When comparing Skype vs Stride (previously HipChat), the Slant community recommends Stride (previously HipChat) for most people. In the question“What is the best team chat software?” Stride (previously HipChat) is ranked 5th while Skype is ranked 64th. The most important reason people chose Stride (previously HipChat) is:
You can access HipChat from pretty much every common platform. HipChat even allows chatting via SMS.
Specs
Ranked in these QuestionsQuestion Ranking
Pros
Pro Easily connect with others due to how popular the service is
There's a good chance that whoever you're trying to reach has Skype already set up and familiar with it, avoiding the hassle of installing and getting to know new software.
Pro Screen sharing
You can show your whole desktop, a select part of the screen or a specific window over Skype.
Pro Cross-platform
There's software for Windows, Mac & Linux and apps are available on iPhone, Android, and Windows Phone.
Pro Group video for free
You can hold video calls with up to 10 people.
Pro Available on Linux
A stripped down, minimalist version of Skype is available for Linux.
Pro File sharing
Skype allows you to send any files (MP3s, images, text, etc.) by simply dragging and dropping then in the chat window making it simple to share things with colleagues.
Pro Cheap fixed phone number
Starting at $5/mo you can get a Skype number.
Pro Send SMS and make regular calls
With Skype Credit bought or a subscription, you can send SMS and make direct calls.
Pro Group chat with archive / records
Pro Powerful 1:1 chat and also group chat
Pro Available on Web, Mac, Windows, Linux, iOS, Android
You can access HipChat from pretty much every common platform. HipChat even allows chatting via SMS.
Pro Powerful @mentions
You can ping people to get their attention even if they are not online by @mentioning them. Depending on how the person has set their account up it can be by notifications via in-app sounds, visual alerts, and even email, SMS, or mobile app push notifications.
Pro Huge list of integrations
Including Asana, Github, Zendesk, WordPress, MongoDB, TeamCity, JIRA, Confluence, PowerShell and more that 40 others.

Pro Cheap
Free with unlimited users, $2/user/month for voice + video calls, screencasts, full history retention and management. (Even enterprise feature like SAML)
Pro Simple, easy to use
An intuitive, easy to overview interface listing both online and offline users.
Pro Embeds files
Things like photos get automatically embedded in the chat thread once you upload them.
Pro Guest access
You can invite people to join conversations even if they don't have a HipChat account. HipChat will generate a link to share and the guest will only need to enter their name to join the conversation.
Pro Desktop client
HipChat has an optional desktop client powered by Adobe AIR.
Pro Good audio and video support
HipChat audio and video works on mobile platforms and web browsers.

Pro "Rooms" for persistent group chat
Participate and keep tabs on ongoing discussions on particular topics or amongst certain groups of people.
Pro Self-Hosting available
If you are worried about third-parties getting access to your data you should consider self-hosting. With self-hosting you are in control over where your data is stored, who has access to it. You will also not be vulnerable to exploits of a third-party provider.
Pro Plentiful GIFs and custom Emoticons
Pro Syntax coloring
Pasted code can be colored based on syntax.
Pro Will be updated to have more functions in the future
A big company with experience will bring in more options like Google Apps One Time Login.
Pro Reliability has been great
Pro Powerful command system
E.g. part, away, all, here etc.
Cons
Con Plagued by bugs on all platforms
Crashes and other bugs are prevalent on Android, Windows and other platforms.
Con Subpar video quality with more than 5 users
Skype has significant problems with multiple users and video quality. Skype recommends that a max of 5 users group chat as video quality is severely affected. Even webcams tested with other chat services showed lower quality when used with Skype.
Con Not a feasible alternative as a professional team chat
Missing key feature such as centralized mgmt, centralized billing, data retention policies, ...
Con Poor quality when screensharing
It is not possible to manually set resolution or bitrate, and Skype often defaults to a resolution so low that text is unreadable. It is also not possible to transfer control over mouse and keyboard.
Con Slow filesharing speed

Con Owned by Microsoft
Con Obnoxiously large ads
Ads take up over 25% of the usable space.
Con Poor Linux support
The version available for linux users is quite outdated, and does not support some of the newer functionality, such as the free group video calling and screen sharing.
Con Requires both ends to be online (if neither end is using a cloud-enabled device)
Messages are sent and received only when both ends are online, if neither end is using a cloud-enabled device. In this case, if you are online 9-17 and your recipient is online 18-3, messages will never be delivered.
Con MIcrosoft (Skype's owner) actively assists eavesdroppers
On the other hand, if you lose your copy of one of your conversations, you may be able to get a copy of it from your government with a little bit of luck and a public records request.
Con Will be discontinued Feb 2019
Slack acquired Stride / Hip Chat. Both Stride and Hip Chat will cease to exist. Sad since they were quite usable.
Con Prioprietary (non-free/libre)
Con Reliability of service has been weak
The reliability of the hosted HipChat service, particularly in the early days of version 4.x, has not been a strong suit.

Con Free plan has limited storage
Free plan comes with 5GB of storage, where as paid plan has "Unlimited".
Con Only one-on-one video calls in free version
There is no option for multi-user conference calls.

Con No emoji
There's no emoji support. Instead there are some strange custom emoticons which only make sense for people steeped in internet subculture and never get updated.
Con API calls are limited even on paid plan to 500 calls in 5min by default
This will force you to contact them when you need more calls.
Con Non-synced notifications
Messages read on one client don't sync their status to another client.
