Leadership turnover is accelerating across enterprise software. In a market recalibrating around AI disruption and tighter valuation discipline, CEO resets are becoming part of the structural shift. This month alone saw notable CEO transitions at PayPal Holdings with Alex Chriss leaving, at Expand Energy with Nick Dell’Osso’s exit, and at Workday with Carl Eschenbach stepping down.
We’ve covered numerous turnaround situations before, and Workday now joins that list. Turnarounds can generate meaningful upside when executed well, but regaining momentum after growth slows or strategy drifts is rarely straightforward.
In many cases, boards turn back to founders or former CEOs during these moments, giving rise to so-called “boomerang CEOs.” Howard Schultz returned to steady Starbucks (SBUX), Bob Iger stepped back in to guide Walt Disney, and Kevin Plank reclaimed leadership at Under Armour (UAA) after a slowdown. Workday’s founder-led transition now unfolds against a similar backdrop, one defined by fears of AI-driven disruption and heightened execution pressure.
Workday (WDAY): $142.63
Market Cap: $38.08B
EV: $39.40B
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