From Fortune · Stephen Messer · · 5m
The SaaS debt trap closes in
Legacy software giants borrowed billions to buy their own stock, betting on AI. The bet is failing, and the reckoning has started.
In brief
Legacy software giants borrowed billions to buy their own stock, betting on AI. The bet is failing, and the reckoning has started. SaaS incumbents funded massive buybacks with debt instead of investing in AI, while customers rebuild their systems with AI-native tools. The strategy is collapsing. Originally reported by…
The wrong debate
Everyone argued about whether AI infrastructure was a bubble. The real problem was hiding in plain sight: SaaS incumbents taking on record debt to buy back stock.
The substrate hardened
Anthropic's annualized revenue crossed sixty-five billion dollars at the end of July, up sevenfold from nine billion at the end of twenty twenty-five. Every quarter it added a Snowflake plus a Palantir.
Model labs dwarf SaaS

Anthropic alone, at nine hundred sixty-five billion dollars, is worth more than Salesforce, Adobe, ServiceNow, Workday, and HubSpot combined. Those five sit at roughly five hundred forty-four billion dollars.
Salesforce's capital choice
In February twenty twenty-six, Salesforce's board authorized a fifty billion dollar share repurchase. In March the company issued twenty-five billion in senior unsecured notes and routed proceeds into the largest accelerated share repurchase in history.
Salesforce had cash
Salesforce entered March with seven point three billion dollars in cash. Management had capital and chose to borrow anyway instead of investing in a proprietary model or strategic stakes.
Claudeforce launches

On August twenty-six at the Q two FY twenty-seven earnings call, Benioff announced Claudeforce. Claude inside Salesforce. Salesforce inside Claude. Thirty-seven prebuilt sales skills. The stock jumped twenty-two point fifty-eight percent in two days.
The earnings surprise
Salesforce marked its Anthropic stake up by two point seven billion dollars in the quarter. That single line item covered ninety-six percent of the earnings surprise. Benioff floated selling the stake to help pay down buyback debt.
What Claudeforce really did
Any Salesforce customer with an API key could have called Claude the day before Claudeforce. The announcement gave every customer a path to replace the Salesforce front end with an AI-generated CRM over a weekend.
Benioff's line
On the earnings call, Benioff said: "This nonsense of the SaaSpocalypse, I think it's time for it to stop." The stock jumped on the statement, not on product news.
“This nonsense of the SaaSpocalypse, I think it's time for it to stop.”
HubSpot runs the same play
HubSpot dropped forty-eight percent at the low. Response: Breeze, an AI agent lineup, and a February twenty twenty-six authorization for a one billion dollar buyback. Another billion added in August.
Workday's signal
Workday dropped forty-three percent, worst year since the twenty twelve IPO. Agentic AI ARR grew over two hundred percent. The board authorized a fresh four billion dollar buyback on top of two point nine billion executed in fiscal twenty twenty-six.
ServiceNow and Adobe follow
ServiceNow authorized a five billion dollar buyback and executed a two billion dollar accelerated share repurchase at one hundred seven point ninety-seven dollars per share. Adobe authorized a new twenty-five billion dollar buyback running through twenty thirty.
Curative cancels Salesforce
A regulated health insurer canceled Salesforce and rebuilt in two months. Curative, with one hundred sixty-five thousand members and more than one billion in ARR, canceled its six hundred thousand dollar Salesforce contract. The rebuild took two months.
Kirkland builds its own AI
On May twenty-eight, Kirkland and Ellis committed five hundred million dollars over three to four years to build a proprietary platform, funded from revenue. Morgan and Morgan doubled it with one billion over ten years for MX two.
Rillet replaces ERPs
Rillet closed a one hundred million dollar Series C at a one billion dollar valuation on August twenty. Customers replace NetSuite, Sage Intacct, Oracle Fusion, SAP, Workday, and Microsoft Great Plains. Slash Financial raised one hundred million at one point four billion in April.
Dreamforce attendance collapses
Dreamforce wrapped September seventeen with roughly forty-three thousand attendees, down from about fifty thousand in twenty twenty-five and roughly seventy-five percent off the twenty nineteen peak of one hundred seventy-one thousand. Five straight years of decline.
Airtable sets the floor
On August fourth, Bending Spoons agreed to acquire Airtable for one point two eight five billion in enterprise value. ARR was about four hundred eighty million growing over twenty percent year-over-year. The operating business cleared at two point sixty-eight times revenue.
Buyback prices versus floors
Adobe retired twenty-three point three billion at an average of four hundred twelve dollars per share against an operating floor near one hundred seventy. Salesforce's ASR at one hundred ninety-eight dollars lands at the equity floor and roughly twice the operating floor.
The death spiral begins
The buyback stops working. Replacement buyers ship. Debt payments do not care. Salesforce generated roughly fourteen billion in free cash flow last year, but committed future cash flow to bond payments instead of growth investments at exactly the moment they were most needed.
The short version
SaaS incumbents funded massive buybacks with debt instead of investing in AI, while customers rebuild their systems with AI-native tools. The strategy is collapsing.


