June 20, 2019

Email on Tap Episode 10, with Lili Crowley, Postmaster, Verizon Media


Our newest video is a little longer than our previous episodes, but it is for a really great reason. Anthony Chiulli, 250ok’s director of product marketing, spent time with Lili Crowley, postmaster at Verizon Media, which includes well-known entities Verizon.net, AOL, and Yahoo, to shed light on a commonly misunderstood function of the email ecosystem.

Many senders find postmasters mysterious, and this conversation with Lili should help marketers understand what is and is not important, what to do for optimal deliverability, and provide a look into the more technical side of email marketing. This fun change of pace for us is packed full of knowledge, and trust us, if you’re a commercial sender, you’ll want to watch the whole thing.


(Keep scrolling for key timestamps and even a full transcript. Plus, find links to our podcast version!)


Total Run Time: 26 minutes
00:20 – How Lili got involved in the email industry
1:25 – What is a postmaster, and what are its responsibilities
3:23 – Basic fundamentals and best practices for optimal delivery
5:37 – Non-obvious, but important signals for marketers
7:15 – What marketers should know about the recent completion of the Yahoo, AOL, and Verizon mail infrastructure merger
9:44 – Key metrics and indicators marketers should focus on and why
13:40 – How AI and machine learning may influence deliverability monitoring capabilities for marketers
15:30 – Similarities and differences in measuring domain versus IP reputation for senders
16:39 – How changes in the email inbox experience and enhanced features affect consumer behavior
19:00 – What makes email so unique and adaptable over the decades
22:30 – Lightning Round


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Transcript

Anthony Chiulli
Hi everyone, and welcome to another episode of Email on Tap. I’m your host Anthony Chiulli, and today I’m thrilled to have as a guest Lili Crowley. She is the postmaster at Verizon Media. Lili, thanks so much for being on the program.

Lili Crowley
Sure, thanks for having me.

AC
How are you?

LC
I’m good, good.

AC
So tell me a little bit about how you got into the email industry and your story.

LC
I worked for Network Solutions for years, which is one of the original domain registrars. And I did data warehousing, and actually sort of involved in their email system, it was a homegrown system. Then I went to work for AOL as a data analyst in their anti-abuse team and I initially was doing lots of anti-abuse work. And then I went to the M3AAWG in San Francisco in 2013, met a bunch of people, and I realized that we have maybe gotten a little out of balance with treating the abuse side and not really paying attention to the postmaster side. So I came back and I said, you know what, I think we can do better. And so we decided that I would focus more of my time on the postmaster side. Which actually, ultimately, makes the abuse side easier, because we’re scooping up the good mail, and hopefully doing better with it, and then giving the abuse team the ability to be more aggressive with the bad mail. So then, over time, it just became, I’m the postmaster of the mail system, and, that’s just how it worked out. It’s been great, though.

AC
For a lot of senders, there seems to be this misconception, certainly, that postmasters are these evil gatekeepers and all they do is block my mail for no legitimate reason. Help explain the role of what a postmaster does and what you focus on.

LC
Right, so the most important thing is we want to make sure that we’re not mistreating mail that’s very good. So, obviously, things like banking mail, transactional mail, mail that people want, and certainly person-to-person mail… We want to make sure that mail is getting in and I think people sometimes feel uncomfortable saying, “Hey, this customer that’s in the order fulfillment is getting blocked. And I know they just started warming up, but can you do anything?” So we want to do something about that mail. We absolutely do not want those customers to not get their mail in, because it gives everyone a feeling of uncertainty. The users are like, “Where did my order go? Where do my bank transactions go? Where do my statements go?” So we want that mail, we obviously want senders to spend a little more time making sure they are aware of the other mail that they are sending. And I think that is where people think that we are being overly aggressive. Maybe they are not as aware of some of their shared pools or a customer that says, “I’m only mailing to engaged people,” but they’re maybe mailing people that have already complained, things like that. Sometimes it’s a lack of awareness of what their customer is doing, and it makes us look like we’re being overly harsh. And then the other thing is, the abuse system is always changing to fight spammers.

AC
Right.

LC
So the problem is we may make a tweak that takes care of like 90% of spammer mail but also hits 20% to 30% of good mail, because nothing is perfect. And so we’re constantly refining, but we can’t just wait because everyone knows the life of our spam run is really short. And so sometimes, you have to be aggressive. So the balance is trying to figure out what that sweet spot is of the mail we want and the mail we don’t want, [LAUGH] and trying not to be too overly aggressive in the process.

AC
Yeah, you touched on an interesting point here; you’re talking about wanted mail and unwanted mail, which I think is kind of an evolution of the historically defined spam versus not spam.

LC
Right.

AC
On that note, what would you recommend as far as kind of the basic fundamentals or best practices for optimal deliverability for a sender?

LC
So, I get asked this question a lot and I’m surprised, the next thing I’m going to say, “Can you tell me what it is that you’re seeing that’s spam to you?” And I’m like, “Really?” [LAUGH]

AC
Right.

LC
So I expect in this day that there’s data available to people, and you should be looking at the same things we’re looking at. Sure, are we anti-abuse people of a larger scale? Yes, but if I’m seeing pharmacy spam, this should not be a mystery. And I’m sorry if they’re masking the mail and making it look like it’s not as obvious in a human-readable format. You need to work on your mail. And so, I think people, they rely on FBLs, and FBLs are important, but remember if you’ve got a spammer squatting on your system, they want to go to this spam folder because they’ll never get complained about, and so they’re flying under the radar. There are other outbound things that people need to pay attention to. They need to pay attention to their pretties, their subjects. I mean, some pretty basic stuff; their trends, if you see a huge spike in mail, that’s a red flag. If you see someone who’s sending to the same number of people again and again and again and no complaints, that’s a red flag. No complaints is as much of a red flag for a new sender probably as much as too many complaints. But the other thing is, expect that you’re going to need a warm-up very slowly on our system. It’s 50 pieces of mail might not sound like a lot, but if you go from 0 to 50 very quickly, the system may respond poorly. So the advice I usually give people is if they see any kind of deferring, pull back. Pull back until you start sending again, and then you keep going. And it’s slow early, but if you do that appropriately, the system can relax more with your mail, versus, ah, too much mail and then it freaks out and you’re upset and then our system’s upset and getting resolution actually can put you slower. You have to kind of go back to the beginning.

AC
If I were to ask you one non-obvious recommendation or tip that you could share with marketers outside of sending to engaged and some of the more common recommendations, are there any non-obvious things that you would recommend a sender pay attention to that maybe they’re overlooking?

LC
Having come from a place that did analysis, if you know your customer and you know a little bit about who they’re sending to, and obviously, that can vary, depending on how many customers you’re responsible for, the data will tell you information about what’s going on and you shouldn’t ignore those signals. Now, obviously don’t give too much credence if you have five seeds and two of them go to spam, that doesn’t mean that 40% of your mail is going to spam. Seeds sometimes can go into spam. But pay attention to what else you’re seeing, pay attention to if the user hasn’t opened the mail, they’re probably not interested in the mail, right? And maybe it’s not perfect, maybe your opens are not always calculating properly. But it should be a signal that if I’m seeing other people opening, I’m not seeing this set of users opening, then I could probably make an assumption that they’re not as interested. So I think a lot of the information is there, people just have to stop and they have to dig through the data.

And also sometimes you can’t look at a million things at once. You maybe have to look at a subset of people and try to understand what you’re seeing and see if you can draw conclusions from there and then extrapolate from that. So that’s kind of a foundation of data analysis. But that’s the nature of, you have to use whatever you have to build your picture. And if you ignore it, then you’re missing out.

AC
Well said. Recently, there was the completion of the Yahoo and AOL mail infrastructures this past spring. What should marketers be aware of or know when sending to AOL and Yahoo subscribers now that the mail infrastructure is complete?

LC
Also, just so you know, Verizon.net, too, and that’s a smaller subset. There are still pretty dedicated customers on those. They’re the same mail system, so while the user bases are different and you do see different user behavior based on patterns that you’ve had in the past. The mail systems are the same, so sometimes people will say to me, “I’m having trouble with AOL and this week I’m having trouble with Yahoo for the same sender.” I’m like, it’s the same mail system. So obviously, week over week, you could have a slightly different experience in our mail system depending on other changes we made to the abuse. But it’s the same mail system so people should treat it as such. When you’re looking at volumes, you should treat, if you’re sending to Yahoo and you’re sending to AOL, you’re sending on the same IP from the same customer. Those volumes now, you gotta send to the same place, you need to adjust accordingly. I think a lot of places that were concerned about that early on have seen some of those challenges go away with the initial ramp up. But they’re the same system, and so people should treat them from that standpoint the same, the rules, everything.

AC
And does that apply also during warming where historically marketers have kind of controlled volume by domain? Those are all grouped together?

LC
Yes, but if they have concerns about their users and what’s going on with individual sets, they should look at the domains separately from the standpoint of user behavior, because the user demographics are different, and so they should not then say, “Well, this worked to AOL, so this will work at Yahoo.” Because those are different customer sets. Also, depending on who you’re mailing from. The AOL demographic does tend to skew a little older, so we get a different kind of customer base. The AOL people have also been, some of them are paying customers, and they’ve paid for other services through AOL and continue to do so. So it’s a different kind of customer, so people should keep that in mind. Even though you’re going to treat the mail system the same way, you’re going to treat the customer bases differently. Just like the data analysis we talked about, where you should understand who you’re mailing to.

AC
Yeah, well said. That’s a good point. You touched on this briefly earlier, but in your opinion, what are some of the more important metrics that senders should be paying attention to when trying to manage their email performance and deliverability?

LC
So the first thing is if you start to mail to us and you start getting deferred, you should slow down. There’s no question. I think people talk about the TSS errors. They hear about them a lot, they’re on our website. I won’t go into the details of that, but a deferral should be a good indicator to you that something’s wrong. And use those signals to determine whether you should be speeding up. Just because you have more mail to send, if the system is telling you, “I don’t want to send right now,” no matter. Piling it on is only going to make your problem worse, it just exacerbates it. There’s a lot of patience involved. Sometimes you have to put the brakes on and make sure that you can. Because if you can’t get any mail in, then it doesn’t matter how many times you try, you’re still at zero delivery. Or you’re inching in a little bit of mail. And I know people get the problem of the backed up mail causing other problems in their system. I just think people need to pay attention to what the system is telling them.

If you’re sending to us newly, and you don’t think that you’re going to the inbox, so you’re assuming that you might be going to the spam folder based on user engagement and you speed up your sending, you’re going to start getting deferred. It’s as simple as that. So people should not ignore that. Then, once, if they are in a pattern of sending that they like, and they see engagement go down, then they need to do their homework.

I can help make sure, if it’s deserved, that people understand why they’re getting deferred and if there’s things they can do to fix that. And I can help them understand why they might be going to the spam folder at times. But I can’t change–if the user doesn’t want to interact with your mail, we can’t change that. If you’re getting bulked because you sent us too much mail and nobody’s responding to it, and you start getting bulked, I can’t magically make the users want to engage with that mail and mark it as ham, right? So at the end of the day, we can only manage the things we can. If the relationship with the user is not strong, if the recipient doesn’t want the mail, no amount of anything is going to fix that. It’s still a basic concept of, you need to send mail people want to look at.

AC
Goes back to wanted mail versus unwanted mail.

LC
Exactly. Exactly, and I know there are more things available to us and the systems are complex, but you can’t just ignore the history of what you did.

AC
And you can’t force engagement.

LC
Right, so when I used to work in data warehousing and network solutions, I worked in the marketing team for a while, and I would pull all the mailings. We were very basic. This was before all these systems that do it. I used to pull the recipients, I’d figure out who we’re going to mail to based on what products they owned, what we thought they might need. And then, also based on how they responded to previous maillings. I looked back a year. If we mailed to them then and they didn’t respond, so I’d pull out people and say, “No, we’re not going to mail to them, they didn’t respond to this.” We got kind of lifecycle on it, and I paid attention to that stuff. It was really painful to keep track of, because I had to make my own database of the users and their responses and keep it over time. But we did it, and we did it because we wanted to make the mailings we were sending really effective. And we wanted to make people feel like when we sent them mail, “Oh, cool, this is the next thing I thought I would get for my lifecycle of products.” So that doesn’t just go away because you have nice new tools. You still should be looking back at your data and seeing who’s interacting with you, what did they buy, do they really want this?

AC
The data tells the story.

LC
Yeah, exactly, so.

AC
We’ll shift gears and talk about AI and machine learning, certainly disrupting and finding their way into multiple use cases within digital marketing. How do you feel about its influence or possibilities in deliverability monitoring services?

LC
I think there’s a lot of potential there. But once again, I think if you’re just saying, “Oh, the system will know,” just shoving everything through and not really paying attention to the signals you’re getting back… Also, AI is great, but if you’re not training on a constant basis, it’s only as good as the last time you’ve trained your data. So it requires care and feeding. What worked three weeks ago because you had a new product isn’t going to work now if you’ve sent a million mails about the same thing, right? You can’t just rely on the same things being effective. So I think there’s a lot of potential, but I don’t think that means that we ignore the basics of how we send mail. So I mean, it’s great, but we have our own AI systems and they’re not foolproof either. So obviously, otherwise we’d all be out of a job because we wouldn’t have any more spam, right? And that’s where we are, so [LAUGH]. So I mean, they’re great effective tools and I think there is a lot to be done. But there’s been research that showed, I think it was called Blue Ocean. I forget the name of that. It was basically a machine that played chess. And then, it played Chess and beat people. But when it got to a certain level of player that it was playing, a human, that the machine couldn’t beat the human. But when you combined a machine and a human, they could beat anybody. So there’s a blend of, I have this data available to me, but a human sometimes needs to intervene and say, “What should we do next?” So don’t just say, “Oh, we’re running this program, it works, we’re done.”

AC
There’s been a shift recently, around domain reputation playing much more of an importance and impact to sender reputation than historical IP-based reputation. Is IP reputation still important? Should senders still be paying attention to reputation tied to their IPs? Or where is kind of the balance in domain versus IP reputation, in your opinion?

LC
So, it can vary for different receivers. It depends on what your system is. They both play a role. So if you have a really bad domain reputation, you can be sending unclean IPs, and that won’t last you forever. Also, you can have a great domain reputation, but if you send on IPs that have a problem or you don’t pay attention to good sending practices, you’re still going to have a problem. So they go hand in hand. I mean, in a perfect world, we would look at things as brands associated to its domain. It’s like saying your phone number is your personality, right? Your IP is just a method of sending something. So I think over time we’ll see more domain influence. But it’s still a process to get that in the shape that it needs to be for us to be able to rely on it. So they’re both important.

AC
Recently, there’s been a lot of evolution and changes in the inbox experience and enhancing with new features and functionalities the way that consumers interact and engage with brands and email within the inbox. Do you feel like this is influencing in a positive way, the way that the recipients engage with brands, with all of these new like AMP for Email and dynamic email and all these other kind of rich features that help recipients engage in new and exciting ways with brands?

LC
So I think it depends on the person and the degree to which there’s, for example, some interaction happening in the inbox. So I know some people are really bothered if an email moves to a different folder based on what the receiver thinks should happen with the mail. So people feel very territorial about their mailboxes, right? And they don’t want something to happen to their mail. They want their mail in a certain way. So I think email’s got a use case that a lot of other communication methods don’t have, right? You’re not going to get your power bill via text. You might get a reminder about it, but you’re probably going to get notification that you need to pay your bill, the amount, sensitive information, in email. So I think there’s definitely opportunity to have more information available to the user from their email box. So for example, your flight information comes in and then it automatically gets added to your calendar, or things like that, where you’re integrating other services around email where it makes sense. Or hey, I’m shopping and I’m going to go by this store that I like, and I got an email in my inbox. There’s some use case for, I’m walking by the store, my email now makes itself known to me. But that’s also a privacy issue. You have to turn on location services, you’re now broadcasting where you are and that you’re near a store. So I think there’s a lot of potential. I think people need to be very aware of how people feel about their privacy. And it isn’t a yes/no for every person. Today, I could be like, yeah, I’m so excited there’s this sale, I’m going to go to that store. Tomorrow, I’d be like, I didn’t really want you to know I was here. You know what I mean? Same person, different experience. That’s the same reason people mark the same sender as spam one day and not the next, even if they want the mail.

AC
It’s interesting, and I think that that’s a perfect dovetail on my next question of you’ve been in email for quite some time, what makes email so unique in its adaptability over the decades with all of these new messaging channels and emergences of new ways to communicate and market to people? We’ve all heard the critics, email is dead, chanted from the rooftops. But in your opinion, looking back, why is email so unique and how has it been able to survive this long?

LC
Right, well, I mean, my opinion is it’s persistent. So texts are nice, but they sort of disappear based on the current way we interact with our texts in our devices, which is usually mobile. Email, you can store it, you can copy it easily, you can interact with it, you can forward it. I mean, you can search on it if you have a powerful enough search engine. And I think some of the benefit of that is that–so text, a lot of it is driven by the device owner or the operating system of the mobile phone that you have. But because we have another layer in there of mailbox providers, they’re providing experiences through their software that make it more what users want. So I think you have another layer away from just your device and your operating system of people providing value to you. Facebook Messenger is great, instant messenger is great, Whatsapp texts are all great. I’m not going to do real actual business there. I don’t mind talking to a customer service department through one of those, but I’m not getting my order confirmation there. I’m not going to be able to find it again, not to remember what platform I had it on. You know what I mean? They’re not integrated right now. That might be a potential place for email to go with sucking some of that information in. But right now, if I want to figure out, what did I buy in 2015 when I had that company? Or, that company came and painted my house, we’re doing this now, oh, I could search for the company that did painting for me. Oh, here’s the quote that they gave me. I can call this company and have them come do a quote because we were happy with their work. And that’s actually a lot easier than if I had a paper receipt that I stuck in a file somewhere and that I’d have to empty my brain to figure out where I put that receipt. So there’s a lot of places for it to, really, a utility, for people to do things, so. That’s interesting.

AC
It’s a very interesting point of view and something I haven’t really thought about is the efficiency of almost archiving and storing. And it’s very easy to search rather than-

LC
I am the archive guru, I archive and scan almost everything I can. I mean, I even did my kids, some of their school records. And I could go into meetings, and they’re like well, we can’t access the record right now. I’m like [SOUND]

AC
And you find it right in your phone in your email.

LC
Right in there. I PDF’d things. I had access to things. I had naming conventions. I mean, I’m a little bit of a freak. [LAUGH] But the point is it’s available to you and it makes, things that can get very disorganized become very organized really quickly. So if you manage your email box well, it can become your reminder system. It’s another fail-safe besides your calendar of ways that you don’t miss things that you need to do.

It can be a distraction. And I would be the first to admit that oh, shopping, but it also can be a huge productivity tool. And so, I can’t say that about the other communications platforms that I use. With the exception of text. “Hey, you need to go do this,” directly to someone.

AC
We’re going to have some fun for our last question; it’s going to be a lightning round. I’m going to ask you four questions that require brief responses.

LC
How brief? Define brief.

AC
Lightning round. Fairly brief. First one, you ready?

LC
Yeah.

AC
Best career advice you’ve ever received.

LC
Look out for yourself first. I mean, the companies, they are interested in you and they care about you. But if things change, they’re not going to be the one who has to pay your mortgage or look after your family. So make sure you always take care of yourself.

AC
Most important lesson you’ve learned in the industry.

LC
Keep people happy. Not to the point where you’re doing things you shouldn’t be doing. But the reality is you could be doing a fabulous job, your team can. One big executive escalation to the CEO of your company, and things can get ugly really fast. And most people, even though the reason they might escalate doesn’t seem very important to you, there’s a reason behind why they’re upset about something. And you need to address that because it will come back to you. And that’s why people are like, “I don’t want to bother you.” I’d rather you come to me than my CEO has to find the chain all the way down to someone who can fix this problem. Bad for everybody.

AC
Biggest pet peeve of yours that you see from senders?

LC
Don’t forget the basics. Come on now. I mean, do your research, do your work. I’ll have people come to me and say, “Do you think this is a good sender?” I’m like, I don’t know. The WHOIS creation date on this domain is like, two days ago. What do you think?

Stuff like that where, let’s use all the resources available to us. Let’s check LinkedIn, let’s check Facebook, let’s see what kind of company this is. You’ll know, you do a Google search and you come up with an address that looks like it’s not a real place, it’s some shady looking building, and they’ve got a PO box in that building. All of these are indicators that you have a problem. And so, pay attention. You’re a detective, do your work, and then come to me. And I’m fine with people coming to me and saying, “This is what I’ve done, this is where I’m lost.” But don’t come to me with a slash 24, and I think they’re fine. I’m not here to fix your life.

I’m just here, you know what I mean? [LAUGH] I can’t anyway, so do your work. So before you come to me.

AC
Last question. This is an opportunity for you to stand on your soapbox. What accomplishment are you most proud of?

LC
Back to when you asked how I got into email. When I went to M3AAWG the first time and I kind of got a “whoa this is bigger than I realize,” kind of the scope, coming back and saying, you know what, we’re not doing a very good job. We need to do a better job of supporting senders. I’m like, if we can’t go to M3AAWG and trust people who are in our anti-abuse community that are vetted, who are we trusting? And I’m like, all we’re doing is putting everybody in the middle and trying to figure out who is bad and good. We should lift the good out of the middle. Let the bad, really obviously bad ones, fall through, and then deal with the middle. And so, that philosophy has really taken where I work and with our team. And it’s just nice to see that people see not only that it’s important, but that there’s value in it. Because it actually makes less work if we do a good job at taking care of the good vendors that are vetting their mail and sending responsibly.

AC
This has been an awesome interview, and I’m so happy that I was able to sit down with you and have this. So thank you very much. And thanks, everyone, for tuning in. We hope to see you on another episode of Email on Tap.

Author: Nicky Copland

Nicky is the senior marketing manager at 250ok. Before joining the team, she spent the majority of her time crafting and implementing communications strategies for the association industry. She was never a brain surgeon, but she played one on the internet.

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