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Dealmaker

A Pocket of Enterprise Software Investors Still Love

By Cory Weinberg · Jan 15, 2026 3:39pm PST
What do you get when you offset investors’ recent loathing of software startups with their lust for defense tech? Fast-growing Onebrief, the latest startup to double its valuation in a short span after raising $200 million this week from Battery Ventures and Sapphire Ventures at a $2.15 billion valuation, including the new investment.Onebrief... What do you get when you offset investors’ recent loathing of software startups with their lust...
Art by Clark Miller. Screenshots via YouTube.
AI Agenda

A $4 Billion Enterprise Software Firm Acquires AI Coding Startup Codegen

By Stephanie Palazzolo · Dec 23, 2025 7:00am PST
This year has been a big one for AI coding startup acquisitions. Who can forget the dramatic Google-Windsurf-Cognition saga from this summer? And this month alone, Anthropic acquired developer tool startup Bun and Cursor bought code review startup Graphite.Another coding deal is sneaking in before the end of the year. ClickUp, a $4... This year has been a big one for AI coding startup acquisitions. Who can forget the dramatic ...
Marc Benioff, CEO of Salesforce, speaks during the 2025 Dreamforce conference in San Francisco. Photo by Getty Images
Applied AI

The Real Winners of the Enterprise Software Market’s AI Agent Free-For-All

By Aaron Holmes and Kevin McLaughlin · Nov 13, 2025 10:30am PST
Something curious has happened in software: Nearly every established seller of enterprise tools started marketing the same general-purpose AI agents that aim to handle everything from drafting emails to customers to resolving IT service tickets. Even old-guard database providers like Snowflake are now in the AI applications game, going head... Something curious has happened in software: Nearly every established seller of enterprise tools...

160 Enterprise Software Startups That Could Be for Sale This Year

By Alix Coutures · Jul 16, 2026 6:02am PDT
Many enterprise software startups that raised money at steep valuations between 2020 and 2022 face diminishing options. Venture capitalists who previously sank funds into these startups have shifted much of their money toward AI. Stocks in public enterprise software companies have fallen sharply. When the startups’ backers push for cash returns,... Many enterprise software startups that raised money at steep valuations between 2020 and 2022...
The Prolonged Write-Downs in Enterprise Software Startups
Dealmaker

The Prolonged Write-Downs in Enterprise Software Startups

By Laura Mandaro · Jul 7, 2026 4:30pm PDT
It’s not easy to run an enterprise software company these days. For the nth example of this, read the latest story by my colleague Laura Bratton, who describes how an Atlanta real estate manager replaced Salesforce software with a custom app developed using Replit and Claude Code—saving $100,000 a year. Yipes. Fears that companies will... It’s not easy to run an enterprise software company these days. For the nth example of this, read...
Shantanu Narayen, Adobe chairman and CEO. Stefani Reynolds/Bloomberg via Getty Images.
The Briefing

Adobe CEO’s Departure and Enterprise Software Stress

By Martin Peers · Mar 12, 2026 5:00pm PDT · 2 comments
The Saaspocalypse may have claimed another scalp! Adobe said Thursday its longtime CEO and chair, Shantanu Narayen, had decided to give up the job as soon as his replacement can be found. Less than two months ago, Adobe had given Narayen an annual grant of stock, to vest based on the company's stock performance 2028, suggesting the board wasn’t... The Saaspocalypse may have claimed another scalp! Adobe said Thursday its longtime CEO and chair,...