Oliver Jay
Former Chief Revenue Officer, Asana · 1 appearance on the record.
computed by AI from the episodes · how this works → · full disclaimer →
31statements → 4claims → 0claims resolved → 3.71/5average certainty → 2.42/5average debate potential → ≈4.5/5argument clarity, estimated → 7said about them ↓
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4 assertions · 1 opinion · 20 insights · 3 disclosures · 3 what ifs · every statement was checked. The predictions and assertions are the 4 claims: statements the public record can support or contradict. 0 are resolved, and 4 name no date, number or outcome precise enough to check. 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.
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Everything Oliver Jay said on In Depth that made the record, most notable first. Filter by type, assessment or year in the ledger →
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”
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: 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…”
Jay: PLG-to-enterprise deals require four internal buyer personas
“For PLG companies moving to enterprise, what we found was one, and kudos to my team for figuring this out, I didn't coin this, my team did. First, we call them Intel agents... The next level we call them or change agents... And so those are change agents, and …”
Attempting to build a better Jira is like trying to replace Salesforce
“I think a lot of companies are trying to be like the better version of Jira. To me, that's like being the better version of Salesforce. It's going to be really hard to do and replace.”
Atlassian had a much shorter route to CIOs than Asana did
“The edge that they had was eventually the route to the CIO, the CTO to then just, all right, let's just Deploy this across the whole organization. That path is very short. Whereas for many PLG companies like us on the distance was really long.”
Oliver Jay: PLG focuses on the user journey, enterprise on the customer journey
“Enterprise, we always use the term customer journey. What's the customer journey? Who are the people in the company who receive different Forms of value along the way that eventually makes the right decision of buying your product, right? And that takes a long…”
Oliver Jay: Enterprise product feedback is ~80% field-driven, unlike PLG aggregate data
“On the enterprise side, it is largely dependent on what's coming from the field. I would say 80% probably, and then 20% is like, what, With that feedback, how can you sort of do the, fulfill your customer's job in a better way with your product, with a more in…”
Jay: Infrastructure and developer PLG tools convert directly to enterprise deals
“If I think about certain dev ops tools, think about like a data dog or the infrastructure layer, the PLG traction Directly leads to an enterprise deal, right? A small team of engineers evaluate the products. They decide Datadog is the right product to go with.…”
Jay: Asana invested in OKRs to open enterprise executive sales conversations
“So at Asana, what we realized was a lot of companies were starting to use Asana as the framework for Goal setting and OKR setting. The reason is because all the work is actually already happening in projects and tasks in the product, and so you might as well s…”
The other half of the tape: Oliver Jay's own voice is left out of every number here. Other people bring the name up 7 times in 1 episode on In Depth. every mention, with the transcript →
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Appearances (1)
| Episode | Date | Speaking time |
|---|---|---|
| The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (A | Jan 4, 2024 | 50m |