How To Fix Email Deliverability Issues W/ Jimmy Kim

Email Marketing With Google

Hey, everyone.

I recently sat down with one of my best friends and Sendlane CEO, Jimmy Kim, to talk about both the current and future trends in email marketing. The funny thing about Jimmy and I is that we met as strangers sharing a hotel room at an event in Vegas.

Since then, we’ve gone on to work together in several capacities, the biggest one being that I’m a co-founder of Sendlane.

Jimmy has over 10 years of experience in email marketing, oversees the delivery 0f 750 million emails per month and has overseen the delivery of over 10 billion emails overall. Needless to say, the guy is an expert in his field.

So, here are my biggest takeaways from the conversation I had with Jimmy.

Overview Of Email Marketing With Gmail


Without a shadow of doubt, Gmail is the industry leader when it comes to email. At last count, Gmail had over 1.5 billion users. What that means is that Gmail sets the overall trends of the industry. While there are other email providers that have significant chunks of users, they’ll all be following the decisions that Google makes over the next couple years.

For email marketers, that means you need to be on top of what Gmail is doing and where they want to go. To give you an idea of where Gmail is going, you first need to understand how the whole email process works at the most basic level.

At Sendlane, here’s the basic process:

  • The user types up an email

  • They hit ‘send’

  • That email shoots of to Sendlane’s servers

  • Sendlane sends that out to the providers (i.e. Gmail)

  • Gmail delivers (or doesn’t deliver) the email

That last layer is the most important one for email marketers since nobody wants to end up getting flagged as spam or not have their email delivered at all. Gmail takes a few things into consideration to determine whether they actually inbox your emails:

  • The reputation of both the email provider (i.e. Sendlane) and the reputation of the person sending it

  • The reputation of the sender’s domain

  • The content of the email

All of that together goes into Gmail deciding whether or not to inbox your message, and there are very specific things that Google is looking for before they agree to put your email into someone’s inbox.

The biggest change and trend that we’re seeing in email marketing right now is that Gmail is putting an enormous focus on delivering unique and appropriate value to people at the right time. Gone are the days where you can just type up one email, send it out to your entire list and expect everyone to get it.

That type of behavior now lands you in the spam box.

To give you an idea of how healthy your account is, you need to look at the following metrics:

  • Open Rate: About 15%-20% is around the industry standard, but it varies by niche

  • Clickthrough Rate: Around 17% is good

  • Bounces: The number of emails returned to sender

  • Unsubscribers: Under 6% or 7% is good

You obviously also want to stay out of the user spam reports.

Now that you have a basic overview of how Gmail processes your emails and determines whether or not they deliver them, let’s go over the 7 rules and laws of Gmail that Jimmy Kim wants you to know.

Internal Health Meter

The internal health meter isn’t something specific that you can look at. Instead, it’s the overall quality of everything that goes into your email. This means:

  • Words your using

  • HTML structure

  • Domain quality

  • Link structure

Google keeps tabs on you way more than you might think, and factors seemingly unrelated to your email affect your deliverability. If the domain on your email is connected to a spammy website, for example, Google is likely going to penalize you.

You can think about your internal health meter much like a bucket filled with water.

You can make mistakes and spill some of the water, but you’re in trouble once that bucket is completely empty.


Email Marketing With Google

Engagement is huge for email deliverability right now because Google is pushing positive user experience hard.

What they’re looking for specifically are things like how many people interact with your email (i.e. by opening it), how fast they click the email after it was sent, how long they’re looking at the email, what they’re doing with the email and a range of other factors.

Engagement with your emails should be one of your highest priorities, which is why personalized messages (something we’ll cover later), are becoming increasingly important.

SEO For Email

If you’ve been around email marketing for a while, you know how easy it used to be. For example, Gary V says that he was getting 90% open rates back in 1997 before inboxes were crowded with messages.

That’s insane!

Back in those days, it didn’t matter too much if you sent out the same email to 500,000 people because the technology wasn’t advanced enough to detect that or do anything with it. Today, Google’s algorithms are looking out for (and rewarding) unique content.

This is why so many affiliate marketers have so much trouble getting their emails delivers. Way too many affiliate marketers are lazy and just copy and paste their emails to their entire list.

You need to be providing unique, personalized content to your list.

Promotional Tabs

While you may think of emails as going to either the inbox or the spam folders, it’s not that simple anymore. Today, you have categories like:

  • Social

  • Updates

  • Forums

  • Promotional

Just because your email doesn’t get sent to the spam folder doesn’t mean that it gets delivered straight to someone’s inbox. If Gmail scans the email and thinks that it’s promoting an offer or a sale, they’re likely going to send that email to the person’s promotional tab.

They’ll only see it there if they specifically look in their promotional folder. The goal behind this, as usual, is to create a better user experience.

Email Curse Words

No, I’m not talking about traditional curse words here.

Email curse words are words that significantly increase your chances of getting sent to the spam folder, never to be heard from again. Let me give you some examples to show you what I mean:

  • Weight loss

  • Apply now

  • Free

  • Act now

  • Click here

These are words that immediately raise a red flag for Gmail because so many people have misused them over the years. However, I’m not saying that you can’t use them at all.

It all comes down to that internal health meter that we discussed.

If you have a full health meter, you’re going to be able to get away with using these words a little bit more than other people. If you have a bad reputation, these words are going to get you sent to spam immediately.


One thing that works well in marketing, but will get you flagged inside Gmail, is the use of different symbols and enhancements in your text. What I mean by this are things like:

  • Bold

  • Color

  • Highlights

  • Italics

These are especially problematic if you use them in your subject line. While they may have worked well in the past, you can be sure that Gmail is going to be flagging emails with these with increasing frequency.

But again, it comes back to your reputation.

If you have a good reputation and can use these responsibly, you shouldn’t have any major problems.


With all of that in mind, we come to the most important step: testing.

What Gmail doesn’t want you to know is that there’s a simple way to check whether or not your emails are going to get sent directly to someone’s inbox or to the tabs or spam.

How you do this is you sign up for three or four free Gmail accounts. What you call them doesn’t matter too much. The important thing is that you don’t open or interact with any emails at all in these test accounts.

What you do with these accounts is you send your test email to all of them to see what happens with you email. Because Gmail doesn’t have any user behavior on you since you aren’t clicking or interacting with any emails, it gives you a good sense of where your emails are going to land in other inboxes.

Two Bonus Expert-Level Tips

Email Marketing With Google

Like I said, Jimmy’s been doing this email thing for quite some time, and he knows what he’s talking about when it comes to optimizing email marketing campaigns. These two tips from him that I’m going to share might make you a little bit uncomfortable, but they’re data-backed strategies that everyone needs to be using.

Purging Your Email Leads

I get it. This one is painful.

You work so hard (and spend money) to add email leads to your list, so why the heck would you want to take them off your list?

The reason is simple: user experience.

Remember when I said that Gmail prioritizes user experience and that all other email providers follow what Gmail is doing? Well, sending emails to people who don’t want them is one way to provide a poor user experience.

Your open rates and click-through rates are two major factors in determining whether you’re providing a good user experience. If only 5% of your list opens your emails, what do you think that tells Gmail?

It tells them people don’t want to see your emails.

So, the basic strategy is that you should remove any subscribers on your list who haven’t engaged with your emails over a period of the last 90 days. Then go another 90 days and remove anyone who doesn’t interact with your emails during that period.

If someone hasn’t opened in 90 days, why would they open at 150 days? What Jimmy and his team have found is that trying to re-engage people just isn’t worth the time or effort.

Simply take them off your list to show Gmail that you also value user experience.

Jimmy did this with me years ago, and he took my list from 600,000 subscribers to 200,000 subscribers. It terrified me to do it, but I also ended up getting about double the clicks that I was getting before I scrubbed the list.

One of the best features in Sendlane is their auto-hygiene features that scrubs your list for you.


The second thing all email marketers should absolutely be doing is segmenting their list to send more personalized and relevant emails. By making the buckets that you’re sending emails to a little bit smaller, it makes it much it much easier to get higher engagement.

So, instead of blasting everybody with the same email, personalize what you’re sending to make the experience more relevant for everybody.

While this does take more time, it’s worth it. The amount of extra value that you get is worth every extra minute that you put into creating segments and custom content.

Fix Email Deliverability Issues Today

Email Marketing With Google

Whether you’re thinking about building a list or already mailing a list, it’s important to start correcting any mistakes that you’re making as soon as possible. If anything, Gmail is going to be even more strict with email marketers moving forward.

You might as well get ahead now.

Remember, email marketing is all about building relationships and a positive user experience rather than just making sales.

If you focus on that, you’re going to be just fine.