Google Workspace: SMB to Enterprise Sales

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What are the pain points? The existing productivity tools are so baked into the organization, so something must be painful for this to be under consideration at the enterprise level. What is that pain?

Usually, the door opener is collaboration. Typically, it's like, "Would you like to more easily work together in real time?" The other thing that happens a lot, unlike in the enterprise is, it's a costs discussion. They're looking to cut costs, especially early on. Early on the value prop was, we can do 80% of what you do today and a lot cheaper. That was literally the value prop in the early days. We've tried really hard to move away from that over time, because of course, we can't win on that but that's also part of it. You have a lot of conversations that happen with CIOs where they're up for renewal, and they’re getting gouged on their Microsoft renewal. They say, let me at least entertain the conversation if for no other reason, but to have some leverage. Usually we'll uncover something like, “Sharing a very large file is really difficult" or, "We have lots more people on video meetings today and they're working across boundaries". The collaboration piece usually is the next value prop lever.

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It seems to me that the Cloud-based and the heritage of Google makes it so much better at multi-user collaboration, and Microsoft has a lot of technical work to do, in order to replicate that and migrate its legacy users over, but it has Teams. How do you think about that? Is Teams sort of a trump card that takes the rug out from underneath Workspace? How do you think about that?

But the other thing that Microsoft is really good at, which I think is part of broadly why they continue to win is, they've got an army of sales folks and customer success folks who are out there as soon as these things are released, making sure that they're getting adopted. I think that's the biggest challenge. Google had a real moment there a few years ago, when there was this license conversion from on-prem perpetual licenses to Cloud licenses. Everyone was reevaluating. We had a real point in time where we could capitalize, but they were so efficient at converting all those licenses, even if folks were still using on-prem stuff. Now, it was a subscription. I think it's the same thing with Teams. They've done a really good job in terms of Teams adoption. The product is decent, they're investing a lot of resources there, so I do think it's problematic. I think what Google is trying to do is capitalize on their more popular services. You've seen a lot happen in Gmail, and as Gmail is becoming this hub for work, where things now pipe into Gmail, so this is their approach as well, to consolidate and try to get stickier with some of that.

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You mentioned the Essentials Bundle, and how there was the strategy of getting a wedge in and then expanding from there. Can you talk me through a textbook case of that being successful? Where does the wedge go in? How does that expand over time? How often would this actually work?

Most often, the wedge would go in one of two places. It would either go into a SharePoint use case, so they're using either SharePoint online, or they're using some legacy version, and it sucks, and it's hard to collaborate. Capitalizing on that with Drive was a great entry point. The other places that we would go in would just be around real time collaboration, or large files. Large files are super problematic for Microsoft. For some reason, they just can't seem to do it and then you have to change where you store it based on how big it is, or who you want to share it with. Those are the best places.

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