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Oliver Jay

Former CRO, Asana · 1 appearance on the record, plus 2 compilation re-airs.

computed by AI from the episodes · how this works → · full disclaimer →

Oliver Jay served as the first revenue leader and CRO at Asana. Prior to Asana, he was Head of APAC and LATAM at Dropbox.

20statements → 1claims → 1claims resolved → 4/5average certainty → 2.36/5average debate potential → 4.3/5argument clarity · the sources → 4said about them ↓

0 supported 1 partly supported 0 contradicted how the 1 claim stands · each chip opens the sources

1 assertion · 1 opinion · 15 insights · 3 disclosures · every statement was checked. The predictions and assertion are the 1 claim: statements the public record can support or contradict. 1 is resolved. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Oliver argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Argument clarity: do they answer the question? how? →

4.3 / 5 directness 4.6 · coherence 4.5 · precision 4 · compression 3.8

answered every one of 39 assessed questions directly

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

270 words/min while actually speaking · 17.6 um and uh per 1k words · 22.3 false starts per 1k · 27.4% of pauses land inside a clause

Measured by listening to the audio itself: 7,599 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

How the interview went all their pushback → series average →

Across 3 rated episodes:

host pushback ▾ 2.3/10
pushed back at the host ▾ 2.7/10
setup questions received 25%

Everything Oliver Jay said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Insight
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 Jul 27, 2022 ▶ 7:49 20VC: 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?
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 Jay Jul 27, 2022 ▶ 9:56 20VC: 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?
Insight
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…”
Oliver Jay Jul 27, 2022 ▶ 10:21 20VC: 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?
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 Jay May 25, 2022 ▶ 2:52 Oliver 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 Jay May 25, 2022 ▶ 4:00 Oliver 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 Jay May 25, 2022 ▶ 7:17 Oliver 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 Jay May 25, 2022 ▶ 15:16 Oliver 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 Jay May 25, 2022 ▶ 41:31 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Disclosure
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.”
Oliver Jay Nov 16, 2022 ▶ 5:18 20 Sales: The Ultimate Guide to Sales Onboarding for New Sales Reps and Sales Leaders, The Biggest Red Flags in the First 30 Days & What Can Be Done to Set Them Up for Success with Leaders from Figma, Dropbox, Miro and more.
Insight
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.”
Oliver Jay May 25, 2022 ▶ 1:14 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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 …”
Oliver Jay May 25, 2022 ▶ 40:41 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Opinion
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…”
Oliver Jay May 25, 2022 ▶ 53:43 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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 Nov 16, 2022 ▶ 4:16 20 Sales: The Ultimate Guide to Sales Onboarding for New Sales Reps and Sales Leaders, The Biggest Red Flags in the First 30 Days & What Can Be Done to Set Them Up for Success with Leaders from Figma, Dropbox, Miro and more.
Insight
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.”
Oliver Jay Jul 27, 2022 ▶ 7:00 20VC: 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?
Assertion Partly supported
Dropbox pioneered the enterprise bring-your-own-application movement
“Dropbox was the company that shattered and started the BYOA move.”
Oliver Jay May 25, 2022 ▶ 2:18 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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…”
Oliver Jay May 25, 2022 ▶ 3:38 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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.”
Oliver Jay May 25, 2022 ▶ 20:42 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Insight
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.”
Oliver Jay May 25, 2022 ▶ 32:29 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Disclosure
Asana reached $20M in self-serve revenue without a sales deck
“When I joined Asana, we had twenty million in revenue, mainly driven from our self-serve business, right? And there was no, we didn't have a sales deck.”
Oliver Jay May 25, 2022 ▶ 35:04 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings
Disclosure
Asana adopted Toyota's Five Whys process for lost sales post-mortems
“At Asana, we had a practice called Five Whys, it was adopted from Toyota, that I think is very effective.”
Oliver Jay May 25, 2022 ▶ 46:15 Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with Harry Stebbings

The other half of the tape: Oliver Jay's own voice is left out of every number here. Other people bring the name up 4 times in 1 episode on 20VC. every mention, with the transcript →

Who brings them up most Harry Stebbings 4

Every mention by year

tap a year for its mentions
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2022 4 mentions in 1 episode

Appearances (3)

EpisodeDateSpeaking time
20 Sales: The Ultimate Guide to Sales Onboarding for New Sales Reps and Sales Leaders, The compilation Nov 16, 2022 4m
20VC: The Memo: What is a Sales Playbook? Does the Founder Need to Create It? Should the F compilation Jul 27, 2022 3m
Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889 · 20VC with May 25, 2022 37m
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