Outlook vs Skiff

If you're a larger enterprise, you're likely using Outlook instead of Gmail (Google Workspace) to manage your email and calendar for work.

That said, most startups and quickly growing companies use Google Workspace, so if you're looking into Gmail vs Outlook, we believe Gmail is the clear winner here. It just has a more user-friendly experience all-around, and has significantly more integrated tools ( most modern tools integrate with Gmail over Outlook).

If you're "stuck" with Outlook and want to make your email experience 10X better, using Outlook in addition to a platform like Superhuman email is the way to go.

• All-in-one email and calendar solution within Microsoft 365
• Tight integration with other Microsoft tools
• Familiar interface for long-time enterprise users
• Standard choice for companies already committed to Microsoft

• Clunkier user experience compared to modern email clients
• Fewer modern integrations compared to Google Workspace
• Limited “Sign in with Microsoft” support across newer SaaS tools
• Most modern startups and tools prioritize Google compatibility
• Rarely a proactive choice for small business owners

Outlook combines your inbox and calendar into a single interface. Giving you the ability to respond to your emails, check calendar availability, schedule a meeting, and send out invites, without switching tools.

For companies already using Microsoft 365, you know it works and that it’s functional. You also know it lacks that modern feel that places importance on speed and focus.

Outlook connects directly with the rest of the Microsoft ecosystem (Word, Excel, Teams, SharePoint, and OneDrive). And that's great if 365 is what you're committed to, but when you're looking to create a tech stack outside of their system, it suddenly becomes a lot less compelling.

Large enterprises rely on the level of oversight that Microsoft provides. It provides strong security, compliance features, and centralized admin controls, but this is a great example of just because flagship companies are using it doesn't mean it's what's best for you and your team.

If your team is a smaller and fast-moving team, this level of complexity will probably feel like overkill.

Outlook itself is included with Microsoft 365, and pricing varies depending on features and region. Most Microsoft 365 plans start around:

• Business Basic: ~$6/user/month
• Business Standard: ~$12.50/user/month
• Business Premium: ~$22/user/month

Skiff was a popular privacy-focused email client that was acquired by Notion and shut down.