An interview with the internet's most famous sales comedian

Published: Wed, 12/01/21

December 1, 2021

Good morning. Now that we’re in the midst of the holiday season, we all have to work twice as hard to get people to respond to our calls and emails -- and that’s just our coworkers! For now, take a break with this week’s edition of The Quota, where we interview the man behind the hilarious sales character Corporate Bro, share a Sales Fail that makes us want to crawl into a hole and hide, and give some advice to a rep whose sales manager crossed the line. Let’s go!

NUMBER OF THE WEEK

Hours per month SDRs spend leaving voicemails.

Source: TaskDrive

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

The Deseret News recently published a fascinating article about the subculture of “summer sales” -- where thousands of (mostly young male) recruits leave their towns during the hot summer months to sell solar, home security, and pest control services door-to-door throughout Utah and the west, sometimes raking in upwards of half a million dollars in a few short months. There is, of course, a darker side to the industry, and it’s clear that the huge paydays are reserved for those at the top, while many others fall far short of what they’re promised, or worse. You can read the excellent article here.
How out-of-control are car prices these days? One shocking example recently made the news, as an Oakland Toyota dealership allegedly listed a 2021 Toyota RAV4 Prime for a mind-blowing $96,000, about twice its initial MSRP. A screenshot of the listing made the rounds on Reddit, and the car-site Jalopnik verified the price with a salesman before the dealership took the listing down, but not before the San Francisco Times wrote up an article. Apparently not all press is good press.
While MLM (Multi-level marketing) is technically sales, there’s a reason why most professional salespeople won’t step foot within a hundred miles of an MLM pitch. BuzzFeed recently ran an article sharing stories from former MLM members who quit the business after realizing they’d been sold a bill of goods. If you need another fifteen reasons to avoid these scammy organizations, you can read the listice here.

MEME OF THE WEEK

Source: Instagram -- Sales Humor

THE INTERVIEW

Ross Pomerantz

An interview with the internet’s most famous sales comedian, Ross Pomerantz aka Corporate Bro

If you follow our Sales Humor page on Instagram, or have spent time consuming sales content on the platform, then you’ve probably come across Corporate Bro. The intentionally-over-the-top, but strangely charming character is played by Ross Pomerantz, a salesman-turned-comedian from California, who’s amassed a loyal following over the last eight years, bringing his brand of humor to the masses, and giving the world a brutally honest take on what it’s really like to work in sales in the 21st century.

We wanted to get to know the man behind the character, so we sat down for an interview with Ross, who told us about his journey from tech sales to tech sales comedy. The following interview has been edited for clarity, and shortened for this newsletter. The full version will be published on our forthcoming website in early 2022.

How did you get into this line of work? Did you accidentally film a video that went viral, or was there some sort of moment when you decided this is what you wanted to do?

My first tech sales role was at Oracle in 2013. While I was there, Vine was still a social media platform that people used. I remember talking with a friend of mine one morning and I said, "Yo, everyone here is such a corporate bro." That's when I decided I'd make stupid little 6-second Vine videos about my experience. The goal was never to be an influencer or 'go viral,' I just enjoyed making people laugh. Growing up I was the kid who always made home movies. I just never thought it could actually be my job. Now, that being said, I've still never gone viral. Meaning, I've never had a video that just took over the internet for a day (1M+ views). My growth has just been a steady grind of trying to put out one video per week. I do wish one video would just blow up though...

Is this what you do full-time?

I do a million things full time. I'm on the senior leadership team at Bravado - the sales community. That's my traditional full time 'day-job.'

I also recently started an investment group for sales professionals called Corp Capital (www.corpcapital.vc). I've always wanted to connect sales savages with the same investment opportunities I've been afforded, especially through my Stanford network. We've done a couple of investments already and I'll be launching exclusive merch and an NFT program as well. I’m also an advisor for a few early stage companies, helping them with GTM -- brand and content is sort of my wheelhouse.

Lastly (though I should probably say firstly), I do Corporate Bro. Every week I try to put out a video. It's hard though. They take a ton of time as I do the majority of the writing (Ben is my creative partner. He shows up in many of the videos as well), obviously acting, and I also edit them all. I take production very seriously.

Tell us about the different sales jobs you've had.

I've had a few different roles. Immediately out of college, I was an apartment leasing agent. I worked in a luxury apartment building in Oakland, California. That was in-person, which I CRUSHED. Between that role and my tech career I also did a short stint in independent minor league baseball as a pitcher. That was always my dream. But, it didn't take long to realize I wasn't going to the big leagues, so in 2013, I became a BDR at Oracle. I did that for 10 months, got promoted, then left Oracle to become an AE at a small company that no one has ever heard of. They got acquired by Akamai for next to nothing. Then I spent 3 years at Glassdoor slanging as an AE. After that I went to start a VR SaaS company called Neurotrainer with a scientist who had a system that could measure the cognitive function of athletes. That was super fun. I ran sales there before getting admitted to Stanford where I went to get my MBA.

How much money do you make doing this? More or less than you made selling software?

Fun fact: I didn't make a cent from Corporate Bro for the first 7 years. Now I'd say, given the amount of speaking gigs I do, that I could pass my full year of earning as an AE in 1 month of speaking. So in short, I make more. However, I'm certainly not rich. The money I make goes back into production and costs that I incur while creating content. I'm saving up to produce my web series.

How is Ross different from Corporate Bro? How are they the same

I'd say Corporate Bro is 65% Ross. Or Ross is 65% Corporate Bro. IDK. My humor is my humor. I think Corporate Bro is just everything I wish I could have said and everything I want to say. It's super interesting because I genuinely have no idea how people would describe Corporate Bro. Ross is certainly much quieter. I'm an introvert. I prefer being alone. Corporate Bro is the life of the party. He's a savage. In reality, I hate when people dislike me. I have terrible anxiety. Corporate Bro is my outlet to be unapologetic. That's why when I meet people in person I always feel like I'm a letdown. I'd say people probably perceive Ross as smarter than Corp. But who knows? Maybe it's all one and the same.

Do you have any advice for those who are just starting out in sales?

Just understand that sales is hard. It will always be hard. Everyone has struggled at some point. But the best salespeople DO NOT tie their quota attainment to their self-worth. It's just a job. And sales is the best skill you can learn. Period. It can unlock so many doors... So my advice is to focus on being mentally tough. To PICK UP THE PHONE. To make mistakes. To realize that no matter how mad someone may get, IT DOESNT FUCKING MATTER. Because, at the end of the day (S.A.D.N.E.S.S.) Sales Are Dope, Never Ever Stop Selling.

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

“This happened a year ago. I was working B2B SaaS sales -- marketing software. My sales manager had always encouraged us to engage with our prospects on social media, so when I was working a seventy-seat deal, trying to land a large auto insurance broker, I followed their Facebook and LinkedIn pages and began interacting with them.

In one post, they shared a picture of one of their employees standing in front of a hospital with the caption, “Congratulations to [employee’s name] for completing his last round of cancer treatment.” So I clicked the “care” reaction on Facebook and went about my day. Later that afternoon, my sales manager called me into his office; He looked like he’d seen a ghost. It turns out, I had accidentally clicked the “laugh” reaction and left it up. I sent them an apology email right away. Needless to say, we didn’t get the deal.”

- Embarrassed, 34 Rolling Meadows, IL

GRAPH OF THE WEEK

Source: LinkedIn Poll -- February 2021

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Dear Quota Team,

I have a problem, and I’m wondering if there’s anything I can do about it. I joined my current company a little less than a year ago, and overall, it’s been a pretty decent run. Comp plan is solid, and I’m hitting my numbers every quarter.

But about a month ago, something happened. My manager and I got into an argument which escalated pretty quickly. Basically, he gave me a hard time for losing a deal that (in his opinion) we should’ve won, even though we got beat out on pricing and literally would’ve lost money if we’d tried to discount to match the competitor’s pricing.

That’s not the real problem though. The real problem is what he said to me when we were arguing. I’ll admit that I should’ve probably just shut my mouth and not tried to defend myself when he was criticizing me, but when the conversation got heated, he said, “You can make excuses if you want, but then you’re just gonna end up like your brother.”

He was talking about my older brother who can’t hold down a job and has had a drinking problem since college. I had told him (my manager) about my brother when we were talking about our families one day, but I never thought he’d bring it up to me like that.

We’ve basically moved on since the argument, and he probably thinks everything is back to normal, but I’m still pissed about what he said, and I’m thinking about it on a regular basis. Should I bring it up to him or am I better off just keeping my mouth shut and focusing on work until one of us either gets promoted or leaves the company?

Bothered in New York

Dear Bothered,

We can see why you’d be bothered by your manager saying something like that. Our personal lives can elicit strong emotions, and they shouldn’t be used to score cheap points or as motivational tools -- which, if we’re being generous, is what your manager might have been trying to do.

There’s no easy answer here; you can either live with it and move on, or bring it up to your manager and let him know it’s been on your mind. If you do the latter, it’s unlikely he’ll ever do it again, but, depending on how mature he is, it might just create more problems for you. So the question becomes: is it worth it?

Not all battles are worth fighting, but if you can’t stop thinking about it, you’ll probably feel better after getting it off your chest. Just be ready for the possibility that this will open another can of worms. And, as an aside, this is a perfect example of why so many people feel like they have to keep their personal and professional lives separate. Good luck!

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Today's email was written by Ken K., Steve R., and Emily H.

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