The first sales reps at Google

What're they doing today?

Happy Cross Atlantic Communication Day! It took about 12 years, but in 1866, a telegraph cable connected the USA and Europe… and that’s when overseas cold calls were born. 🙌 

In today’s Follow Up:

  • The first sales reps at Google 👀 

  • Sales in the news 🗞️

  • Sales weapon of the day 🛠️

  • LinkedIn Influencers & Memes 🖼️ 

Sales Fact of The Day

67% of sales reps will work on a hybrid or fully remote basis in 2023.

Source: Hubspot

The First Sales Reps at Google

It’s a common question for many sales reps:

Take a bet on an early stage start up? Or work for an established company?

Startups = high risk + high reward

Established = low risk + low reward

If you’ve ever faced this dilemma, then boy do we got the story for you today.

25 years ago, 3 sales reps based in the bay area made the decision of their lifetime.

The company they joined started as a school project to organize internet search results and it turned into the 4th largest company in the world… Google.

Right now, Google:

  • Does $279 billion in revenue

  • Has over 170,000 employees and over 30,000 salespeople (give or take, we aren’t statisticians over here)

  • $80k average base salary for a sales rep

But things weren’t always this way.

Out of Google’s first 20 employees, only 3 were salespeople.

These 3 people were responsible for driving the early go-to-market strategy for the unknown company.

So we did some digging and found out who the first salespeople at Google were, and what they’re up to today:

Kendra DiGirolamo


Kendra joined Google as an Ad Sales Coordinator in 1999. She only spent two years at the company and left 3 years before the IPO.

Kendra was a career sales and ops person. After spending time at Google she worked as the National Sales Manager for Internet Broadcasting, Sr. Analyst of Enterprise Merchandising Ops at Best Buy, and CSM at Driscolls.

It seems like she lived a pretty normal life and according to her LinkedIn.

It’s unknown how much she made off the Google IPO, but it looks like she’s doing just fine today.

Chris Skarakis


Chris completed his undergrad at Chico St. in 1988 before getting his MBA at USF. He worked as a strategic financial analyst for a few years before taking over as Google’s head of Business Development in 1999.

Chris was responsible for all early wireless deals and relationships with Google. He held down relationships with libraries including Harvard, Oxford, University of Michigan, New York Public Library, and the National Library of Congress which allowed Google to build out their book scanning operations and led to the creation of “Google Books”.

After leaving Google, Chris has put most of his effort into music and philanthropy. He founded, the “Twitter for music” and is on the board for Kanye West's Foundation.

Chris left right around Google’s IPO. Although we’re not sure how much he cashed out, his philanthropic donations lead us to believe his bank account still looks good.

Steve Schimmel 


Steve Schimmel’s story is a little more interesting. In 1994, he graduated from Babson College and moved to San Francisco. For a year, Steve couldn't get a job. But one day, “he took to the streets” and saw two men that changed his life.

One was a homeless man asking people for money, and the other was a homeless man standing on a milk crate wearing a sandwich board that said, “Repent! The end of the world is coming.”

The next day, he put on his best thrift store suit and took a 5 AM bus to the financial district, where he held up a two-sided sandwich board stating his virtues and passed out resumes as people rolled into work.

This landed him a job as an associate equity analyst, but it didn’t take long for him to realize he didn’t enjoy equity research and wanted to start his own company.

So he did just that, but ran out of money and needed to look for a steady job again. That led him to his next job at Netscape, but when Netscape was sold in 1999 and it was time for Steve to hit the job market once again.

This time, one of his former managers from Netscape hired him to be employee #13 at a small startup started called “Google”.

During his time at Google, he negotiated their first $100k and $1m deals, was on the design team for the original ad program, ran a cross-functional external technology evaluation team, negotiated 3rd party technology licenses, and founded and ran the Google Wine Club….bro was wearing a lot of hats.

He cashed out in the IPO, and at 32 years old, he retired.

Back to the question: Startups vs Large Companies

The real answer is…. it all depends on your risk tolerance, what you want from your career, and your belief in a company.

Most startups won’t be the next Google.

If you want a steady paycheck, no (major) worries that your company will fail, and no expectation to do things outside of your role, a large company is likely the best option for you.

But if your goal is to end up like our friend Steve and retire at 32, a start-up is your best chance.

Here are a few questions to ask yourself if you’re considering a startup:

  1. Do you believe the startup still has a chance to 10X or even 100X?

  2. Do you believe the startup will still be around in 10 years?

  3. Do you truly believe in the product?

  4. Is equity a part of your compensation?

If the answer to any of those is “no”, then the specific startup is likely not a good choice.

Which would you rather work at?

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Sales Tip of The Day

Stop over thank-ing and sounding desperate on sales calls.

“Thank you so much for meeting with me, do you still have 30 minutes?”

“Glad we could connect here, so the agenda I have for our call today is xyz…”

Sales in the News

  • The breakdown of how a SaaS sales rep can make $1,000,000 / year.

  • Understanding the difference between an inbound vs outbound call center.

  • A Commercial Real Estate sales team goes viral for posting a video from their sales floor that looks like a scene from Wolf of Wall Street.

  • From Reddit: A guide book for mediocre sales people!

Sales Weapon of The Day

PhoneBurner: A virtual phone dialer that allows sales reps to make 4X the calls per day. Easily dial 60-80 contacts per hour, and stop wasting time on connection delays.

A word from our LinkedIn Influencers:

Why do prospects still ask where we got their number… it’s 2023 😂 

Sales Meme of the Day

And that’s a wrap!

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