Social Selling With Corporate Bro | Confident Negotiator Podcast #6

By RED BEAR May 7, 2024 | 15 min read

In this episode of The Confident Negotiator Podcast, host Rob Cox welcomes Ross Pomerantz, widely recognized as Corporate Bro, for a candid discussion about humor in the sales profession. Ross recounts his transition from a typical enterprise software sales role to becoming a viral internet personality, captivating over half a million followers with his satirical takes on the sales profession. 

This episode delves into how Ross harnesses the power of humor to navigate the highs and lows of sales, the importance of emotional intelligence in crafting his sketches, advice for how salespeople can use social media, and practical tips for keeping spirits up during challenging negotiations. Don’t miss these invaluable insights sprinkled with humor — perfect for anyone looking to add a lighter touch to their sales and social media tactics.





Transcription of the Video:

Disclaimer: RED BEAR does not necessarily agree with all views expressed in this interview. They are funny, though. Enjoy.

Rob Cox: Hello everyone, and welcome to The Confident Negotiator Podcast. I'm Rob Cox, and with me today is Ross Pomerantz, but you may better know him as his internet name, Corporate Bro. Ross, thank you so much for joining today.

Ross Pomerantz: Just a damn honor to be here. Thanks for having me.

Rob Cox: Well, we're honored to have you on here. Ross, as Corporate Bro, you've built up quite the social following. At the time of this recording, you've amassed 530,000 followers on Instagram, over 220,000 followers on LinkedIn, over 30,000 followers on YouTube, and over 250,000 followers on TikTok, all through humor about being a salesperson. So tell our audience a little bit about how Corporate Bro started and some of the additional projects that you're working on now.


Ross Pomerantz: Sure. I guess I'll give you the quick story. In the interest of time, I was a sales guy, and people always ask me, they're like, "Well, how do you know all this stuff?" Well, dude, I lived it; I was a sales heathen. I started my career as many washed-up athletes do, realizing you have no hard skills at Oracle, like Big Red Machine, if you will, where a lot of salespeople that I meet still got their start. It's kind of funny, not to say and not to take away anything from our military, but it's like if you went through Oracle, you have an instant bond. It's like, "I know what you went through; we were birds of a feather; we're kin with the same scars." So while I was there in 2014, I started making Vines, if you remember Vine, that platform, TikTok, pre-TikTok back when you could only do six-second videos. So you had to tell a story in six seconds, which was good times.

I mean, sales was really hard. I was in business development, so I was effectively an SDR at the time, and I didn't know that's what I was getting into. I was like, "Oh, business development at Oracle; they sponsor the Warriors. The Golden State Warriors, that's going to be sweet." It turned out it was a sales job, and it was painful and it was hard, and I was working in this place called Redwood Shores. It was more specifically Twin Dolphin, which is a building in Redwood Shores where they put all the salespeople. Across the street, all the engineers, all the business people, all the every other function was together or at this beautiful campus. But we were in this frat house across the street, all the salespeople, and I was like, "Why is no one talking about this? This whole thing exists, and you would never know. So I'm going to document it. I'm going to start making silly little videos."

It wasn't like I got to tell the world. It was more like this job is really painful, and I lose a lot, and it's demeaning in a lot of ways, and so what's the best way to combat that and get some catharsis? Well, humor. So things from the chairs that lean back too far back when the headsets were wired and you'd stand up and forget it was on, it would choke you out. Little things, the fire alarm going off, whatever it was, I was like, "I'm just going to make little videos for my team." Spread from team to team. Other teams were like, "When are you doing another video?" I was like, "Whenever inspiration strikes," what ended up happening was one of the teammates, fellow sales savages at Oracle, sent my stuff to the illustrious publication known as Total Frat Move and BroBible, two separate ones.

Those were like Barstool, pre-Barstool, and they wrote about my account, and it just so turned out sales. It's a big profession. A lot of people were doing it, and it was like, "Whoa, that guy's me," and I had no expectations of it taking off or becoming a thing. It just, as people know, it's the oldest, largest profession on earth; sales is probably the largest profession that still exists, that enough people do around the world, and I basically learned that it doesn't matter what you sell, where you sell it: quota is too high, product sucks, and marketing doesn't do shit.

And those three universal truths just hit across the board. So I've been doing that ever since, I think I'm into my 10th year now. People ask if I went viral at some point. No. It's been a real slow, steady grind. Some people become overnight successes on social media, not me. Do I wish I went viral? Sometimes. I still do, still want to go viral. But yeah, it's been a lot of fun. I've learned a lot of things, but that's effectively where it started, and I continued to do it alongside my sales role up until 2020. I graduated from business school and was like, "You know what? I'm just going to do this full time and make this my business." So that's where I'm at today, four years later.


Rob Cox: Well, thank you for that, Ross. That makes a lot of sense. I've personally been following you for several years now. Back when I started in B2B SaaS, marketing and sales, and I said, "Okay, this humor is coming from a real place; it's very specific." So it's interesting that it resonated with so many people. You've given us some of the background there on how Corporate Bro came to be. When did you realize, though, that the everyday comedy of sales was something that so many people could relate to? What was the inflection point?

Ross Pomerantz: Yeah, the inflection point was in 2015, so I guess it was about a year and a half. I was messing around on Vine. It was when those articles got written, that was the first time... Growing up, I was always the goofy, weird, funny guy in the friend group. That was the role I filled. I wasn't the cool guy, I wasn't the best athlete. Though all my friends were all playing sports, we're all athletes. But the way I filled the gap was I was the self-conscious, funny guy. So I also never assumed that I was funny, generally. I was like, "Oh, it's funny because it's Ross."

But when those articles were written and people started discovering my page and just following, that was kind of when I was like, "Oh, shit, this is making sense to people, and they don't even know who I am; these are random people." I had a few thousand followers at that point, and then when those articles came out, it jumped me over 10, and that's when I decided I should probably apply some, we'll call it intellectual rigor to the process. I should try to have my scripts, I should try to produce once a week. I should try to really focus and streamline this, which I still haven't figured out, but the goal then became, "Let's produce at least one thing a week and start getting consistent."

Rob Cox: Cool. Now, your sketches often highlight the absurdity of sales situations. In your opinion, how can salespeople maintain a sense of humor and perspective during challenging negotiations?

Ross Pomerantz: Oh, I mean, I would say it's easy, but you have to just step back and realize nobody's going to die. Nobody's going to die. The world's not going to end. You get so caught up in sales and your number and feeling like you are as good as your number and your self-worth is tied to your number; it's just not true. And being able to step back and look at it from a third-party, what is really happening here? That's what happened to me at Oracle. I was like, "They are all 20- to 40-year-olds selling million-dollar deals to Fortune 100 CEOs. We have no idea what the fuck we're talking about." I feel like I'm taking crazy pills. Why am I the only one who thinks this is ridiculous? And I think it's the same thing in any negotiation. It's like two people want something; they're both trying to do right by their business.

Most of them don't own the business that they're trying to do right by. They're trying to make somebody else a lot more money than they're making themselves, but all we want to do is go home and watch TV, watch the next Netflix show. It's not that serious. So I don't know; for me, maybe it's just because it's my way of hiding pain, but humor was just always the best way. And people say humor is the best medicine, so if you can't laugh at what you do in sales, I mean, shit, we do so much losing, so much rejection, so much stupid shit happens. How can you not laugh at it? If you take it too seriously, you won't last very long. That's what I think. So it's just perspective.

Rob Cox: Excellent. Riding the highs and lows.

Ross Pomerantz: Yeah. And there are many of each.

Rob Cox: Yep. Social selling, you've obviously taken the leap that many salespeople are afraid to do with building a large social following. Do you think sales professionals should leverage their social media platforms to enhance their personal brands and connect with prospects?

Ross Pomerantz: The short answer is yes, but the long answer is it's not for everyone. Just like anything, not everybody's good at it. Not everybody will come off in some sort of authentic way; some people will be cringey, some people will try too hard, some people will try to be funny, and it's not funny. People will try to be something that they're not. And I think that's probably the biggest issue is if you're true to yourself, which maybe like, I'm not an on-camera personality; I'm not a social media type person. Well, maybe you try writing; maybe you're a good writer, and you can post things, interesting things, thoughtful things on LinkedIn, but you're not a camera person. You may be none of those things, that may not actually help you in any way, shape, or form. I do think it's an advantage to do it. I think it can open some doors. I mean, they talk about brand building; any company that's trying to brand build for themselves, it's creating trust with people who you don't know through repeated touch points, and therefore those people feel like they know you.

It opens doors, it breaks down barriers. So, I mean, I'd be lying if I said... I mean, obviously, this is my job now. It opens up a million doors, and doors continue to open, and that's because people feel like they know me through social media. And obviously, social media isn't entirely who I am; there's a lot of pieces of me people don't know about and intentionally so, but again, short answer is yes, everybody should do it or try it, or think about it. But you can't just go into it and be like, "I'm just going to start doing this today and then be really inconsistent about it." You need to be somewhat intentional and kind of have a plan.

Rob Cox: Got it. So finding your right format, like you said, some people may be better writers, some people may be better on video, some people may be better at posting pictures or something like that. So finding the right format for social selling.

Ross Pomerantz: Yeah. And you're also trying to; it's not always building your brand as a subject matter expert. You don't need to try and be a thought leader. I mean, the joke is all the SDRs; it's like, "I've been cold calling for six months, and here's 10 best practices." And I'm sure they've learned things, and I'm sure some of those things are good for other people, but it's also about just developing who you are, your own personal brand as a human being. Do you seem approachable? Do you write and communicate in a way that others would want to communicate with you? Even if it has nothing to do with sales, because that's not really what people are looking for, they're trying to connect with other humans. It's not like, "Oh, I want to buy from that guy; I like that guy; I like that tone; I like that approach." So it doesn't have to be thought-leader-type cliche stuff on LinkedIn. It can really be about yourself.

Rob Cox: Excellent. Let's move over to humor. You're a very funny person, your sketches are very funny. Do you think salespeople can infuse their sales pitches and negotiations with more humor, and how can they do that without crossing boundaries?

Ross Pomerantz: Yeah, I mean, short answer is yes, and that's the entire thing. I have a whole workshop on... So humor is the single greatest tool of influence; it builds a power dynamic in a positive way for yourself but also removes barriers of standoffishness. It's a double win on both sides. So if you can harness humor, it is actually, scientifically, the most powerful tool of influence that there is and get people to do things. It's a level of perceived, at least intelligence. The best way to do it, in my opinion, is self-deprecation. Be really self-aware; that never fails to... If you're going to make a joke and you miss, it should be about yourself. I wouldn't say joke about the prospects X or Y; I mean, if you have the rapport, this is lame, but I'm just like, their sports team got absolutely blown out last night. "Are you still recovering from that absolutely tragic, humiliating loss, right?"

You got to be on that level. But when in doubt, it's like, own that you're a salesperson. That's what it was for me is like, "Look, I know talking to a salesperson is somewhere between jury duty and a root canal, so I appreciate you just getting on the phone with me for 10 minutes." And they're like, "Oh, yeah. Well, I was kind of not looking forward to this call." Like, "I know you weren't; I know you weren't. I don't like me either, for what it's worth." And you kind of go from there. So its self-awareness meets self-deprecation. I think that's the easiest and best way to do it. Even making jokes about your product, nobody's perfect, and if you try to sell perfection and sell yourself as perfect, you will fail. It'll come off as contrived, I should say.

Rob Cox: Excellent. That makes sense. Now, Ross, how do you balance the fine line between poking fun at sales stereotypes while still respecting the profession and the hard work that salespeople do?

Ross Pomerantz: It's hard. I get people; in fact, we just had somebody write into the podcast. They're like, "I'm thinking about transferring it. I've been a product manager for 12 years. I've been told I've got a great personality for tech sales, but every time I listen to the podcast, it seems like Ross hates his job or hated the job and doesn't want me to..." And I think, for me, it's taken a long time, but I've more or less earned the right to shit on the profession. The profession is broken in a lot of ways as a lot of things in life are broken. A lot of professions are broken, the world's changing, as it always is and always will.

I have enormous respect for the job, but of course, I'm going to call out the bullshit. That's my whole brand, is calling out bullshit, whether it's marketing or sales, or otherwise. I still fundamentally keep coming back to, I think sales is the most important skill there is period. In life, for anything you want, whether you are in marketing, you want to go into data science, or you want to convince your friends to go to a restaurant or whatever your significant other to do X, Y, or Z. It's all sales; everything in life is sales. To get where you want to be is sales, whether you're selling a physical product or yourself, or whatever it is. So that, to me, is what the true kernel of truth at the root of all of this is. It's like we are all trying to sell something. The whole world is trying to sell something, so it helps to be good at it.

And of course, there's people who are bad at it, and there's things that happen that are bullshit, and you got to make fun of those. And I think it kind of adds power to it. And having done it, it gives me... I've earned the right to do it, I think? It depends on who you ask. I realize when I say that I sound like such an asshole, but I do think over this: I've sold for 10 years. People often wonder; they're like, "Did you actually work in sales?" I'm like, "Yeah, dog. I sold SMB, mid-market, enterprise. I've sold products you could sell in one call and products that took 18 months." So I've kind of seen it all, doesn't mean I was the best; certainly wasn't the best. I was a bit too busy thinking about videos and the next thing I could make fun of. But yeah, to me, it's all about pulling out kernels of truth, and I think that's why it works.


Rob Cox: Again, your humor seems to come from a very real place, from someone who's definitely been in the sales profession. So that's great. Ross, you've been-

Ross Pomerantz: It's dark.

Rob Cox: Sorry, it's a dark place?

Ross Pomerantz: It's the dark pain where it all comes from. Comedy is tragedy; it just flipped. So.

Rob Cox: A little bit of time. Yeah. Ross, you've been very generous with your time. I really do appreciate it. Is there anything else that you'd like to share before you wrap up?

Ross Pomerantz: No. I mean, people should go listen to Demoted, the podcast, or I just launched a newsletter called Silly Valley News. It's not just about Silicon Valley; it's more of like, I want to arm you with probably six news stories written in a comedic way for you to just kick off your week. So when you're struggling on your phone call to talk to your prospects about something, you could bring up relevant news. Be a little bit smarter. Yeah, that's pretty much what I'm working on right now. I mean, obviously, videos and content; you should follow it all, but those are the kind of new things that I'm working on right now.

Rob Cox: Excellent. Well, Ross, thank you again for your time. Be sure to catch Ross at Corporate Bro on most social channels and check out his new podcast, Demoted with Corporate Natalie. It's very funny. And you said it was Silly Valley News, is that right?

Ross Pomerantz: Silly Valley News. Yep. Yep.

Rob Cox: Excellent. This has been The Confident Negotiator Podcast. Thank you for listening. We'll see you next time.

Ross Pomerantz: Thanks for having me, Rob.

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