You Want Your Sales Team to Make a Lot of Money

23 Feb 2024 · 1 min
0:49

In this monologue, Jason M. Lemkin recounts his first venture investment in Pipedrive, a SMB CRM that later sold for $1.5 billion. He describes hiring the company's first sales representative—a former employee of his—despite the founders' cultural resistance because the business was 100% self‑serve. Within three months the rep generated more revenue than any founder, prompting both frustration and admiration. The rep identified existing multi‑seat self‑serve customers, such as AOL, and directly called them to upsell additional seats, dramatically increasing revenue from a $2 million base. Lemkin uses this story to illustrate the power of early sales hires and proactive upselling in self‑serve startups.

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