ChatGPT CTO Hire Investment 
SaaStr
JUNE 20, 2025
The Infrastructure Bypass Midmarket software companies are caught in a “pressure cooker” with fast-moving AI startups developing applications far more rapidly than traditional software companies on one side, and tech giants investing billions in proprietary AI tools on the other.
SaaStr
OCTOBER 25, 2023
For part one of this Ask Me Anything session, Jason covers everything you need to know about hiring your first VP of Sales, what he really thinks about AI, what the future of lead generation in 2024 looks like, and much more. But only if you do it every week at the same time and never stop. Let’s jump right into the questions.
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Crafty CTO
APRIL 17, 2023
In a recent conversation, we laughed about how tough it is to stay up with the AI Emergence, and I pointed out that it’s almost a full time job just keeping up with him , let alone everything else happening in the AI world. Willison is prolific, to no small degree, because he’s skilled at applying tools like ChatGPT.)
Andreessen Horowitz
DECEMBER 4, 2023
To improve the efficiency of spend on cost of goods sold (COGS), most growth-stage leaders can optimize seat-based spend or renegotiate consumption-based contracts in a quarter or 2. Focus on performance management of your product and engineering teams as early indicators for what R&D investments are working, and which aren’t.
Sales Hacker
SEPTEMBER 20, 2024
Read more about true differentiation in sales data in Primary Venture Partners’ article on why they invested in Operator. The Co-Founders brought in an insanely talented team: Pleasant Middelhof , (COO), Jeremy Jonas (CTO), and Carl Gunderson (Software Engineer). Like chatGPT but more powerful, built just for sellers.
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