Oliver Jay, former CRO at Asana and early Dropbox sales leader, discusses the competitive market dynamics that dictate why software startups must move quickly.
“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, and that category leader gets like 70, 80% of the market share”
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More from Oliver Jay
What-if
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 JayJan 4, 2024▶ 19:15The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana)
What-if
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 JayJan 4, 2024▶ 19:22The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana)
Insight
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 …”
Oliver JayJan 4, 2024▶ 2:53The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana)
Insight
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.”
Oliver JayJan 4, 2024▶ 3:35The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana)
Insight
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 …”
Oliver JayJan 4, 2024▶ 6:46The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana)
Insight
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…”
Oliver JayJan 4, 2024▶ 12:49The new PLG playbook | Arming the next generation of product-led companies | Oliver Jay (Asana)
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