Oliver Jay
Former Chief Revenue Officer, Asana · Former CRO, Asana. On 2 shows, 2 appearances, plus 2 compilation re-airs not counted. The Shows tab opens the full record on each.
Oliver Jay served as the first revenue leader and CRO at Asana. Prior to Asana, he was Head of APAC and LATAM at Dropbox.
2shows
2appearances
51statements
1resolved
0supported
0contradicted
0%fully supported
11said about them ↓ Everything Oliver Jay said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Better execution on Dropbox Paper could have prevented Notion's rise
“One can argue there if Dropbox paper Had, you know, maybe launched at a different time or a different way, there would be no notion, potentially.”
Oliver Jay: Dropbox could have eliminated Box with better enterprise execution
“I would say, there's a scenario where there is no box, and I think that was, Dropbox could have made that happen”
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.”
Running PLG and enterprise requires operating two completely separate companies
“Winning the enterprise is really, and winning a more traditional PLG motion, it's almost like two separate companies. I think it's a very different way you think about building product, different way you interact with customers, and certainly a very different …”
PLG companies mistakenly believe they can seamlessly blend into the enterprise
“I think the big mistakes companies make over and over again when I see is when they try to blend, they think they can just seamlessly evolve. And as they scale and Into an enterprise company. I think it's a lot more complicated than that.”
Jay: The 'PLG trap' happens when companies run out of organic accounts
“As you build the security stuff, it does unlock major expansion in, within your customer base, right? The companies where you have good organic usage, many of those companies will start paying you 25, 50, a 102 hundred K. And so you're taking in this data and …”
Jay: Pitching team productivity fails to resonate with enterprise executives
“As an executive, all I care about is driving enterprise value. And then really the only things that drive enterprise value are driving more revenue, lowering costs, risk mitigating, right, on that level. And so your pitch at that point is like, well, look look…”
Dropbox and Slack's enterprise value came from securitizing rogue employee usage
“And so Dropbox and Slack, if you ask me what's the company value, well, the company value was securitizing, in a way, the bottoms-up problem that we created for them, which is all this rogue usage.”
Software companies cannot become category leaders without winning the enterprise market
“All categories have to go through the enterprise. All winners have to win through the enterprise. There's very few, I really can't think of many of any companies that have become the category leader without winning the enterprise.”
Jay: PLG companies must start executive value sales concurrently with expansion sales
“Phase three starts the same time phase two starts, because it takes that much time to identify the problem, identify the path, and then start building the right team to execute that, that play. It takes a long, long time.”
PLG companies mistakenly segment sales teams by company size instead of motion
“This is something that I see a lot of PLG companies get wrong, which is they confuse segments and motions. If you take a step back, traditionally enterprise companies are set up and they are split by segments, SMB, mid-market enterprise, right? And of course y…”
Notion would not exist if Evernote had executed on team-level value
“One can argue if they executed better, there would be no notion as well, right? But they just got stuck on the individual user value, and the team user value, like, they didn't really, it doesn't really, it didn't really resonate, right? The product didn't rea…”
Very few PLG companies outside of DevOps have truly broken out
“There really aren't many successful PLG companies outside of like the DevOps ones like Datadog and Atlassian that have actually really broken out.”
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: Most SaaS companies cannot successfully emulate Dropbox's growth model
“Dropbox is a really interesting case study, and it is one that I think too many people look to emulate, but they just can't. Because what happened with Dropbox, amazing product, perfect market timing.”
Only 5% of PLG enterprise customers expand beyond their organic base
“And I would say maybe five percent of your enterprise customers are able to actually leverage that access to IT's interest and security to drive a bigger deployment.”
Inbound product-led sales roles are 70% customer success and 30% sales
“The job is realistically is 70% CS, 30% sales.”
Software category leaders eventually capture 70% to 80% of market share
“We look at every single category that's been created, it's very noisy in the beginning, but there's a period of like, there's like a two to three year window, where there's a massive competition, but coming out of that, the category leader is kinged or queened…”
The other half of the tape: Oliver Jay's own voice is left out of every number here. Other people bring the name up 11 times in 2 episodes across the shows. every mention, with the transcript →
Who brings them up most Kyle Parrish 7Harry Stebbings 4
Every mention by year
tap a year for its mentions
In Depth 7
20VC 4
2024 7 mentions in 1 episode
One line per show, most statements first. The link opens Oliver's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| IN DEPTHLEDGER | Former Chief Revenue Officer, Asana | 1 | 31 | — | full record on In Depth → |
| 20VCLEDGER | Former CRO, Asana | 1 +2 | 20 | 0% 0/1 | full record on 20VC → |