Salesforce stock hits longest losing streak on record amid AI acquisition anxiety

Salesforce just set a record nobody on its board wanted. The enterprise software giant’s stock has fallen for its longest consecutive stretch ever, driven by growing investor unease over its aggressive push into AI, and specifically, its latest multi-billion-dollar acquisition.

The company announced on June 15 that it would acquire Fin, an AI customer service platform, for approximately $3.6 billion. Instead of cheering the deal, the market punished CRM shares, extending a brutal losing streak that has seen the stock drop roughly 33-37% year-to-date through mid-June 2026.

The Fin deal and why Wall Street isn’t buying it

Fin builds AI that handles complex customer queries across multiple channels, with reportedly high autonomous resolution rates. The deal is expected to close in Q4 of fiscal 2027, pending regulatory approvals.

Salesforce built an empire on subscriptions. Companies pay per seat, per user, per month. That model has generated massive recurring revenue for two decades. AI agents that autonomously resolve customer issues don’t need seats. They don’t need licenses. They could, in theory, reduce the number of human users a company needs on the Salesforce platform.

The stock suffered a five-day decline of approximately 13% during one particularly rough stretch, part of the broader year-to-date collapse that has made 2026 a year Salesforce shareholders would rather forget.

An acquisition spree that’s raising eyebrows

Fin isn’t an isolated bet. Salesforce has completed over a dozen AI and data-focused acquisitions in the last 12-18 months.

Salesforce reported $11.13 billion in revenue for a recent quarter, a 13% increase year-over-year. Part of that growth came from Agentforce-related enhancements, which suggests the AI strategy is already contributing to the top line. But mixed guidance from the company, citing competition and transition costs, gave investors another reason to hit the sell button.

The $50 billion buyback and what it signals

Salesforce has also implemented a $50 billion share buyback program. A massive buyback alongside a massive acquisition spree creates a capital allocation question of whether Salesforce can afford to do both aggressively without stretching its balance sheet or sacrificing the R&D spending needed to stay competitive.

Microsoft has Copilot deeply embedded in its enterprise stack. Google is pushing Gemini into every workflow it can find. Salesforce is trying to compete with all of them while simultaneously managing a transition that could reshape how its customers pay for software.

The year-to-date decline of 33-37% creates a valuation that looks more attractive than it has in years. Revenue is still growing at 13%. The AI acquisitions, if properly integrated, could position the company as the dominant platform for enterprise AI agents. And the $50 billion buyback provides a mechanical bid under the stock.

Disclosure: This article was edited by Editorial Team. For more information on how we create and review content, see our Editorial Policy.