After some testing, it’s time to take the wraps off a new feature we’ll be launching next week on WordPress.com VIP! On the wider WordPress.com service, we have been offering direct, live chat support to more and more users in an effort to serve them as efficiently as possible. It’s been well-received and the customer response has been off-the-charts amazing. Live chat support has been a really successful and helpful service for our customers, adding another—much faster—channel to our support offerings.
We took a look at WordPress.com VIP, and we noted that while your developers and business people know where to reach our team and ask for help, it’s not quite as obvious to the users who are creating and curating content for your sites.
So, starting next Tuesday, we will begin offering live chat support to all users with access to VIP site dashboards. Your users will see this box in the lower-right corner of your site dashboards:
Clicking on that box will expand a text area where they can enter a question:
We’ll be standing by to assist your authors and editors and get back to them right away to assist them with their WordPress.com questions as quickly and efficiently as possible.
The WordPress.com VIP team is super-excited to bring this feature to your editorial teams. Live chat support will help them get their work done more efficiently, and free up your developers to focus on more non-support projects!
If you have questions about this feature, we invite you to contact us at support@vip.wordpress.com at any time either prior to the launch of the feature or once it’s up and running. We’ll be happy to discuss it with you and let you know more!
WordPress VIP Lobby 
It would help us understand the problems are users are having if we can feedback / stats on the usage of this for our sites
Paul
Thanks for the feedback — we’re still working on the livechat roadmap, but tools like that are something we’re definitely interested in.