The Expert’s Guide to Email Marketing

Table of Contents

Our goal at SendGrid is to make sure you have all the tools and resources you need to be the go-to person for email marketing at your organization. For this guide, rather than just tell you what works from our perspective, we decided to get advice from some of the email experts that work with us, and use SendGrid themselves.

The Expert’s Guide to Email Marketing taps into the email knowledge of some of the industry’s best senders. This guide is designed to help novice and other experts alike in improving their email marketing programs.

Visit any of the above sections to learn more about the email marketing experts who work at these successful companies, and how they use email marketing to reach customers and drive engagement.

Whether you’re at a 5-person startup, or a 5,000-person corporation, we believe that educating customers about email is the best way to make them excellent senders. Use this guide to take your email marketing to the next level.

Chapter 1: Subject line strategy with SendGrid

The subject line is a window into the content of your email. If your recipients haven’t decided whether or not to open your message based on who you are as a company, they’ll absolutely decide if they’re going to open it based on your subject line.

Jill Guest -Sr. Customer Growth Marketing Manager

Jill Guest is SendGrid’s Sr. Customer Growth Marketing Manager. Jill works to ensure we deliver marketing email and in-app messaging that educates, inspires, and delights our customers and community. She joined the SendGrid team in 2011 and has since scaled the email marketing program from 3,000 to almost 700,000 loyal subscribers.

Best practices

Before we create and send a new email, there are a few things we keep in mind when it comes to the subject line:

1. Write content first – Rather than create the subject line and then the message and the call to action, we think about what action we want the recipient to take when reading the message. Once that’s taken care of, we develop a subject line that is descriptive of the email and tells how the message will provide benefit.

2. Limit characters – Try to limit the number of characters used when possible. It’s easier, and more intriguing, for people to read a full subject line rather than just a portion of your intended sentence.

3. Include special characters and emojis sparingly – If you’ve opened your inbox lately, you’ve probably seen companies trying to catch your eye with an emoji or other character within the subject line. While this might be ok for emailing a customer about a new sale, it may have a jarring effect on an enterprise business client.

4. Keep personas and segments in mind – If you have the capability, and know who your customer personas are, it’s extremely beneficial to write subject lines that speak specifically to those audiences. At SendGrid, there are different types of customers who use our products, and we actively try to speak to them differently.

Avoid “spamminess”

If there’s one thing that customers really dislike, it’s the feeling that they’ve been tricked. To prevent this as a sender, you should make sure that subject lines and message CTAs are closely tied.

This prevents the reader from feeling “duped” or making them think the message should be marked as spam because it was misleading.

Another thing to keep in mind is to think about the use of all caps in subject lines. This may seem like a way to grab attention, but in reality, an all caps subject line looks spammy and may get you sent to the junk folder.

Keep things fresh

It’s always a good idea to keep things consistent in your emails so that recipients know what they’re getting, but you also want to make sure your subject lines are interesting and grab attention. One of the ways you can do this is by changing things up every now and then.

• Caps – At SendGrid, we usually use caps in our subject lines the same way you would title an article. However, for urgent or account-essential communications, it may make sense to include some all-caps words, but more than that you risk looking like a spam message.

• Test – Subject line testing is a consistent and simple option for different campaigns, especially if you don’t have anything else planned. However, it’s good to tie the subject line test to larger sending strategies that can be applied to future messages rather than just the copy for that particular send.

• Use Your Content – Oftentimes, recipients can see a small amount of text as a preview after the subject line. Use this to your advantage! You can ask a question with the subject line and have an answer in that text, or in a less formal situation, ask a joke.

• Use Their Name – For a more personalized touch, you can use a name substitution in the subject line, but you need to be careful. If recipients fail to provide their name, or if they provide a fake name, this could backfire by looking unprofessional in their inbox.

• Use Your Name – For some sends, it may make sense to have the email come from you, rather than from your company. This can provide a more informal avenue for having a conversation with customers.

Your subject lines are a reflection of your organization. So, by all means, have fun with them and work on keeping them interesting, but you also want to make sure your tone and structure are consistent, and reflect what customers see on your site or app.

Learn more about SendGrid

SendGrid is a proven, cloud-based customer communication platform that drives engagement and business growth. SendGrid is a leader in email deliverability and its cloud-based platform successfully delivers over 25 billion emails each month for Internet and mobile-based customers like Airbnb, Pandora, HubSpot, Spotify, Uber and FourSquare as well as more traditional enterprises like Intuit and Costco. Learn more at

Chapter 2: Image testing with Pandora

Pandora uses images in every email. Not only do images make messages more visually appealing, they provide our readers with a clear action to take after they’ve opened the message.

David Hampian – Sr. Marketing Manager

For the past 4 years, David has managed Pandora’s owned media marketing channels, including email, mobile push, and in-product notifications. He spends his days developing and executing marketing campaigns that not only empower music makers by helping them reach millions of fans with just the right station or concert, but benefit music lovers by leading them to their next favorite song or show. David’s campaigns drive over 1M incremental listeners, 4M incremental hours, and 6M station creates to Pandora each month. His career mission is to enrich lives with music.

Image direction comes from the Pandora brand team. One of the things the brand team does is update an image library that email marketers can source from as they’re creating messages.

We also have a brand design team that’s responsible for creating all of the templates and appearance of Pandora marketing emails. Since we have this resource, it allows us to get a lot of customization and improve the look and feel of messages depending on the type of campaign we’re sending.

Most importantly, before sending an image to everyone, we run tests to determine what works best and generates the most clicks. Our tests include everything image-related, including:

Featured images

For a long time, it was difficult for us to get album art included in messages, but when we were able to implement it, we tested and found that it generates the most clicks in emails. We add a play symbol over the album to make it even more obvious to recipients that they can click on it to hear the album music.

Hero images

A more recent addition to our emails is hero images. One of the issues we have to take into account is that their inclusion means it pushes our content further down, which means recipients have to scroll further. To get the best of both worlds, we’ve been trying to incorporate the hero image into the body of the email.

This way, the image and the message are combined in a way that doesn’t push all the content below a giant hero image that isn’t providing very much value to the reader.

Moving images

In addition to the current images we use in messages, we’ve tested gifs and animations. One of the best uses we’ve found for gifs is in educational messages and tutorials. Showing users how to perform a specific action, or use the app for the first time are good examples of when gifs can be leveraged well.

Gifs and videos can be difficult to create, and require a lot of time from designers. Don’t rely on having the best looking gif if it means you’re sacrificing relevance or context with recipients.


Pandora doesn’t use video because we haven’t found a good way to incorporate it yet, however, we will include links to videos within messages. Rather than have the video play within the message, we provide an image of the video player with a play icon over it, inviting readers to go watch it on YouTube or the blog where the video is hosted.

Keeping templates consistent

Whenever we create a new template that will be sent over and over to people, we test into it by creating a few ideas and then choosing the one that performs best. Once that winner is chosen, we keep a standard “skeleton” template that has a consistent header, logo, tagline, social widget placement, and unsubscribe links. Then, we make those messages feel new by swapping images in and out based on what’s relevant.

Learn more about Pandora

Pandora (NYSE: P) gives people music and comedy they love anytime, anywhere, through connected devices. Personalized stations launch instantly with the input of a single “seed” – a favorite artist, song, or genre. The Music Genome Project®, a deeply detailed hand-built musical taxonomy, powers the personalization of Pandora® internet radio by using musicological “DNA” and constant listener feedback to craft personalized stations from a growing collection of more than one million tracks. Tens of millions of people turn on Pandora every day to hear music they love. 

Chapter 3: Keeping email relevant with bounce exchange

In order to keep messages relevant to their customers, Bounce Exchange uses a few different effective segmentation techniques to ensure visitors to their site receive messages that relate to them.

Ofir Caspi – Product Manager, Email and CRM

Ofir Caspi is currently the Product Manager for Email and CRM at Bounce Exchange, a position that allows her to help companies embrace behavioral email techniques. Previously, she was the Email Marketing Manager for Uniqlo where she oversaw the US email marketing program, and before that was the Supervisor of Email Marketing and CRM at Gilt Group. Ofir is passionate about email and uses her knowledge and experience to implement excellent email programs.

More than demographics

When people first discover the concept of segmentation, they usually begin with demographics, like age, gender, location, etc… Unfortunately, from my experience, these segmentation strategies don’t really move the needle when it comes to email marketing.

Not only can demographic segmentation take a ton of time and resources to put in place (data warehouse, anyone?), it usually doesn’t make sense. Speaking to actual shopping habits and behaviors in your users is far more impactful. In this case, you’re providing your users information that they’ve shown you they want to learn more about.

A vital segmentation strategy

Once you’ve embraced the idea that segmentation can be much more powerful when it’s based on actions, you can start to create a really powerful behavioral email marketing strategy.

Address behaviors visitors have on your site within these emails. Users want to engage with things that interest them and that they have shown interest in. If they weren’t shopping for grills, don’t send them discounts for grills. If someone is on your site and shows an affinity towards a specific type of product, use that product to speak to them. If they’ve shown actions that display disinterest, help them find something they like.

For a basic technique you can implement today, separate recipients into two groups:

• New leads and potential customers (prospects)

• Returning customers

Note: we’re talking about “customer status,” here, not “visitor status.” You’ll hear a lot about new vs. returning customers; in my opinion, this is a much more impactful segmentation technique than, say, new vs. returning visitors.

If you’re tracking who’s coming to your site, what they’re looking at, and what they’ve purchased in the past, you have the opportunity to make messages far more relevant to them. These are very different people, so let’s treat them as such.

For instance, existing customers returning to your site have higher intent and need less marketing than first-timers. There’s no reason to bombard a returning customer with generic value propositions. However, for prospects, you may want to make those propositions even louder and more apparent. I think this basic form of segmentation is something many marketers forget or take for granted. One-size-fits-all may be easier, but it’s not nearly as effective.

Too much is too much

There’s a misconception that more is better when it comes to email. Send more email, get more revenue, but that isn’t necessarily the case. The more you message someone, the more likely they are to get email-fatigue and unsubscribe.

When someone unsubscribes from your email list, you’ve lost the option to message them ever again, so that long term value is gone. As an email marketing rule-of-thumb, you want to say that each email you send is generating more revenue than you’re losing from unsubscribes. An email is no longer worth sending if the scales tip the other way, and then it’s time to put it out to pasture.

This begs the question: How often should you ping your list to maximize email revenue without incurring email-fatigue (and unsubscribes)?

To solve for this, I like to look at revenue-per-recipient-per-email. When you break down every part of an email campaign this way, you can make sure that the revenue generated per recipient is consistent through all parts. Let’s say a particular campaign has four parts. If I see that there’s a drop in engagement and revenue after the third email of a campaign, I’ll kill the fourth email completely.

I rely on testing a lot for this. I’ll segment my lists and test whether sending a third or fourth email generates enough revenue to continue sending. If it does, I’ll keep it. If not, it’s dead. I also like to test timing and cadence to make sure email is delivered when it’s most relevant to customers.

Ultimately, the goal of segmenting is to be more relevant. 20% off for everyone is not relevant. New products in a line you know I love is relevant. A relevant message is going to drive conversions and revenue way better than a message with no context and no relevance every time.

Learn more about Bounce Exchange

Bounce Exchange is the leader in behavioral automation software and analytics. Their behavioral marketing platform drives incremental revenue per visitor and enhances the value of all other marketing channels by increasing purchase intent. This technology is employed by marketers to build complete profiles of their site visitors and then, based on these profiles, direct marketing efforts towards the most productive actions possible. The platform is live on thousands of digital properties across a diverse array of industries. Headquartered in New York City, Bounce Exchange is widely recognized as a leader in employee retention and workplace culture. Internet Week, Crain’s New York, Computerworld and Fortune have all awarded the company for being among the best places to work in tech.

Chapter 4: Calls to action (CTAs) with

One of the ways drives donations for school projects is through implementing the right CTAs in our email marketing program. From thinking about the reader experience, to surprising and delighting readers when they click on an email, CTAs are an essential part of our strategy.

Morgan Kazan – Director, Email Marketing

Morgan is responsible for donor and teacher email marketing efforts. She focuses on retaining donors through targeted, personalized campaigns, as well as ensuring teachers are knowledgeable about all aspects of using through email. Prior to joining the team in 2011, Morgan was the Promotions Manager at the Big Apple Circus, driving ticket sales through email marketing and grassroots partnerships. She also worked in the music industry promoting artists through retail marketing.

A call to action, or CTA, is the link at the end of a marketing email that drives the recipient to take an action. The CTA tells the recipient what you want them to do with your message, like make a purchase, open the app, or read a new piece of content.

Make things obvious at a glance

A general guideline we follow regarding CTAs is that they should be very obvious. We want recipients to glance at an email and know immediately what’s being asked of them. People don’t always have a lot of attention for emails, so we want to make sure they know where to click and how to engage as easily as possible.

In the past, we’ve used video in email, and our goal was to have recipients watch the video and then donate. We found through trial and error that our recipients only pay attention to one or the other, and not both. Now we try to keep emails limited to one very clear CTA.

Twice a year, we’ll do an “email audit,” where we look at all of our triggered email templates and make sure we can identify the CTA. As the email marketer, you might know what action you want a recipient to take, but that may not be conveyed clearly. There shouldn’t be any confusion or second-guessing about what a recipient should do with the message they just received.

Create intriguing messages

Another way we drive more engagement and traffic back to our site is by providing a preview of something within an email, and then inviting readers back to the site to see the complete asset.

Jasmine Penny – Email Marketing Associate

Jasmine is responsible for campaign-based teacher and donor email marketing efforts at Before joining the Marketing Team, Jasmine worked part-time at as a Donor Experience Agent. She recently graduated from the University of New Haven with a BA in English.

We tested including a thank-you note within messages to donors by creating three different versions of a thank you message to see what worked best:

1. The full thank-you note from teachers within the email, as well as a CTA to donate again.

2. An excerpt of the note with a CTA to go back to the site to read more.

3. No thank you note, but a CTA to go to the site and read it there.

We thought the winner of the test would be the full note because it added so much value, but we didn’t see that in the results. The clear winner of our test was the second version where we provided the excerpt. This version not only drove traffic back to the site, but it also drove donations.

Think like your recipients and personalize

When creating emails, we like to put ourselves in our customer’s shoes. If someone receives an email on their phone, chances are they don’t want to look at a wall of text. They want to know what they’re looking at quickly and what’s being asked of them. For us, we’ve found that simple messages with short paragraphs and a blue hyperlink CTA, resonate well with our donor base.

We strive for making our emails feel like 1-to-1 communications. Both in terms of language (using “you” and “you’re” in our subject lines) and with serving up personalized content. For CTAs, we use our data to link donors to more personalized projects. This might include projects that are similar to those they’ve donated to in the past, or projects that are close in proximity to their location.

Learn more about makes it easy for anyone to help a classroom in need. Public school teachers from every corner of America create classroom project requests, and you can give any amount to the project that inspires you. Since 2000, more than 2 million supporters have donated over $400 million to classrooms in need.

Allie Kranick – Sr. Marketing Manager, Brand & Retail

Originally from Pittsburgh, PA, Allie grew up in St. Petersburg, FL, attended Florida State University, and has happily lived in Denver the past three-and-a-half years. She’s been at Ibotta since June 2013 and is a Senior Marketing Manager, helping lead the Brand and Retail division of the Marketing team. In her free time, you can find Allie trying to keep plants alive, spending time on a rooftop patio, or buying new flavors of La Croix.

Ibotta views email as an avenue for providing users with helpful, informative content that solves a problem for them. We want to do more than just show people what rebates we’re offering, we want to help recipients cook dinner, plan for a barbecue, or stock their bar for a party.

Planning ahead

One of the ways we make our email timely and relevant is by planning our campaigns around holidays and promotional windows throughout the year.

Not only will we identify which campaigns we’ll be sending about a year in advance, we’ll also start working on specific content months in advance of sending in order to stay on track and have things ready to go.

We’ve learned in the past that things are constantly changing and new campaigns come up, so if we have our scheduled content ready to go ahead of time, we can more easily handle unforeseen changes.

One of the key windows for our promotional emails is roughly from August through January, which includes:

  • Labor Day
  • Back to School
  • Thanksgiving
  • Holidays

In order to make sure we have content and themes ready for the dates and holidays we schedule for, we try to prep things three to four months ahead of time. In fact, a trick we’ve used in order to get ahead of our holiday content, is brainstorming in September with holiday music playing as a way to get in the right mindset!

Providing solutions

Rather than simply updating recipients weekly or monthly about new offers available through the Ibotta app, we want to provide app users with a solution to a problem they may be facing.

By thinking of the target persona that’s receiving and engaging with our different email campaigns, we create content around their needs that promotes products Ibotta has rebates for.

Some of the newsletters Ibotta sends include:

  • The Booze-letter – With a large beer, wine, and spirit section, we’ll send out an alcohol-specific newsletter to customers who use those rebates.
  • Meal Solutions – Ibotta has also found that recipes resonate very well with our recipients. We’ll send newsletters that include rebates for everything in a meal so that we’re solving the “what’s for dinner?” question, as well as showing what’s available in the app.
  • Seasonal Themes – Whether it’s “Dads and Grads” or “Spring Cleaning,” we make sure we’re sending content that’s relevant to our users around the time that they’ll be going shopping.

Maddie Groves – Senior Marketing Associate

Born and raised in Philadelphia, PA, Maddie moved to sunny Colorado a few short weeks after graduating from Penn State in 2012 with a primary degree in Public Relations. When she’s not working as a Senior Marketing Associate at Ibotta, you can find Maddie at the yoga studio, scoping out Denver’s live music scene, or curled up with a good book and her cat, Bubba.

Adding personality and personalization

Before sending, we take a look at our recipient engagement, like the last time a person engaged with an email, or the last time they opened the app. Based on this information, we might change the type of subject line or message they get.

For instance, if someone hasn’t opened the app or engaged with an email in a long time, we’ll be a lot more playful or humorous with the content of the message because they may have already decided to stop using Ibotta already. If that’s the case, an interesting, fun, or funny message might draw them back in.

Along with that, we definitely love to test things within our campaigns. We’ll test a cheeky, fun subject line against one that’s purely informational to see what’s working better with a certain segment of recipients.

Learn more about Ibotta

Headquartered in the heart of Denver, Colorado, Ibotta has been revolutionizing the consumer shopping experience since 2012. With a dedicated team that’s constantly growing, they’ve helped build the local startup community and have become one of the fastest growing tech companies in Colorado.

Ibotta easily allows consumers to earn cash back on everyday purchases at their favorite stores. Initially solely in grocery, users can now earn at over 300 retailers nationwide, including Best Buy, JCPenney, KFC and more. With exclusive rebates and bonuses rolled out every week, Ibotta makes it fun and easy to earn.

To download, search “Ibotta” in the App Store or Google Play, or visit!

Chapter 6: The best advice for email marketers

All of our experts were asked to provide one or two pieces of advice for email marketers that are getting started with implementing their programs:

Jill Guest

Take a data-driven approach to evolving your email program and challenge your assumptions. Some of the best gains we’ve made in email marketing is through testing concepts I never thought would work! By testing macro (different types of content, segmentation techniques, and designs) and micro (subject line, button color, or email signature) strategies and elements of your messages, you can consistently grow engagement rates, as well as your personal knowledge of what your subscribers want.

David Hampian

Start simple. Sometimes email marketers will get caught up in the design and appearance of the messages they’re sending. The fact is, content drives the click. You want to gain your recipients’ trust by providing personalized, relevant messages they want to open. Then you can start tinkering with how messages look.

Ofir Caspi

Send more diverse emails to more inboxes, not more of the same emails to the same inboxes: Employ methods to yield the highest identification/match rate. This way you can send highly relevant messages to the right person and then just multiply that over and over. Most companies identify less than 15% of visitors, that number should be closer to 50% — email should be a goldmine, people!

Send personalized and relevant emails: Set up your email program to send personalized, relevant messages to customers. Send fewer emails with more relevance. It’s a lot easier to do this from the jump than it is to slip it into a mature email marketing program. This way, you can keep your messages relevant. Relevant messages are GOOD. Less is more if less is done better.

Morgan Kazan and Jasmine Penny

Sign up for as many emails as you can from other companies! This is a great way to get subject line, content, design, and even seasonality inspiration. This may seem obvious, but a lot of times the best place to get new ideas is to look at what other people are doing in your industry and in other areas.

Allie Kranick and Maddie Groves

Try whenever possible to personalize your message and content to your audience. No two consumers are the same, and the more personal a consumer feels their experience is with your brand, the more connected they are likely to be.

Testing your communications is just as important as your email content itself. By tweaking certain aspects of your emails and optimizing the results, you can find the message that resonates best with your audience.

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