Building Sales Team

"In those early days, it's more inbound in nature, and so the type of sales reps you might need are not necessarily going to be outbound, heavy kind of hunting sales reps... making sure that the profile, the folks you're bringing on early match that target buyer in addition to match the motion around how you're going to be acquiring customers."

"We shouldn't force the merchant to choose, do you want to talk to sales? You want to do self-service? Should give them the options, whatever path that they want to go on. And so a lot of that has been building into the self-service journey over to sales and then from sales into self-service."

"you're going to have to hire somebody who knows sales... there's a lot of knowledge in how to build a worldwide sales organization; maybe knowledge of customers, territories, territory splitting, rep profiles. There's just a litany of stuff that you really can only learn by doing trial and error"

"Attach to yourself a pilot AE, so account executive, or an SDR and see how that works. You kind of separate yourself from the mothership of the sales engine and you actually prototype this separately in a little bit of a vacuum, not under pressure of them top-down quota relief."

"If your money collection is going to happen through sales team primarily, then you absolutely should be hiring sales way before growth. In fact, in the sales led companies, growth teams are not necessarily needed even that much."

"Enterprise salespeople are not good chasm crossers because they're used to doing horizontal coverage model... You want somebody that looks more like a sales engineer than a salesperson. You want somebody very diagnostic, very committed to the integrity of the problem solution framework."

"You need to hire one rep and you've got to hire two because otherwise, there's no A-B test. You have to A-B test humans. You've got to hire two as hard as it is, and there's just one cheat code to those first two."

"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."

"In sales, I'm actually not sure what the tip of heuristic is in product... But the thing about sales is there's no efficiency... it's rules of eight. Eight SDRs, outbound reps need one manager, eight AEs, eight sales execs need a director above them."

"I have this theory that maybe you shouldn't hire any salespeople until series A, right? Because seed is all about experimentation and proving out that experiment, and then obviously series A is about exploiting that learning."

"I always say you need people that can cosplay a founder, which is selling the vision, getting them excited, running through a wall to get the deal done and getting creative on ... None of my deals look exactly the same, every deal looks different and that's okay because every organization has slightly different opportunities."

"It's usually 50/50. So it's 50% OTE. So it's 50% base salary, 50% OTE... In technology, it could be anywhere between eight and 12%. So rounds out around 10%."

"We would hire a ton of really smart people that had never done sales and had them do sales. There are a lot of disadvantages to that, but I do think it led to a ton of innovation. That's how we got our very innovative go-to market motions because a lot of those people then moved into different functions at the company."

"The point at which you should start to hire someone else to do that is when you, as the founder, absolutely cannot meet the demand... And then the other time to do that, apart from just being maxed out, is when you are moving in to and usually up to a customer that both wants and expects to meet with a salesperson."

"Generally speaking, it is to contingent on your sales motion, but it's going to be that you can reliably, at a pretty okay win rate, so maybe 15% or 20% or 25%, turn first meetings into eventual customers and do that in a reliable fashion. It's not like, "I engaged 10 arms-length parties and I got two customers closed." It's like, "Hey, that's great. That's a good start. 5X that, 10X that.""

"Generally, what you want to do is you probably don't want to start with a VP of sales to start... what you want to do is you want to hire a couple early-stage pioneer sellers to take that sales motion. The downside of seeking to hire a VP of sales... is that person hasn't been selling for a hot second."

"What we haven't done is built a modern technical sales compensation plan that actually aligns the needs and incentives of the business, the customer and the rep... I think that setting up a longer horizon where if the customer you sign up today ends up renewing tomorrow, the rep should get a kicker on it."

"we've had this team for almost two years now that that's been working on sales automation and data to just make our sales teams more efficient."

"We hired our VP of sales over a year ago actually. And the go-to-market team is now over 80 people inside the company... if you want to sell to the Fortune 500, it is very hard to do that purely by swiping a credit card."

"The litmus test I have always given my sales team is if you are an account executive in my org and I put you in front of 10 engineers at our company, it should take them 10 minutes to figure out you aren't a product manager."

"SDR is typically in charge of generating pipeline... account executives are closers. It's their job to take somebody from, 'Okay, hey, I'm interested in learning about your solution, I have a legitimate problem. I potentially could make a decision,' to, 'I now believe that your product is the best in the market for me and I'm willing to pay for it.'"

"I strongly believe that sales is a skill and so you want salespeople with actual sales experience in your organization, but I think there's value in pairing them with more nontraditional backgrounds, in particular consulting or banking background. Those folks are really good at more quantitative and analytical aspects of sales."