The E-Mail Marketing Pocket Bible

by Daniel Pereira

If you are an email marketer you know that ISPs are making your life harder.

A lot has worsened in 2015 and you have probably seen your deliverability rate fall to the ground. We all have been screwed at some level and this new scenario is forcing us to take email strategy and governance to a whole new level.

Every digital marketing campaign starts with the same purpose: capture interested and engaged leads.

Although not always worried about the “interested and engaged”, everyone know that leads are equivalent to gold in the internet universe.

That’s the first possible conversion, the top of the funnel.

And, in the end, leads are the best way to keep contact and create a relationship with potential buyers.

That’s probably why more than 50% of growth hacking tips I’ve seen include some form of e-mail.

So, now it’s very common that websites develop any number of lead capturing strategies that goes from pop-ups and exit intents to landings pages, free content, webinars and more.

And what do you do with leads? Send them lots of e-mails, of course.

Yes, you should be feeling guilty too. Users want stuff for free, but this doesn’t mean that they want to be bothered with a sequence of e-mails from your company.

I know what you’re thinking:

– but they have opted-in!

I know that, because that’s what I used to think too.

But nowadays, there is a price to pay if you are still thinking like that.

Here’s the hard fact: ISPs have been getting harder and harder on spam fighting policies for high volume senders and it doesn’t matter if you are a viagra spammer or not.

But guess who’s helping make things even worse!


Those who have opted-in.

And it was a simple UX change that caused this:

more evidence to the report spam button.

Take a look:

Gmail Spam Button
Outlook Junk Button
Yahoo Spam Button

That’s when “report spam” became the new “unsubscribe” for users.

By making it too easy to report spam, user behaviour is another big thorn on your side.

Even my company transactional e-mails (with a simple order confirmation) sometimes get complained…

Yes, people are reporting spam at transactional e-mails.

But that’s not all.

In the past, it was ok to think that if the customer have not unsubscribed or haven’t clicked into report spam they still want to receive your message, even if they didn’t open or click it.

Maybe they are saving it for later, right?

Damn, right!

In my case, 75% of my leads take an average of 55 days to make their first purchase.

But major ISPs don’t care about that.

They have “improved” their SPAM algorithms and now track user engagement by analyzing opens, clicks and replies as a way to understand if you might be a candidate for their spam folder.

In other words, if most of your emails are sitting unopened in users inbox you are going to get into spam anytime soon.

But why I decided to write about it?

Yes folks, I also have been screwed.

Very badly.

All of a sudden, 100% of my company emails got into the Spam Folder on all major ISPs and it was not my fault (sort of).

I decided to switch to a new cheaper bugged e-mail automation software, but let’s not get into that.

Anyway, it took me by surprise.

The first symptom was a weird delay on our email delivery (also known as email throttling).

Then our sales started dropping…

So we went after some advice!

People told us: check your sender score!

It was 97, not bad.

Blog posts told us: check black lists!

We were not there!

eBooks told us: switch to a dedicated IP!

We did it… and it got even worse.

— “This cannot be happening” was all I could think over and over…

So here the second reason I decided to write this guide: there are no experts and there’s no good advice available anywhere.

There are so few articles you can trust or people willing to help on email deliverability & governance that I decided to write a full guide on what I have learned during the hard process of getting out of the spam folder.

This is also a guide on how you too can keep your levels of deliverability at a maximum.

So let’s begin.

Step 1) Understand How User Engagement is Measured

Regardless anything else you have read, these are the main types of user engagement you need to be aware of:

  1. Email Reported as Spam
  2. Email Unsubscribed
  3. Email not read
  4. Email read, then deleted
  5. Email read, then clicked
  6. Email read, then replied to / Sender in Contact List

These engagements levels will have different weights depending on the frequency of email received from a source (usually a domain).

So take note:

  1. This range go from very bad (1) to very good (6).
  2. For your peace of mind, user engagement must be from 4 to 6.
  3. But from 5 to 6 is even better
  4. If you are a high volume sender being at 3 is already quite dangerous
  5. 1 and 2 is dangerous to anyone, which means that algorithms are working toward to classify your email as spam.

And remember, do everything you can to avoid high complaint rates (user who report your email as spam) at all times. You should never go beyond 0,3%.

Step 2) Email Technology Set UP

  1. Choosing a email system is hard and there’s a lot of crap out there. If you have a good team of engineers/developers choose to create your own system. After using tools such as mailchimp and hubspot, I can guarantee you that pays off (it’s much cheaper and reliable) to set up your own system using Mandrill, Sendgrid or Amazon SES. A great unexpected upside that we got from this was that by having our landings pages made on our application we could smooth user login, using the first conversion as a first step on his account creation (and a lot more cool stuff I’m not going to list here).
  2. If you can’t develop your own system go for the big players. Reach Hubspot or Pardot or Vero and ask for discount by the end of their sales process (they can go up to 75% of discount from their list price and this segment is getting a red ocean of competitiveness — this is no joke).
  3. There are some interesting options for self-hosted email out there. We are currently using Arp Reach with Amazon SES (best email service to deliver to hotmail if you don’t have a certified dedicated IP) for our promotional/manual emails, but you can also use Sendy.
  4. Add your domain to the only whitelist that matters:
  5. Have a SPF, DKIM and DMARC records in place (all of them). They help you certify which services are allowed to send e-mails in your behalf and guarantee to ISPs trustworthy of e-mails from your domain.
  6. If you use Google Apps (and I hope that you are), I advise you to follow Google Help on how to setup them or contact your email service or marketing automation tool to help you with that. Check Google on SPF Records, Google on DKIM and Google on DMARC.
  7. Make sure to setup SPF and DKIM for each one of the services you use to send email in behalf of your domain (e.g.: ticketing systems, CRM systems, etc.) and not only your email and email marketing/automation service provider.
  8. There’s no need to setup SPF2.0 (sender ID). It’s obsolete and it makes no difference to improve your deliverability with hotmail/outlook/live ISP and mentioned in some articles in the web (I have tested).
  9. Avoid too many DNS lookups in your SPF Record. Use the Email Stuff Checker here to find out how many lookups yours have.
  10. Setup a Reverse DNS (also known as PTR Records) whenever possible. Many email service providers help you with that. This is how you have to do it in Mandrill (system I use for transactional e-mails).
  11. There are some wizards that may help you with SPF Records. I recommend this two: SPF Wizard or Unlock the Inbox.
  12. Should you go with dedicated IP? Only if you are a very high volume sender (Over 1MM emails / month) and if your are planning to have an Email certification from a company such as Return Path in the long run (more on IP certification later).
  13. If you decided to go with a dedicated IP understand that it takes time for it to get good credibility with ISPs, even using the IP warm up option in email service providers. So expect worse results at the beginning and up to 3 months to see it get at good levels. Every single new IP is seen as a potential source of SPAM by ISPs.
  14. Although sender score of shared IPs might be lower than dedicated IPs, a few spam complaints won’t hurt as much as if you have your own domain. In the end what matters is not shared IPs sender score but email service provider quality in first place. Good email companies have strong governance on complaints and unsubscribe rates to have their shared IP at the best possible performance. Bad email software companies have no idea what’s going on and this might hurt your domain. Amazon SES does a great job by being very rigorous when allowing new users to send through them (and they only have shared IP option).
  15. I personally recommend a mix of dedicated IP and shared IP, but it really depends on your sending volumes and setup.
  16. Still undecided? Mail Up has a good post about that.
  17. If you go with dedicated IPs, don’t have too many. Two is a good number.
  18. Remember that if you decided to use dedicated IPs make sure they are at your SPF records with the ip4 syntax.
  19. Should you use a different domain for your promotional emails? This is a good idea if you want to avoid affecting your team email communication. With our problem, my company email address started to get into spam folder of anyone I was trying to email, so this forced me to use my personal email in order to communicate again. Companies such as Buffer use to send newsletters, for example. The rule of thumb here is: use a domain that relates to your branding to avoid confusion.
  20. Whatever domain you use avoid using e-mail addresses such as or to send e-mails.
  21. It’s better to use people names as senders, but don’t forget to say that they are from your company. Buffer send messages from “Courtney from Buffer“. Got it?

Step 3) Feedback Loops

  1. After initial setup steps, check if your setup is okay with MX Toolbox or Google’s Check MX.
  2. Have a Feedback Loop System in Place. A feedback loop allows you to be notified from all major ISPs everytime an email user report you as spam. This will allow you to automatically or manually remove emails from your list. One of the worst thing you can do nowadays is keep sending emails to users who have marked you as spam.
  3. Good email sending service providers will automatically set up a feedback loop for you. For example, if you use Sendgrid or Mandrill don’t worry, they do it.
  4. If you send emails through your own servers or use a sending service that does not automatically set it up for you, go and do it yourself by manually registering in the feedback loop of major ISPs. Here’s a full list.
  5. To register at them you must create an e-mail specifically for compaints reports. Create both and
  6. Add those e-mails to
  7. Have a privacy policy page in your website. Some feedback loops will ask you that.
  8. Some feedback loops will notice you about complaints, but won’t tell you which user has done it (which will not help you on identifying which user to remove from your mailing list). So it’s important to add the recipient email address automatically in the html of each message (e.g.: this email was sent to “” because you have subscribed to our newsletter)
  9. If you are having problems with Gmail you can contact them through this page.
  10. If you are having problems with Hotmail you can contact them through this page.
  11. They usually don’t answer you, but I think they consider it somehow.

Step 4) Email formatting, Content and Frequency

  1. If you want better deliverability try to balance text and images ratio. The More text you have (and less image) the better. Always.
  2. Use Google Bulker Senders List as a guide. It offers great advice.
  3. Use List-unsubscribe Header (both automatic link and mailto: options). You might have to ask your email service to add this. This will give your e-mails, in Gmail, that nice and easy to use unsubscribe link. But only if you have good reputation, if not they will keep “report spam” as the easiest option for users.
  4. Use nice clean responsive e-mail layout. Here are three sources of templates I have used: Zurb Responsive Email Templates or Responsive Email Patterns or Lee Monroe Really Simple HTML Template.
  5. Keep your e-mail branding / desing as close as possible to your website (but remember: don’t use too much images).
  6. Include header and footer with a. social network links; b. web view link; and c. unsubscribe link.
  7. Prioritize Good Content over Promotional / Sales Emails — that’s the only way to have your email list engaged with you in the long run.
  8. Keep your e-mails subject aligned to your content. If you play with subjects with open rate objective but fail to deliver an aligned content, be prepared for a higher complaint rate.
  9. Use a welcome e-mail to align with the user communication frequency and content.
  10. It’s also good to allow users to switch from daily to weekly or monthly e-mails.
  11. Ask users to add your company e-mail to their contact list and to take it out of promotional inbox.
Nice example from Copy Hackers asking users to move their e-mail to primary folder in gmail

Step 5) Lead Generation and Email List Management

  1. You have to avoid sending to incorrect emails addresses at all costs. Although it might be a simple typing error from a user, ISPs think that you might have purchased a email list with a lot of non-sense emails used to bloat lists or that you are inserting inactive e-mails who won’t report your e-mails as spam. So your lists should never have over 5% of inactive/disengaged users.
  2. To help you with that there are some tools on the market, such as: Kickbox, Brite Verify and Verias.
  3. Mailgun offers a free API email validator that you might want to try.
  4. Many of those services allow you to verify emails right at the opt-in forms, which saves you time and let user correct mistyping. But the verification may take up to 3 seconds (or more) and may impact user experience.
  5. Always use a checkbox (remember to let it unchecked) to ask users to confirm that they want to receive newsletter or promotional emails.
  6. Always use double opt-in email to validate user intention and engagement. Trust me, although this may reduce your conversion or lead capture results, it will give you more piece of mind in the future.
  7. All those steps are also important to avoid Microsoft Spam Traps.
  8. Create a routine of list cleaning: for example, you should remove any e-mail address which has not engaged with your e-mails for more than 3 months. But this depends on your e-mail sending and lead capturing volume, so you are the best person to choose cleaning frequency.
  9. Do not send more than one e-mail a day. Although this may seem obvious, be aware that having different landing pages, lead capturing boxes and e-mail systems (for transactional, promotional, etc.) can make this happen without you notice it. But ISPs and users will surely do.
  10. Avoid sending e-mails on weekend if you can.

Step 6) Monitoring Tools

  1. Always use monitor tools to keep a close eye on your performance.
  2. Use free tools from major ISPs, such as: Google Postmaster and Microsoft SNDS
  3. And choose a paid tool such as: Inboxtrail or 250ok. Other options here.
  4. If you are brazilian, use Inbox Monitor 360

Other Observations

  1. No matter what you do, you may see a higher complaint rate during weekends (which will affect your delivery rates on monday). Users who do not check promotional emails during the week, use report spam button more often as it represents a faster way to clean their inbox on weekends.
  2. Every effect on your e-mail strategy usually takes 24h to take effect. ISPs algorithms don’t work on real-time. They usually process results in 24 hours.
  3. Hotmail/Live/Outlook is the worst ISP to deal with nowadays. If they represent a big portion of your mailing list, you really have to consider investing in a Return Path certification. I’m not sure how Return Path have landed this deal/partnership with microsoft, but it’s surely making them very rich.

A note on Email Certification

  1. If you want to make e-mail deliverability a priority you should invest in an email certification service.
  2. The most famous one is Return Path and although very expensive, as said they have a partnership with microsoft (hotmail, live & outlook) which gets you in the inbox once you are certified.
  3. If you follow all of the steps above it’ll be a piece of cake to get certified. But it’s very hard to keep certification as any slip may take you into suspension.
  4. The other option out there is Surety Mail but it seams to not have much efficiency with Hotmail.
  5. To avoid high costs with certification you may consider certification of only one dedicated IP designated to microsoft recipients.

How to Get Back into the Inbox

First, understand that it’s possible!

What we did was:

  1. Do all the steps above;
  2. Monitor your feedback loop every single day to take out complainers e-mail addresses;
  3. Use inbox monitoring tools to correct wrong decisions (content, subject, etc.) as fast as possible;
  4. Send emails only to engaged contacts (this meant reducing our mailing list from 200,000 emails to 20,000 — hard but it was the only way to start reverting our domain reputation on ISPs);
  5. Keep volume constant, don’t vary too much your sending intervals and volume;
  6. Don’t send e-mails on weekends;
  7. Create a re-engagement strategy and send it to very low number of e-mails. If you see bad results, consider building your mailing list from the ground up;
  8. Wait, be patience and test a lot of different content strategies to improve engagement;
  9. After two weeks of the first signs of improvement, start capturing leads again with all best practices in place.
  10. Have in mind that your master objective is: engagement. period.
First sign at Google Postmaster that we were in the right direction. We are currently at the medium level.

If you still want to use 3rd party systems

  1. For simple email newsletter I do recommend Mailup (mailchimp is awsome, but too expensive). Mailup have a innovative pricing system and really help their customers improve deliverability.
  2. For automation system, if you are a SaaS I do recommed Pardot or Hubspot
  3. If you are an E-commerce I do recommend Klaviyo.
  4. There’s also some cool behavioural tools like Vero or even Mixpanel
  5. Leadsquared is a tool I’m Looking forward to try soon.

Final note:

Like it or not this is the new level of governance you must adopt in order to deliver your companies emails to users inbox.

If your levels are still ok, the recommendations above might improve it to even better levels.

If you are not delivering well, keep in mind that it takes time (3 to 4 months) to get out of this hole. It’s very distressing but it does revert and get back to good levels.

Well, that’s it! I hope it helps you somehow!

Good luck and if you think someone else might benefit from this post share and recommend it! :p

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