Enterprise Software

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The Real Cost of AI: A Survey of the Unpredictable Token Economics

By The Information Partnerships · Sep 21, 2026 9:04am PDT
For decades, enterprise software budgeting was a predictable exercise: negotiate a subscription fee, project the number of seats you need, move on. AI has broken that model. Pricing tied to tokens — the metered unit behind most AI billing — has turned technology spend into a variable cost, and an unpredictable one. The Information’s survey of... For decades, enterprise software budgeting was a predictable exercise: negotiate a subscription...
Pro subscription required icon Pro subscription required icon Art by Clark Miller.
Deep Research

Can AI Tollgates Become the New SaaS Model?

By The Information Staff · May 7, 2026 11:49am PDT
AI agents are forcing enterprise software companies to defend the business model that made them rich: charging for every human user. Companies like ServiceNow and SAP are starting to redraw the boundaries around their software, with some restricting how outside agents get in. Others are testing new usage-based pricing models to reflect how AI... AI agents are forcing enterprise software companies to defend the business model that made them...
Art via Mike Sullivan
Sunday Insights

Atlassian and HubSpot Join Shift From AI Flat Fees

By Laura Bratton and Aaron Holmes · Apr 26, 2026 8:00am PDT · 14 comments
Dozens of enterprise software firms have shifted away from charging customers flat, per-user subscription fees as AI threatens their seat-based pricing model. By the end of 2025, 79 of the 500 software companies tracked by former OpenView partner Kyle Poyar, including HubSpot, Adobe and Salesforce, had begun charging customers additional fees... Dozens of enterprise software firms have shifted away from charging customers flat, per-user...
Atlassian and Figma Lead the R&D Arms Race
By Laura Bratton · Apr 12, 2026 8:00am PDT · 4 comments
Sunday Insights

Atlassian and Figma Lead the R&D Arms Race

By Laura Bratton · Apr 12, 2026 8:00am PDT · 4 comments
Wall Street’s sell-off of enterprise software stocks resumed in earnest late last week, sending stocks such as ServiceNow and Snowflake down around 8% or so on Friday, as jitters over the impact of new AI tools on older software firms intensified. But the panic may be too indiscriminate. One way of sorting out which software firms may have more... Wall Street’s sell-off of enterprise software stocks resumed in earnest late last week, sending...
Art via Clark Miller
Exclusive

Microsoft Lowers Sales Staff’s Growth Targets For Newer AI Software

By Aaron Holmes · Dec 3, 2025 6:00am PST · 7 comments
Executives at Microsoft and other enterprise software firms heralded 2025 as the year artificial intelligence would be capable of automating tasks that involve multiple steps, such as generating dashboards based on company sales data. But as the year comes to a close, Microsoft has lowered expectations for how quickly it can get customers to... Executives at Microsoft and other enterprise software firms heralded 2025 as the year artificial...
Sridhar Ramaswamy. Photo by Getty
Exclusive

Snowflake Sets $100 Million Target in AI Sales Push

By Kevin McLaughlin · Apr 29, 2025 10:46am PDT
Snowflake and other enterprise software firms whose success predates the rise of ChatGPT are trying to recast themselves as artificial intelligence companies. They’ll have to persuade corporate customers to choose their offerings in what has become a very crowded field. The pressure is particularly acute for Snowflake CEO Sridhar Ramaswamy, who... Snowflake and other enterprise software firms whose success predates the rise of ChatGPT are...
Cohesity CEO Sanjay Poonen. Photo via Getty
Exclusive

Cohesity Plans Employee Share Sale, Deferring IPO

By Natasha Mascarenhas and Kevin McLaughlin · Feb 25, 2025 3:31pm PST
One of enterprise software’s bitter rivalries—between data security firms Rubrik and Cohesity—came to a head last year when Rubrik went public in an offering with a nearly $7 billion valuation. Now Cohesity, which is still private, is pitching investors on the notion that it’s the better deal. The Santa Clara, Calif.–based... One of enterprise software’s bitter rivalries—between data security firms Rubrik and...
Photo via Getty
Google and Microsoft Force Customers to Pay For AI
By Jon Victor and Aaron Holmes · Jan 16, 2025 11:26am PST
Photo via Getty
Applied AI

Google and Microsoft Force Customers to Pay For AI

By Jon Victor and Aaron Holmes · Jan 16, 2025 11:26am PST
For the last two years, enterprise software companies have been trying to convince customers to fork over more money for new artificial intelligence features, such as generating notes from conference calls and ginning up images for slide presentations.Now, the software firms are no longer asking. Google said Wednesday it would automatically... For the last two years, enterprise software companies have been trying to convince customers to...
Sridhar Ramaswamy. Photo by Getty.
The Briefing

What Snowflake’s CEO Shake-Up Means

By Martin Peers · Feb 28, 2024 5:00pm PST
Big news tonight in the enterprise software sector—and we’re not talking about Salesforce introducing a dividend (although that’s notable). No, the real headline is an AI-inspired changing of the guard at Snowflake, until recently a fast-growing enterprise software hotshot whose 2020 IPO turned into a blockbuster. Snowflake CEO Frank Slootman is... Big news tonight in the enterprise software sector—and we’re not talking about Salesforce ...
Photo by Bloomberg.
Exclusive

Palo Alto Networks Woos Customers With Years of Free Software as Cloud Security Sales Slow

By Aaron Holmes · Apr 14, 2023 6:00am PDT · 1 comment
The slowdown in enterprise software spending is forcing some software firms to go to extraordinary lengths to win business. Palo Alto Networks, for instance, is giving away cloud security service—literally. The company, which is the biggest stand-alone security software firm measured by market capitalization, is offering its cloud security... The slowdown in enterprise software spending is forcing some software firms to go to...
True Value

Why ‘Battered’ SaaS Valuations Look Out of Touch With Reality

By Akash Pasricha · Aug 15, 2022 1:29pm PDT · 3 comments
Valuations for publicly traded enterprise software companies such as Salesforce and Workday have plunged from pandemic-era peaks, thanks to rising interest rates and worries that customers will cut software budgets during an economic slowdown. But there are signs the sell-off has gone too far. For the first time since at least 2019, the... Valuations for publicly traded enterprise software companies such as Salesforce and Workday have...
Adam Selipsky. Photo by Tableau
The Briefing: Amazon’s Unexpected AWS Choice
By Martin Peers · Mar 23, 2021 5:01pm PDT
Adam Selipsky. Photo by Tableau
The Briefing

The Briefing: Amazon’s Unexpected AWS Choice

By Martin Peers · Mar 23, 2021 5:01pm PDT
Amazon surprised the enterprise software industry with its choice of Adam Selipsky, chief of Salesforce’s Tableau unit, to succeed Andy Jassy as CEO of the cloud unit. Selipsky is a onetime lieutenant to Jassy, who is moving upstairs to Jeff Bezos’ job. So he has the experience for the role. But Selipsky had been seen as a possible... Amazon surprised the enterprise software industry with its choice of Adam Selipsky, chief of...
From left: Snowflake's Frank Slootman, Palantir's Alexander Karp and Asana's Dustin Moskovitz. Photos by Snowflake, Bloomberg and Julie Mikos.
True Value

Five New Software Stocks: Why Investors Love Some and Hate Others

By Ross Matican · Sep 15, 2020 6:02am PDT · 2 comments
Five enterprise software companies are going public this month, cashing in on the sector’s enormous popularity with investors. But while investors love some of the companies, such as Snowflake, giving it a valuation of nearly 100 times’ last year’s revenue, they hate others. Sumo Logic, for instance, may get a valuation of just... Five enterprise software companies are going public this month, cashing in on the sector’s...
Box CEO Aaron Levie. Photo by Bloomberg.

What Box Founders Learned from Tough IPO

By Eugene Kim · Apr 18, 2017 10:02am PDT · 3 comments
When going public, an enterprise software company needs an explanation of their business so simple that it can be written down on a cocktail napkin. That’s one of the lessons Box’s co-founders Aaron Levie and Dylan Smith learned after the cloud file storage company went public in 2015. And it’s a good lesson for the current... When going public, an enterprise software company needs an explanation of their business so...
Cloudera co-founder Mike Olson. Photo by Bloomberg.
Exclusive

Enterprise Cos. Cry Foul Over ‘Open’ Data Alliance

By Steve Nellis · Mar 3, 2015 7:01am PST · 3 comments
When three big enterprise software companies announced last month they had agreed to a set of common tools for analyzing big data, it may have seemed like just another boring partnership in the world of business software. But the agreement between Pivotal, Hortonworks and IBM was much more. The creation of the so-called Open Data Platform set... When three big enterprise software companies announced last month they had agreed to a set of...