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Tips to keep your sales team's emails landing in inboxes and out of spam folders

Worried your emails aren't making it to their final destination? Here are 9 ways to optimize your emails for deliverability.
John-Henry Scherck
January 20, 2016
Email deliverability

 "I'm sending you an email invite right now, but be sure to check your spam folder"

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Do your sales reps have to say this to leads over the phone? Hopefully they don't, but if you run aggressive outbound campaigns, getting your company's emails into inboxes can be an issue. Not all emails make it to their final destination, sort of like this cat:

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If your SDRs' emails aren't getting any love and you think deliverability may be the issue, three questions need to be asked:

  • Has your company spammed in the past? i.e. history of the domain that's sending the email.

  • Have the servers that send your email been spamming? i.e. history of the IP address the domain is sending from.

  • Are you spamming right now? i.e. content of the email being sent.

Every domain and IP that sends email has a reputation with email service providers. If your marketing team or sales reps have demonstrated a tendency for spamming, it can cause issues with email deliverability for the entire company.

You need to protect your company's sender reputation, because a few bad campaigns can cause problems for years.

Nine things you can do to keep your sales team's emails landing in inboxes:

1. Reign in overly aggressive reps that could cause users to hit the spam button

Some reps don't have enough leads to work, so they go back and work contacts (not prospects, contacts) that are completely unqualified. This can make for a busy-body, nervous-energy induced, nagging feeling of "I need to keep moving or I will die" that leads horrible emails like this:

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image via Moz

If prospects aren't opening your emails, viewing your collateral or responding to your calls, why are your reps bothering them again? Eventually, they will be forced to hit the spam button in their email client to silence the inbox assault so they can get some work done. Make sure your most aggressive reps aren't stepping over the line.

User reported spam is a huge tip off for email service providers that your sending something people do not want to deal with. Rather than harassing people that aren't going to buy, get your reps some new leads to work.

2. Don't send big email attachments

Your marketing team worked hard on all the high-res sales collateral and sleek pitch decks -- but all those big images can add up. Big attachments can cause your reps emails to get denied inbox entry.

If your sales team is sending large attachments in cold emails they could be going right to the spam folder. Instead of using attachments, send your sales documents and presentations with DocSend. Not only will sending DocSend links not risk your deliverability, your team will be able to measure document usage and engagement with prospects.

3. Be cautious of false positives with FullContact, Rapportive, SideKick etc.

There are a lot of tricks for finding someone's email address. Tools like Rapportive, FullContact and SideKick have become popular with SDRs. But these tools shouldn't be trusted blindly, they can trigger false positives:

Just because your Chrome extension of choice serves up the correct profile picture, or populates a prospects full name, it does not mean it's a "direct hit." You can see a few false positives in the screen grabbed GIF above. After a ton of misfires to nonexistent email addresses your deliverability will suffer.

4. Verify a single email address for a one-off pitch by pinging the email server.

One of the best ways to tell if an email address is correct is to ping the mail server by using a service like MailTester.com. But pinging non-existent email addresses from your office IP can hurt your deliverability, especially if you have 100 SDRs doing it on a daily basis. Instead of doing this from your office IP, use a free proxy like hide.me, and then use the proxy to head over to MailTester.com and try out any email address likely to be a hit for a prospect.

Each attempt will be met with green for a match:

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or Red for a non-existent email:

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5. Use a service like BriteVerify or NeverBounce to clean lists

Avoid sending emails that produce a "hard bounce," (i.e. sending to email addresses or domains that don't exist) at all costs. This gif illustrates how an email service provider reacts to one hard bounce from a sender... and then hundreds of hard bounces from the same sender:

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If you are buying or creating prospect lists with hundreds of fresh email addresses to feed your SDRs or marketing team, make sure they've been cleaned and verified. These third-party services also watch out for honeypot email addresses, which are spam traps - they will decimate your deliverability.

6. If attempting hyper-growth, scale outbound email volume at a reasonable rate

Just because you want to 100X your run rate doesn't mean you should 100X your outbound email volume. You need to build up your reputation with email service providers and warm up your IP address first.

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If you are an established company and dipping your toes in the outbound pool, start sending outbound emails gradually and test everything you can. Figure out which subject lines work and ditch the ones that don't as fast as you can. Even if your company needs to grow at light speed, you want to gradually ease into higher volume outbound email. If you go from sending 2000 new emails a week to 20,000 new emails a week, you will be growing at a suspiciously fast rate in the eyes of ESPs.

7. Be technically authentic

This robot is both technical *and* authentic

Gmail cites authentication as one of their top recommendations for helping get your email delivered to their users’ inboxes. By publishing your Sender Policy Framework (SPF) record, Domain-based Message Authentication, Reporting & Conformance (DMARC) policy, and signing messages with DomainKeys Identified Mail (DKIM),  the inboxes you're sending to will have some verifiable information to determine if your email deserves to end up in an inbox, or if it should be sequestered to the spam folder. If you've never heard of any of this stuff, ask your engineering team to make sure it's set up ASAP**.**

8. Don't send emails with tons of images

Spam filters can only process text and code, not images, so spammers love sending big images that contain their spammy messaging to try and bypass email filters. If you look at the top 10 reasons emails end up in spam filters, six of them have to do with sending too many images.

This can be especially tricky for SaaS sales, if you are sending large animated gifs in your emails to help explain your product you may be shooting yourself in the foot.

9. Don't make over the top or spammy sounding claims in your pitch

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We have nothing against Dr. McLaughlin's Electric Belt, but it's unlikely he'd make it past the Gmail spam filter with this type of cold pitch. MailChimp recommends avoiding the following when drafting an email:

  • Spammy phrases like “Click here!” “Once in a lifetime opportunity!” or

  • Excessive exclamation points!!!!!!!!!

  • USING ALL CAPS (especially in the subject line).

10. Set up Google Postmaster Tools to Measure Your Email Deliverability

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Google Postmaster Tools helps senders analyze their email deliverability. The dashboard provides a baseline of how your email is performing in terms of deliverability and will let you know if your company has any outstanding deliverability issues. If you start having problems with making it into inboxes, Postmaster Tools can help you figure out what's going on.

If you want to take a deep dive and learn the ins-and-outs of Postmaster Tools, Return Path has an awesome guide.

Following these best practices, your emails should be hitting their targets.

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The second email deliverability starts hurting, so does your growth. With these tips, you're better armed to get your emails to their proper final destination.

Wondering how you can boost the effectiveness of delivered emails? With DocSend, you’ll be able to share sensitive materials with external business partners while getting real-time, actionable, feedback on document engagement, so you can be in full control of your business outcome. Say goodbye to email attachments once and for all, and click here to get started with a free trial of DocSend!

image credits: bertknotDavid Morris, GSGCHans Splinterindiamos, GIPHY, 4GIFS.TUMBLR.COM

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