Today’s episode features millennial comedian and tech sales icon Ross Pomerantz, also known as Corporate Bro, or, increasingly, Corp.

After selling SaaS solutions in Silicon Valley, Ross exited the full-time tech sales employee route in favor of focusing on, well, a lot of other stuff: comedy, filmmaking, advising, investing, speaking, acronyms, writing, and more… but, mostly, influencing (sorry Ross, had to). 

He also recently launched an impressive project, an eight-part comedy web series called Sales Are Dope (S.A.D.), all about working in sales at a Silicon Valley tech company, with plans for a second season. Ross, aka Corporate Bro, has garnered a massive social media following of about a million and growing across platforms like Instagram, LinkedIn, YouTube, and, yes, even TikTok. And Threads, too, I guess.

Ross has done enough jokes about getting old in tech both over the years in social reels and in his recent comedy series that I realized we needed to get his/Corporate Bro’s take on what it’s like in tech for anyone anywhere near 40 or older. He’ll take you through his own tech career journey and share more about how that professional experience has informed his comedy. Also, we discuss how Ross himself will also one day turn 40…or will he? We’ll get into some of his options.

If you aren’t into profanity (or are listening around kids), or are easily offended, fair warning: this episode is NOT for you, and we’ll catch you next time. 

It was a blast to sit down with Ross to bring some humor into the mix on a topic that can obviously be heavy and serious, and I hope you love listening as much as I loved recording.

"I do think leadership and experience are often underappreciated. It can be a huge difference-maker in tech in motivating people and giving them perspective and wise words, whatever it may be, but also even catharsis and therapy to the younger folks."

- Ross Pomerantz

In This Episode:

-Why Corp thinks tech companies are youth-dominated

-Where will Corporate Bro be in ten years? Hint: maybe drop the “Bro”

-How Ross’s humor plays differently with Gen Z vs. older people

-Ross’s feelings about facing ageism - his first “ism”  

-How Ross works well with both younger and older people alike 

-A new “ism” facing Corporate Bro and some of his fellow tech sales colleagues 

-Allusions to the Big Island of Hawaii, a place we both love

-What athletes and tech sales professionals share as they age

-Targeted advertisements for those over 40 and where they can go wrong

-His casting limitations for comedy skits and his hopes for more diverse representation in season two of Sales Are Dope (S.A.D.)

-Ross’s true feelings on influencers and TikTok

-Some colorful, out-there facts about some of Ross’s fellow San Francisco residents

-What Taylor Swift and Corp have in common

-How bicyclists feel about Corp

-How he handles people who recognize him as Corporate Bro in the street/at the bar

-What it feels like for him to get older

-What tech companies are sleeping on regarding the value of older employees 

And much more.

Make sure to follow Ross on socials, and above all, go watch Sales Are Dope! All the links are below.

Resources:

-Sales Are Dope (S.A.D.) Series: https://www.youtube.com/playlist?list=PL3NoHBNSs00Y7I82f6h_6KyWM3b9pjmmQ

-Gavin DeGraw clip mentioned: https://www.tiktok.com/@corporate.bro/video/7196785042696457518

Connect with Ross Pomerantz:

-Website: https://corporatebro.com/

-LinkedIn: https://www.linkedin.com/in/corporatebro/

-Instagram: https://www.instagram.com/corporate.bro/

-TikTok - https://www.tiktok.com/@corporate.bro

-Threads - https://www.threads.net/@corporate.bro?igshid=MzRlODBiNWFlZA==

Connect with Maureen Clough:

-Instagram: @itgetslateearly - https://www.instagram.com/itgetslateearly/

-YouTube: @itgetslateearly - https://www.youtube.com/channel/UCGrHwk-y7ERaq7bCSjZYf1A?sub_confirmation=1

-Website: itgetslateearly.com - https://www.itgetslateearly.com/

-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/

-Facebook: It Gets Late Early - https://www.facebook.com/profile.php?id=100088694515585