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The Labor Gap No One Talks About: Why AI Will Fill the Jobs Humans Won’t Do in Tech

Sep 1, 2025

Will AI take away jobs in tech? Some of course. Even more often, already, it’s leading to headcount being rebooted and used in new ways. Salesforce for example has already repurposed headcount from 1000s of support agents into sales. Same headcount, but different...

From Zero to $25B in 17 Years: The Inside Story of HubSpot’s Domination Strategy

Sep 1, 2025

When HubSpot rang the NYSE bell on October 9, 2014, at $25 per share, most observers saw another marketing automation company going public. What they missed was witnessing the birth of one of SaaS's most consistent wealth-creation machines. The scorecard after 10.7...

Dear SaaStr: As a Founder, What Were the Sketchiest Things a VC Asked You To Do?

Sep 1, 2025

Dear SaaStr: As a startup founder, what's the shadiest thing a VC asked you to do (to get their funding)? I don’t think anything is truly shady in venture. Deals are generally made at arm's length, and founders don’t have to sell any shares if they don’t want to. But...

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