Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908

(beeping) Three, two, one, zero. You have now arrived at your destination. Sam, this is such a joy. You know I always love our chats, but, uh, thank you so much for putting up with my dulcet tones once again.

Get out of here with that. It's always great to see you. Always great to hear from you.

You know, fake humility is always good to have.

(laughs)

Um, but, uh ... (laughs) But, uh, for those that missed our first show, tell me, how did you make your way into the world of tech and, most importantly, sales? What was that entry point for you?

So, definitely not a direct line from university or school straight into it. Held a number of random jobs in a number of different industries. So, studied environmental science, did environmental consulting. I was on the purchasing side of the house, that got me on the phones, uh, at a silicon wafer distribution company. Won't even get into-

(laughs)

... or unpack what that means. Take a whole show. Um, but ultimately, uh, got my start on both the technology and sales side at Salesforce back in 2010. Um, was fortunate enough to stumble my way into the Dropbox organization as one of their first five salespeople back in 2011. Uh, and it's really snowballed from there. And so, have been having the opportunity to learn from and work with some amazing teams between the Dropbox crew/now mafia. Uh, I think a number of folks have been on this show with you. And, uh, then also ended up on, on a couple of small growth teams at Quip, which brought me back to Salesforce, and then now, been holding things down with the Loom crew for the last, roughly, 18 months.

I mean, actually it's perfect timing 'cause we released a show, uh, just, just recently with Zhenya, and obviously he spent time, I presume, with you at Dropbox. And-

He did. Yep.

... so I'm, I'm fascinated to hear. When we think about Salesforce and Dropbox, two such iconic companies, if we were to isolate, like, one or two takeaways for you from each, what would you say those are that've really shaped how you think today as a sales leader?

So, I think Dropbox, with it being a decently early pioneer, if we want to call it, on the product-led side of the house, I think the, the early learning for me particularly is we were building the direct sales motion in tandem with the product-led side, is-

Yeah.

... security's not enough. You need to find more value than just security when you're thinking about a consolidation plan. I think a learning for me along the way was we were really trying to take the density of user engagement and our, our de facto was going and selling to IT or CIOs around, "How do we roll this up and how do we protect the house," so to speak. Um, which when you put it in those terms, like, you're basically positioning your service as a liability as opposed to a value add. Uh, and effective in certain ways, but, you know, in a, a environment where I think that we have to make sure that we are continuing to align with the goals of our customers, align with the impact, and particularly on the future of work side of things, like, what are we doing to enable a more effective and efficient workforce? And so I think, for me, really taking that lens, particularly when I went to Quip, which was my next opportunity, um, and really focusing on the workflow and the day-to-day engagement and impact, and then how do you roll up that positive, that additive, um, experience as a core part of your value prop. That was a key takeaway for me through Dropbox.