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.
why aren't all 20 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Oliver Jay: Repeatable sales playbooks require at least 20 ramped AEs
“I don't think you create that playbook until you have at least 20 ramped AEs, where you have the right to say this is a playbook.”
Oliver Jay: Startups in existing categories should hire a sales leader first
“If your product and your business is going after an existing category, and you're just a much better version of it, so there's already, sometimes already budget, but certainly it's pretty clear who the buyer is and what are you solving? I would lean towards a …”
Oliver Jay: Category-creating startups should hire frontline reps before a sales leader
“On the other hand, if you're trying to actually create a new category, what you're selling is fundamentally the first piece of that kind of software solving that admit problem at a company. I think you're better off with hiring some hungry and smart customer f…”
Software companies can run PLG and enterprise sales simultaneously
“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 have to pick one or the other. And at Asana, we pioneered and we try to do both at the same time. And I think the results we…”
Non-developer PLG startups miss significant growth without sales teams
“Almost every other persona. Sales make sense, right? To compliment, not to say that you have to lead with sales, but sales can really help you move up and get to the larger, more strategic conversations. So I think it depends on your product. But generally spe…”
Wait for 20 ramped AEs before building a repeatable sales playbook
“I don't think you create that playbook until you have at least 20 ramped AEs.”
Early sales teams need collaboration over manufactured internal competition
“I think if you really need to rely on sort of like having people with the same cohort to drive competition, I think you may have hired the wrong people in my opinion, right? Because in that early stage, I'm actually trying to foster more than anything, a cultu…”
Cold outbound fails without company-wide marketing and product alignment
“If what you mean by going outbound is you're just going to get some salespeople to go buy some lists and just start cold emailing, LinkedIn bombing people. It won't gonna work because your entire conversion process is designed around a different buyer, articul…”
Oliver Jay: Asana reached $20M revenue without a sales deck
“When I joined Asana, we had twenty million in revenue, mainly driven from our self-serve business. And we didn't have a sales deck.”
In tech, you either build or sell product; everything else is support
“And if you're going to operate, you either build product or you sell product. Everything else is supporting one of those two.”
Outbound sales requires distinct buyers, messaging, and larger deal sizes
“For outbound to be successful, generally speaking, you're selling to a different buyer. Probably a more senior persona. You're probably selling a different value. And so therefore you need different messaging. In terms of the sales process, absolutely, you'll …”
The best tech companies put sales on equal footing with product
“A lot of times in tech, frankly, I think sales people are second class citizens. Because they're not building a product and all that, and I think I would love to change that, because I think the best companies are the ones where sales, collecting customer feed…”
Jay: Support tickets reveal future sales obstacles during rep onboarding
“A lot of times the best way to do that is actually get the team exposed to support because the tickets that you get coming in is basically a reflection of what you're likely sales obstacles that you're going to get.”
Oliver Jay: Founders must drive sales until the initial playbook exists
“If that playbook hasn't been written, founder must be involved. You have to talk to the customer to hear the feedback firsthand so that you can then incorporate it into your product and eventually get the product market fit.”
Dropbox pioneered the enterprise bring-your-own-application movement
“Dropbox was the company that shattered and started the BYOA move.”
Pure self-serve works in developer tools because developers avoid sales calls
“There are some categories where you can get really far with a self-serve only model. I'm thinking about Atlassian and how far they went in the sort of in that DevOps world. It makes total sense, right? No developer really wants to get on a phone or get cold ca…”
Startups should hire product-passionate reps over generic playbook followers
“PLG is on the rise. You want this, I want this person to convey this passion and this love for the product to their customers, as opposed to just following some playbook.”
Sequence sales onboarding: product first, market second, sales methodology last
“I would sequence product knowledge first, and then sales knowledge, right, you know, kind of like, and then, oh, so I would do product first, market first, second, and sales last.”