Jason M. LemkinCEO, SaaStr · Co-Founder of SaaStr AI, SaaStr Fund, Adobe Sign

You Want Your Sales Team to Make a Lot of Money

23 Feb 2024 · 1 min

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0:49

Jason M. Lemkin recounts an anecdote from his first investment, Pipedrive, an SMB CRM he invested in when it was ~ $2M ARR and 100% self-serve. He placed a former employee as the first sales rep; the rep quickly out-earned the founders in three months and found immediate upsell opportunities by identifying self-serve customers who had purchased multiple seats (e.g., AOL with 20 seats). The story highlights cultural resistance at self-serve companies to hiring salespeople, and the revenue opportunities in converting multi-seat self-serve accounts to larger purchases.

Chapters

Remember, the first investment I ever made was a company called Pipedrive, which sold for a billion and a half, you know, SMB, CRM. And I put in the first sales rep there. He used to work for me. And the founders got mad at him. They got mad at him because in three months he was making more than any of the founders. They're, they were pissed. I'm like, guys, I know we're, we're have different backgrounds and cultures, but this is what you want. But it took him a long time culturally, as self serve, because Pipedrive was 100% self serve at the time. They'd never had a sales rep. And I put the guy in and what he did was he went, he looked all these self serve customers. He's like, it was, this was. The company was at about 2 million revenue at the time. And he's like, okay, who's bought more than one seat? He just did a reverse sort. And he called them, I remember he called AOL back in the day and he's like, you guys have 20 seats of pipedrive, would you like to buy more for your sales team? They're like, thank you very much.