The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
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Founders should never hire a VP of Sales before an individual seller
“But in no circumstances do you really want to bring in a VP of sales before you have a seller, because they're gonna come in with the preconceived notions That ultimately might not mesh with your particular business model.”
Startups should treat customer logo rights as mandatory, not optional
“So one, I don't ask for it. It's something that's a requirement. So I think just the assumed close there is really important. You know, as part of working with us, we we're excited by we want to support our customers. We love to show off the great companies th…”
Software sales leaders recruit within too narrow a candidate profile
“I think there's a challenge from software companies and sales leaders thinking too small inside of a box in terms of the profile of who they're looking for.”
Early enterprise sales require product-customer fit, not product-market fit
“You don't need product market fit In order to sell an enterprise, especially as that first seller, what you need to find is product customer fit.”
Startups should hire their first sales rep before reaching $1M ARR
“I think they should make that first hire as soon as they have a product that they really want to be testing out in the market, and so I think it's a lot sooner than a million ARR, to be honest.”
Logos matter far more than revenue in early-stage sales
“The, those first sales, I don't think about revenue as being important. The revenue or the currency that matters in those first sales are the logos. You need to be acquiring logos. You need to be able to say, hey, this company works with us. That gives you cre…”
Salespeople must never let champions sell to executive buyers alone
“There is not a world that I would ever be comfortable living in where I want to outsource my job to a champion at a prospect.”
Optimists make poor enterprise sales reps; skepticism is required
“People are great fun at parties, but they make for shit sellers. You need someone who is a lot more skeptical, who questions everything.”
Top sales performers would fail standard modern hiring rubrics
“The best salespeople I've seen in the last several companies I've been in, none of them would be hired today based on the rubric that sales leaders have.”
Promoted mid-market account executives often fail in enterprise sales
“I've seen mid-market account executives get promoted into enterprise in my past and flame out pretty quickly.”
Founders rely too heavily on cash over equity for early sales hires
“When it comes, especially to early sales hires, there's not enough emphasis placed on, on equity in sales. They give out equity for other roles. And I think equity is, is often something that founders don't really think of when it comes to salespeople. They re…”
Sales teams avoiding traditional outbound outreach are doing sales wrong
“Traditional outbound is the most important thing, Harry, and if you're not doing it you are doing sales wrong, and the reason why is because pipeline is the most important thing if you want to hit your quota, as we just established, and the way that you build …”
Mark Goldberger closed $13M in revenue during his first year at Navan
“I closed about thirteen million dollars of revenue that first year.”
Asking for an executive buyer intro is the only true champion test
“When it comes to thinking you have a champion, there is only one way to know if they really are a champion for you. You have to test them. And the way that you test them is asking them to take you to the executive buyer.”
Creating sales urgency without discounting requires deep customer pain
“If you don't have enough pain, there's Not a world where I can get you to have the urgency you need short of discounting.”
Sales leaders must allow reps to fail in low-stakes deals
“So you need to create space for them to fail when the stakes are low so they can succeed when the stakes are high.”
Sales managers should cap mistake severity rather than prevent errors entirely
“No matter how much you say the stove is hot, people still want to touch it in order to find out that it's really hot, and so it's my job to make sure the burner's on simmer and not on high, so it's not a catastrophic wound.”
Ramp's enterprise sales team is trending to hit over 300% of quota
“This quarter the enterprise team at ramp is trending to hit more than 300% of their quota, which is pretty insane.”
A new sales rep's silence in their first month is a red flag
“If someone is not asking a lot of questions, if they're not vocal in that first month or two, to me, that's a red flag that I want to at least dig into.”
The B2B payments market size is $115 trillion
“When you think about the size of this market, payments alone, B to B payments, are a 115 trillion dollars.”
Customer success must be involved before closing enterprise deals
“You need to be introducing that implementation and that CS team before the deal is ever closed, right? Implementation, onboarding, how we're going to make you successful as a customer is part of the sales process.”