Most Sales Operations professionals will face the typical scenario of a sales rep complaining about their email not being delivered. It will be easy to dismiss this as their email content not being compelling to the prospect. They are receiving the email. It’s just being ignored because the rep sucks at writing them. Obviously, that will be a possibility. More often than not, it will actually be the case.

However, the diligent Sales Ops pro should do their due diligence and look further into the issue. Perhaps the problem resides in the guts of your tech stack. It’s worth it to check on a regular basis, say a couple times a year, just to make sure that everything in your stack that touches emails is firing appropriately.

Here’s how to track down, diagnose, and fix your email deliverability issues:

Sometimes your sales reps suck at writing emails. Less often, the fault is in your stack.

TL;DR

There’s a lot of moving parts that affect email deliverability in a Sales organization. The most important cog in the system is the source of the email address and determining if the data can be trusted. Following the journey of the lead data from creation to contact by a Sales rep, and testing each stage and system that data touches determines if it’s a system or process issue that’s causing a deliverability problem.

If everything checks out, the human factor may be the cause. It’s up to Sales Ops to establish best practices for email personalization and to help Sales leadership train and keep their reps accountable to follow best practices to ensure email deliverability.

The Scenario

The sales team is telling you that they are suspicious that their emails are landing more and more in spam folders. As a Sales Ops pro, you are responsible for helping remove these kinds of obstacles.

• Where do you go to research the issue? 
• Based on what you learned, where did your thought process lead you? 
• How do you go about solving this issue? 

The Research

1. Check to see if emails are being bounced back. If Sales receives an automated reply from the Postmaster or Mailer Daemon indicating a spam filter has blocked their email, have them send it to you. Check the SalesLoft/Outreach.io bounce rates for anything above 5%.

Next, dig into the Postmaster response: 

• Which domains are sending these messages? Only one domain or multiple? Common domains (gmail, yahoo, outlook) or custom domains? Are bounces from a single email address on a domain or on all addresses in that domain?
• Hard bounce (5xx) or soft bounce (4xx)? Does the email address exist at all or did the user just spell it incorrectly?
• Is it certain sent emails or all emails that are getting these responses? 
• Was it a one-off email, or part of a bulk mailing to 500 leads/contacts?
• What’s the frequency of bounces? Once in a while, or every day multiple times per day.

2. Check sender reputation using services like mxtoolbox.com, Google Postmaster Tools, mail-tester.com, or dnschecker.org. See if they flag anything in the DNS record as unfavorable. Are you Authenticated? Does SpamAssassin like you? Are you blacklisted anywhere? If they catch anything that could be improved on the back-end of your email service, it will show here and you can address it in Admin.

3. Check Email Deliverability settings in SFDC.

• Ensure Bounce Management has been enabled and that Return bounced emails to sender is checked.
• Enable Email security compliance with standard email security mechanisms.
• Set up a DKIM key to improve recipient confidence in authorized emails.
• Test Deliverability on your own addresses to make sure Salesforce is set up correctly to deliver emails.

Also, check email deliverability settings in other Sales Engagement services that you forward emails through, like Outreach.

• Require opt-out links
• Setup hard bounce limits
• Create a special governance profile for frequent offenders – spam jail, lol.

4. Are all emails sent being tracked? Are all prospecting emails being sent through Outreach? Are all emails to prospects in Opportunity being logged to SFDC?

5. Verify for clean data. How old is the contact information in the database? 

6. Dig into the content of the emails. Ask questions like:

• Do we have permission to email the prospect?
• Is this being sent to the right audience? Right personas in the ICP? If not, emails may be manually marked as Spam. 
• How often are we emailing them? Every day or every few weeks?
• Are we A/B testing email subject lines to see what resonates with a prospect?
• Are subject lines:
  • In all caps?
  • Using a ton of exclamation points?
  • Contain emoji?
• Does the body:
  • Have embedded video, Flash, or Javascript?
  • Have large attachments?
  • Have a ton of images and little text?
  • Have excessive links? Have any links?
  • Using non-standard formats and fonts and colors?
• Does the To: address have the prospect’s name included and not just the email address?
• Does the From: address have the user’s real name, or a personalized sender, or a generic one?

A little bounce is acceptable. If the bounce rate goes over 5%, then it’s time to investigate further.

The Thought Process:

You are going to want to start from the data source and work your way forward through each stage in the data journey to the transmission of the email itself.

Most of the stages in that process are controlled by Sales Ops, and so much of the work to resolve the current issue and prevent any future bounce problems is on you.

The last stage, when the Rep personalizes the email in the Outreach sequence (or any one-off emails), is still on SalesOps. You have to do your best to make sure best practices are communicated by Trainers, understood and encouraged by Sales Management, and followed by Reps.

Ensuring the technical administration of the tools follows best practices for email deliverability is vital. Equally important is that Reps don’t deviate from email best practices. 

Finally, a little bounce is acceptable. If the bounce rate goes over 5%, then it’s time to investigate further.

The Solution

What Sales Ops can fix:

First to Last in Data journey: 

1. Where are we getting our 3rd party contact data from? Is it a trusted source? How old is the data? Does it match the ICP and Personas we want to be targeting?
   • Are marketing-sourced leads being properly enriched?
   • Make sure that ZoomInfo is connected properly and is updating Contact information in SFDC with verified email addresses. 
2. Is the Data cleaned well prior to import? Spellchecked? No added characters? Unnecessary spaces? Phone numbers, zip codes, State codes all uniform? Text PROPER?
   • Export to CSV and run standard list of data cleansing formulae.
3. Is the Data Import into SFDC working correctly? Are all the fields mapped correctly? Not trying to upload excessive numbers of records at one time?
4. Are there duplicate contacts in SFDC?
   • Scrub the Contact list to remove invalid email addresses to make way for the good ones.
   • Use default Dedupe tool in SFDC or 3rd party app like Cloudingo
5. Are fields mapped correctly between SFDC and Outreach.io? Are directional updates set up correctly?
6. Are Zaps firing correctly?
7. Check bounce rate from all sending platforms: Outreach.io and Salesforce.

What you need other people’s help in fixing:

Make sure the Sales team is sending all emails through Outreach and that every email is logged in SFDC.

Inform the Sales team that if they notice that an email bounced to an address, don’t try sending it again. Have them check for these things first:

• Are you sending the email through Outreach and/or logging it in SFDC?
• Is the Contact’s name listed in the To: line, in addition to the email address?
• If this is a one-off email, are you following email best practices?
  • natural language subject line with normal punctuation and no sensationalization?
  • One or fewer attachments, less than 5MB?
  • One or fewer links?
  • One or fewer images?
  • Copy of reasonable length?
• Have you confirmed with the Contact that they haven’t accidentally manually marked you as Spam?
  • Contact your prospect and ask them to add you to their list of Contacts in their email program.

Once everything on this list checks out, then Report it to Sales Ops so we can start fixing it on our end.

Finally, just because the email isn’t being replied to doesn’t necessarily mean that the emails are going to spam. It may be that Sales isn’t being compelling in their outreach and no one wants to reply to their canned pitch.

• Best practice is to A/B test the heck out of email sequences.
  • Subject lines.
  • First 14 words in the body (what shows up in the email preview in Gmail)
  • Email body length
  • CTA
  • Frequency of emails
  • Multi-channel: is it just email or is it a combination of all messaging that causes low response rates/marked as Spam.
  • Cadence of the outreach sequence. Too many emails or too few when compared to the number of other channels being used.

Conclusion

It’s probably the Sales Reps fault their email isn’t being “delivered”. It is, it’s just that the Prospect doesn’t want to read it. The email sucks.

When that’s not the case and your Rep is not at fault, as a Sales Operations professional it’s your solemn duty to your organization to track down the real culprit: your stack needs to suck less.

Happy hunting! 

Resources consulted:

• https://bobcares.com/blog/550-email-blocked/
• https://www.shellblack.com/administration/email-deliverabilty-and-html-status-reports/
• https://nethunt.com/blog/how-to-make-sure-your-emails-dont-go-to-spam/
• https://coherentpath.com/rarelogic/blog/how-to-prevent-emails-from-going-to-spam/
• https://foxbound.io/blog/the-quick-guide-to-bounce-codes-and-email-deliverability/
• https://support.outreach.io/hc/en-us/articles/115004605147-Understanding-Bounced-Emails