The agile enterprise’s trick to winning with AI? Tidying up.

In a recent Fortune column, Freshworks CEO Dennis Woodside makes the case that mid-market companies winning with AI are outexecuting, not outspending, the competition

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Derek Korte

Derek KorteManaging Editor at Freshworks

May 21, 20261 MIN READ

The most common explanation for why enterprise AI investments stall is that the technology isn't ready. The more honest explanation? The operating environment underpinning it all wasn’t.

That's the argument Dennis Woodside makes in Fortune, drawing on research, Freshworks customer examples, and a pattern he's watched play out across the mid-market. When Seagate's IT team had three months to replace the platform running its global operations for 30,000 employees, they faced a choice: replicate the existing configuration and reconcile the mess later, or rebuild from the ground up. They rebuilt. A year in, the AI agent on top of that clean foundation deflects roughly a third of incoming tickets and resolves issues 27% faster than the industry standard.

The decision to stop dragging the past forward before layering intelligence on top is a common strategy across agile enterprises transforming their service operations with AI, Woodside argues. 

Those businesses don’t win by outspending or outscaling the competition. They win by making smarter decisions about where to start and what success looks like. That discipline, it turns out, might be a more durable AI advantage than an outsized technology budget. 

Read more from Woodside on LinkedIn. 

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