Salesforce Borrowed $25 Billion to Buy Its Own Stock. That Was the AI Strategy

Salesforce issued $25 billion in senior unsecured notes in March 2026, with maturities running to 2066, and routed the proceeds into the largest accelerated share repurchase in history. Senior notes on its balance sheet went from $8.5 billion to $33.3 billion in a single quarter. All of it happened five months before the company announced Claudeforce.

That is the core of what Stephen Messer, writing on Fortune.com, calls the SaaS debt trap — the bubble he argues nobody is watching while the market argues about data centers. "The bubble nobody is looking at has more legs than the one everyone is arguing about," he writes. When their multiples collapsed, SaaS incumbents took on record debt, bought back their own stock, and packaged it as an AI strategy. He calls the endpoint "a debt-driven death loop that ends in a Bending Spoons offer letter."

The substrate has hardened

The numbers behind the pressure are stark. The SaaS index fell 6.5% in 2025 while the S&P 500 rose 17.6%. Median SaaS revenue multiples went from 18x in 2021 to about 3x. IBM dropped 13.2% on February 23 — its worst single day in more than 25 years — after Anthropic demonstrated Claude Code modernizing COBOL. Jasper's revenue fell from $120 million to $55 million in one year.

On the other side of the ledger, Anthropic's annualized run rate crossed $65 billion at the end of July, per Bloomberg, up sevenfold from the $9 billion it exited 2025 on. The New York Times reports Anthropic is on track to top $100 billion in annualized revenue this year and could list as soon as November. Q2 2026 revenue alone was $11.5 billion, up 14x year over year.

Put in market-cap terms: Anthropic, at $965 billion and expected to trade at double that at IPO, is worth more than Salesforce, Adobe, ServiceNow, Workday, and HubSpot combined — those five names sit at roughly $544 billion of public equity as of September 18. Add OpenAI at $852 billion, and the two leading language-model labs approach two trillion dollars in private value.

The Salesforce sequence

Messer walks through the mechanics. Salesforce's board authorized a $50 billion share repurchase in February 2026. The initial ASR delivery retired 103 million shares in one quarter at a $198.34 reference price — roughly 80% of the expected total. A separate $6 billion five-year term loan closed the Informatica acquisition. Critically, Messer notes, Salesforce entered March with $7.3 billion in cash. "Management had capital and chose to borrow anyway."

Then came August 26 and the Q2 FY27 earnings call, where Marc Benioff announced Claudeforce — Claude inside Salesforce, Salesforce inside Claude, thirty-seven prebuilt sales skills. He also told the sell side: "This nonsense of the SaaSpocalypse, I think it's time for it to stop." The stock jumped 22.58% in two days.

But the earnings surprise, Messer points out, rested heavily on a $2.7 billion markup of Salesforce's Anthropic stake — a single line item that covered 96% of the beat. That Anthropic position is worth about $5 billion, close to two-thirds of the entire Salesforce Ventures strategic portfolio. On the same call, Benioff floated selling the stake to help pay down the buyback debt. "Two paper gains, one cash event. Neat," Messer writes.

The deeper problem: Claudeforce effectively gave every Salesforce customer "a first-class path to replace the SFDC front end with an AI-generated CRM over a weekend." Front-end lock-in was a big piece of the moat.

The whole category is running the same play

• HubSpot: Down 48% at the low, worst in the category per Bernstein. A $1 billion buyback authorized in February 2026, doubled by another $1 billion in August — $2 billion in seven months.
• Workday: Down 43%, its worst year since the 2012 IPO. A fresh $4 billion buyback on August 27, on top of $2.9 billion executed in fiscal 2026. Cash fell from $5.4 billion in January to $3.4 billion in July. Co-founder Aneel Bhusri's defense: "no amount of vibe coding is going to produce an HR or an ERP system."
• ServiceNow: Dropped 18% in a single day, its worst on record. A $5 billion buyback authorized January 28; a $2 billion ASR executed January 30 at an average price of $107.97. More than 20 million shares retired in Q1 alone.
• Adobe: Down 28% in 12 months. A new $25 billion buyback authorized in April despite the broken stock. Prior buybacks of $23.3 billion were executed at an average around $412; the stock now sits at $250. CEO Shantanu Narayen is out December 1.
• IBM: Down 22% through February, with total debt around $55 to $61 billion and no frontier model in response to the Claude Code COBOL threat.

"Not one incumbent has a strategy for saving the business," Messer writes. "All of them have a program for managing the stock price."

The buyers are moving

The replacement is running ahead of the coverage. Curative, a health insurer with 165,000 members and more than $1 billion in ARR, canceled its $600,000 Salesforce contract and rebuilt in two months — confirmed by Business Insider after founder Fred Turner disclosed it on 20VC. Curative targets eliminating 80% of its SaaS spend in 2026 and cutting headcount from 650 to 400.

Three law firms committed $1.5 billion combined to build their own AI: Kirkland & Ellis put in $500 million over three to four years on May 28; Morgan & Morgan doubled it with $1 billion over ten years for MX2 on September 14; Latham & Watkins bought its own Nvidia GPU servers to run open-weight models on-premise. Meanwhile, roughly $150 billion of venture capital flowed into AI developer tools in 2026 alone — Cursor at $60 billion, Cognition at $25 billion.

The floor has a name: Bending Spoons

On August 4, Bending Spoons agreed to acquire Airtable for $1.285 billion in enterprise value. Airtable's roughly $480 million ARR, growing over 20% year over year, with 500,000 organizations and 80 of the Fortune 100 as customers, cleared at 2.68x revenue on enterprise value — or 4.7x on equity once its $965 million of net cash is counted. Airtable peaked at $11 billion in 2021.

Apply those floors to the incumbents and the math is unforgiving, Messer argues. Adobe trades 14% below even the friendly equity floor; Workday 8% below; HubSpot 29% below. Every one of the five has room down to the operating floor. Adobe retired $23.3 billion of stock at prices more than double the operating floor.

Messer notes the debt itself is serviceable — Salesforce generated roughly $14 billion in free cash flow last year, and the March 2026 notes carry weighted-average coupons north of 5%. The issue is what the capital structure signals: "A growth compounder just committed a large chunk of its future cash flow to bond payments instead of growth investments, at exactly the moment the growth investments were most needed."

Dreamforce wrapped September 17 with roughly 43,000 attendees, down from about 50,000 in 2025 and 75% off the 2019 peak of 171,000 — five straight years of decline. Benioff called for the SaaSpocalypse nonsense to stop. Dreamforce 2026, Messer counters, "may be remembered as the day it actually began."