YouSendIt, the file transfer and business content collaboration service, has been trucking along of late, in spite of competition from plucky upstarts like Box. The startup has 98 percent of Fortune 500 companies on board in some form or another, and last we heard, YouSendIt had over 600K paying customers along with 30 million registered users.

In May, the company found a new CEO in Brad Garlinghouse, the former head of consumer products at AOL. Prior to AOL, the exec spent five years in various senior positons at Yahoo. Peanut butter manifestos notwithstanding, the CEO (and team) has parlayed past connections into a significant partnership with his former employer.

YouSendIt has announced that its Attach Large Files app will be integrated into the “Compose Message” window in Yahoo Mail. This means that users can now compose emails and attach files via YouSendIt (whether they be personal files, like video and photos or work files like CAD and PowerPoint) within the message.

The integration is significant for YouSendIt both because it’s the first partner app to be included in Yahoo’s compose message window, but more significantly, the integration gives the company direct, always-there access to Yahoo Mail’s sizable user base. Today, the mail client has over 300 million users, who are sending more than 200 million attachments from their inboxes every day, said David McDowell, the senior director of Product Management at Yahoo! Mail.

Since it turns out that more than a handful of people use email to communicate on a daily basis, if this trend continues, the company thinks that easy-to-use apps and services with their hooks in email will play an integral role in collaboration in the future.

Be that as it may, as many readers have likely experienced, the major email providers put a cap on their attachment size, generally in the range of 15MB to 25MB. Since this is a pain in the ass because we’re all increasingly using email to send large files, this is where YouSendIt swoops in. Now users can send up to 50 files or 100MB in a single email.

Since its initial beta release in the app gallery of Yahoo Mail last year, eight million users have registered and have sent more than 20 million files. Now, that growing list of users can not only compose an email and attach a mess of hefty files via YouSendIt but also verify when a file has been downloaded, ensure that only the intended recipient can download a particular file, and set advanced security options (like setting the amount of time a file is available for download or how many times it can be downloaded.

The company’s partnership with Yahoo continues its march across the major email platforms. In addition to Yahoo Mail, YouSendIt is now available within the attachment functionality of Mozilla Thunderbird, AOL Mail, Gmail, and Hotmail.

It’s a smart approach: Take email by storm and let the rest follow.

Find YouSendIt at home here.

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