The Do’s And Don’ts Of Email Marketing Strategy

Email Marketing Strategy
The Do’s & Don’ts Of Email Marketing Strategy

LAUREN KASHUK: Welcome to the Google Small Business Community. I’m Lauren Kashuk and today we have Sendgrid’s Regan Peschel, the head of strategic sales and small business for Sendgrid. Welcome, Regan.

REGAN PESCHEL: Thank you. Thanks for having me.

LAUREN KASHUK: Today we’re going to be discussing the basics do’s and don’ts of email marketing strategy. But before we do that, Regan, why don’t you tell us a little bit about Sendgrid and what you do at Sendgrid.

REGAN PESCHEL: So Sendgrid is a cloud-based email delivery platform. So we work with everyone from developers who want to jump in and create a developer account for their in-app notifications, all the way to people who are marketing professionals, and even people who are just getting started in marketing. They can jump into our marketing platform and start sending emails today.

LAUREN KASHUK: Our community is really excited to hear helpful tips that you have about what to do and what not to do when it comes to email marketing. Before we get into the specifics of that though, we have an initiation question that we ask every single person that’s in the community. So, question is if you could Hangout with anyone living or dead who would it be and why?

REGAN PESCHEL: That’s a great question. I think I would choose Jim Gaffigan just because he’s so funny.

LAUREN KASHUK: And if you were having that Hangout with Jim Gaffigan, what’s the most embarrassing thing that you’d ask him?

REGAN PESCHEL: I’m not sure I’d ask him an embarrassing question, because I do you really like him and I think he’s hilarious. But I think it would just be fun to maybe have a drink and sit there and chat with him for a while and laugh really hard.

LAUREN KASHUK: Jim Gaffigan would be good to get a laugh from 101 in a Hangout.


LAUREN KASHUK: So shifting gears back to email marketing – why we’re here – a lot of businesses face a lot of challenges when it comes to just understanding the basics of successful email marketing strategy. Can you speak a little bit about what those challenges are that you have come across?

REGAN PESCHEL: Yeah, absolutely. So I always say small business owners know their business the best. Like they understand the passion behind it. They understand their product. They’ve built, probably in the last how many ever years they’ve been working on it, their entire foundation for their business.

So as they set foot into the marketing effort, you want to make sure that you’re understanding what is your message that you’re going to be sending to those end users? What is your message that you’re going to be sending to the customers?

What you want to do is have a clear strategy going into that so that you can most impactfully effect that relationship that you’re building.
So the first thing that I always tell people is understand how you’re getting your email addresses from people. So some of the common places that small business owners might collect email addresses would be, maybe trade shows, or maybe they organically had a conversation, or they had a service and they’ve exchanged email information.

Another common place would be through your website. So a website is a really great place to start collecting and nurturing relationships with people who want your services. So on your website, if you already have one, you want to make sure that you’ve got a place where people can easily go in there and sign up with their email address.

And you want to take the chance to set what we call expectations around what they’re going to receive from you. So that’s a great time to say, OK, hey, here’s what you’re signing up for. You’re signing up for a newsletter. You’re going to be getting it once a week, or maybe you’re going to be sending it once a month. And I also want to collect probably their first name and/or their last name.

Now, the reason you do that is, again, just to have clear strategy going into your email efforts. So once I’ve collected that email address, ideally the best next thing to do is make sure that you’re doing what’s called an opt-in in or a double opt-in. A confirmed opt-in means they’ve given you their email address. And then you’re going to send them a secondary email. And then they actually have to open that email and confirm that it was them. So that really eradicates a lot of spammy behavior in terms of people putting in fake email addresses, maybe they fat fingered it, and you’ve got a true one-to-one relationship organically started from day one.

So once you have that email list, now you’re starting to collect those folks, and then you can start putting that strategy into action.

LAUREN KASHUK: And the strategy that you speak about, can you talk a little bit about what makes a really great email marketing strategy?

REGAN PESCHEL: Yeah. So a great email marketing strategy is going to have a lot of different components to it. The first one is what I call everything pre-send. So that would be understanding, again;

  • What is the content that you want to put inside of your marketing emails?
  • What is the message you’re trying to deliver to the end users?
  • What is the brand that you’ve got built into that?
  • So do you have a logo that you want to incorporate into that content?
  • Do you have certain images that you want to incorporate into that content?
  • Do you have a specific subject line that you think might be compelling to your end users?
  • Do you have an idea around how frequently you’d like to send that message to those end users?
  • Are you going to be baking in, let’s say, coupons or things that could be compelling to them?
  • Are you aware of when I get people who click and open, what I’m going to do next with that?

So again, strategy is a lot of different things. But the clearer that you define your strategy and you understand what each of those things do, then you can start pulling some levers and making some educated decisions.

The second half of strategy is everything that happens after you push send. So when you hit send and you’ve sent out – let’s say you have an email list of 400 people and you’ve hit send and it’s gone off to the what we call the ISPs, which is, again, Gmail, Yahoo, MSN, all the major ISP providers – you want to know that once you’ve sent it, it’s actually going to get to the inbox.

So there’s a whole other world lives behind that that you have to understand the ins and outs. And it doesn’t need to be complicated. You don’t have to be super technical to understand it. There’s some really basic rules we can provide you, and guidance, to really understand, OK, if I’ve hit send to those 400 people, what am I going to do to make sure that it’s getting through not only to the ISPs and they like it, but they want to deliver it to the inbox?

LAUREN KASHUK: Speaking about breaking through the clutter and getting to the inbox, I’m sure that a lot of businesses have problems with their emails going directly to spam.


LAUREN KASHUK: Can you speak about how to avoid that obstacle?

REGAN PESCHEL: Yeah. So there’s definitely certain things people do that cause them to get to spam, and they should be getting to spam, right?

So if you’re putting in spammy content, or you’re sending email that has nothing to do with your business, or if you’re putting in subject lines that are very spammy, or maybe you’ve purchased a list. So maybe you bought a list that has like 2,000 people on it but has nothing to do with your business, a lot of things, bad things, can happen from doing something like that.

And so to avoid that, again, you want to grow your list organically and only acquire email addresses from people that you’ve had personal relationships with. Meaning, you’ve either met them or they went directly to your website and said explicitly, I’d like to sign up for this.

So if you’re looking through all of that and you’ve said, OK, now I’ve created a compelling message, I’ve got clear content, I’ve got a great subject line, I have my brand baked in here, I’ve got everything that I need to have, and I’ve also acquired my email addresses appropriately, and I’m starting to send and I’m still getting some issues?

Some of those issues usually are around throttling or blacklisting. Throttling is when you send out the email and for whatever reason, the ISP says, I’m not going to put your whole email through. I’m going to hold onto it until I decide what it is that you’re sending and if I like it or not. So that’s where having a trusted partner in this is really important.

Because you’re going to be able to see am I being throttled, am I landing on a blacklist, and what’s causing that. Is it the content of my email? Is it the frequency that I’m sending? Is it something, is there a link in my email? Some people don’t realize, inadvertently, they might have a partnership with someone and their partnership link sits inside their email and they think in good faith, I’m sending out something that my end users probably want.

But at the end of the day that link may lead to something to a website that isn’t so hot and the ISPs might actually hold your email. So get really clear about – especially if you’re just starting out – making sure that it’s just your content that you’re sending and that you’re aware of what you’re sending and how it’s being perceived in the community.

LAUREN KASHUK: And how would a business go about finding a trusted advisor that you speak about?

REGAN PESCHEL: So I always say there’s definitely tons of resources online. You can Google a lot of things. You can get a lot of information on the internet and just start reading through it. You can also talk to other people. Maybe you have a friend who happens to be in a marketing position. Or maybe you’ve got some friends who are a lot like your own customers.

You could draft up your own emails and start putting them together and show them to your friends, or the people who are similar to your current customers.

So, again, I’ll use a knitting shop as an example. If I own a knitting shop and I’m about to start an email marketing campaign, I might put everything together. And before I hit send, I might actually pull in two of my customers and say, hey, I’m going to send you this email, I want honest feedback about what was working or what wasn’t working when you opened it. Right? So is it something in the subject line that compelled you to open it? Was it something in the actual body? Did you not get to open it because something prevented you from opening it?

And again, that’s where we can sort of drill in a little more granularly and give really specific advice. So some of the things that might prevent you from even being able to have someone open your email are images, for example. So images are a tricky subject. You definitely want to have imagery, and you want to have compelling imagery in there, and pertinent compelling imagery.

But what you don’t want to have is only images. For every one image, you might want to have two lines of content, at the very least. You can be a little more content heavy, but you never want to be just images and you never want to be just text.

If you do just images, when you send out that email, a lot of your customers, just based on their browser when they open it, won’t have what’s called images enabled. And that means that they don’t ever get to see the images. So all they’re left with is either a blank email or potentially just a couple lines of text. So I always try and use the rule where if any one of these two things went away, would my message still get to that person? And you kind of always want to operate in that way.

LAUREN KASHUK: So keeping in mind that balance between images and content, something else I know that a lot of businesses struggle with are just the subject line. So they sit down to write this email for their business, and they don’t even know where to begin. Can you give a little advice on how to best write a really compelling subject line?

REGAN PESCHEL: Yeah. So the first piece of advice I would give is as a small business owner, you, again, know your business, and your industry, and your customers better than anybody. So I would just sit down and literally start jotting out some key words that make sense for what you want to have your message be. What is your brand? Get familiar with your brand. Be able to articulate it, whether that’s in writing or even just talking to a friend. Narrow down some of that and then you can start seeing a theme coming through.

Then what you want to do is you want to transfer some of that knowledge into essentially what is the subject line. So subject line, again, I think old school thinking was keep it longer and put in as much as possible because that might be the one chance that someone gets to read your message. It has evolved quite significantly.

We actually are finding that if you use shorter subject lines, you’re going to get a better click rate. So people might open it and actually engage with your email. A few reasons for that is everything is moving, obviously, very mobile-centric. So even as a small business or a medium business owner, you want to make sure that you’re looking at who are my end users, and who are my customers, and are they actually opening it on their desktop or are they opening it on their mobile device. It is statistically, I think they say it’s something like 48% of all email that’s opened today is opened on a mobile device.

So, again, that kind of leads into rendering your templates and making sure that they look as good on mobile as they do on a desktop, and also making sure that any messaging that you’re sending can be consumed in either version.

LAUREN KASHUK: So knowing that 48%, as you said, of all email sent are being read on mobile, can you think of maybe some examples for some businesses that you’ve seen that have done it really well, whether it’s been on the web or on mobile, but have really understand the marketing space?

REGAN PESCHEL: Yeah. So we have tons of clients who do it very, very, very well. We definitely see people who come in with a strong proclivity for understanding what mobile rendering should look like and what mobile templates should look like. And then we have people who are very green and have just started and we’ve been able to make an impact with them.

One company that I would say that we’ve had a huge impact with is called Commissions Inc., which is a broker real estate marketplace where it lets brokers and homeowners come into one community and find each other so that they can have a better experience around home buying and home selling.

What we’ve done for them is – and they, by all means, had a lot of sophistication already coming into it. They weren’t super green, but they had a lot of improvement to make. So when they came into our company and we looked at their emails and said, OK, what does your content look like, what does your subject line look like. Also, more than that, what we looked at is what does your list look like?

So your list, again, kind of referring back to what I was talking about before, is very important. So when they first started sending emails, they were sending a couple thousand emails per month. Now they’re already sending several million emails per month. And a lot of that is because they probably couldn’t get away with sending what they were sending before to that really large user base until they fine-tuned a lot of the stuff we’re talking about. So that could be playing with the subject line, it could be the content, it could be the frequency in which they send.

Another component to that would be when you’re looking at your lists, you want to say – and small to medium-sized businesses get clear on how old is your list. Right? Like have you had it for 10 years and it’s this list that you haven’t really had a lot of interaction with but you know you just don’t want to let go of it? Or is this a brand new endeavor for you and you’re going out and organically collecting email addresses?

If you have a 10-year-old list and you’re continually sending sort of like this random message that comes out every three months, and it’s a newsletter, and it isn’t necessarily super compelling, you actually could be hurting your reputation more than helping it.

Again, this goes back to the strategy part – you want to get clear on if I do have a 10-year-old list, maybe you send out for a while and start tracking clicks and opens. So who’s clicking, who’s opening, who’s actually engaging with my email, and make really great decisions around that.

So once you can say, OK, this person, for example, hasn’t opened my email in five months, I probably lost this person for whatever reason. I may or may not resend to them in the future, but I’m going to segment them out and hang on to them and put them in a different bucket. And for now, I’m going to really put all my energy in trying to grow the what we call the engaged users.

LAUREN KASHUK: Speaking about engaged users, what’s the healthy amount of time that you should be seeing some sort of response from them. You mentioned five months.

REGAN PESCHEL: So different schools of thinking have different ideas around this, different ISPs. Ultimately, the ISPs. So, again, like Gmail, Yahoo, MSN, they get to decide what that timeline is that they think is appropriate. And different ones have more conservative timelines and other ones have different longer timelines. 30 days is very conservative, but that is something that people try and shoot for. So if you haven’t clicked or opened an email in 30 days, some people believe you should stop sending to them.

Again, I think it all goes down to how good your brand is and how engaged your users are, because that may not be true for everyone. Some people may not open an email within 30 days but they are absolutely going to click on it in 90 days or 120 days. So what you want to do is instead of maybe cutting them off at 30 is you decide what your what we call sunsetting policy is. And that sunsetting policy is what we’re talking about.

I’m going to send for a while and watch and see how many people actual stay engaged. And then maybe just pick a time and say after four months I’m going to stop sending to this group of people. And then just take those engaged users, and then later, as you’re growing your list and you’re having more organic one-on-one growth of conversations, then you can go back to that engaged list and even pepper in some of those older people and do what’s called a win back campaign.

LAUREN KASHUK: Let’s say that I’m just not having success across the board. I’ve been focusing on my subject line. I’m having friends come in and read my emails before they’re going out. I’ve even revamped my email list and made sure that all of my most active customers are reflected, yet I’m not getting any response or I’m not seeing any sort of impact on my business. What would you recommend to our businesses to do?

REGAN PESCHEL: So I guess first deciding do you want to do it on your own or do you want help. Right? So there’s two ways to do it. If you’re doing it on your own, again, you want to continue reading and just sort of consuming information out there and figuring it out. And just like a project, you’re going to dedicate time to that and figure out how to self-serve your way through that process.

There’s much easier ways to do that. If you’re currently working with an email service provider, I would connect with them and see if they can help you around some strategy. With Sendgrid, for example, if we’ve done everything right and we can see the client’s done everything right and they’re still not getting through, then it indicates that there’s something else maybe going on.

That’s when, if I was the small business owner, I would reach out and say, hey, it looks like I’ve done everything, can you guys take a deeper dive here and see is there something weird going on with just Gmail, or is something weird just going out with Yahoo? And when you have all the data analytics that are telling you that story, then you can actually start fine tuning and course correcting that.

A lot of the data we provide back to people is clicks, opens, bounces, but also hard bounces, soft bounces, deferrals, how long did it take for that email message to get bounced back to us, why was it bounced back to us. There’s some really important information in there. And some of the people that you’re sending to – again, depending on how small or large your list is, and how old it is – it might have nothing to do with you at all. It might have to do with you’re sending to smaller domains.

Smaller domains, if they no longer exist no matter how much you keep trying to send it’s not going to happen if that domain has shut down or it doesn’t exist anymore. So you need that pertinent data to say, oh, OK, that’s why this is happening. So I’m not doing anything wrong. I’m going to keep going with my strategy, but this particular thing happened.

So the advice I always give people is peel into that data and get as granular as you can so that you can make educated, empowered decisions around your small business.

LAUREN KASHUK: Let’s do a deep dive on data that you spoke talk about in analytics. What tools are available for small businesses that maybe want to analyze their emails?

REGAN PESCHEL: So, again, if we’re operating under the understanding that it’s a small business or a medium-sized business, and let’s say you have a lot of capital, great. Then there’s some really awesome external tools that you can purchase that would sit on top of what your current email provider is.

If you’re on a budget or if you want to do it very methodically and start either on your own and then adopt some internal analytical tools, that might be a good strategy as well. Most ESPs should have some sort of analytical tools available. But the analytical tools that we have, for example, again, would be around your sending and how it’s performing. So click tracking, open tracking, bounce reports.

Also, we’re going to give you a list of down to the email level of how that person performed. So, again, the analytical tools that you’re going to look at, you can go and grow into incrementally. So just like any small business, you don’t want to sort of jump from here to here, right? You want to start utilizing those tools, looking at that data, applying it back to your business, and fine tuning. And then if you’re seeing a real uplift from email, which is what you want to have happen, all of a sudden you have some revenue coming from that stream, that’s when it would be smart to start adding some additional things in there as well.

LAUREN KASHUK: And what data points do you think are the most important to focus on?

REGAN PESCHEL: So the data points for someone emerging into this endeavor, in terms of doing a brand new email marketing campaign, really basic ones, right?

You want to get that really sorted out before you do anything super complicated. You can go as far as you want, but the basic ones that you absolutely should know – who’s opening, who’s clicking, who’s bouncing, and what is your spam complaint rate. So I would say those four things are probably the most key.

  • Again, who’s clicking, who’s actually clicking into your email after they’ve opened it.
  • Who’s opening your emails in the first place.
  • How many bounces do you have?
  • And then also what is your spam complaint rate?

There’s things called spam checker apps that you can use ahead of time that will really alleviate a lot of this as well, at least for that fourth one for spam. So if I’m going to send out to this list of 2,000 people, before I even hit send I might run my list through a spam checker. And the spam checker’s essentially going to, in layman’s terms, look at it and say this is how spammy you look on a scale of one to five.

So already I’ve got a really clear picture of, oh, something either is working really well on this or there’s a red flag. So then I don’t want to hit send because I don’t want to hurt my reputation. Yet, I’m going to take that spam checker score and maybe have a conversation again with myself, with my friends, with a business consultant, or maybe with your ESP.

LAUREN KASHUK: And how much do spam checkers cost? Or you said some are free?

REGAN PESCHEL: There’s free ones. Oh yeah, absolutely. Yeah. There’s great tools that are free on the internet for sure.

LAUREN KASHUK: Are there any top of mind that you can recommend to our businesses to look into using?

REGAN PESCHEL: I actually can’t think of any off the top of my head business wise. We have one built into our product that before you even launch your campaign, it’s just a button you click on. You run it through and then it sends it out based on what your score is. So you can look at the score first and decide if you’d like to send it out.

LAUREN KASHUK: That is so helpful to know that there’s spam checkers out there that exist.


LAUREN KASHUK: So let’s just kind of wrap this all up. If you could really give three actionable pieces of advice for our businesses for what they can do to really see some great email success, what would those be?

REGAN PESCHEL: So number one, I would say know your audience, and know how to curate a list and know how to craft a message. Right? So that’s really just saying, I understand who I’m talking to and I’m really focusing my message toward them. So again, to go historically, I think marketers used to sort of make everything about, not them per se, but their product or their company.

That was something that worked, I guess, for a while, but it’s evolved significantly. And the new school of thinking is really make it about your customer. So when you send to your customer, make sure that, again, you’re personalizing. You’re using their first name. You’re putting it maybe in the subject line. And you’re really understanding who am I sending to and what would they want to hear from me rather than what would I want to tell them.

So shifting that paradigm a bit is really important. The second thing is really setting expectations. I think that’s super important. So when you collect email addresses, make sure you’re giving people the chance to understand what they’re actually signing up for. So the last thing you want to do is put all this work into your small business, you’re really excited about it, you’re moving on to this next marketing endeavor, and you’ve collected an email address, and someone might just inherently think, oh, I’m getting an email once a week from this person, but you send it to them twice a day.

That’s a really good way to very quickly get someone to unsubscribe. So, again, instead of giving them that chance to – you lost them in that first swoop, start maybe a little bit slower or keep going at that pace and give them the chance to what we call preference what they would like to do.

There’s what’s called a preference center. So in your emails, you’re going to have an unsubscribe link at the bottom of every single email. That’s a really important piece of information for everyone to know, like no matter what you send in marketing emails, always have that. And then also give them a chance to say, I’m not ready to unsubscribe, but I want what you’re sending me. I just don’t want it twice a day. I want it once a week.

LAUREN KASHUK: So know your audience, make sure that you’re clear with the expectations, and give them the preference of what they’d like to opt-in to versus what they wouldn’t.

REGAN PESCHEL: Yes. And then the third take away is just really this idea or this concept, you can think of it as the three R’s. So sending to the right email, to the right person, at the right time. And that really kind of encompasses everything we’re talking about.

Know your audience and sending it to the right person, meaning you’ve sent it to only people that really want it because you know because they’ve double confirmed in. Then know the right messaging in terms of cadence. So you’re not going to be sending five times a day. Whatever place you start out, you can always tweak and you can slit test, but just make sure that you’re going at a cadence that isn’t going to sort of kill your email marketing campaign right out of the gates.

LAUREN KASHUK: To recap, we want to target the right message, to the right people, at the right time.

REGAN PESCHEL: That’s right.

LAUREN KASHUK: Three R’s. That’s easy to remember for our community. And we’re actually out of time today. Regan, thank you so much for joining us.

REGAN PESCHEL: You’re welcome. Thank you.

Matthew Brewin

Hey, name's Matt. I'm a blogger on, Certified Digital Marketer, and Partner at Internet Profits Ltd.

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