Jason Lemkin: evaluation

Transcript context

…Amazing advice. Wow. There's so much there. I'm going to follow a couple threads there. In terms of the level, I know a lot of people make the mistake of going with a VP of sales pretty quickly. What's your advice? I know you talked about general attributes, but what's your advice for the level and seniority of these first two hires? Two things, one that's evergreen and one that's maybe especially apropos for today's environment. The evergreen one, which I've talked about for over a decade, and I think folks that have been through it will see it, which is you need two sales reps hitting quota closing deals before you're ready to hire a manager for them. Almost all VPs of sales, their job is to take you from rep three to 300, to take you from three to 300, to take something that's just starting to repeat, a script that's just starting to work, leads that are just starting to come in. Then take Lenny and Jason, the two reps I have, as quirky as they are, they're crushing it. Then I'm going to hire a more heterogeneous type of person going forward. I'm going to hire the person from Cloudfare. They can't all be like Lenny and Jason, they're pretty quirky, but at least I can learn from them. What's working? What are the objections? How do we get around that feature gap? We're one year old, we're two years old. We've got a lot of feature gaps. This integration doesn't quite work. How do we box around those issues? How do we sell our 10x feature? Because if you're a startup, your product isn't very good, your software is not very good, and you have a competitor, but you have some 10x feature that is driving people to buy you something you're doing that does not exist in the marketplace. The really good reps get insanely good at selling that, and the folks off the street, the new VPs often doesn't even understand the 10x feature. It's too subtle. It's too subtle. Why? The fact that your product is localized in Portuguese magically means you can win these deals. I'm making up something that doesn't quite make sense. So you need two reps that are hitting quota and then you hire VP of sales. If you hire it before then, you're doing a Hail Mary. It ain't going to work. It never, ever, never, ever, ever, never, ever works. You're asking them to find product market fit to be the first rep, to be the second rep and scale it all at the same time. It's mission impossible to do all four at the same time. So that's the biggest mistake is, Lenny, I can't get sales going at my company. I can't do it, but I raised $4 million in my C+ round. I'm going to go out and hire the VP of sales. That VP of sales will not be there in eight months. You know what else? 2 million of the four will be gone because they'll never understand the product. They will never understand. There's so many things we could talk about, but if there's one thing I could reinforce for this audience, it's that early sales team, they've got to be product gurus for your product audience. They've got to be product experts. Later as you scale, they can't be or you can't scale. When I started, when I came out of my own startup and started interviewing other folks, I remember I would interview a lot of folks at places like GitHub back in the day. I'd be like, "Do you have a technical background? Are you an engineer? startup and started interviewing other folks, I remember I would interview a lot of folks at places like GitHub back in the day. I'd be like, "Do you have a technical background? Are you an engineer? Have you ever built any software?" They're like, "No, I don't. I don't know. I don't know," and I was like, "I was curious how you could do it," but GitHub was so well-established that it's 10 questions. It's 10 questions and grab a sales engineer. It's 10 questions and grab ... So you got to be really good at 10 and then you grab a sales engineer. That doesn't work in the early estate startups. So you've got to find these sales folks that are a bit of product savants and dropping the VP of sales in that isn't a product savant, which is a big issue. That's all mister or miss process. This is the issue. They're all mister or miss process. So the second point I wanted to make, and I was on the fence for years of when you hire a VP of sales, do they need to carry a bag? Do they need to sell themselves or not? Does it matter? Does it matter? I wasn't sure for a long time. The reason I wasn't sure for a long time, it's not that you don't want a VP of sales carrying a bag. I do think a VP of engineering also should commit code. We can talk about that.…

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