PLG vs. Enterprise: Mistakes We Made in Sales with Calendly's CEO

6 Jul 2025 · 0 min
0:05

Calendly's CEO explains how the company's 2020 sales expansion backfired. They hired aggressively to chase enterprise deals, but relaxed qualification rules meant prospects talked to sales unnecessarily, slowing deals and raising customer acquisition costs faster than revenue grew. The hybrid model cannibalized their self-serve business.

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