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Square Loses Its Second Major Leader in 3 Months

By Leo Sun – Updated Apr 18, 2019 at 10:15PM

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The payment company is seeing big turnover.

Square's (SQ 3.97%) head of payments, Mary Kay Bowman, recently resigned to join Visa (V 1.74%) as its new head of seller solutions. Bowman joined Square in 2015 after spending over a decade on Amazon's payments team.

Bowman's departure comes just three months after CFO Sarah Friar, who joined Square in 2012 and guided it through its IPO, left to become the CEO of Nextdoor. Will the loss of two key leaders in such a short time hurt Square's prospects this year?

Square's Register.

Image source: Square.

Don't jump to conclusions

Investors shouldn't immediately interpret Friar and Bowman's departures as bearish headwinds for Square, since companies lose and replace key leaders all the time. Square already replaced Friar with Amrita Ahuja, the former CFO of Activision Blizzard's Blizzard unit; the choice was well-received by investors.

The loss of Bowman was more abrupt, since it was announced by Visa instead of Square. However, her position probably won't stay vacant for long since Square is arguably one of the most promising players in fintech.

Will Square lose its focus?

But as a Square investor, I'm slightly worried that Friar and Bowman's departures could cause the company to lose its focus. Over the past few years Square aggressively expanded beyond a single product, the Square Reader, with a wide range of hardware devices and an expanding ecosystem of fintech services.

This ecosystem now includes customer relationship management (CRM) software, payroll services, food deliveries (through Caviar), HR and inventory management tools, e-commerce and web design solutions, Instant Deposits, small business loans (via Square Capital), and other services. It also recently launched a software development kit that lets developers directly integrate Square's payment services into mobile apps.

Square bundles all its hardware and software services together to lock in businesses and boost its revenue per customer. That's why it launched Square of Restaurants, which merged Square's payments, analytics, and Caviar deliveries into a single platform.

Square's Terminal.

Image source: Square.

On the consumer front, Square launched the Cash App, a popular peer-to-peer payments app that surpassed PayPal's (PYPL 4.79%) Venmo in cumulative downloads last year according to Sensor Tower and Nomura Instinet. Square also offers a physical debit card, the Cash Card, which is linked to the app.

Prior to her departure, Friar stated that Square was mulling the development of savings products and brokerage services for Cash, and that it was building "an ecosystem of financial services for individuals in the same way" as it did for businesses. Bowman would have likely overseen all those expansion efforts.

Did Square let two potential CEOs leave?

Friar and Bowman's departures wouldn't be worrisome if Square had a full-time CEO. However, Jack Dorsey still serves as the CEO of both Square and Twitter (TWTR), so Friar was widely seen as the company's public face.

Yet the loss of Friar to Nextdoor, a social network for neighborhoods, wasn't as damaging as the loss of Bowman to Visa, which is expanding its own digital ecosystem. Visa is also partnered with Square's rival PayPal in digital payments.

Visa stated that Bowman will lead its "strategy for acceptance products and solutions, driving the design, development and delivery of new services and solutions that will transform the payment experience for both sellers and consumers." Simply put, Visa wants to be more like Square.

I personally think Dorsey should have stepped aside and promoted a top leader like Friar or Bowman to the CEO role. The move would have given both Square and Twitter more focused leaders, and allowed Square to retain its key fintech architects.

What Bowman's departure means (and doesn't mean)

Bowman and Friar's resignations probably won't derail Square's near-term growth or trigger a serious "brain drain" yet. But over the long term, investors should see if their successors alter Square's ecosystem expansion strategies.

Check out the latest Square earnings call transcript.

John Mackey, CEO of Whole Foods Market, an Amazon subsidiary, is a member of The Motley Fool's board of directors. Leo Sun owns shares of Amazon and Square. The Motley Fool owns shares of and recommends Activision Blizzard, Amazon, PayPal Holdings, Square, and Twitter. The Motley Fool owns shares of Visa and has the following options: short January 2019 $82 calls on PayPal Holdings and short January 2019 $80 calls on Square. The Motley Fool has a disclosure policy.

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