What Comes Next for Square After CEO Departure?

Alyssa Henry, the long-serving CEO of Square, recently announced her resignation, leaving investors and industry experts speculating about the future direction of the company. While a Block representative declined to comment on Jack Dorsey's tenure at Square, Henry's departure is raising questions about the company's trajectory.

Founded in 2009 by Dorsey and Jim McKelvey, Square revolutionized the way small businesses process card payments by providing them with white card readers. Over the years, Square has evolved to include the peer-to-peer Cash App and the Australian buy now, pay later service Afterpay.

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A domain name system issue was to blame for the most recent outage that Square's merchant segment experienced, which lasted from September 7 to September 8. While the company issued a public apology for the disruption, it undoubtedly led to concerns among sellers who rely on Square for payment processing.

Some people consider Henry's departure to be a potential reason for investor concern as Square experiences a slowdown in growth. David Koning, a senior analyst at Baird Equity Research, noted that Dorsey's continued oversight of the company is seen as positive, given his recent focus on Square's strategic direction.

Darrin Peller, an analyst at Wolfe Research, suggested that Henry's resignation may stem from a desire for a break after nearly a decade with the company, as well as Dorsey's increasing involvement in day-to-day operations. Peller also highlighted concerns about Square's recent performance, both internally and among investors.

While Square's gross payment volume increased by 12% in the second quarter, there has been a decline in gross payment volume per current merchant since Q3 2022, according to Block CFO Amrita Ahuja. She discussed Square's new sales strategy, which included distinct inbound and outbound teams for various industries.

Analysts have varying opinions on the implications of Henry's departure. Mizuho Securities Senior Analyst Dan Dolev sees potential in Dorsey's renewed focus on Square, suggesting it could lead to greater synergy between Square, Cash App, and Afterpay. Dolev also believes that a shift away from Bitcoin and towards the core point-of-sale (POS) business could be a positive long-term move for the company.

Henry's tenure as CEO has been instrumental in transforming Square into a software-led technology company, especially during the challenges posed by the global pandemic. While her departure marks a significant transition for the company, Block has expressed gratitude for her contributions and wishes her success in her future endeavors.

In the wake of Henry's departure, all eyes are on Jack Dorsey and his plans to steer Square towards continued success in an ever-evolving market. The coming months will undoubtedly be pivotal for the company and its investors.