Founding Conversature

Alex Kracov: So before Gong, you started a company Conversature, which was an early pioneer in what became the conversation intelligence category. I love to know what led you to start the company, and why did you pick this emerging product category?

Chris Orlob: Well, it is generous of you to say that we were an early pioneer. I don't know if I can describe myself in that company as lofty as that. But when I started, or shortly before I started that, I was a regional sales manager at a company called InsideSales.com. At that time in my life, I was desperate to start a company. I just wanted to be an entrepreneur. Anything that's like legal, ethical and scalable, those were my criteria for what kind of business I could start.

I remember, one day, I was trying to help a few reps ramp faster that were on my team. I was hamstrung. I couldn't listen to their calls, at least easily without riding shotgun. And so I stumbled across this industry that's been around for a while called speech analytics. This is almost like old school clunky versions of Gong but for call centers. And so I found an industry analyst for that industry. He worked at Gartner or something like that. I got him on the phone. I was like, why doesn't this exist for b2b? Because as a sales manager, I have this problem. And he goes, I don't know. That was enough for me. I had saved up enough life savings at that point where I was like, okay, this is what I'm starting.

So shortly after that, I left my job. Horrible timing. It was like right after - I think my son just turned one years old. And so lots of reasons to not be starting a company. I went. And my co-founder, who's my current co-founder in my existing business in pclub, he joined me. And that's how that got started.

Alex Kracov: I think my first job out of college, I worked at Yelp. I remember my manager barging in to the calls. That was the only way. The worse.

Chris Orlob: Especially whispering in your ear, I can't do this.

Alex Kracov: Go past that objection. It was just like the craziest thing. And I do nothing about sales at the time, and I'm still not amazing at sales. But yeah, it's so much better now. As a founder, I could just go listen to all the Gong calls. It's a thing. So yeah, it's funny how far it's come. I'm curious how far along did you get into the business. Did you have a working product? Did you have customers?

Chris Orlob: We are working with air quotes around it. I think we did that business for about 18 months, and maybe generated like $20,000 or $30,000 in total revenue. And so I mean, my hair is pretty grey. That comes from that period of my life - just like living off of life savings, watching my bank account go like this every two weeks so that I can pay my family's bills. So we got to a minimally working product, a handful of customers. It was like a really long story that led us to finally throwing in the towel. There were a number of reasons that we eventually did. This was like October 2016. We finally decided we were going to stop pursuing this business.

I told the handful of customers we did have to go check out Gong. A few months before that, Gong had announced their avocado seed round. It was like $6 million. And so now they were like out in the world. One of our customers, the CEO, one of the first customers we closed, their implementation was not going well because we had a "working product." He forwarded me the press release from Gong. And he goes, it sounds like your space is heating up. He almost meant it as, like, get your shit together. I remember that day. This was in June 2016. I got that. It was 3 PM. I closed the blinds. I went to sleep. I didn't wake up till 5 AM the next day, because I was so despondent. I was like, we're done. Gong is going to crush us. I knew of Amit, the CEO of Gong. I knew who he was. I knew he had been working on this. And so that was a devastating day for me.

But then, fast forward a few more months, it just didn't work out. We told our customers go checkout Gong. I was scheming about how I was going to get in front of Amit. Because that was the job that I wanted. I was like, this isn't going to work, but I want to see if I can work for Gong, or Chorus, or exacqVision, which were the startups in that space at the time. I was lucky enough that Amit reached out to me first, so now I can kind of play coy. I still have the LinkedIn message. I joke about how coy I was playing with him. But I was really excited. He was like, hey, I heard you're closing up shop from some of your customers. I hope it's not true. But if it is, I would love to have you come run product marketing over here, which I've never done. I've never worked in marketing. For some reason, at that point in my life, I wanted to try my hand at product marketing. And so after interviewing some of the other companies, too, I decided to join Gong.

Joining Gong

Alex Kracov: And so you started in product marketing at Gong, which can mean a number of different things. Do you remember what your early conversations were with Amit, where it was like, hey, you're doing marketing now. You should focus on X, Y, and Z. What was sort of your mission at the beginning?

Chris Orlob: Amit had no job description for me, and I think he did that intentionally. He was just, like, I saw how you can market your own business on a shoestring budget. I'm going to see if you can do the same for us. And so my first boss at Gong was Udi Ledergor, who's still over there. He's Chief Evangelist. At the time, he was VP of Marketing. Eventually, he went on to become CMO. He had me typed my own job description. He's like, you just tell me what you want to do here and what kind of impact. And so it was much more an external facing role than what a lot of product marketing is. A lot of product marketing is equipping internal customer facing people to tell the narrative. We didn't have those people. Amit was selling at the time. And so my job, or at least a huge part of it, was more or less evangelism. It was being very loud in different social platforms, getting on stage, doing webinars, and just trying to get Gong on the map and build that initial velocity, that we eventually got too.

Alex Kracov: That's the fun part of the super early stage. I remember when I joined Lattice in marketing, Jack was just like, okay, go do marketing now. And it's like, alright, I'm going to go figure out what that means and all the different things. That's the fun puzzle.

Chris Orlob: I don't mind the lack of structure. In fact, I almost prefer it. I don't like structure imposed on me. I guess it's just kind of fair. I like creating structure and imposing it on others.

Alex Kracov: Yeah, me, too.

Chris Orlob: I think that's why I like to be an entrepreneur now, and I'll probably never have a normal job again.

Setting the Foundation for Gong Labs

Alex Kracov: And so in your first couple of weeks at Gong, I think you launched a data experiment by ungating an e-book. Can you share that story?

Chris Orlob: Yeah, well, I wanted to do this with Conversature. I remember me and my co-founder being like, can you imagine when we have dozens or hundreds of customers, and we take all their transcripts and anonymize them in published reports? Like, according to data, here's what the best salespeople do. We're like, we just got to get enough customers to do it. And so, obviously, we never got to that point with Conversature.

But inside of my first week at Gong, I became aware of this campaign we were running, which was the same thing but it was an e book. It was like a PDF e-book where it was like we analyzed 25,000 sales calls. Here are five things the best salespeople do differently. I'm sitting here steaming at the ears because I'm like, this thing will go viral. And we're hiding it behind a landing page. This is good. And so I emailed Udi and Amit. I'm like, can I turn this into an article? They're like, yeah, go for it.

I wrote this article over the weekend. Again, this was within week one. I had to decide where I was going to place it. Was this a LinkedIn article, whatever? For some reason, we decided Sales Hacker at the time was the best outlet for us. And it actually turned out to be a good idea. Because we published it, and it got thousands of shares immediately. And we were off to the races. There's this moment we had where we're like, alright, is that it? Is that our next campaign? We did the data thing. And we're like, well, there's probably one or two different angles we can take. Let's get our data science team to analyze some more calls, and let's try this two or three more times. 100 articles later, they're still going with that. You would just find different ways to cut the data and different questions to answer. And so that became - I mean, Gong still does that to this day. The impact that had on the first two years of the business was incredible, though. Just the word of mouth, and the virality, and the inbound demand that was generating.

Alex Kracov: Why do you think the data play worked so well? Why do you think people in sales are just so hungry for this data content play?

Chris Orlob: I think there's two reasons. One is just there's never been any data validating what actually works in sales, aside from Neil Rackham in the '80s. He did the SPIN selling experiment where, apparently, he and his team did shotgun ride along with 30,000 salespeople.

Alex Kracov: Interesting.

Chris Orlob: And so this is like the closest thing, real data, the world had ever seen. The other thing though which is kind of dumb is just how much of the data validated what people wanted to hear. You go through the comments and they're like, "I totally agree with this data. I've known this for years." And you're like, well, I agree with the data. That's a weird thing to say. It doesn't matter if you agree with the data or not. It's just there. It's fact. But a lot of people just loved that their notions of what works in sales, or at least many of them, were validated with data. I don't know what the brain science is behind that. I'm sure there's something super interesting if you got into it. Dopamine just flowed in or something like that. But I don't know. That's the best I got.

Alex Kracov: Yeah, I imagine just a bunch of VPs of sales running to their founders or whatever and they'd be like, see, I told you. See, I told you. The data is real, right? It also fits into the social psychology, if you share things that you believe in and reaffirms. I don't know. It makes a ton of sense. People always say, I don't know, data is a great way to get PR and all that. So I'm sure that worked well.

Chris Orlob: Totally.

Alex Kracov: I'm curious how did you actually work with the data science and product team. Because I've tried this in the past, and it can sometimes be a challenge to get the resources, get them to focus on things that help marketing. It usually requires exec sponsorship. Are they just fully bought in?

Chris Orlob: Amit was adamant about this. We hired a data science firm within a couple of months to work with our data science team. Their entire job was to work with me to analyze different cuts of the data and answer different questions. It was not just like exact by. It was like Amit is like, I want to see an article like this every two weeks. And so the entire company was behind this.

Alex Kracov: Then why did you end up picking LinkedIn? It seemed as like a primary distribution channel. I think you were pretty early to that. Why did you go there?

Chris Orlob: Just simple. Sales leaders are on LinkedIn, right? It's where our market congregates and still does. That's where they are. We tried other avenues that never really worked, in addition to LinkedIn. Even to this day, I don't have Twitter figured out. Like this morning, I'm like, I'm going to get Twitter working. And I don't know if I ever will. Maybe I don't need to. But that's why we chose LinkedIn in the beginning. It's just that's where salespeople and sales leaders were, and that's where they spent their time.

Sales Experience in Marketing

Alex Kracov: Makes sense. I've heard you say you are like a sales guy in disguise running product marketing. I'm curious, how did your background in sales helped you do marketing?

Chris Orlob: There's this guy named Eben Pagan who I learned a lot from as a marketer. He's a direct response marketer. He sells information products and teaches entrepreneurs how to be very good marketers. One of the things he said in one of his seminars really resonated with me, which was: if you want to learn how to sell one to many, which is what marketing is, you will be best served by first figuring out what works one-to-one. Because if you know what works one-to-one, it is far easier to scale that out into a one-to-many way.

I'm not saying, like, to be a good marketer, you have to have sales experience. Because that's an exaggeration. But it helps, right? If you're a product marketer and your job is to put together a sales deck for salespeople to use, and you've never had to go eye-to-eye or toe-to-toe with another human being and ask for their money, you question whether that's the right person to put that sales deck together. Right? I mean, just having that skill set of what works on a one-to-one basis amplifies, in many cases, your ability to market well in a one-to-many way.

Alex Kracov: I assume you just so deeply understood the ICP because you ruled the ICP, right?

Chris Orlob: That's what I've done my entire career. I tell people this: sales technique is important. But the more fundamental piece of knowledge you can get is understanding your buyer so well that you can peer into their soul. If you can get to that point, everything becomes far, far easier.

Scaling Gong's Marketing

Alex Kracov: I'm curious how Gong's marketing scaled over time. How is it different in the early days, from zero to one million, then 1 to 10, and then 10 to 100 and beyond? Were there things that were noticeably different? Or is it the same, just on steroids? How did you sort of think about that?

Chris Orlob: At least, while I was in marketing there, it was the same but on steroids up until 20 or 30 million in revenue. I won't say who it is or what company it works for. But there was this other semi-famous CMO at the time. He goes out to a cocktail party with Udi. He asked Udi. He's like, how many people are in your marketing team? And Udi was like, three, not counting me. The guy's eyes popped out of his head because Gong is super well-known at this point. He's like, I have a team of 40 content writers, and we're not doing the same work as you guys. Please do not tell my CEO that you only have three people on your marketing team.

I don't say that as like, oh, we were so talented. It was more just like we found something that was so high leverage, which was Going Labs, that we just tripled down on it. We could have gone and messed around and done a bunch of other things. And we did. But it was clear that the number one marketing priority during that entire stretch of time was Gong Labs, because it has an incredible number of benefits to the business. It creates virality and word of mouth. It positions us strategically how we want to. It creates inbound demand, and it creates other opportunities for more marketing. People would invite us to come on stage at conferences and present that stuff. So it was the same playbook, just like you said, on steroids for a while there.

Transitioning from Marketing to Sales

Alex Kracov: Yeah, it seems like you just had an extreme content market fit. What you put out there just accelerated crazy. Alright. So you eventually transitioned to a sales role at Gong, where I think you led the growth segment. You had a good thing going in marketing. So I'm curious, why did you switch to sales? What was the growth segment? Who were you selling into?

Chris Orlob: Growth segment was typically mid-market accounts, as the world defines it. I'm trying to think back why I made that decision. I think there were a number of things. One is, I got tired of not being able to call the shots. In product marketing and in a lot of roles like that, you're at the mercy of the sales leader. And I hated that. My ego was too big to handle it at the time. And so I wanted my head on the chopping block. I wanted me to be accountable for a number so that I am now charting the course rather than responding and reacting to somebody else's demands. That was a big one.

The other one is, I wanted at the time to be a CEO. And so I wanted to get a breadth of go-to-market experience, not just like one bucket. Now, I had already had sales leadership experience, but I hadn't had second-line sales leadership experience. This was a second-line role. And so I learned a lot about people leadership in management in a way that I haven't before, having only spent some time in frontline management and as an account executive, and then as a marketer. So that was the motivation. I was trying to round out this swirling resume that eventually leads up to a C-suite role.

Alex Kracov: Makes a lot of sense. I'm curious, what was the sales pitch in those days for Gong? Did it evolve? Is it the same pitch today? What did you start with, and how did you think about making the case to the customers?

Chris Orlob: No, our pitch changed quite often. But it wasn't ever huge pivots. It was like derivatives of something that came before. The first pitch that we really tried was the science of sales, basically turning Gong Labs into a sales narrative. That kind of worked, but that's not really the product that Gong was delivering at the time. There was a little bit of a disconnect between Gong Labs and what the product could actually do at the push of a button for a customer. You can wire up Gong, press a button and have it tell you all the things that are different between your best reps according to data.

And so we ended up positioning away from that and moving toward a narrative that was a little more successful, which at the time, we called it the three pillars of revenue success. It was like, there's three things you need to get right. There's people success. You need to make your reps successful. There's deal success. You need to manage your pipeline. Then there is strategy success, which is like rolling out strategic initiatives through your sales organization. Our point was, you can't execute well on any of those three if you don't have visibility into what's going on in frontline conversations. And so Gong opens up this black box. It gives you that visibility and helps you power those three dimensions of running a successful revenue organization.

That worked really well. Based on what I see at Gong - it's been a while since I've been there. It's been like 15 months or something - it still feels like they don't say that exactly. But what they're going to market with, to me, feels like a derivative of that. Right now, they talk about unlocking reality. You're blind to reality without visibility in the frontline conversations. It powers a number of important things for you to make good one.

Alex Kracov: Yeah, my outside perception of the positioning change over the years was more like, alright, call recording, sales coaching. We'll get insight into that. Then it's now become this whole analytics engine to help with forecasting and leadership and all that stuff, which is interesting.

Chris Orlob: Yeah, that's totally true. Because one of the problems we had on the sales side during the first couple years is, we were positioned as a coaching tool, a call recording tool, for enablement. If you're positioned as coaching or something like that, you tend to start your sales cycles in enablement. Those were really tough sells. I don't know why we struggled so much with enablement. I think a lot of it is because they don't have as much power as you would think. And so we started to reposition as not just coaching but also pipeline management and strategy execution so that we could get in front of the chief revenue officer. Because we had huge sales problem of like so many deals would just get stuck with a director of enablement, and they wouldn't go anywhere.

Alex Kracov: Super interesting. We're dealing with that problem now at Dock, so that's a great lesson for me. Because we sell into sales orgs. It's like, alright, we have a product like growth. So it could be the sales rep end user. Then there's enablement, and rev ops, and CRO. It's like, where's our entry point? We actually have figured out the same thing as it works way better when it's a top-down sale. We get the CRO involved. The enablement person helps move it along, but they're not the decision-maker.

Chris Orlob: Funny enough, I'm finding the opposite to be true selling pclub to businesses. Because when we first started selling to businesses at pclub, I had the same scar tissue. I was like, we're going straight to the VP of sales and CRO. Those still work. But the deals where we start with enablement and then go to the VP of sales actually work better for us at pclub. I think it's because we're selling a skill development platform, which enablement squarely owns. And if you start with the top and then get punted down, enablement is obviously going to be running the sales process, and they feel like it's being imposed on them. Versus when we go to enablement now and get them bought in, as long as we did our job well, they're very eager to take us to chief revenue officer. So it's weird.

Competing with Chorus

Alex Kracov: Super interesting. Yeah, it's like the psyche of a champion. It's like it needs to be there. You need to incept them. Make it their own idea, where it's like they're going in, where it's like, oh, the annoying boss is telling me to do it. That's like, okay. Go away boss. I know what I'm doing. We're going to get into pclub in a minute here. I'll stay with Gong for just a couple more questions. I remember Gong being super competitive with Chorus. I feel like that was the main head-to-head competition. How did you think about the competition at the time? Were there others? How did you win head-to-head? Because I feel like Gong won this battle at least, as I think about it.

Chris Orlob: It was definitely Chorus head-to-head. ExacqVision was there early, but they dissipated over the course of a couple of years. Our competitive deal strategy was very based on pattern interrupt. Because most people would come to us and they're like, yeah, this is basically the same thing. Our CEO trained us. He's like, you need to interrupt that thought pattern. Where we go, no, these are totally in a different league. I can't remember exactly what the talk track was there. But we would make a point that it's like, course is okay. They're a little bit cheaper. Gong is lightyears ahead. And people are like, that's a bold thing to say. Our talk tracks that followed that would change throughout the years just based on what actually was different. But we very much shied away from spreadsheet comparisons. We tried to get out of that mindset as much as possible, and instead just interrupt the entire thought pattern around us being even vaguely in the same ballpark as Chorus.

Alex Kracov: I heard you say in another presentation, it was like how you sell is more important than what you sell. I think the example you just gave is a really good example of that. It's like that feature parity battle is just a losing battle for everybody.

Chris Orlob: Totally, yeah.

Leading a Sales Org

Alex Kracov: Can you talk a little bit about why consistency is the key to a great sales process? How did you define those different stages at Gong?

Chris Orlob: I think consistency is the key to running a sales organization. I don't think it's necessarily the key to an individual being successful. Because if you run a 50-person sales organization, you have to have everybody marching in the same direction, or else you just can't manage them. What you'll always find in a 50-person sales organization, some of the best people don't follow the process. But you can't manage them.

Now, that speaks to why consistency matters so much to the sales leader. Well, if you don't have the same language, and stages and exit criteria, and nobody has a shared understanding of what we're doing, then you are useless as a sales leader. What can you do? Nothing. That's why consistency matters so much, right? It's just being able to manage at scale. There's probably a lot more answers to the question, why does consistency matter? That's the big one. That was just like, if you don't have that, it's going to be wild west very, very quickly. There will be no predictability in your revenue and your revenue motion.

Alex Kracov: I think the last thing you did at Gong was help the company transition to a multi-product company. What was that second product, and how did that transition impact the sales process?

Chris Orlob: I don't think I was there long enough to fully speak to how it impacted the sales process. Because that was like my last hurrah at Gong. I did this multi-product revenue job for probably six or seven months, and then I was out. That first product was Forecast. So up until that point in our history, we just sold Gong. And that was it. There was no modules, no pricing or packaging differences, no additional products. And so Forecast was the first separately monetized Voltron product that we sold. It was hard launching that thing. We launched it at breakneck speed, six months from basically idea to the product hitting the market was a very grueling pace.

How it changed our sales process, though, I can only speak to this lightly. Because again, I left shortly after. It changed discovery quite a bit, because reps had to more comprehensively diagnose the customer's problem to see if there was an opportunity to offer a multi-product value proposition. So that was a big piece. There was a lot of questions of like, do we even want new business reps selling multiproduct? Because it could complicate the deals and slow down the sales cycle. Or, should we just have them take down the logo, and then expansion reps can go sell the additional products? I'm trying to go into the recesses of my memory during that time, but it was complicated. Launching a second product is not for the faint of heart.

Alex Kracov: On a personal level, I'm curious what this whole Gong experience was like for you. I mean, it must have been wild. Being there in the early days, seeing you grow, how were you able to keep up with the company growth and scale yourself?

Chris Orlob: Yeah, well, I've loved my time at Gong from start to finish. I have so much affinity for that time in my life. There are so many complex emotions that happen to a person when you go through that journey. Because you start at the beginning, a tiny company, you have no idea what the potential is. It keeps growing and growing and growing. And you start to worry. You're like, is this thing going to scale past my capabilities? I worried about that all the time. And so I obsessively was trying to keep my skills up to date and at pace with how the business was growing.

The best way I can describe it is, there's this complex inner life you have when you're an early employee, and you scale with the business. The hardest part of it is like you make so much impact early on. One Gong Labs article changed the game for us. Then as you grow, you feel your impact diluting just a little bit more, even if you're still in a leadership position, just because the company's big, right? The time I left Gong, we had I think 1,200 employees. And so I went from being, to some extent, the face of the company to just another senior leader who was running a different part of the business alongside many, many other people. That kind of messes with you a little bit. It messed with me, that's for sure.

Alex Kracov: Yeah, it was very weird for me at Lattice, too. It just changes on a personal note, the friendships you have and your position. It's also weird being the scary boss, when you're like, wait. It's just weird, the perceptions of other people at the company as it evolves. So yeah, I don't know. Definitely, it's a mind journey for yourself to go on.

Co-Founding PClub and QuotaSignal

In 2022, you left Gong to go start your own businesses. And so you're the co-founder of a company called QuotaSignal, that I think helped improve the sales interview process. Then you also started pclub, a sales learning platform. Why did you start not one but two companies? How did you think of these companies working together? Because from my perspective, it seems like one is the community, and the content one is maybe the software. How do you think about it?

Chris Orlob: So pclub.io, that's our core business. That's the one me and my co-founder are, by far, most focused on. Probably 10 years ago, we tried to start the same business. One of the businesses that we get inspiration from for pclub is a business called Pluralsight. Pluralsight is a Utah company. They do around $500-million revenue. They're the same thing as pclub but for technology folks. It's a large online learning library for software developers and technology people. Back in 2014, they had just crossed the 100 million in revenue. They're in my backyard basically, because I lived in Utah at the time. My co-founder and I were like, we should try to start this, but for revenue teams. Imagine a big online learning company for sales and revenue and marketing and that kind of thing. It just fizzled out. We never really did anything with it.

But then, fast forward to 2022, almost a decade later, we started QuotaSignal which is the Interview-as-a-Service company. But at the same time, I created my first online course to see if we could just bootstrap some cash. I figured I'd make $1,000 a month or something. It just took off like a rocket ship. So I was like, okay. Let's do another one. So we created a second one, and then we created a third one. Within a couple months, these courses were doing well into the six figures a month. And so we decided, as this was happening, we were raising a little bit of money, like a pre-seed round. And we're like, let's focus on pclub. QuotaSignal is cool. But it's really hard to hire or sell hiring technology and services in an environment where nobody's hiring. And pclub just feels easy compared to this. And so our vision started to shape with pclub. We went from selling just to individuals to selling to businesses. I've got a contract out for a quarter million dollar deal right now with pclub, and it's just grown crazy. That's pclub.

The genesis behind P club years and years ago, when I was an SDR, me and my co-founder went to an amusement park together with our girlfriends, who are now our wives. All of us are like best friends. I told them, I was like, I can't play the drums anymore, which was previously my life stream. Because I got tendinitis in all my limbs, and I've decided I'm going to get rich. I don't know how but I'm telling them. I'm like, I'm going to make a ton of money. My co-founder, he just says things in a smart way. I remember exactly what he said. He goes, "If you want to do well for yourself economically, you should learn to sell. You should get really good at it." That inspired me to double down on this SDR job. Now, how does that relate to pclub? That 12-year journey or whatever it was, I became obsessed with skill acquisition. Because it helped me rise from lower class in life to doing pretty well for myself. And so I became very interested in learning, very interested in skill building. And I still am. That's the mission behind pclub. The mission is, we help people acquire economically valuable skills so that we can raise prosperity. There's a lot of just complex backstory to all of this.

Alex Kracov: What does pclub look like behind the scenes? Are you in some ways almost like a teacher and just coming up with a curriculum, and content, and videos, and different things? Is it just you in the videos? Do you have other people? How do you sort of think about the content that you're selling to these enablement teams?

Chris Orlob: Yeah, I mean, we have a couple dozen courses now. I did maybe the first five or six. I have a head of course production. His job is to go find the top tech revenue practitioners to teach courses on very finite distinct skills. And so it's becoming less and less about me, Chris Orlob, doing the courses, and more about other people. And so he runs that part of the business. I have a head of sales who's running the B2B. But I'm very involved with it. Any deal over $20,000, I'm involved. I have a head of growth marketing who runs the consumer side. I'm also super involved in that part of the business. Her and I are like tag team. She does certain things well, and I do certain things well. Then my co-founder has an engineering team, and we're building all the software that supports all the courses and makes intelligent recommendations based on skill gaps and all this stuff. So my day-to-day is kind of a cluster. There's no day the same. I can't really fit in a routine anymore, which is kind of sad. Because I like having the first couple hours of my day be the same. But it's really hard for me to fit in the time to do that these days.

Alex Kracov: I just found your life - I feel like I always have a plan for every day. Then I wake up, open up my laptop. And it's like you get punched in the face of one way or the other. And you're like, okay, I'm going to do that now.

Chris Orlob: Exactly.

Alex Kracov: What's been the surprisingly hardest part of building the company? What's something that's been unexpectedly hard for you?

Chris Orlob: We're getting away with murder. It has been shockingly - I don't want to say it's been easy, because I've worked harder on this than I have anywhere. But we were really fortunate. We started this company. I already had a big audience on LinkedIn. And so it was not a cold start company. In hindsight, it's not shocking that we grew as fast as we did and just got that initial traction. The hardest part for me at least is context switching. Because we have these two revenue lines. We have the consumer revenue and the business revenue. Anytime I put more focus on one, the other one suffers. Then I go back and put the focus on. It's like playing Whack a Mole.

And so trying to build a self-managing company is the hardest part right now. How can I build this company in a way that's not so dependent on my hands, so I can take a step back and dissect the company from the outside and think about what we should be doing differently rather than so much day-to-day execution?

Alex Kracov: Makes a lot of sense. It's relatively easy in the sense that, yeah, you have this giant LinkedIn following. You did the smart thing. You go build the audience and go build the customer base, and then go sell the product into them, which I think is what I've tried to do a little bit but nowhere near as successful. But yeah, I know. It makes sense. So most people know you from your viral LinkedIn posts. How have you thought about curating that audience over time? I know it started in the Gong Labs' side. But yeah, can you take us behind the scenes a little bit of how you think about your own channel?

Chris Orlob: The more I'm asked questions like this, the more I start to realize I'm probably not that great of a strategic thinker. Because I don't plan this stuff out. I just go, and then I iterate it over time. If you ask me, like, what's your strategy for LinkedIn, I would tell you: publish every day for a year, and you'll never worry about money problems again. That's my strategy.

Now, I'm sure I could articulate a better strategy. But I never had some master plan of how I was going to do it, how I was going to build the audience in a certain way. I just had, if you want to really condense it, it's just I want to create concrete value for people. And if you do that and you do that consistently, and you have a unique, insightful taste or take on things, then a snowball starts to form. And as long as you're consistent with it, then it's all downhill from there.

Alex Kracov: One of the things I've struggled with just in the chaos of building a company is carving time out to write and think about things and make genuinely interesting posts and things like that. How do you think about your own content schedule? Are you bulk writing a bunch? Do you have a team helping you a little bit? How do you think about that?

Chris Orlob: The first thing is like, to me, getting LinkedIn posts and stuff like that out the door is as important to our business as breathing is to a human. Because we generate a lot of B2C revenue from that. We get a lot of inbound demand. And so if I'm not doing that, I'm kind of killing - not killing, but slowing down our revenue. So it's not nice to have for our business. Right now, it is very much the nexus point of our entire marketing and go-to-market. So that's one.

How do I tackle it? Just through chaos, I've tried to outsource this. I've paid people twice, and I've used none of their posts just because I can't get their voice to match mine. I had this moment. The last time I did this, that failed. This was only a couple months ago. I paid some guy $6,000 a month to see if he could do this, and he couldn't. The realization I had is, this is a super strength of mine, like writing. It doesn't make sense to outsource a super strength. Outsource things that you're okay at and bad at, or maybe even good at. But don't outsource the super strength. And so I finally made this decision that I wasn't going to try to hand that off to somebody else.

I don't bulk write. It just burns too much brainpower. I can't imagine sitting down for five hours on a Sunday and trying to write everything in advance. That sounds like I'd rather put bike spokes on my eyeballs. And so I don't do this every day. But I do do it most days. I try to find a 90-minute window every day where it's just content creation. It's usually like 45 minutes of that on LinkedIn. 15 minutes, I'll do a very quick and snappy podcast episode. I'll try to fit some YouTube videos. And although I'm not a YouTube expert, yeah, I aspire to be. But I'm not there yet.

Alex Kracov: That was actually my next question. I was curious how you're thinking about YouTube. Because I'm trying to do that. That's why you're actually on this podcast, too. How do you think about YouTube channel? And why are you picking that as potentially your next LinkedIn distribution?

Chris Orlob: Yeah, well, I mean, if I had my druthers, I would do everything. I would be like three days or three times a day on LinkedIn, five or six times a day on Twitter, once a day on YouTube, once a day on podcast. Just immersive content team. But we're still a small team, so I can't do that. And so YouTube just feels like the most natural place to go from here. I'm still not sold on Twitter. I still just screw around with that. I have no idea if I'm going to be able to build an audience. But it's obvious that there's enough sales-oriented professionals on YouTube. That's why I'm doubling down there. Instagram is interesting to me, but this is another bike spokes on the eyeball thing. I don't want to take this and be talking to my phone six times a day. It just doesn't sound fun to me.

Alex Kracov: Yeah, I think YouTube. I'm very bullish on YouTube as a future channel too, because I think it just has such an amazing distribution engine built into the platform. I think B2B content is pretty underserved there. I think, over time, that just becomes more and more of the channel. So we'll see. We'll see what happens.

The Future of Sales Tech

Alright. I'd love to end today's conversation talking a little bit about the future of sales tech. Sales tech stacks are sort of consolidating, and there's this war going on between - I feel like all the major players outside of the CRM category - Gong, Outreach, Clari, ZoomInfo - are all sort of going after each other, building each other stuff. I'm curious if you have any insights into like, how do you think this plays out, future of sales technology? What do you think happens?

Chris Orlob: I mean, we've seen this movie before in sales tech, in marketing tech. It is just the bundling and unbundling ebb and flow of how these categories evolve. Right now, we're in a bundling phase because everybody is trying to copy each other and have a big Frankenstein solution. That's what the market wants because the economy is hurting right now. So they want the all-in-one one vendor, cheaper price total. But I'm sure within the next couple of years, that entire category is going to start to unbundle. People are going to want point solutions that are best in class. There's going to be new startups that start attacking these bundled companies, and then they're going to unbundle their solution. Then the economy is going to ebb and flow again. Then they're going to bundle. You can predict this stuff almost with precision.

Now, what are those categories going to look like in the future? I have no idea. I almost don't want to ever be asked about my predictions of where sales tech is going to go. Because I don't know. I have no idea. I know a lot of people who have opinions on where they think it's going to go, beyond what I just shared like bundling, unbundling. They know something I don't. I don't know how to predict the future.

Alex Kracov: Well, thank you so much for the time today, Chris. I learned a lot in this conversation. If people want to reach out to you - I'm sure they already know you on LinkedIn - where can they find pclub and then the different businesses you're up to?

Chris Orlob: Yeah, LinkedIn is probably the best. You can follow me. You can connect. If you're interested in staying on the cutting edge of sales skills, you can go to pclub.io. Those are probably the best places.