Salesforce Stock Slips After Buyback Spree, AI Worries Mount
Fell after the company named Miguel Milano as operating chief and disclosed a record $27 billion in buybacks. The move comes as investors question how AI will…
NEW YORK — Salesforce stock slid after the company promoted revenue head Miguel Milano to operating chief and said it had spent a record $27 billion on buybacks in the first quarter. The stock slipped another 4% in extended trading on Wednesday, while software shares stayed under pressure from artificial intelligence worries.
The move lands at a sensitive moment for Marc Benioff’s company. Salesforce shares have tumbled 27% this year, CNBC reported, and investors are still weighing whether AI tools will help the business or make its core software look less essential.
AI pressure hits Salesforce stock
Few companies have been hit as hard by the “SaaSpocalypse” as Salesforce, according to Yahoo Finance. The company built its name in software-as-a-service, but the rise of generative AI has raised a new threat: customers may use “vibe coding” and other AI tools to build custom software instead of paying SaaS vendors to do the work.
That fear has already shown up in the share price. By mid-2026, Salesforce stock was down nearly 60% from its high at the start of 2025, Yahoo Finance said. The latest drop on Wednesday added to that stretch of weakness and kept attention fixed on whether management can prove its AI push has real upside.
Benioff, who has run Salesforce since co-founding the company in 1999, has argued that AI will affect the business in a positive way. To back that view, the company took on a large amount of debt to buy back beaten-down shares. The $25 billion in accelerated repurchases, together with normal repurchases funded by cash flow, brought total buybacks to a record $27 billion in the first quarter.
Salesforce said the bonds it issued carry interest rates ranging from 4.5% to 6.7%. That matters because the company is choosing debt at a time when it believes its stock is cheap enough to buy aggressively.
Leadership shake-up adds to the signal
Milano’s promotion is another sign Benioff is widening the leadership bench. Milano returned to Salesforce as chief revenue officer in 2023 after earlier stints at the company in Europe from 2011 to 2020 and later at Celonis, where he served as chief revenue officer. He also made his first appearance on Salesforce earnings calls last year.
Robin Washington, a Salesforce board member who took on the role of chief operating and financial officer last year, will keep that title. Srini Tallapragada, president and chief engineering and customer success officer, is leaving after 14 years and will serve as special adviser to Benioff for the next year to help with the transition.
Salesforce also tapped Rohan Kumar, a longtime Microsoft executive who joined in June, as chief platform and engineering officer. The company has been pushing its Agentforce AI services, which are designed to automate tasks, but the market has not rewarded the effort yet.
That gap is what makes this latest stretch so important. Traders are not just watching buybacks and titles. They are watching whether Salesforce can show that its AI strategy protects revenue, steadies growth, and gives Salesforce stock a floor after a rough year.
The next test comes in how quickly Milano settles into the operating chief role and whether Benioff’s bet on debt-fueled repurchases looks smart enough to slow the slide.
