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Outreach emails that are designed to target top candidates take a lot of time and energy for recruiters to create. (At least, they should, if you want them to be effective and make the recipients feel like true VIPs!) So, it’s frustrating to think that all that good work might end up in a spam folder — never to be retrieved, opened, read, and enthusiastically replied to by the prospective candidate.

Emails end up in spam folders or get bounced for many reasons. The recipient’s mail system and security settings have a lot to do with that process, of course. Most spam filters and mail servers use a scoring method to decide which messages should be relegated to a user’s spam folder. The higher the spam score assigned to your email, the more likely your message won’t make it to the recipient’s inbox.

There are several things you can do, however, to help keep your candidate outreach emails out of the spam folder. Here are a few strategies.

When formatting outreach emails, think plain and simple.


You want your outreach emails to dazzle potential hires, of course. But if they’re HTML-heavy and bloated with images, color formatting, and other bells and whistles, spam filters will be inclined to reject them outright. Avoid DIV tags (HTML coding), which is generally good practice for emails anyway. And make sure not to leave tables empty.

Also, be careful about generating bad markups. (This often happens when copying and pasting from Microsoft Word.) Just type plain text in the compose field. Plain text works great — really. It will be less likely to send up a red flag with spam filters and will look professional to all recipients.

Subject lines should be brief — 32 characters or fewer, including spaces, is ideal, so they fit on small device screens — and straightforward. Be careful about the words you choose to include your message, especially in the subject line. Even seemingly benign words like “Success” and “Great” and “Boss” could be flagged by a spam filter. Phrases like “Apply now” and “Call now” and “Urgent” can also put your email on the short path to a spam folder. (Note: When crafting your outreach emails, take the time to do a quick search online for current lists of spam trigger words.)

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Timothy Massad is currently a Senior Fellow at the Kennedy School of Government at Harvard University and an Adjunct Professor of Law at Georgetown Law School.

Mr. Massad served as Chairman of the U.S. Commodity Futures Trading Commission from 2014-2017. Under his leadership, the agency implemented critical reforms of the over-the-counter swaps market; harmonized many aspects of cross-border regulation, including reaching a landmark agreement with the European Union on clearinghouse oversight; enhanced cybersecurity for critical market infrastructure; improved the resilience of major clearinghouses; and took many actions to ensure commercial businesses were not burdened by Dodd- Frank reforms.

Under his leadership, the agency declared virtual currencies to be commodities, brought enforcement actions against unregistered Bitcoin platforms and approved a Bitcoin swap.

Previously, Mr. Massad served as the Assistant Secretary for Financial Stability of the U.S. Department of the Treasury. In that capacity, he oversaw the Troubled Asset Relief Program (TARP), the principal U.S. governmental response to the 2008 financial crisis. During his tenure, Treasury recovered more on all the crisis investments than was disbursed. Mr. Massad was with the Treasury from 2009 to 2014 and also served as a counselor to the Treasury Secretary.

Prior to his government service, Mr. Massad was a partner in the law firm of Cravath, Swaine & Moore, LLP. Mr. Massad had a broad corporate practice with a focus on corporate finance, financial markets and derivatives. His practice was heavily international. While resident primarily in New York over his 25 year career with the firm, he served as co-manager of the Hong Kong office for five years and also in the London office. He was

one of the principal lawyers that drafted the ISDA Master Agreement governing derivative transactions as well as the original User’s Guide. He also had an active pro bono practice, representing UNICEF and Covenant House, among others, for many years.

Mr. Massad has a J.D. from Harvard Law School and a B.A. from Harvard College. He currently lives in Washington, D.C. with his family.