Oliver Jay, former Head of Sales at Asana, cautions early-stage founders against claiming they have a repeatable sales playbook prematurely.
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“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.”
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More from Oliver Jay
Insight
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…”
Oliver JayMay 25, 2022▶ 2:52Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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…”
Oliver JayMay 25, 2022▶ 4:00Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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.”
Oliver JayMay 25, 2022▶ 7:17Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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…”
Oliver JayMay 25, 2022▶ 15:16Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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 JayMay 25, 2022▶ 41:31Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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 JayJul 27, 2022▶ 9:5620VC: The Memo: What is a Sales Playbook? Does the Founder Need to Create It? Should the First Sales Hire Be a Leader or a Rep?
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