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Expert Interview Series: Part 7

Expert Interview Series: Part 7 Data protection, privacy compliance, and avoiding the email spam trap during the Holiday season with Dennis Dayman Res...

Expert Interview Series: Part 7

Data protection, privacy compliance, and avoiding the email spam trap during the Holiday season

with Dennis Dayman

Resident Chief Information Security Officer, Proofpoint

Holiday email marketing is a technique-sensitive topic. More so because the volume of emails sent and received reaches an astronomical figure during these busy days. With this surge, spam filters also get extra alert on the kind of sales and marketing emails being sent by brands. While this can put your email deliverability rate at a huge risk, it can be absolutely detrimental for your Holiday email campaigns and conversions.

So, to help you get the maximum out of your Holiday email strategy, we got in touch with Dennis Dayman, the Resident Chief Information Security Officer at Proofpoint. We got some great insights into how spam traps work, sending frequency, trigger words, and anti-spam regulations.

Here’s sharing all those amazing recommendations with you all.

You have extensive experience when it comes to spam traps. Now, speaking about Holidays, most Holiday email subject lines are bound to have words like discount, free gift, sale, and deals. Will they trigger spam filters? If yes, what’s the way out?

Dennis : I think for years now, it’s been known that words like FREE and DISCOUNT no longer trigger spam filters. Why? Well, most platforms today use reputation scores and other items to determine if the message is wanted or warranted – meaning, does it have complaints or is it content that people want to see and if so, are they interacting with it?

For instance, Gmail and other mailbox providers see how people interact with an email today. Did they look at it, how long did they look at it? Did they ignore it? How long did they scroll through it?, Did they folder it?, Which folder did they put it in?, etc. These indicators are the most important in anti-spam filtering as it really gets away from the misnomer that content and words like FREE get blocked more. Think about it today, using the word FREE by a known and good sender/brand of an email isn’t fair to them, right?

What’s funny about this is that spammers do attempt to hide their emails by throwing all sorts of “acceptable” words and stolen copy from brands into their spam thinking it will confuse content filters, but in reality, those filters are looking to see if the receiver liked the message and if not via their interactions or actions upon it.

So, go ahead! Use some of these words if you need to.

What other factors do we need to consider during this time so that we can keep the spam filters at bay?

Dennis : Know that simplicity should be the key goal in email design. You will only have 5-8 seconds to let them know what your email is about.

Today, most emails are opened on a mobile device and it can be a deal breaker if your email is not responsive. Layout, design, and fonts will become particularly important in how fast you can garner the attention of the reader and present your point to them. This means that you must ensure a responsive design for your emails to read well across all devices and content that can be seen and not hidden in a preview pane. Writing a catchy subject line that matches the holiday mood also helps; try to make it unique as well as specific. I don’t know about you, but during the holidays my inbox is slammed not only with end of year work email, but also tons of marketing, so like many, I use subject lines and pre-headers as two things that I use to decide whether to open and review your emails or not, so make sure you use that to grab attention.

Something else to consider that I think is glossed over during the marketing calendar is the different makeup of your subscribers’ beliefs and celebrations such as Kwanzaa and Hanukkah. Make sure you segment your lists properly not just by location, but by beliefs, faith, and backgrounds if you can as well.

By doing these things, users will happily and quickly interact with your emails thus showing mailbox providers that users do want your email and thus increasing your internal reputational scores.

The sending frequency is an important aspect during the Holiday season. How should one go about it? Do you recommend pausing the automation workflows?

Dennis : During the holidays, most retailers start sending daily. And there’s nothing wrong with that, as most subscribers expect it. Some retailers even start sending multiple times per day, which can make sense when done because of non-openers.

Your messages need to be short, but also engaging. Too many times, your readers will not check their email inbox as much during the holiday season. To make sure your offerings are read and engaged with, try to promote them across social media channels as well, and include social sharing buttons in your emails to obtain greater engagement.

Also, know that some of your targets might be traveling and in different time zones, so be sure to consider that what worked for them at their time, may not again for a few weeks.

I would also heavily review campaigns from last year. Look for both strong-performing emails and those that had high unsubscribe or complaint rates. This is your best starting point for determining which messages you should and should not send, as well as the cadence for your messaging.

Also, stay connected with other divisions like support who send email on behalf of your brand. Everyone should be mapping out the holiday email send calendar, and remember to allow for pre-holiday sending, remailing and extended sales, which will also increase the overall sending volume. You don’t want your brand over sending emails and upsetting the receiver.

How far do you agree with the thought of investing in another sub-domain for the Holiday email campaigns?

Dennis : Don’t make sudden and unexpected changes to the “From” email address. Why take away familiarity of your brand when in today’s world of email, you are fighting for the digital screen landscape with other major senders. This is your calling card!

By changing and adding a sub-domain, you are now needing to spend more time building up the email reputation of that vs. using the current one already set for marketing and that critical time to look at your current list makeup to understand who would want a holiday timed email and what targeted advertisement. If you start sending from a brand new sub-domain it will have no sending history and will be treated with greater suspicion.

Changing the email address also kills any whitelisting people have done for your emails and thus again puts you in a danger zone of emails having to go through filters.

Cyber attacks are constantly on the rise and emails are equally vulnerable. So, how to steer clear of the security issues, especially during the Holidays? What should the subscribers and email marketers take care of?

Dennis : You need to know that cyber-criminals take advantage of us during the holidays because of the overload of content coming into us. Like I mentioned above, try not to make too many changes from the normal way you might send in terms of identification. Consumers are already dealing with a lot and if you give cyber-criminals a chance to get into that break from the norm, they will try as hard as possible to trick your customers that they are you and the customer needs to do something immediate or urgent, thus ruining your reputation if it was a false thing.

So, if you change domains or add sub-domains, then criminals might work that to their advantage and send fake emails about bad orders to your customers and in the hustle and bustle of the holidays asking for billing updates because of a failed order and we don’t want customers clicking on malware or fake banking credentials just because we want to get the email task completed ASAP.


  • 91% of cyberattacks start with email
  • 20% of emails are considered suspicious
  • 70%-80% increases in email attacks each quarter
  • Research shows that 43% of organizations that experienced a security incident in the last 12 months reported that Business Email Compromise (BEC)/phishing attacks account for more than 50% of the incidents.
  • And there has been a 2,370% increase in losses due to business email compromise (BEC) over the last few years.

Your people are your most valuable asset, your greatest weakness, and your best defence. So, try not to confuse your readers with too many changes and try not to give a leg up to the bad guys who will exploit changes.

Privacy and data protection have become quite significant with GDPR regulations and the CCPA in place. How should you design your controls to steer clear of any violations?

Dennis : So I wish I had an easy answer to this, but this is a VERY complicated answer that would take hours, so let me walk you through some of the basics here.

The California Consumer Privacy Act (CCPA) and the General Data Protection Regulation (GDPR) are laws that emerged to give individuals greater power over their personal information. Both regulate organizations that collect and use data in a variety of different ways.

The CCPA protects “consumers” who are natural persons who have to be residents in California to be protected. However, with GDPR it only protects “data subjects,” and does not specify residency or citizenship requirements and who are natural persons. So as you can see, the laws start out to be different. However these, and many more laws, have the similar goal of giving individuals more control over their personal information.

Again, there are so many more differences in these regulations that it would take hours to explain, but overall, GDPR compliance does not equal CCPA compliance, which makes it difficult to say if you are using one of them to cover the other, things like definitions and applicability will not be the same across the board.

The best thing to remember in all this is to obtain explicit permission to collect, process, share, sell the data that you may obtain. You also should build privacy controls to give users the most options to control, edit, and delete their data if any of these regulations apply to you and/or them. You need to put the people first when it comes to the use of the data. Ask yourself this question every time, in whose best interest will this purpose serve? The brand? or the customer? Yes, we know that GDPR states that the “processing of personal data for direct marketing purposes may be regarded as carried out for a legitimate interest.” (This is verbatim from the text of the regulation.)

However, that doesn’t mean that you’re scott free. You also have to consider the balance of interests and ensure that your “legitimate interest” is not overridden by the interests or fundamental rights and freedoms of the data subject.

Be sure to do your own homework, though in determining how and what regulations apply to you and the customer.

Would you recommend any tools to improve email deliverability during the Holidays?

Dennis : The tools I’d recommend would be first to set up feedback loops of those mailbox providers that offer them. This way you will know quickly if your content is being sent and usually in mass quantities over the holidays. They are provided to aid senders in keeping a better list. Senders should also use feedback loops to watch for signs of what their subscribers want and exceptions that will allow them to take action such as suppressing them if there are complaints. It’s important to learn from the complaints you receive because they can help you evaluate and fix issues before they get out of hand in the next series of campaigns.

Second, get an email marketing monitoring tool, which offers innovative ways for brands to monitor key deliverability and reputation metrics, identify potential issues, and take action to resolve them. Email monitoring tools allow you to watch and measure campaigns after you send emails that then allows for you to take the best steps to correct issues found and ensure the best possible inbox delivery on the next campaign and not perform the same mistakes.

Lastly, obtain a list validation service. List validation services can scan your email marketing contacts for possible bad or invalid addresses. Many online companies offer list cleaning services, but accuracy varies and is never 100%. Cleaning a list may solve an obvious problem, like stale addresses, but it can hide bigger issues with your audience collection and management procedures. You won’t discover or solve ongoing audience issues like abuse complaints, spam traps, or blocklists, so be careful not to be sold on those services by some validation companies if they use it as a selling point.

Lastly, would you like to share any pro-tips that would help our readers make the most of the Holiday season and drive maximum conversions?

Dennis : I think your time is better spent on making sure you’ve prepared for this season, especially not knowing where the marketing conditions are going to be. This year AGAIN is a bit different from normal preparations for the holidays. The last few months have been tough on all of us. Most shoppers are still reeling from the economic and emotional rollercoaster of COVID-19.

One of the top things you can do is show true empathy for them during this time. Show them how much you care about them in your communications and help them find ways to do business with you during this socially distanced time.

In other words, remove the roadblocks and friction for them. Make sure you can help them:

  • Meet more stringent budgets this year by offering bigger discounts.
  • Offer the best ways to pay online and via any app available.
  • Make it easier for them to obtain your products by offering free shipping or free shipping to local stores.

You should also anticipate how the next four months could look and have some different strategies prepared.

Right now, we all could use a bit of holiday cheer and some fun things to do. If you start planning for the holiday season now, you might be able to help alleviate some of the stress that is associated with holiday shopping, as it is sure to be exacerbated by the current pandemic.

Holidays should be about reaching maximum people rather than struggling with your email deliverability rate and inbox placement. We are sure that this interview with Dennis Dayman would help you make your email strategy more fruitful and to get unmatched results.

We would love to hear your thoughts on the same. Head to the comment box below.

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Prajakti Pathak

Prajakti is the Content Lead at Email Uplers. She brings with her a rich content creation experience of over 10 years. A creative mind and a good hold on syntax make her traverse her writing through different forms of content including blogs, interviews, infographics, case studies, etc. While writing is her first love, she’s also an avid birdwatcher.



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