Email Expert Talk 4: Anna Ward, Head of Deliverability at Postmark

In our series ‘Email Expert Talk’ we discuss all things email with distinguished experts who know about the struggles and strategies of working with high volume emails. We talk about how they cope with daily challenges, what their opinions are on the latest industry developments and how they manage to stay on top of the ever-changing email landscape.

In this fourth edition of Email Expert Talk, we are speaking with Anna Ward. As Head of Deliverability at Postmark, Anna is primarily occupied with maintaining superior inbox rates, lightning-fast delivery speed and providing full transparency into sending and bounce-handling processes for customers.

Six years ago, Anna stepped foot into the world of deliverability, during which she “gained experience fighting fires in monstrous mail queues” as she so grippingly describes herself. Now she focuses on improving the sending experiences of customers by practicing the nuances of sending reputation and building trust. Let’s see what she has to say about this!

What does a typical day at work look like for you?

Anna: “My typical day starts with checking and updating various internal statuses, pouring over dashboards and creating new visualizations to understand changing trends. With that comes a good chunk of data analysis, investigating any abnormalities and potential risks.

“From there I start working with customers that are encountering complex deliverability concerns or issues. Our team keeps meetings and interruptions to a minimum, so I also set aside time to chip away at quarterly projects and research. I think it’s important to break up every work day with a run and a picnic lunch!”

What are the most common deliverability challenges you encounter and how do you tackle them?

Anna: “Our customers’ mail is mostly transactional, so almost all of our deliverability issues come from vulnerable online forms. Bots are crawling the internet looking for sites that post or send submitted content, allowing them to spread spam for free that puts your network at risk.”

“The first solution to this is to make sure your forms are protected via captcha, honeypot fields, filtering source IPs or domains, etc. Secondly, never automatically send content submitted to a form. Many bots enter their spam into a ‘First Name’ or ‘comment’ field, so try to never include form submission content in your email auto-replies without manual or automated review first.”

“Another major issue I see is not properly distinguishing transactional mail from other messages (like marketing/promotional, legal notices, etc). If an online form gets compromised, you will see that it immediately affects your marketing messages as receivers try to block the spam. At the same time, email marketing mistakes could quickly affect the reputation of your transactional mail. Ideally, your messages will be identified with their own subdomains, (transactional example) and (marketing example). You may also seek out an ESP that specializes in supporting different message streams or a specific type of mail, which separates your messages further by network/IP. Not only does this help separate their reputations when issues arise, but it can help you acutely optimize deliverability for each message stream.”

What result/performance data do you most rely on for tuning your delivery settings?

Anna: “Not every bounce response is helpful (some are downright silly!), but there are specific types of bounces that tell a story about the state of a sender. For example, a lot of hard bounces usually mean there’s a problem with the list source – perhaps a vulnerable signup form getting bot submissions or excessive typos/errors in data entry. Soft bounces like full mailboxes and temporary issues tells me list management is the likely issue — these addresses are old and unresponsive. There are also what I call “Priority Bounces”, such as this one from Gmail: “Our system has detected that this message is likely suspicious due to the very low reputation of the sending domain.” In my book, any sender who receives this bounce requires immediate intervention!”

“I could spend all day identifying trends and anomalies for each receiver (which I often do!), so Postmark created the SMTP Field Manual — a free open-source bounce response index to encourage others to share our passion.”

What kind of information that you’re currently missing would make your (professional) life easier?

Anna: “I understand that email delivery is a black box for senders. Once the message is out of my own mailserver’s hands, I don’t have much reliable info about what happens to it later. This is especially the case when it comes to spam filters and firewalls. These exist on the receiving MTA, the various routing and forwarding mailservers, and individual mailbox providers. That’s not to mention the more manual applications by corporate/university/community network administrators and any additional rules set by the recipient themselves in their own inbox.”

“Sometimes I have a clue on why a message is getting blocked, such as a specific bounce response, the source of an asynchronous bounce, or even access to someone who knows the recipient personally. But my job would be a breeze if I had more details about which hop specifically in the delivery led to the message being blocked and which services or rules are being used to decide that block. For example, if I knew mailserver ABC was rejecting the message because of a fuzzy checksum by tool XYZ, I could confidently and immediately move forward in repairing the issue.”

What advice would you give to someone who is just starting out in email deliverability?

Anna: “I tend to think there are two sides to email deliverability — The first is the relational side of understanding business models, marketing techniques, seasonal trends, and list management and acquisition. You’re working very closely with your customers, you are maybe even involved in some compliance work and calling out negligent behavior.”

“The second side is more technical, delving into the art of managing an MTA’s software, setting up rate limiting and bounce processing, analyzing raw delivery logs for global issues, and even building compliance automations and queue alerts to minimize risk on your mailservers/IPs. On this side you’re working more closely with reliability/operations engineers to allocate and optimize resources, making sure every mail volume shift is handled smoothly and efficiently.”

“So take your time shadowing people in this kind of work and try on some new tasks/responsibilities you’re curious about. Since deliverability work always affects multiple teams, the end goal is to craft the type of position you want for yourself. Pretty much every company structures and evolves their deliverability team differently, so you can likely create your own role that includes a healthy mix of relational and technical tasks to your taste.”

Looking forward, where do you see email deliverability in 2025? What new challenges will we be facing and what current issues may be tackled by then?

Anna: “New standards and new technology for email seems abundant, but adoption across all senders/receivers/mailbox providers is inherently slow. While we do see those eager for more dynamic content (AMP for Email, for example), increasing concerns around security and personally identifiable information (PII) makes me think by 2025 the medium itself will look mostly the same.”

“One thing that does have the ability and necessity to change quickly is spam filtering – how we adapt to the ‘darkness of the internet’. More and more receivers are relying on machine learning to determine what is spam, and as storing and accessing data gets cheaper, a sender’s historic performance can become an increasingly real-time metric.”

“At the same time, we’re seeing increased interest in sharing data used for anti-abuse, so abusing one provider could mean immediate action taken by another as well. My expectation is that by 2025 we’ll have some more efficient and anonymized data sharing options, so understanding a sender’s reputation and performance isn’t so scattered and variant by receiver.”


[Originally posted here.]