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Join for freePosted: Mon 27th Jul 2026
Writing a brilliant email is pointless if it never reaches the inbox.
In this session, we tackle deliverability head-on. The do's and don'ts, the common reasons emails get blocked, and the quick wins that can instantly improve your delivery rate.
Plus: why subject lines, send times, sender details and pre-headers matter more than you think.
How to build a top-tier sender reputation to avoid the spam folder
How to instantly improve your inbox rate by managing your list and boosting email engagement
How to win back silent subscribers to boost your deliverability
Bring each session to life with a 30-day Constant Contact free trial, helping you turn insights into action.
Both speakers are employees at Constant Contact, the AI-powered marketing platform that has helped millions of small businesses and nonprofits grow for over 30 years.
Thomas Nettesheim is a sales engineer, bringing over 14 years of experience in supporting small businesses, nonprofits and franchises.
As a subject matter expert, he frequently leads educational webinars that cover product overviews, best practices and the essential role Constant Contact plays in effective marketing strategies.
Sophie Dunlea is Constant Contact's UK marketing lead. Also based in London, she works closely with communities and partners across the UK who share a passion for helping small businesses get seen, connect with customers and grow through smarter marketing.
With a background in events and large-scale partnerships, Sophie specialises in helping businesses turn simple marketing ideas into meaningful results.
Constant Contact offers email and digital marketing tools that make it easy for your small business or nonprofit to get the attention and revenue it deserves. Constant Contact has joined Lunch and Learn to share its extensive marketing expertise.
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Lightly edited for clarity.
Caitriona: Hello, everyone, and welcome to today's Lunch and Learn as part of Marketing Mondays. My name is Caitriona, and I'll be your host today.
Marketing Mondays is a free five-week webinar series from Constant Contact and Enterprise Nation, designed to help small business owners improve their email marketing with practical, easy-to-implement advice.
Whether you're looking to improve open rates, avoid spam folders, grow your subscriber list or use AI more effectively, each session offers actionable insights to help you market smarter and achieve better results.
In this session, we will tackle deliverability head on: the dos and don'ts, the common reasons emails get blocked, and the quick wins that can instantly improve your delivery rate.
We are joined by Thomas Nettesheim, who is a sales engineer at Constant Contact, and Sophie Dunlea, who is the UK marketing lead at Constant Contact.
Both Thomas and Sophie are employees at Constant Contact, the AI-powered marketing platform that has helped millions of small businesses and nonprofits grow over the past 30 years.
You can also take your learning one step further with a 30-day Constant Contact free trial, allowing you to test new ideas and follow along as you learn. We'll be sharing a link to the trial in the chat box during the session.
Please add any questions to the Q&A as we go. The session is being recorded, and we'll share the recording and resources afterwards.
I'm now going to hand over to Thomas and Sophie for their presentation.
Thomas: Perfect. Thank you, Caitriona, and thank you everybody for taking the time today.
As you could tell by the title, today we're going to talk about how to avoid email jail and why deliverability is everything.
To lay the foundation, I want to start with what deliverability is. What does that mean?
You've probably received emails. We were even talking before we got started today about how there are going to be a bunch of emails. We all have businesses and nonprofits that we follow, and sometimes we see those emails go into the spam folder.
Why does that happen? That's what we're going to talk about today.
Email deliverability is the gatekeeper that decides whether your message lands in the inbox or that dreaded spam folder.
We'll unpack that a little bit, how you can get that reputation clean and how to get those emails in the inbox. Then we'll also give you some best practices, picking up on last week.
If you joined us last week, we really focused on why email is still relevant and why it is still a hugely impactful opportunity for you to continue to make those connections with the people in your community.
So we're going to make sure that if you take the effort to make beautiful emails, we will do our very best to help you get into that inbox.
We're going to have three topics today.
We're going to talk about building that top-tier sender reputation and how that happens, instantly improving your inbox rate, and winning back silent subscribers, which is often an overlooked group.
There's so much focus on getting new people, but let's talk about those people who engaged with you at one point, then maybe fell off a little bit or lost interest for a little bit, and how to wake them back up.
A quick introduction. My name is Thomas. I'm a sales engineer at Constant Contact. I've been here for 14 years, and I have done a lot of webinars and sessions.
I've done some time in London for other sessions as well, so I'm really excited to share some time with you.
Sophie, would you like to do a quick intro?
Sophie: Yes. Thank you very much, Thomas. Hi, everyone. It's lovely to meet you all.
My name is Sophie, and I lead marketing in the UK for Constant Contact. I focus particularly on our go-to-market strategy, including our partnerships, such as our partnership with Enterprise Nation, any different community or brand partnerships, events that we attend and run for our customers and prospects, content marketing and connecting with our current customer base as well.
I'm really looking forward to this session with you all.
Thomas: Wonderful. Thank you, Sophie.
With that, let's go ahead and get started with how to build that top-tier sender reputation to avoid the spam folder.
I want to start here because, when it comes to email, there are a couple of concerns that we want to unpack.
One of them is that we get a little worried about unsubscribes. If you're going to send out an email campaign, we think: "Oh no, if I get too many unsubscribes, then I'm going to get myself into trouble."
Especially with GDPR compliance, making sure that you are staying compliant, getting those permission-based lists and sending out those campaigns, it can feel concerning if you get higher unsubscribes.
But I want to put your mind at ease and maybe talk through how we might be looking at the wrong thing.
This gives you a little chart of positive and negative impacts to deliverability.
We are going to talk through how you hold the power, pretty much, for email deliverability. But this is one thing that subscribers can do.
You've got your positive actions: replying, adding you to their address book, and opening and clicking.
Then you've got these neutral ones, and notice unsubscribe is actually a neutral action.
If somebody wants to unsubscribe because they're no longer interested, that's OK. You want to have as clean a list as possible.
Of course, you want people to stick around as long as possible, but unsubscribing is more of a neutral action, as opposed to the ones on the right.
Marking as spam, of course, is the big one that we want to focus on. But I also want to double click on leaving emails unopened.
The key here is making sure that your content is relevant.
We unpacked that a little bit last week, and we will in the next three sessions as well. Make sure you stick around for the save-the-dates and follow through on the rest of the sessions.
Marking as spam and leaving emails unopened are the biggest indicators to email service providers, such as Gmail and Yahoo, that maybe your content needs to go into the spam folder, or at the very least into some other folder besides the inbox.
So how do we do that? How do we make sure that you are staying relevant?
There are really four buckets that email service providers are going to look for. Number one is your past send history.
That includes whether you've consistently been sending, or whether you've sent things in the past to purchased lists or third-party lists.
With GDPR compliance, you really don't want to do any of those things anyway. By the way, email marketing is GDPR-compliant, provided that these things are in place and that you have good measures to stay in line with permissions.
Your past send history is something that will be looked at. We're going to talk through consistency and making sure that you are sending out at least one campaign per month as much as possible.
The next thing is: are you who you say you are?
No bait and switch. Don't make it look as though it comes from a company but then have it come from a Gmail address.
Those are things that email service providers and security software will look for.
If you're just sending from a Gmail address or something like that, it can look a lot like a spam or junk email.
As much as possible, having a domain that is attached to your brand and your website is going to be key. There are even options like authentication that you can attach to a tool like Constant Contact to ensure that everything looks like it's coming from you.
Has the recipient engaged with the sender's emails before? Are they opening? Are they clicking?
That's going to help email service providers know: this is somebody who's actually interested in your content. I'm going to go ahead and push it through.
Finally, do these people want to hear from you?
You're hearing a pattern here. This is all permission-based. This is ensuring that the communications you send out are expected.
I always give the example of looking at how you handle your inbox. When you handle your inbox, you're going to look at a few things. You're going to look at that from name. You're going to look at that subject line and ask: is this relevant to me?
Take that same action and turn it around, where you're wearing the other hat as the sender. Make sure you're writing and acting in such a way that you would want to open it yourself, and make sure that you are accommodating those permissions.
I talked through these briefly, but audience engagement is something that is in your control: those opens and clicks.
If you're not getting the opens and clicks you're looking for, how can you pivot? What can you do? What are some ways that you can fine tune the content a little bit?
Even asking questions like, "What would you like to hear from us?" and gathering that feedback, those things are really important.
Then there is the fact that they recognise and trust you. Are they recognising who you are based on what you put in the from information?
We talked about those seven things about the email last week, so make sure you catch that recording. But your from, your subject line and your pre-header are all critical because that's the doorway to whether people are going to open up and come inside to see your email. So make sure you're recognisable there.
We talked briefly about consent and not buying or purchasing a list.
The key here is: are people expecting to hear from you? If they are, they're more likely to open and less likely to mark you as spam.
As I mentioned before, have some sort of consistency. What are you able to allocate time-wise, without overdoing your bandwidth, but still staying top of mind?
The key here is that even if the person doesn't need you right at that moment, they eventually will.
You want to make sure you're on their minds and that you're sending, even if you're seasonal, even if there is a lag, or even if there is time when you're not necessarily offering that service.
Even if they've been engaged for a while but haven't actually called out to you, or they haven't gone to your website just yet, that's OK.
If you're staying top of mind and getting those touch points, you're being locked in, and hopefully they'll connect with you when the time is right.
Another misconception is the promotions folder. The promotions folder is obviously not as good as the primary inbox, but one thing to keep in mind is that the promotions folder, or the promotions tab in Gmail, is not the spam folder.
There has been behaviour modification recently. We've gone through and set these precedents. Things like Gmail have set these standards of social and promotion.
So when somebody is in the right framework and the right headspace of, "I want to see what's on sale" or "We've got these things coming up", they will look there.
I'll give you an example I've seen quite a bit recently. It's been the Christmas in July thing.
Sometimes, with seasonality, the bottom half of the year, July and August, is a slow season. So they'll say things like Christmas in July, and it gets you in that space.
If your email goes into the promotions folder, that is not you being dead in the water. People are going to be looking into that.
Of course, we want to be in that primary folder as much as possible, and your subscriber is able to move it into that primary folder. But just keep in mind that the promotions folder is not a deal breaker.
That is something that can be used, but we'll continue to go through some best practices to get you from that promotions folder into the primary folder.
I'll pass over to Sophie to instantly improve that inbox rate.
Sophie: Thank you very much, Thomas. Next, we're going to move on to the second part, which is instantly improving your inbox rate.
The first element we're going to talk about is sending those emails regularly. It's the number one key step.
As everyone knows, it's important to stay top of mind with your subscribers.
Even if your product or service isn't actually needed at the moment they receive the email, you've almost planted that seed so they can remember you when they're actually ready to purchase your product or service.
With sending regularly, consistency definitely builds trust within your subscriber base.
If they keep seeing your name or business name pop up, it's building that trust, which is really important.
As Thomas mentioned with Christmas in July, even if you are a seasonal business, it's important to send out content not just within the season that your business flourishes in.
It's important to keep up those regular touches with your customer base. That Christmas in July example is a way to look at something familiar as a way to wake up the slow season. Again, keep sending regularly, even if your business is seasonal.
The third one is setting reminders and plans. I don't know if some of you were here for our session last week, but we talked about having that calendar and content plan for sending your emails.
It's really helpful within those calendars if you have specific holidays in there or big days associated with your business. You can map out when you're going to send your emails and reminders so that your email sends don't get lost among the other items you're doing as well.
Next is encouraging your subscribers to take action. If you think of what types of engagement are important when it comes to improving your inbox rate, your call to action is definitely number one. You should have one within your email, and it should be clear and easily noticeable for your subscribers.
You can also use sentiment or feedback trackers. You can have an option for your subscribers to share their suggestions. You can have a reply-to option.
This is really important. You should avoid using a no-reply sender address, as these can sometimes discourage interaction and can actually hurt your sender reputation as well. We would always advise having a reply-to option with any emails you send.
You can use "read more" or "go to your website" as well, linking your website within your emails to have that consistent flow.
Another good option is "refer your friend" or "share your story". It's being able to provide that wow experience and actually use your customers for personal marketing as well.
Next is segmenting your list. I'm sure everyone has heard about segmentation and personalising your emails, but it's a really important tactic to have within email marketing.
If we're sending information that's not of interest to a group of our subscribers, ensuring that we're able to segment that list is important for improving your deliverability.
Having segmentation and personalised emails will definitely go a long way. Studies show that personalised emails achieve up to 29% higher open rates and 41% higher click-through rates.
So the data is definitely there to show that segmentation and personalising those emails are great.
Here on the slides, we have an example of one of our Constant Contact customers, who talks about the buying habits of their customers and how important it is to make sure emails are specific to those different buying habits.
Next is managing your bounces to keep your list clean. Think of your contact list or subscriber list as a living asset. It requires regular maintenance, just like other business databases, like your accounts or your website.
You want to manage your bounces, as high bounce rates can tell ISPs that your list is outdated or low quality. These can actually trigger spam filters for future campaigns as well.
So ensuring that you manage those bounces and keep your list clean will definitely go a long way.
For example, you can choose not to send emails to people who can't actually receive your email. Maybe the email addresses you're sending emails to are non-existent. Maybe your emails are undelivered or blocked. Or sometimes the mailbox is full.
Managing your list, tackling these issues and managing those bounces is definitely going to help your list stay clean and help your deliverability rate overall.
Next, tips for maximising your inbox placement. Something we would definitely recommend is not sending an email with just a single image. You need to ensure that your email has text complementing any images you include as well.
Spam filters can often struggle to read single-image emails, so ensuring that you have text helps to avoid situations where they might be flagged by default.
You also don't want any misleading language. For example, in your subject lines, if you have the letters "RE" instead of referring to, or "FWD" instead of forward, this might be misleading.
Spam filters can think that you have already started a conversation with those subscribers when you haven't. So we would suggest avoiding these within your subject lines.
Interestingly, I know sometimes it can be debatable, but having emojis in your subject lines is OK when used appropriately.
If you add an emoji at the front or the back of your subject line, it can help tell your subscribers part of the message you're trying to portray. I think it goes with the saying that a picture tells a thousand words.
Using emojis to your benefit can definitely help your subject lines and your emails.
Again, with all caps, you can use these when appropriate too. One tip we would have is, instead of having your whole subject line in caps, maybe choose one or two words within the subject line to put in caps.
For example, if we wanted to use the words "be intentional", maybe you can have "intentional" in all caps but "be" in lower case.
You can play around with that, but you can definitely use caps within your subject line, just making sure it's appropriate.
Finally, the word "free". Free can definitely be a useful tactic within your subject line, depending on how you phrase it and what you're actually offering your subscribers.
For example, if it's a free consultation or a free dessert with purchase of a main course, you can use it in those situations.
It's important to test your different subject lines for your different segments. You can do A/B tests on using all caps, not using all caps, using the word free, not using the word free.
You can test these within the different segments and see what works best for your audience based on your subscribers too.
Lastly, check your emails for errors. This is a very important step and can sometimes be overlooked.
You should use this step to ensure that any links or landing pages you're sending your subscribers to are active and correct.
Various email tools have this built in. For example, Constant Contact has a check for errors option that you can use before you send out your email.
This will help identify common mistakes you're making within your email. Then, the next time you create and send your emails, maybe it's something you'll pick up on before you even complete your email.
Previewing and testing your emails before sending is also a great thing to do.
In the day and age we live in today, previewing your email on mobile devices as well as desktop is a good tip because a lot of people read their emails when they're on their commute to work, their commute home, on their phones, at their coffee break or their lunch break.
Ensuring that your email fits mobile devices as well as desktop is a good tip for avoiding deliverability issues and improving deliverability within your subscriber base.
Now I'll pass to Thomas for the final section.
Thomas: Perfect. Thank you so much, Sophie.
We're going to wrap up with a group of people that maybe you've started building your list for, and maybe you've been doing some email marketing, or maybe you just want to set the precedent right out of the gate.
We're going to talk about winning back silent subscribers. We'll start with a welcome email or some sort of automation at the start to help with building out that relationship.
Whether you're using Constant Contact or another tool, if somebody does subscribe, you have a list builder tool, you're connecting with people on LinkedIn or in person, having a way for them to join your list is going to be key.
Then, having that follow-up that goes out is important.
So having a welcome email, some sort of email that gives them an incentive of some sort, as we discussed last week, is useful.
You can also use an automation to reach out to people who have not engaged after a certain amount of time.
That's something that can be helpful for winning back silent subscribers, the ones who joined your list but haven't taken any action recently.
One thing you can do is communicate with them and maybe even call out something like, "Was it something that we said?"
Have a little bit of fun with that, just to offer up some sort of incentive or connection.
As we mentioned earlier, maybe fine tune your communications a little bit. Find out how they would like you to communicate with them.
Some may prefer social media. Some may prefer an email campaign. That's totally fine.
Then also offer up that incentive and social proof, showing that somebody else has had a successful interaction with you, whether that was for a purchase or a consultation.
Being able to share those testimonials can hopefully help revive some of those silent subscribers and get them interested.
Like I mentioned at the top, they may not have needed you at that time, but if you send out a reminder along with a success story, that might revitalise that relationship.
Ask them if they would like to set a different frequency. Maybe they don't want it monthly. Maybe they want it quarterly or something like that. That's totally fine. Just have some sort of conversation about that.
Here's a quick timeline of things that you could do for those who are potentially inactive.
After 30 or 60 days of inactivity, you can send a less frequent campaign to them. Maybe switch to monthly or bimonthly. Again, whatever makes the most sense for your cadence.
After 60 to 90 days of inactivity, you could send out a campaign that says: "We haven't heard from you in a while. What would you like to do? We would like to continue this relationship with you. What would be the best way for us to stay connected with you?"
After 120 days, you could maybe send out one more email asking: "Do you still want to receive these emails?"
Maybe highlight a missed event or some missed content that would have been relevant to them.
Then at the six-month mark, you could consider unsubscribing them because they may not be interested or may not need your services anymore.
This is something you could try as you get started and as you are starting to send out those particular campaigns.
By the way, having a tool that has segmentation and tools to help you build out this list is going to be key. It will help you make informed decisions on how you want to do those communications.
We have Jason now at Rapido Trains in the UK. I think this is a really good quote because a lot of times we focus on numbers and not quality.
It's a useful exercise. Having a big mailing list doesn't mean anything. Saying 81% of people I send emails to open them does. I'd rather have 81% of 10,000 as opposed to 3% of two million people.
Again, focus on quality, not necessarily quantity, and make sure that as you are building and connecting, you are meeting people where they are and sending out those campaigns.
Some final thoughts, and then we will share the next webinars coming up and have a couple of minutes for questions.
The first one is be consistent. Find some sort of cadence that works for you.
The second one is be intentional. Make sure that you are personalising, like we talked about last week.
The third is be personal. People want to know about you. They want to hear from you.
Ultimately, be you. Make it so they know exactly who they're working with, and you've built that impression and connection. Sophie?
Sophie: Perfect. Thank you, Thomas.
I know there are a couple of questions in the chat about items that we're going to talk about a little bit more over the coming sessions.
Next Monday, 3 August, we have a session about how to use AI without sounding like a machine.
Our next session is on 10 August: smarter ways to grow your contacts list.
I know there are a couple of questions in the chat about QR codes and using sign-up forms to grow that list. We'll talk a lot about that within this session.
Then the final session is really exciting. We'll have a panel session with Barrett from Constant Contact, a representative from Canva and a representative from Chelsea Women's Football Club as well.
They're going to talk about their experience in marketing and email marketing specifically, and share some tips and tricks with you. That session is on 17 August.
If anyone wants to look into tools that you can use for email marketing, Constant Contact has a 30-day free trial available.
If you scan this QR code, you can sign up. You don't need any payment details. You can simply sign up, go in and see what the platform looks like, start creating some emails, and even send out emails within the free trial.
Caitriona: Thank you, Sophie. Thank you, Thomas. We've had lots of questions come through, so let's try to get through a few now.
We had a lot of questions around GDPR, so I think we can handle this one with Simon's question. He's asking: how do mailing lists comply with GDPR?
Thomas: That's a great question and something that is critical, especially with GDPR compliance.
The key is: are they expecting to hear from you? Do you have measures to show that paper trail of these people signing up for your list?
In order to be GDPR-compliant, you just have to show that permission.
So having sign-up forms on your website, having QR codes when you're doing in-person events and having follow-ups, where you can send out a LinkedIn message that's just an initial message saying, "It was great talking with you. Here's a link to sign up."
All of those things are a great way for you to get people to subscribe and sign up. Having that paper trail is going to be key for you.
Caitriona: Thank you. We had a question from Liz, who was asking about suggestions for layout tools.
I know Sophie has answered this question in the chat, but I feel this could be really interesting for the other attendees as well.
Did you want to talk a little bit more, Sophie, about the layout tool options that Constant Contact has?
Sophie: Yes, absolutely. With Constant Contact, we have hundreds of different email templates that you can use.
Once you sign up for a tool like this, for example, you can include your brand kit, which includes your brand logo, your colours and so on.
Then you can use the different templates available, change them to suit your brand, create your email and send them out.
With Constant Contact, we have an integration with Canva. So you can use the email templates available in Canva, create those to suit your brand and send your emails within Canva as well.
Without needing to change from Canva to Constant Contact, you can send emails directly to your list once you have a Constant Contact account and that integration is available.
Caitriona: Thank you. Then we had a question from Reese.
They were asking: when segmenting email audiences, would you recommend using dynamic content to personalise messages within each segment, or is it more effective to create separate campaigns for each audience?
Thomas: That's a good question, and the answer is you could do both. You can do segmentation or dynamic content using a tool like Constant Contact.
The way that it would work is based on the details you have for that contact. Maybe they're in a specific place, or they have a specific field, maybe prospect versus existing.
You could leverage that and have a single campaign with those dynamic blocks based on that information. Or you can do it as two separate things if you have very different messages.
Sometimes, even for the sake of your own visibility when you're looking at your dashboard of campaigns, it's nice to have either folders of the different types of campaigns or, at the very least, different naming conventions.
That way, you can see: this one was specifically for my prospects, this one was specifically for my clients. It's really up to your flow and the best way to do that.
But yes, you can do dynamic content as long as you have a way to identify how the system should push those campaigns out to those different audiences.
Caitriona: Great. Thank you. We have another question here. I know we touched on it a little bit over the course of the session, but at what point should you stop emailing inactive subscribers?
Thomas: We talked briefly about the six-month mark. Usually that's a good indication if they haven't opened or clicked over that six-month time frame.
You can maybe have one last-ditch call-out, or something like that, just to maybe hit them in a different way than the email campaigns.
That can be a great way to have a last-ditch effort to connect with them.
If they don't follow up, or if they don't answer or anything like that, then that might be a good time to unsubscribe them, at that six-month mark.
Caitriona: Thank you. Thank you so much, Thomas and Sophie, for your presentation and for being here with us today.
I've posted the links for the upcoming sessions, so please do check them out in the chat, as they cover some questions that people were asking as well.
The session is recorded, and we'll share the recording in a follow-up email this afternoon with further resources.
Thanks again, Thomas and Sophie, for sharing your expertise with us. It's been a really useful session. I hope everyone enjoys the rest of their day.
Thomas: Thank you, everybody.
Sophie: Thanks, everyone.
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