Zillow is a fully remote real estate technology company with more than 60 assistants across the U.S. When Zillow standardized on Google Workspace, its assistants had to adapt from Outlook, the calendar system many of them had relied on for years

Becky supports three senior leaders in Zillow’s finance organization. After spending most of her career in Outlook, she had grown accustomed to features like Scheduling Assistant that she found especially useful for complex executive scheduling.

When Zillow moved to Google Calendar, Becky found that some of the scheduling workflows she relied on in Outlook were less intuitive to replicate.

Vimcal EA helped bridge that gap by giving Zillow’s assistants a more advanced scheduling layer on top of Google Calendar, while their executives and the broader company could continue working in Google Workspace.

The challenge: Preserving familiar scheduling workflows after moving off Outlook

Before Zillow moved to Google Workspace, Becky had spent most of her career using Outlook.

“For an assistant who’s in calendars all day, every day, I think there are some considerable differences,” says Becky.

One of the biggest changes was how she viewed availability across large groups.

In Outlook, Becky had relied on Scheduling Assistant, which made it easier to scan attendee availability in one dedicated view.

Google Calendar still provides ways to compare availability, but Becky found its native workflow less intuitive for the kind of high-volume scheduling assistants handle.

“There are times we’re scheduling meetings for 30 people. Having 30 people in the room and looking at all of the calendars side by side was just not getting us where we needed to go,” says Becky.

The challenge wasn’t that Zillow needed to abandon Google Workspace.

The company had already standardized on Google Calendar, and Becky found many of Google’s collaboration tools useful in a fully remote environment. The assistants needed a way to preserve some of the scheduling functionality they had relied on in Outlook.

How Vimcal EA helped Zillow solve their challenges

1. Preserving a familiar Scheduling Assistant-style workflow

For Becky, Vimcal EA’s Scheduling Assistant is the feature she relies on most.

It gives her a clearer way to compare calendars, drill into availability, and coordinate large groups without requiring anyone else at Zillow to change calendar platforms.

“The Scheduling Assistant functionality is extremely helpful,” says Becky. “Being able to really drill down into what people’s availability is and see it more clearly.”

That context helps Becky judge which conflicts are actually movable. Vimcal EA gives Becky visual context that helps her quickly understand what may be flexible.

“It is helpful to just see at a glance: am I potentially scheduling over something that someone isn’t going to be able to move, or does it look like maybe it’s just a one-on-one that would be a little bit more easily adjustable?” says Becky.

2. Seeing multiple executive calendars clearly at once

Becky supports three senior leaders in addition to managing her own calendar.

With Vimcal EA, she can open all four calendars side by side in a Monday-through-Friday workweek view and see them together on one screen.

“I support three executives. I also have my own calendar. I can actually open up all four of our calendars side to side in a workweek view and see everything,” says Becky.

That reduces the need to scroll between calendars and mentally keep track of where open time appeared.

“Being able to just see them all laid out like that is helpful instead of having to scroll and try to remember where availability was from someone else’s calendar,” says Becky.

3. Adding context that helps EAs make better scheduling decisions

Vimcal EA also surfaces information that Becky can use when deciding which meetings to move.

For example, when rescheduling an event, she can see how many times it has already been moved.

“Even when I go to reschedule something, it’s saying, ‘This has been rescheduled three times.’ That is helpful because I’ll take note of that personally. Maybe I don’t want to move that person’s one-on-one again. I’ve already moved it two times. Let me see what else I can do,” says Becky.

That extra context helps her keep the people behind the meetings in mind.

“The reschedule counter is not functionality that I’ve seen elsewhere.,” she says.

The results of using Vimcal EA: A smooth transition to Google Calendar for assistants

For Becky, Vimcal EA helped preserve some of the scheduling workflows she had relied on in Outlook while Zillow continued using Google Workspace.

Zillow’s leaders and broader workforce continue using Google Calendar, while its assistants can use Vimcal EA for the scheduling workflows they rely on most. For Becky, that has made the transition from Outlook easier without requiring anyone else to change how they work.

Moving forward with Vimcal EA

More than six months into Zillow’s use of Vimcal EA, Scheduling Assistant remains the feature Becky holds “most near and dear.”

She is also beginning to explore functionality such as Calendar Audit, while already using reschedule history to make more thoughtful decisions about which meetings to move.

For Zillow’s assistants, Vimcal EA has helped make the shift from Outlook to Google Calendar easier by preserving the kind of scheduling visibility Becky had relied on before.

As Becky puts it:

“It seems like something that’s small, like just one piece of functionality, but it’s huge when you’re doing this all day, every day,” says Becky.