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pitdesi notes Sequoia and Benchmark led a Series A in 2023 reportedly investing…
Brief
pitdesi reflects on a 2023 Series A where Sequoia and Benchmark reportedly put $25M on a $145M post-money valuation, using it to argue that deal execution — not contrarianism — makes returns. Bret Taylor’s parallel announcement: Sierra raised $950M from Tiger Global and GV at >$15B, with >$1B to deploy and adoption by 40% of the Fortune 50.
Why it matters
pitdesi notes Sequoia and Benchmark led a Series A in 2023 reportedly investing $25M on a $145M post-money valuation, arguing the takeaway: you don’t have to be contrarian to make money — you have to win the deal (tweet dated 2026-05-04).
Key details
- Bret Taylor announced Sierra is raising $950M led by Tiger Global and GV at a valuation over $15B, giving the company more than $1B to invest; Sierra now serves over 40% of the Fortune 50 and its agents power billions of customer interactions (announcement referenced 2026-05-04).