Ask the Expert: Lili Crowley, Postmaster, Yahoo!

Ask the Expert: Lili Crowley, Postmaster, Yahoo!

Countless myths abound in the world of email deliverability. That’s why there’s no one better to clear up these common misconceptions than the leading experts in the world of email. Every month, we’ll bring you a Q&A with leaders from inbox providers, spam trap networks, antispam systems, and more in our new Expert Series blog. 

In our third Expert Series blog, we chat with Lili Crowley. Lili has been the Postmaster at AOL/Yahoo! for almost 10 years. Prior to that, she worked for Network Solutions, the very first domain registry and registrar for .com, .net, .org, and .edu. Lili has an extensive background in data extraction and analysis and loves assisting senders and receivers with email.

Now, let’s dive in.

10 questions with deliverability expert Lili Crowley

1. As a postmaster at Yahoo!, what does your role entail? 

In a nutshell: a little bit of this and a little bit of that—or actually, a lot of this and a lot of that! I handle issues that come through our ticketing system, internal escalations (from social, concierge, legal, etc.), and executive escalations as well as requests from email service providers, vendors, and other industry contacts. Plus, I support teams with whatever issues I can and improve communication and processes among them.

2. Yahoo! is known for deferring email from new domains and IPs. Can you explain why and what steps senders can take to minimize this?

Why not defer new email, at least in part? This gives us and our users a chance to form an informed opinion. For example, if you know you have a new IP, build that in and send small, consistent emails to increase volume. And when the deferrals start, ease up on sending, then continue when the deferrals stop. 

3. You’ve said email deferrals is Yahoo! telling senders to “back off” for a bit before sending more volume. For those senders not in control of their mail deployment infrastructure, how do you recommend they respond to deferrals?

We recommend backing off for a few hours and sending fewer. If you follow this procedure at the beginning, you can avoid issues later.

4. At a conference a while back, you said, “Email deliverability isn’t that hard if you send [email] people love.” Can you explain what you meant by that?

Look at it this way: there are companies that send me an email, and I know it’ll be well-crafted, interesting, and relevant to my interests. There are other companies that even though I like them as a consumer, send too frequently (think many times per day), and I delete a lot of it.

Then, there are the ones I’m on the fence about because of the tendency to send not-so-great email way too often. My point is I’m a consumer as well as an email person, and I’m not one to mark an email as spam, but a lot of users do. So my advice is to strive to be in the first bucket: send well-crafted, interesting, and relevant email tailored to users’ interests. 

And while it seems like I’m saying that content governs deliverability, the truth is it does—but not like you think. It’s not about avoiding dollar signs in subject lines or never using the word sale—it’s not about a list of words to avoid at all. However, it is all about creating content that interests people and then sending it (only) to the people who’ve expressed interest in it. The days of successfully blasting giant databases are over.

5. A common deliverability trope is “quality over quantity.” From a postmaster’s perspective, can you explain to senders who place more importance on quantity why this approach doesn’t make sense from a filtering perspective?

If you want to reach the 1,000 people who will buy from you, why send to 99,000 more than that and risk filtering and deferring because of the ones who don’t want your email campaign? That’s taking a good, solid approach and diluting it. 

Many senders have successfully reduced volume without reducing revenue. And since inactive subscribers, old addresses, etc., are far less likely to buy from your email, you’re usually not throwing money away by focusing your sends on those most likely to engage or purchase.

6. How much of inbox placement is determined by Yahoo! filters compared to local user settings/behavior?

It’s both, in parts. We make some decisions on the email and rely on users to let us know if we get something wrong. For example, if you send 100,000 emails and we bulk most of it and users don’t seem concerned, I’m not sure we’ve got it wrong.

Obviously, with malicious email, we’ll make different decisions to protect our users.

7. If a customer notices TSS04 blocks and continues to send email, will that have a negative impact on their sender reputation?

It won’t necessarily hurt their reputation indefinitely, but it’ll make it harder to get out of the deferrals loop. The best response to TSS04 is to ease up sending until the deferrals stop, then begin resending slowly.

8. If a sender notices a portion of their email landing in the spam folder, what next steps do you advise they take?

It depends on their answers to several key questions. What’ll likely lead you in the right direction is: who are you sending to and why? Did you generate complaints or see an increase in complaints recently? Are you sending content that a lot of other senders also send (affiliates)? However, less likely but worth checking: are you failing DMARC with a quarantine setting, and are we doing what you told us to do?

Then, look at users who interact with your email. Is this less than usual? If you notice positive trends in your sending drop-off, assume the spam placement may be related and try paring your list down to see if you can target the most interested users.

holiday-email-sending9. If a sender expects to see a significant increase in sending volume (for example, over the holidays), how do you recommend they approach that?

If they send without deferrals, they can continue to increase their sending volume until they get deferrals, then slow down. That said, keep in mind that volume thresholds will change over time for everyone.

10. It’s an email best practice to suppress email subscribers after a certain period of inactivity. With techniques like prefetching becoming commonplace, how do you recommend senders create effective sunset policies?

Well, first, what’s your ideal measure of engagement? Is it opens or clicks or sales? I would think it’s clicks and sales. So if you see lower engagement with a set of users, test that theory with results that you can measure. Usually, your data and statistics can help tell the story, but you have to look carefully at what you have available to you.

Thanks to Lili! And be sure to stay tuned each month, as we’ll chat with another expert in the world of email marketing to provide you with further insight into the ins and outs of email deliverability. 

Until next time, check out Twilio SendGrid’s Email Deliverability Services packages to get started, or contact our Sales team to learn more about improving your email deliverability.

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