if they were like, oh, I'm not successful because my company's not investing in me, I'd probably tell them, you're never going to be successful. It's not going to happen if you are letting somebody else hold your success hostage right now, don't get me wrong. Like I said, managers and enablement should take responsibility for training people, and P Club wouldn't exist if that weren't the case. But the best salespeople that I know don't let another person hold their success or their development hostage. They take learning into their own hands by reading great books, not just sales books, but books on business acumen and how to improve that. Or if reading's not their thing, they take or listen to podcasts or take some courses or do something to compound their skillset over a very long period of time.

Ted Blosser: Do you have a story? And you don't have to name names unless you have some of a rep who let's say was underperforming or was in a slump and they had this mindset shift you were describing of like, Hey, the way I could get out of this slump or the way I can improve true sales performance is actually through learning. Do you have any examples of that? And also maybe where they focus that time, how do they approach, Hey, maybe I'm losing all my deals, I don't know about the product and I need to go spend 45 minutes a day on the product for a month. So just, I'm throwing out an example like that. But do you have any great example for the people out there who are like, look, I want to learn to essentially bust out of this slump. Any stories around that?

Chris Orlob: I'll give you one. It actually wasn't a turning point. It was more just like time caught up with this guy in a very positive way. So I'm going to call him Matthew because I'm using income figures and I don't want to tell the world who it actually is. I think now he's probably about 30 years old, but he was the first person I had ever met who clocked in a $500,000 W two while he was still in his twenties. He did that by age 28. He started as an S D R at a bi company, and then he moved on to another company and then he moved to Gone as an SS M B A E, and he rose through the ranks to an enterprise seller and he's still there and he's just crushing it. And he was struggling for a while, his first year or so at Gong, he was struggling, but I also knew what his habits looked like.

They looked very similar to the ones that I described about me earlier on. He was sucking up information, he was reading, he was spending a bunch of time honing his craft. And so there wasn't this epiphany he had where he was like, oh, learning is how I turn this around. It was more just like the compound interest of learning eventually caught up with him while he was struggling. He was learning and he was still learning and he was still learning. And one day he woke up and he wasn't struggling again, and then one day he woke up again and not only was he just not struggling, he was crushing it so much that some people almost didn't like it because they liked the struggling guy.

Ted Blosser: What a professor Orisha. That's what was asking. It reminds me of there's this movie clip or show clip Halton Catch Fire where during the interview he goes, what are your credentials? And he showed him his W two. But you were going to say something, you were going to close out that story.

Chris Orlob: I don't think I taught him that much. I think he probably taught me more than I taught him just because he didn't report to me. I observed him a lot like he was on different teams and one of the things he taught me is how much of personal productivity is dependent on your ability to manage your energy, not just your time. That was the first time I was exposed to that concept where he does manage his time well, but he also treats himself like a million-dollar racehorse. He's not working himself into the ground and exhausting himself, and he's not filling his body with junk food. I'm sure occasionally he has a couple of slices of pizza or something like that, but he manages his energy in such a way to maximize life when comes work or when he's at work, he's working. When he's not at work, he's absorbed in what he's doing. He did that really well. So I don't think maybe I taught him something. Maybe he was observing me and he learned something, but I wouldn't know what that looks like. I probably learned more from him than he learned from me.

Ted Blosser: It's a great story. Let's transition out of the rep persona and let's move into, let's take it as the frontline manager. I think there's an ongoing debate, and I've seen this myself. Some managers spend a lot of time in training with the Andy Grove approach of, Hey, learning and training is your highest leverage point with a larger team. But then I see other managers who crush it because they're a little bit of a stick approach. They manage through fear. Maybe not everyone loves working for them, but they just focus on the numbers and moving deals along and maybe put learning a little bit more to the side. So where do you sit in terms of what's the best balance for sales managers when it comes to learning and training for their reps?

Chris Orlob: Well, I think it's a false dichotomy. So first, I would never encourage a sales manager to lead by fear of holding people accountable. Yes, but I think that's a different leadership style. I think you need to do both of those things because you can't be a super coach and a trainer who doesn't hold people accountable. You will fail as a frontline manager and you can't just hold people accountable and not make people better because you are not doing, you are shirking the most fundamental part of your job, which is to extract performance out of talent, the talent being the person, and the number one way to do that is to improve their skills. So I would actually say depending on how we're defining the word learning and training and coaching, that's job number one. Probably right after good hiring actually I would say that's probably even more important, but that's job number one of a manager.

As long as we're defining learning, training and coaching as building skills that show up in such a way that improves performance. So I give a lot of trainings and I create courses and I work with other people to create courses. And one of the things I consistently say while I'm delivering those is my job is not to make you smarter. If you take this course or this training and you walk away and you have more information crammed into your brain, but your behavior didn't change, you failed and I failed. My job is not to make you smarter. It is to change your behavior in such a way that shows up on sales calls and gets you more performance. It just so happens that that whole process starts with giving me or me giving you information. This is like step one. And so to me, I mean, what I wouldn't say is that's the only job of a frontline manager because it's not. They've got to hire people, they've got to fire people, they've got to hold people accountable, but your job as a manager is to get leverage. It's to get things done through other people, and the best way to do that is to improve their skills so you can get more done through the people that you have in your purview.

Ted Blosser: Hey everyone. We're in the middle of a conversation with Chris Orlob, ceo at pclub.io. We're talking a lot about learning in general and also the sales enablement profession. If you're looking for a sales enablement platform that also has a holistic learning capabilities of an LMS look no further, you've got to check out WorkRamp. WorkRamp is building what we're calling the learning cloud. This helps you enable your employees, your customers, and your partners, all on one seamless end-to-end platform. If you want to learn more, visit us@workramp.com and get a demo Today. I'm going to try to exercise on the fly here. I think this will help even solidify your last answer is when you think about a frontline manager and the exercise will be, I'd love to see how you would break up by percentage, some of the core functions of our frontline manager

I just listed a few out. You could add others if I'm missing them on the fly here. If you think about hiring your team, that's one big one. If you think, which includes things like interviewing, obviously, if you then think about coaching, so using Gong for example, or being on sales calls, coaching, spending that time training. If you think about the actual deal management, like, okay, I'm on a deal, or I'm going to help you close. I'm in the front lines with you closing deals. And then maybe lastly is spending time managing up like, Hey, you're probably managing up to senior leadership. Those are just four. You could add or swap out others, but where do you think the percentages fall for the best? You were one of the best sales leaders at Gong. How did you even break it out or what was your philosophy on where you spend time?

Chris Orlob: Yeah, I thought about this a lot weird. I love deconstructing things into their component parts just like you and I are doing right now, and I have six different models at one point for sales management, and it confused me, right? There was too many of 'em, and so now I'm actually looking at mine. To me, there are three super sections of being a frontline manager. There's manage the people, manage the selling and manage the business, and so each one of those three, you can deconstruct into finer points. So underneath manage the people. You've got hiring and recruiting, you've got running effective, you've got coaching and development, you've got running team meetings, you've got motivating, and you've got performance management. That's the the people bucket, the the selling bucket. You've got co-selling with your reps, you've got deal strategy and pipeline management. You've got building and managing the sales process, and you've got managing metrics and KPIs that facilitate the selling. And then finally you have this third master bucket, which is managing the business, which to me, the things that get nested under that are forecasting, managing sideways, managing up, and then your organization's operating rhythm. What's the cadence of meetings and other rituals you do to facilitate?

Ted Blosser: Oh, it much better framework than my crappy three or four-part framework. Now

Chris Orlob: We didn't really have a fair playing ground there,

Ted Blosser: So how would you break that up? Do you think about third or third or is it varying? Does it depend on tenure?

Chris Orlob: Would say? Yeah, I mean, the sales managers listening to this are going to hate to hear this, and I actually stole this joke from, what's his name, David Brock, who wrote a book on sales management. I can't remember what it's called, but I would say 50% of your time is spent on managing the people. 50% of your time is spent managing the selling, and 50% of your time is the business. I mean, frankly speaking, frontline management is not a 40-hour-a-week job. It's just not. I mean, if you figured that out, either your company is probably a lifestyle business or some part of that is being neglected or something, I don't know, which could very well be true, but that was not my experience.

Ted Blosser: I wrote this LinkedIn post that literally the hardest job in a company is frontline management. One of the few parts of the business that has so much work right in front of it where you're doing obviously the frontline management and you have to manage up. Think about even the co-job. I'm pretty much managing down all day. I only have half that equation.

Chris Orlob: CEO's easy.

Ted Blosser: It's easy, easy job, right? Yeah. You know what I'm talking about, but yeah, maybe a little bit to the board, but frontline management is extremely difficult.

Chris Orlob: I mean, everybody wants a piece of you. You got eight reps that want a piece of you. You've got your peers right in marketing and CS, they want a piece of you, your boss, and even your boss's boss probably. It is a thankless job. Bless the people who are in frontline management. I totally agree with that. It's the hardest job. I mean, I haven't had all the jobs in a business. It's the hardest job I ever had in a business. So

Ted Blosser: I want to move to the last persona, and this will be the last major question and we'll jump into the learn lightning round. Let's go into enablement. Give us, I'm assuming you've been around enablement even when you're in product marketing, you probably interacted with enablement and you, I'm assuming also sell to enablers as well too with PCL and direct obviously to reps. Give us your thoughts on the state of enablement, where it should go, what you think about, I don't know if you have any hot takes on this, but this would be really helpful for people to understand your perspective.

Chris Orlob: To me, the job of sales enablement probably is one of the professions that has the biggest divide between really great superstars and then just a sea of people who need to uplevel their game. There's a lot of people, not people because it's not just them. There's a lot of enablement functions and businesses that are just not creating value for the business, but then you go into some and they're transforming the business. One of the best enablement people I've ever met, I hope he listens to this, his name's Kyle, and I don't even know if his job's VP of enablement anymore, but he works for Drift and he has worked for Drift for six or seven years, and I think one of the reasons he's so good at it or good at enablement is he has credibility I've never seen before with his sales team, which a lot of enablement people lack, so I actually spoke at their kickoff in Las Vegas this year back in February, and I got to observe how he interacted with his sales team.

We went to dinner a bunch of times. We had the event and his salespeople. I went to a bar with a couple of his salespeople and they're like, yeah, we just need to get back to the point where Kyle is coaching reps individually. You don't hear reps speak most heads of enablement that way, and so this one's a tough one to crack the code on because I think there's probably a couple different profiles of what makes somebody good at enablement. Sometimes you're the sage, right? Kyle is the sage, he's the one with the credibility. He is able to teach, he's able to train his team to teach. He has credibility. Some enablement, people are facilitators and there's nothing wrong with that, but there needs to be a healthy respect and if you're in a situation where your sales team doesn't see you as credible and won't, and if that's the case, you shouldn't be teaching, you should be the facilitator of finding other experts and putting them in front of your salespeople to learn, right? You are now the curator and the project manager. There's probably a third profile. This is the first time I've really thought about this. Well,

Ted Blosser: Lemme actually ask you about that first profile. It actually is coincidentally, I wrote a post about this morning, but what do you think if you say, Hey, I want to be that first profile, I want to be the credible person. Sales reps are like, I want them to come help me more. Is there an activity that that enablement professional can do to build that credibility? Would you say

Chris Orlob: You better be obsessed with learning sales, right? Not only should you have a track record where you were once successful in a credible way, but if that's who you want to be, you better be ahead of the game. You better be sucking up all the information you can now who you are. That's your professional identity, and so being the person who consumes knowledge at a rate that is just an order of magnitude higher than anybody else in the business, that's probably what it demands of you.

Ted Blosser: That's cool. If you think about that, even your second profile, I don't know if you had the third, I'll let you think of it while I'm talking, but that second profile is like, look, a sales team could probably care less if you became a master of program management. And they're like, I probably don't care. But yes, it'd be great if you could be a facilitator manage programs well, but they do care if you're very credible and understand the art of sales even more because a sales rep doesn't have as much time to go learn the art. They're kind of learning on the fly. I don't know if you had that third or those first two actually are pretty wide encompassing.

Chris Orlob: Yeah. I think the second one, I'm just starting to come to some realizations as we talk, where if you are the program manager kind and you want to be an enablement, you can still create value for the business. Maybe you can't deliver the knowledge with your own hands or with your own voice, but you can get really good at diagnosing microscopic skill issues throughout the organization and then bringing in a solution to address that. You just created value for the organization. But if all you do is play calendar Tetris with the sales team and get something on the calendar and put a few tasks in Asana or something like that, a virtual assistant can do that. There's more than one way to create value for your business if you're an enablement function.

Ted Blosser: I like that, and if you think about that second persona type a business might have different needs, a business might have enough of the first type and they need program management also. I've seen different founders depending on, hey, if you're early stage and there's a lot of stuff to do, I'm okay with program management, or if I'm early stage and I got a little bit of a product-market fit issue, you might want that first type of persona. So love the way you broke that down

Chris Orlob: Or if the business, yeah, I was going to say, or if the business is getting very large and difficult to manage and you've got multiple programs going on at once, that's another opportunity for that.

Ted Blosser: Totally, totally. Well, Chris, we're coming close to the end of our time. We walk through three key personas, your perspective around learning on each. I want to close this off with our section called the Learn Rapid Fire Round. I'm going to ask you just a few questions. Give me some one, two line answers for each of these, but I'm very curious for you, what is one podcast book blog that's top of mind for you right now?

Chris Orlob: I would name a newsletter, it's called Ultra Successful by Julie Gertner. She's a PhD. She's a performance coach for anonymous people who have a net worths of a minimum of $50 million, so big-time entrepreneurs, and big-time executives, and her newsletter, it's a paid newsletter. It's like nine bucks a month, the best nine bucks a month. I spend, she writes what she learns about these people in her coaching sessions, and it's almost like the anti-self-help newsletter because she's talking about like, Hey, if you do want to be ultra-successful, which if you don't, it's fine, blah, blah, blah. I'll make that caveat, but if you do, here's what it actually takes, and this is what these people are like, and she's very real about it. She's not talking about the feel-good stuff that you would read in your typical mainstream self-help book. She talks about how they are very tenacious how it demands a lot from them, and how they sharpen the ax and are constantly learning. So it's a very real look into if you measure success with finances, which there's more noble ways to do it, it's a very noble look into financially successful people. Sorry, not a noble look, a very real look, an authentic look into it. That's

Ted Blosser: Awesome. It's like Tony Robbins, what does he charge? A million per client once a month type of session, but that sounds like it's called ultra-successful, is that right?

Chris Orlob: Ultra successful.com. Okay. We'll put those. I don't read it as much as I used to, but it has been responsible for several months of inspiration for me, just with one of her pieces

Ted Blosser: That's cool. Yeah. All right. Next question. If you could learn from one person, it could be alive or dead; who would you want to learn from?

Chris Orlob: Richard Branson? When I first became an entrepreneur, I knew about Richard Branson. I didn't really think of anything of him, but now that I've started to learn more about myself as an entrepreneur, he's kind of like the ultimate person because his job, he is never managing the businesses, he's just constantly starting new businesses, and I personally love that. I love to create, I love the concept of creating a mini conglomerate where you have an ecosystem of businesses where when one becomes successful, the other becomes more successful, and he's the best person in the world at crafting an empire like that. And he's also just kind of a fascinating, outrageous personality. I think it'd be really fun to talk to.

Ted Blosser: I just finally listened to podcasts with Mr. Beast, and you sound a lot like him from a motivation standpoint and him building; I think he has five different brands and business lines now, but you're the Mr. Beast of sales content. Alright. Last question, I'll ask you who, and this is going to be a nice shout-out; who's the bestseller you would want to give a shout-out to or that you've learned from personally?

Chris Orlob: Jameson Young. 

Ted Blosser: Who is Jameson Young?

Chris Orlob: He is the SVP of Sales at Gong. We hired him as the VP of sales this time in 2017, so he was like the first sales leader at Gong. I was still doing product marketing, and I learned more about how to sell successfully from him than probably anybody. And that's saying something. There were a lot of people at Gong that I learned from, but he's incredible.

Ted Blosser: That's a great shout-out. Hopefully, it doesn't sound like he's Matthew from earlier, so maybe even better. Maybe even better. Alright. Well, Chris, thanks so much for spending time with us. This was an awesome recording, and best of luck on PClub. We'll be able to promote that here as well too. But I appreciate you jumping on.

Chris Orlob: Thanks Ted.