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Post initial setup, a primary concern will be the log-on issue. If your organization is fine with a separate log-on for your email provider, then this step will be quick. However, that's not typically what businesses want or users expect. In general, users expect to sign onto their desktops and have their email and file sharing sign-ons happen as part of that one-step process. Not surprisingly, this is called Single Sign-On (SSO) and it's enabled in one of three ways: through the use of a back-end directory service like Microsoft Active Directory (AD); an identity management service, like Okta (one of our Editors' Choice winners in that category); or several compatible web services that include SSO along with other apps and email services, like Google G Suite Business and Microsoft Office 365 Business Premium (two of the top providers reviewed here). Which method you choose depends on how your business is configured today and your long-term cloud services strategy. It's definitely a conversation you'll need to have either with your in-house IT staff or your outside IT consultant.
What about the time you clicked on that PayPal link that wasn't really a PayPal link? "Phishing" is a term applied to either websites or emails that pretend to be something they're not in hopes of getting a user to click on something they should have ignored. This tactis is done in hopes of then getting users to provide confidential information they would have otherwise kept to themselves, typically like passwords, financial information, or other personal data. While there are security measure that fight this, the mechanics behind phishing are, unfortunately, also consistently becoming more sophisticated. Even some dedicated antivirus and business-class hosted endpoint protection suites are having trouble keeping up.
Your next major concern will be compatibility. It's not a shock that most businesses run on Microsoft Windows and use some form of Microsoft Office. Being able to use common third-party clients such as Microsoft Outlook can often be a concern, and even today, compatibility with Microsoft Outlook isn't necessarily guaranteed. This is especially true when sending and receiving meeting invites. It only takes one garbled meeting invite to realize how frustrating this can be in the real world. Even if using Microsoft Outlook isn't a concern, portability is. If the service is entirely web-based, then is there a means for me to take my email offline and send email when I connect?
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