The Ledger, every show

“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.”

“I would say, there's a scenario where there is no box, and I think that was, Dropbox could have made that happen”

“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.”

“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 …”

“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.”

“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 …”

“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…”

“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.”

“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.”

“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.”

“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…”

“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…”

“There really aren't many successful PLG companies outside of like the DevOps ones like Datadog and Atlassian that have actually really broken out.”

“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 …”

“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…”

“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…”

“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…”

“I don't think you create that playbook until you have at least 20 ramped AEs.”

“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…”

“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…”

“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.”

“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.”

“The job is realistically is 70% CS, 30% sales.”

“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…”

“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 …”

“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.”

“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.”

“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.”

“And if you're going to operate, you either build product or you sell product. Everything else is supporting one of those two.”

“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 …”

“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…”

“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…”

“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…”

“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.…”

“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…”

“A lot of the early unicorns, like when unicorns were still a big deal, 80% of them were sort of built on Asana.”

“We didn't have the dynamic that Dropbox and Slack had where you have 30% of a company using it, especially when you go outside of the big tech companies. And so, A lot of times it would be like five percent of employee base”

“You want to go after executives, you got to find a different way to create that demand. You can't just rely on your organic user base to organically create you know, create those opportunities.”

“What I find is that Human behavior is very hard to change, and so human behavior will lead you to spend most of your time on those three big enterprise accounts that are already healthy, and you're just trying to milk more from them. Makes sense. And you don't…”

“And I think for PLG companies that are moving into enterprise, your likely bottleneck is not number of heads, number of AEs. Your likely bottleneck is how many companies do you actually have real product market fit on a large scale?”

“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.”

“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.”

“Dropbox was the company that shattered and started the BYOA move.”

“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…”

“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.”

“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.”

“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.”

“Facebook was one of the hardest enterprise accounts for us to crack, because their V-one, like, non-mobile version was still so widely used, right, and caught tasks.”