Peloton's internal marketing docs, WeWork's legal operator, and Microsoft CEO's paycheck

Matt Turner is out on parental leave so this week you're stuck with me, Alexei Oreskovic, Business Insider's West Coast bureau chief and global tech editor. I've got my own weekly newsletter focused exclusively on tech that goes out every Wednesday if that's your cup of tea, just click here and you'll be able to hear from me every week.

The holiday sales season is in full swing and companies are peddling their products everywhere, in some cases to hilarious effect. Elon Musk set the tone by inadvertently smashing the window of his new cybertruck during its big debut (luckily it's not due to go on sale for another 2 years).

And Peloton, the maker of the $2,000 fitness bike, is getting a lot of attention for its viral ad. The TV spot involves a woman who makes her husband a video diary of her workouts as a thank-you for giving her the thoughtful gift of exercise. Critics have slammed the ad as confusing, sexist, and clueless and it's since been meme-ified.

As Patrick Coffee reports, Peloton's internal marketing vision was supposed to avoid this kind of fiasco. The company's internal brand positioning deck , one of several elucidating documents that Patrick obtained, outline Peloton's ideals and highlight what Peloton is, and what it's not. From the document:

Who we are: Confident, motivating, empowering, modern
Who we are not: Goofy, Preachy, Cultish, Over-the-top

Perhaps words like "empowering" and "modern" mean different things to different people. Wall Streets seemed pretty clear though: Shares of Peloton plunged 15% amid the PR crisis.

WeWorks new ad man and its behind-the-scenes legal mastermind

At the opposite end of the marketing spectrum, WeWork has launched an ad campaign to repair its tattered image. The ads are the handiwork of Maurice Levy, the former chairman of ad giant Publicis Groupe who became WeWork's interim marketing chief last month.

As Meghan Morris and Patrick Coffee report, the ads will portray WeWork as customer-centric and forward-thinking. Hopefully, the ads won't appear in newspapers alongside any tequila ads .

Speaking of WeWork, don't miss Julie Bort and Dakin Campbell's fascinating look at WeWork's top in-house lawyer, Jen Berrent . Although not nearly as well known to the public as some of the other WeWork executives, Berrent was one of the most powerful insiders at the company.

As Bort and Campbell report, she is considered the legal mastermind who found ways to protect the company and its CEO, no matter what tricky situation presented itself. With Neumann now gone and Berrent still there, she's someone worth keeping an eye on.

Microsoft CEO Satya Nadella Sean Gallup/Getty Images

Microsofts compensation is in the spotlight

Microsoft CEO Satya Nadella is finishing 2019 with another strong year under his belt. The company's market value crossed the trillion-dollar mark for the first time in April and is on track to finish the year up 50%. And Nadella earned some bragging rights by stealing the Pentagon's $10 billion cloud contract from under Amazon's nose (although Amazon is challenging the decision in court ).

But for as great a job as he's done, Nadella's hefty compensation package has become a sticking point for some investors. During Microsoft's annual shareholder meeting this week, one shareholder asked the company to justify the fact that Nadella's pay package was 249 times larger than that of the median employee.

As Ashley Stewart writes, it fell to Chairman John Thompson to respond. And he thinks Nadella is worth every penny.

I'd sure like to be worth that many pennies too. Anyway, that's it for this week. It's been a pleasure hosting the newsletter this week.

Alexei

Cities of the future

We're hosting an event focused on smart cities in Washington, DC on Tuesday, December 10. The event will explore the impact of various technologies transforming cities, mobility, digital equity, the evolving regulatory and policy environment and the investment opportunities these innovations create.

Speakers include Lindsey Parker, chief technology officer for the City of Washington, DC, and Michael Sherwood, the director for innovation and technology for the City of Las Vegas.

Click here for more information, and to apply to attend!

Finance and Investing

PIMCO's flagship hedge fund has lost more than 14% in 2019 a rare stumble for the $3 billion credit strategy

The fund is run by Dan Ivascyn, the chief investment officer of the bond giant, and Jon Horne, a managing director at the firm. The fund has made money in four of the last five years.

'A lot of people don't need to pay back their debt': A student-loan expert explains why popular repayment advice is false and shares how to save up to 50% on interest payments

Travis Hornsby has consulted on over $750 million worth of student-loan obligations. He advocates for refinancing student loans under three strict criteria.

Tech, Media, Telecoms

The Derek Jeter-backed startup BlueJeans Network, last valued at over $700 million, just cut 40% of its workforce as Silicon Valley's focus on profitability grows

The change at BlueJeans shows how Silicon Valley's growing focus on profitability is now trickling down to smaller startups too.

News Corp. has tapped Viacom's former tech chief as its next CTO

David Kline is set to leave Viacom after its merger with CBS closes on December 4. He joins News Corp. in January.

Healthcare, Retail, Transportation

A former Sequoia partner just joined a $313 million VC fund that's focused on digital health. He told us how he's planning to pick his next investments.

Michael Dixon, who spent 10 years atSequoia Capital, is joining a new venture fund focused on digital health.

We asked C.H. Robinson's new CEO everything about the brokerage giant's strategy for the years ahead from tech recruiting in Minnesota to the trucker shortage to the trucking recession. Here's the full interview.

Bob Biesterfeld became CEO ofC.H. Robinson, the largest brokerage in US trucking by market share, this year. He thinks the "truck driver shortage" could be addressed by better utilization of the industry's resources, as well as simply treating truck drivers better.

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