Sophos has been a much easier product to configure and eventually manage, with preset rules and policies to start off right out of the box, saving administrators time from adding every category and or site. However you can add/import all know good company sites (internal url's) …
Before Sophos, I would receive scammers regarding tradeshow lists. People wanted me to pay for lists, but these people weren't actually from the tradeshows. I can now block those, and have received much fewer of those scams. I am also able to open emails within quarantine to view them before deleting, releasing, allowing, or blocking. I use this to my advantage, and am able to make better decisions on what to do with the emails.
If you already have Webroot AV, it makes sense to continue with the same vendor. It's pretty cheap compared to some solutions, so it might be the case that it's this or nothing, in which case this is a no brainer. If you are an MSP, this is an easy product to sell, and requires very little maintenance. you do need to monitor it but it runs itself most of the time. If you are a customer with >50 users, you should really be looking for a product that is a bit higher up the food chain
Sophos does an excellent job of category-based content filtering. It's easy to configure and flexible for many environments with the ability to tighten or loosen restrictions as requirements determing.
Sophos' built-in capabilites can force safe search rules to protect against content work-arounds like Image search and search engines in general.
The Sophos XTreme architecture also helps improve the overall performance of the Web Content Filtering solution. It is very quick and very transparent when in use on the network.
Enforcing organisational policies regarding internet usage, such as blocking access to certain types of websites (e.g., gambling, social networking, etc.)
Sophos has been a much easier product to configure and eventually manage, with preset rules and policies to start off right out of the box, saving administrators time from adding every category and or site. However you can add/import all know good company sites (internal url's) as well as local sites for a safer settings. (know sites)