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January 27, 2025 - Articles

Email Peeps 59: Al Iverson

“Al

You’ve been around the block a few times. How did you get to where you are today?

I first got involved with email as an admin and spam fighter in 1996 or 1997, and I sent my first double opt-in confirmation email in late 1998 or early 1999, while managing marketing efforts for my friend’s jazz club. I helped grow their email list entirely organically, from zero to more than five thousand subscribers. Not bad in those early days of email marketing.

At the time, I worked for a pre-press company, which I had joined as “team lead” for their service bureau print department, but then I later ended up as a unix administrator based on my ability to help them set up and manage their first internet servers. One thing led to another … building spam filters … moving to an ecommerce platform to help guide (and police) client email marketing efforts … to managing deliverability for a large email service provider for fifteen years. And now a bit later, I’m working for Valimail, a DMARC provider, helping folks understand how to protect their domains against phishing and spoofing, living somewhere in-between email deliverability and email security.

Incidentally, when I first worked in “deliverability” in the year 2000, the term hadn’t been coined yet – my initial title back then was “Consumer Privacy Manager,” but it was very much email operations and deliverability/compliance work. I first used the word “deliverability” on my blog in 2003.


What are some signs that you may have a deliverability problem?

You don’t know if you don’t monitor. What are you monitoring and how? I find inbox monitoring (seedlist testing) to be really valuable, even though not everybody agrees and some people believe it to be inaccurate. I don’t believe it’s inaccurate per se, I just think that it has limits to what it can tell you. For example, how the seeds perform at Gmail will only match how SOME Gmail recipients will see the mail. Gmail filtering is very individualistic and based on user-level feedback. One person’s spam is another person’s valuable content. But inbox testing still tells you how the default Gmail filters will treat your messages, and that’s valuable intel.

To actually answer the question, I think identifying falling signals is your best way to identify if and when you have a deliverability issue. Watching that seed list testing – or if you don’t have that, watching for significantly slipping open rates and clickthrough rates. (Open rates are less accurate than in years based, but still widely used, by myself included, as a directional measure to monitor campaign success.)

In this modern age of domain reputation, I think Google Postmaster Tools – watching it for indications of low domain reputation – can also be a very important tool to identify an actual or potential deliverability issue.


What’s the biggest misconception about email deliverability?

That technical settings alone will get you to the inbox. “I’ve got SPF, DKIM and DMARC in place, but my mail is still going to spam. How can that be?” Because spam filters look at MORE than just the technical settings. Spammers can comply easily with technical requirements and most of them do. What those technical settings do is make it easier to identify mail and tie it to a reputation, so that mailbox providers can decide whether or not to drop it in the inbox, spam folder, or reject it outright.

At least a couple people every week post on Reddit, asking for help, saying they’ve got all the technical bits right, but they’re still going to spam. Did they warm their IP or domain? Do they have high engagement or low engagement? Is their mail actually wanted?

People really get confused – the message around email authentication and deliverability is a nuanced one. SPF, DKIM and DMARC do not guarantee inbox placement. But I personally guarantee that it’s a lot harder to reliably get inbox placement without them.


What are your tips for email marketers wanting to specialize in a deliverability career?

Run screaming for the hills after reconsidering your poor choices. Tech is in a contraction right now and things are tough, and deliverability as a career option is affected by this. Look to excel in your particular area of expertise, wherever that may be, and make a career of it if you can. But there really aren’t entry-level deliverability roles out there right now.

If you’re already in the space and looking to move, networking is an absolute must. Go to conference meetings for M3AAWG, ESPC, Inbox Expo, etc. Connect online and offline as much as possible. It really is about who you know.


What’s in your email marketing toolbox?

Most of my tools are custom built or just typical unix/free software utilities.

Hardware: 

  • Amazon EC2 virtual private servers (multiple) for spamtrap tracking.
  • Google Cloud virtual private server for web hosting/email tracking.
  • A hosted server used as my mail server (MTA). (I’ve also used Amazon SES.)
  • A hosted virtual private server that I use to run DNS queries to track MX, SPF, DMARC and BIMI DNS records for millions of domains.
  • A couple of Mac Minis that I use for ad-hoc DNS/data projects. I love to write little scripts that will scour DNS looking for something interesting, but might take four months to run.
  • An M2 MacBook Pro for my work daily driver, and an M1 MacBook Air for my weekend and graphics daily driver.
  • A fancy SHURE microphone and Logitech webcam that I use for making videos and participating in Zoom calls and podcasts.

Software:

  • Custom newsletter management software to handle signups and unsubs, track opens, and build newsletter content. (I have push-button automation to generate my weekly newsletter, which saves me tons of time. It automatically pulls headlines and intros to the past week’s blog posts and builds the newsletter for me.)
  • I’ve also used various email marketing platforms like ExactTarget/Salesforce Marketing Cloud, Responsys, Mailchimp, Aweber, Beehiiv, Sender and a few others.
  • Wombatmail, my DNS tools website that I use for various bits of deliverability and inbox testing. Some of these I share with the public, while some others are reserved for my use only.
  • A very old but legally owned copy of Photoshop from somewhere around 1999. It runs fantastically well under emulation on my M1 MacBook Air. I use this to create all of my blog graphics. (I incorporate stock photos, but avoid using A.I. in my graphics or content.)
  • I run my blog Spam Resource on Blogger, a very old Google-owned blog platform that I think works fantastically well.
  • Fathom Analytics, which I use to track website traffic to my blog. I find it MUCH easier to use than Google Analytics.

Al Iverson


Do you recommend using double opt-in on your sign-up forms?

I do recommend double opt-in, and CAPTCHA, especially for newsletter and other smaller senders. Bad guys love feeding garbage into signup forms, and it will happen to you tomorrow, if you haven’t run into it yet today. Everybody gets hit eventually. 

Also, I know of evidence that shows that a particular blocklist was hounding after single opt-in senders on a particular email service provider platform, leading to blocklistings that were causing deliverability issues at a big mailbox provider. I’m being a bit coy because I don’t want to pick a fight, but at the end of the day, it was a big blocklist provider picking a fight with a big email service provider, and the only way to avoid it was to be using double opt-in, so you weren’t showing up on the blocklist’s radar.

Life (and deliverability) are a lot more fun and successful if you’re able to avoid that noise.


How is AI being used in the deliverability space?

On the mailbox provider front, machine learning is undoubtedly being used by MBPs like Gmail to finetune their spam filtering, to improve the decision making around what mail goes to the inbox (or doesn’t). On the sending platform front, there are things like Mailchimp’s Omnivore that I think of as A.I. adjacent that attempt to analyze list data to determine the chances of a send having poor deliverability or not being in compliance with their policies.

I’ve seen some sending tools basically try to figure out what content goes through to the inbox or what doesn’t, and claim that it’s A.I., but it tends to just be brute forcing a zillion combinations of content bits to see if there’s some version that hasn’t gotten fingerprinted by a mailbox provider’s spam filtering yet. I think those are spammer tactics and not something I would endorse or engage in.

A.I. can undoubtedly be a great help for marketing strategy; thinking specifically of personalization as a starting point. But it tends to get away from deliverability pretty quickly. 

I’m often the annoying person in the room advocating for healthy skepticism about relying on A.I. too heavily, too quickly when it comes to email deliverability and email security. The first steps, in some cases, have involved fumbles, like Apple Intelligence highlighting phishing emails as “important” in a recent iOS beta. They’re to be forgiven, but what we should remember from that is that while looking to A.I. to make things better, we should make sure we’re not throwing away current filters, expertise, and best practices. (A.I. being allowed to bypass existing spam filters, authentication or security checks was probably partly to blame for that initial Apple bug.)


What’s your favorite email campaign of all time? Why?

I signed up for tons of marketing emails. It’s tough to pick just one fave, but I love discounts, and I love good food. I love it when my favorite Miami steakhouse, Red South Beach, lets me know about a special treat or what they’re serving for Miami Spice (restaurant week). Is that sad? There’s nothing technically special about the design of it. Most of the senders I get emails from don’t even use animated GIFs. (They could learn a thing or two from Really Good Emails, who seems to have completely mastered the animated GIF-in-email game.) RGE drove me to try to up my own design game, which is why the Spam Resource logo is now animated.


I noticed that you have a newsletter. Tell us why we should sign up!

You should sign up for my weekly Spam Resource email newsletter if you care about your emails getting to the inbox, and you want proactive warning of when something changes at Gmail, Yahoo or Microsoft that will impact your ability to succeed with your email marketing efforts. Or if you want to learn more about why DMARC matters and how a BIMI logo can help improve engagement. Or if you care about the email ecosystem and want to learn more about how to productively contribute to keeping email a useful channel for years to come. Or if you want to learn why Spamhaus actually isn’t evil and what they actually do to help block badness in email.

My newsletter isn’t huge. It’s only 1374 subscribers at the moment. But it’s a direct connection between myself and 1300+ people who care about email deliverability. II’m very lucky to have this audience and I try very hard to share useful things that I think people will find valuable.

Much love,
Andy

Email: [email protected]
Twitter: @emaillove

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