Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889

Three, two, one, zero. You have now arrived at your destination.

Oj, this is such a joy to do. I heard so many good things from Danny Herzberg before the show, and many other guests, so thank you so much for joining me today.

Oh, I'm so happy to be here.

That is very, very kind of you. I've been looking forward to this one. But I wanna start with some context. So you've worked in some of the most incredible hypergrowth companies, from Dropbox to Asana. Tell me, how did you make your way into sales and come to lead some of these incredible sales orgs?

Uh, you know, I... First couple of years my, in my career was in finance. I, I, I was in first starting equity research at Morgan Stanley and covering tech companies. That was my first exposure to how the, sort of the intersection of tech and business. Um, then I went over to venture, uh, and, and I worked at NEA for a bit. Uh, loved, loved my time there. In that experience, I really saw how amazing some, uh, investors were bas- sort of leveraging their operating background to help founders.

Mm-hmm.

So I got that curious about operating, and all the GPs I really admired, they were like, "Hey, you should operate, and if you're gonna operate, you either build product or you sell product. Everything else is supporting one of those two." And I was like, "Oh, interesting." And, and just one thing led to another. I just hap- ... It was like 50/50. I went down the sales path, and that was the, that was the path I ended up on.

I love that. I love that kind of simplicity of you either build or you sell. Um, I do wanna ask that, you know, when we look back at the time, six years Asana, four years Dropbox, at pivotal moments of scaling for both companies, when you think back to that, and if you isolate one or two key takeaways from each, what would you say they would be, looking back and reflecting?

So, drop- Dropbox, I think for me, number one, is that, uh, technology is just fundamentally diff- uh, adopted differently in businesses. B2B businesses, uh, are, uh, no longer by the traditional top-down way in terms of how technology is used in, in companies. Uh, employees get to pick, right? And that started with Apple with the iPhone in, in probably around, what, 2000 and, 2010, right, when people had this BYOD move, and Dropbox was the, was the company that shattered and started the BYOA move. And so th- I think that's number one. And so as a result, number two is that, you know, PLG is fundamentally is a very different kind of go to market than traditional B2B sales. I think that's the main thing I took from Dropbox. Had the opportunity to then apply that to Asana. And, I think what I learned at Asana was, if I had to pick one thing, it would be this concept of product-led growth sales and traditional enterprise sales. You know, at, when I first joined Asana, and even today, when I talk to a lot of people, I think there is this predominant view of that you can, you got to pick one or the other. And, at Asana, we pioneered, and we, we try to do both at the same time. And, and I think the results were quite positive, and I think it dem- My takeaway is that it is possible. Uh, it's hard, but it is possible.