“The New Clippy”: Benioff Uses Salesforce’s Biggest Product Launch in Years to Challenge Microsoft

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“The New Clippy”: Benioff Uses Salesforce’s Biggest Product Launch in Years to Challenge Microsoft Sheryar Siddiq Wed, September 23, 2026 at 12:46 AM EDT 4 min read CRM MSFT Marc Benioff is never one to pass up a chance to take a jab at Microsoft Corporation (NASDAQ: MSFT ), and Dreamforce 2026 was no different. The Salesforce CEO used the company's flagship annual conference in San Francisco to announce AIforce, the biggest product launch Salesforce, Inc. (NYSE: CRM ) has made in years, and to once again refer to Microsoft's Copilot as "the new Clippy," doubling down on a dig he made two years ago. Salesforce is positioning AIforce as an open, provider-agnostic layer rather than a single proprietary assistant. It's intended to work across multiple AI systems, including Anthropic's Claude, via a specific integration called Claudeforce, which Salesforce claims guarantees zero data retention by the model provider, as well as ChatGPT, Slack, and other environments. Salesforce, Inc. (NYSE:CRM) made the announcement alongside an additional strategic marker: a fiscal 2030 revenue target of $63 billion, which management reiterated at Dreamforce. Benioff portrayed AIforce as the solution to what he calls the "Fantasyland" problem, arguing that competing AI solutions, including Copilot, lack the dependable, controlled business-data layer required to consistently run enterprise operations. It's a continuation of a public feud that's been going on since at least Dreamforce 2024, when Benioff first compared Copilot to Clippy, Microsoft's widely mocked, uninvited desktop assistant from the late 1990s, saying, "We all know now that Microsoft Copilot is basically the new Microsoft Clippy, that customers have not gotten value from it." He's returned to that theme several times since, including at Davos, in an October 2024 written critique saying that Microsoft "lacks the data, metadata, and enterprise security models to create real corporate intelligence," and on a podcast where he labeled Copilot a "tremendous disservice" to the AI sector. Salesforce, Inc. (NYSE:CRM) shares closed at $255.65 on September 15, after a nearly 34% rally in the previous month following a rough start to 2026 that saw the stock tumble as much as 37%. That momentum was fueled by Salesforce's most recent quarterly results, which featured $11.35 billion in revenue, exceeding Wall Street's projections on both the top and bottom lines. Analyst reaction to the Dreamforce announcements was also favorable, with Stifel raising its price target for Salesforce, Inc. (NYSE:CRM) to $300 from $275 while reaffirming a Buy rating, citing six distinct revenue channels laid out by the company for monetizing its new AI stack, including additional core licenses, premium SKU upgrades, Agentforce spending, Data 360, Agent Fabric and Guardian, and APIs, MCPs and related infrastructure. Institutional posture shifted in similar directions for the two competitors. Salesforce, Inc. (NYSE:CRM) saw hedge fund ownership fall slightly, from 101 in the first quarter to 99 in the second. Microsoft Corporation (NASDAQ:MSFT) experienced a greater fall, from 282 funds to 273, though both declines predate the Dreamforce event and are more likely to reflect broader software-sector positioning moves than a direct read on this contest. Salesforce's pitch for AIforce as an open layer that brings Salesforce data, permissions and business logic into Claude, ChatGPT and other AI interfaces could still be an important competitive distinction, particularly for companies that want to use Salesforce context across multiple AI environments. The emphasis on regulated data access and zero data retention in Claudeforce directly addresses enterprise trust problems, which have hampered AI adoption elsewhere. However, Salesforce's stock has a documented history of rallying on analyst upgrades and conference announcements before reversing those gains, as seen with earlier JPMorgan and Citi buy calls in 2026, and pricing and adoption uncertainty around Agentforce remain unanswered questions even as new products pile on top of it. Microsoft's competition is also far from theoretical, considering Copilot's distribution advantage via Office and Dynamics 365. Investors should keep an eye on whether this round of enthusiasm lasts longer than previous Dreamforce-fueled surges, with confirmation likely to come from the next quarterly report, which will show whether Agentforce and now AIforce adoption numbers are translating into the kind of Data and AI revenue growth analysts are projecting with their newly set $300 price targets. Given the remaining uncertainty around how quickly Salesforce can convert AI adoption into meaningful revenue, the more reliable signal for investors will be concrete adoption and revenue-conversion data in upcoming earnings, rather than the announcement itself or the pre-Dreamforce rally that followed Salesforce's latest earnings report. While we acknowledge the potential of CRM as an investment, we believe certain AI stocks offer greater upside potential and carry less downside risk. If you're looking for an extremely undervalued AI stock that also stands to benefit significantly from Trump-era tariffs and the onshoring trend, see our free report on the best short-term AI stock . READ NEXT: 33 Stocks That Should Double in 3 Years and 15 Stocks That Will Make You Rich in 10 Years Disclosure: None. Follow Insider Monkey on Google News .

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