Brad, thanks for taking the time to participate in the interview series! It's great to be able to talk to you. I always kick it off something like this -- you've come a long way in your career. I think I first met you when you were working for Bronto, but that isn't even where your involvement in email began. Tell me more about how you got started in this whole email thing?
It's great to chat with you as well, Al, and thanks so much for the invite!
While I've got a great story about selling vacuum cleaners for some other time, my foray into email actually began with a Craigslist ad. I was working on contract for IBM in Global Customer Support, and I saw a posting for a Director of Support for an email startup located nearby. I answered the ad, got the job, and became the first (official) Director of Support for what's now known as iContact.
I would imagine that as an early employee of iContact, you ended up wearing a lot of hats all at once. How did you end up transitioning from more of a generalist support/support management role to a more specialized deliverability focused-career path?
So. Many. Hats. For a 5-person ESP startup, "customer support” included almost everything that wasn't direct sales or software development. I quickly discovered there were many factors that would prevent mail from being delivered, and that there were a lot of ‘hows' and ‘whys' I didn't know. I really got a trial by fire in the deliverability and compliance space -- including things like a week of twice-daily calls with AOL to try to resolve some large-scale blocks in the early days.
As I learned more about that side of the business, I discovered there weren't a lot of thorough resources dedicated to optimizing deliverability at the time. Instead, I'd spend hours poring over headers or message code looking for issues. Having studied forensic science, I really relished the process of investigating and addressing complex problems that had no obvious solution, and I suppose that's why I gravitated towards deliverability.
Which do you think is better for senders, dedicated IP or shared IP? Kind of a loaded question, I know. Having worked for different platforms with different types of clients, different volumes, and different IP strategies, I know that the very short answer is "it depends.” But, tell me more. Have you found an excess of pain via one path versus the other? Or have you experienced any success that you might want to share specific to IP strategy? Or does this all go out the window, anyway, now that Yahoo and Google effectively require DKIM to send email at any significant volume?
You can firmly count me in Team Dedicated, all other things being equal. Until every receiver system is able to adequately assign domain reputation in a shared pool environment, there will always be a non-trivial amount of reputation resting on the IP(s). I appreciate the (relative) certainty present in a dedicated environment: it's much easier to demonstrate to a sender that their bad practices are the problem if they're the only ones sending from that IP!
All DMARC, all the time! It feels like the last 100 discussions I've had with clients, potential clients, customers and confused marketers were all specific to DMARC. DMARC is just so foreign to so many people, and not an easy concept to absorb. What's your recent experience been like? Lots of scrambling and confusion? Training efforts still ongoing? Or do you think you've hit a critical mass of understanding across those you're talking to?
I'll start by saying it took me a LONG time to fully grasp DMARC, and I'm not embarrassed to say that. It's a complex concept that relies on other protocols while simultaneously making those protocols more complex (I'm looking at you, domain alignment). But, once I began to really understand how it all works, something just "clicked” in my head -- and I'm seeing a lot of the same reactions from folks I've been working with.
I continue to get lots of questions, but the average sender seems to have at least a cursory understanding of DMARC going into our conversations. I think a lot of that stems from an increase in the availability of information and education on the topic. My own introduction to DMARC was via reading RFCs and explanations from highly technical folks who wrote the specs, while senders today have access to many more accessible and easily-digestible sources (present company included).
OK, that's enough email talk. I see you've got a Jeep logo on your wall behind your desk, and a photo of a Jeep off road on your Facebook profile, so I'm guessing that's your Jeep and you like to go off-roading? How often do you take it off the beaten path, and how crazy are you with crawling it up and down rocks like all the crazy Youtubers do?
I previously had an older "project” Jeep that I was a little more adventurous with, but my new one stays mostly on-road. I love to take it out on the beach and the occasional nature trail a few times a year, but you won't find me fully articulated on a giant boulder anytime soon. I do have some friends who've been into that, though, and it's pretty fun to watch.
I end up working some sort of food or drink into every interview. Steak fingers, margaritas, raisins and more. Raisins being in the category "should not exist,” because raisins ruin everything. What is one foodstuff or ingredient that you believe simply should not exist, something you can't believe that people knowingly enjoy?
Corn. Raw or cooked, I have an actual physical aversion to eating corn. What's really strange is that I love a lot of foods made from corn: corn tortillas, polenta, and cornbread to name a few. Maybe it's texture, or smell, or something else; I'm honestly not sure. I think corn should exist only as an ingredient in those other awesome foods, but never on its own.
You've mentioned karaoke as a hobby before. There's really two different ways karaoke can go -- you get a small group of friends together and rent a room at a karaoke bar, or you go to a "regular” bar that has a karaoke night and you get to sing your guts out in front of a whole bunch of strangers, who may or may not be forgiving of your (lack of) signing skills. Are you team "belt it out in front of the whole bar” or do you find it better when it's just you and that group of friends off in a side room?
Karaoke is one of those things I can enjoy in most any iteration, but what makes it great is the interaction between the singers and the audience. I love having the best of both worlds -- taking a group of friends to a bar full of strangers can make for a really fun outing. Venue aside, the key is having a group of people -- friends or strangers -- that like to sing along. The quality of the singing isn't nearly as important as the camaraderie (or maybe commiseration?)
Finally, deliverability is one of those practices where an ounce of prevention is often as valuable as (or more so than) a pound of cure. If you could convince every email marketer to take one step, make one change in practices, make one improvement somewhere in their data, practices or configuration, to help inoculate them against future deliverability problems, what would that step be?
I always cheat on these questions a bit because I just can't choose one single practice, so I'll choose something that's a bit of a copout: Listen to the experts.
Email marketers know their business, their audience, their brand better than anyone -- but they usually don't know deliverability. Our corner of the industry exists for a reason; though I do want to clarify that not every piece of expert advice is the best. There has to be some discernment involved, and that can be tricky at times. But if the consensus among people in the know is to follow a certain practice, you're generally going to see better results if you do that thing.
To paraphrase an infamous public official, I'd love to see marketers acknowledge the "unknown unknowns,” the things they don't know they don't know. When we're able to admit we don't know everything, it's so much easier to learn from others with different areas of expertise.
Brad, thanks so much for your time and words and knowledge and opinions! It was great to connect with you today.
Brad, thanks for taking the time to participate in the interview series! It's great to be able to talk to you. I always kick it off something like this -- you've come a long way in your career. I think I first met you when you were working for Bronto, but that isn't even where your involvement in email began. Tell me more about how you got started in this whole email thing?
It's great to chat with you as well, Al, and thanks so much for the invite!
While I've got a great story about selling vacuum cleaners for some other time, my foray into email actually began with a Craigslist ad. I was working on contract for IBM in Global Customer Support, and I saw a posting for a Director of Support for an email startup located nearby. I answered the ad, got the job, and became the first (official) Director of Support for what's now known as iContact.
I would imagine that as an early employee of iContact, you ended up wearing a lot of hats all at once. How did you end up transitioning from more of a generalist support/support management role to a more specialized deliverability focused-career path?
So. Many. Hats. For a 5-person ESP startup, "customer support” included almost everything that wasn't direct sales or software development. I quickly discovered there were many factors that would prevent mail from being delivered, and that there were a lot of ‘hows' and ‘whys' I didn't know. I really got a trial by fire in the deliverability and compliance space -- including things like a week of twice-daily calls with AOL to try to resolve some large-scale blocks in the early days.
As I learned more about that side of the business, I discovered there weren't a lot of thorough resources dedicated to optimizing deliverability at the time. Instead, I'd spend hours poring over headers or message code looking for issues. Having studied forensic science, I really relished the process of investigating and addressing complex problems that had no obvious solution, and I suppose that's why I gravitated towards deliverability.
Which do you think is better for senders, dedicated IP or shared IP? Kind of a loaded question, I know. Having worked for different platforms with different types of clients, different volumes, and different IP strategies, I know that the very short answer is "it depends.” But, tell me more. Have you found an excess of pain via one path versus the other? Or have you experienced any success that you might want to share specific to IP strategy? Or does this all go out the window, anyway, now that Yahoo and Google effectively require DKIM to send email at any significant volume?
You can firmly count me in Team Dedicated, all other things being equal. Until every receiver system is able to adequately assign domain reputation in a shared pool environment, there will always be a non-trivial amount of reputation resting on the IP(s). I appreciate the (relative) certainty present in a dedicated environment: it's much easier to demonstrate to a sender that their bad practices are the problem if they're the only ones sending from that IP!
All DMARC, all the time! It feels like the last 100 discussions I've had with clients, potential clients, customers and confused marketers were all specific to DMARC. DMARC is just so foreign to so many people, and not an easy concept to absorb. What's your recent experience been like? Lots of scrambling and confusion? Training efforts still ongoing? Or do you think you've hit a critical mass of understanding across those you're talking to?
I'll start by saying it took me a LONG time to fully grasp DMARC, and I'm not embarrassed to say that. It's a complex concept that relies on other protocols while simultaneously making those protocols more complex (I'm looking at you, domain alignment). But, once I began to really understand how it all works, something just "clicked” in my head -- and I'm seeing a lot of the same reactions from folks I've been working with.
I continue to get lots of questions, but the average sender seems to have at least a cursory understanding of DMARC going into our conversations. I think a lot of that stems from an increase in the availability of information and education on the topic. My own introduction to DMARC was via reading RFCs and explanations from highly technical folks who wrote the specs, while senders today have access to many more accessible and easily-digestible sources (present company included).
OK, that's enough email talk. I see you've got a Jeep logo on your wall behind your desk, and a photo of a Jeep off road on your Facebook profile, so I'm guessing that's your Jeep and you like to go off-roading? How often do you take it off the beaten path, and how crazy are you with crawling it up and down rocks like all the crazy Youtubers do?
I previously had an older "project” Jeep that I was a little more adventurous with, but my new one stays mostly on-road. I love to take it out on the beach and the occasional nature trail a few times a year, but you won't find me fully articulated on a giant boulder anytime soon. I do have some friends who've been into that, though, and it's pretty fun to watch.
I end up working some sort of food or drink into every interview. Steak fingers, margaritas, raisins and more. Raisins being in the category "should not exist,” because raisins ruin everything. What is one foodstuff or ingredient that you believe simply should not exist, something you can't believe that people knowingly enjoy?
Corn. Raw or cooked, I have an actual physical aversion to eating corn. What's really strange is that I love a lot of foods made from corn: corn tortillas, polenta, and cornbread to name a few. Maybe it's texture, or smell, or something else; I'm honestly not sure. I think corn should exist only as an ingredient in those other awesome foods, but never on its own.
You've mentioned karaoke as a hobby before. There's really two different ways karaoke can go -- you get a small group of friends together and rent a room at a karaoke bar, or you go to a "regular” bar that has a karaoke night and you get to sing your guts out in front of a whole bunch of strangers, who may or may not be forgiving of your (lack of) signing skills. Are you team "belt it out in front of the whole bar” or do you find it better when it's just you and that group of friends off in a side room?
Karaoke is one of those things I can enjoy in most any iteration, but what makes it great is the interaction between the singers and the audience. I love having the best of both worlds -- taking a group of friends to a bar full of strangers can make for a really fun outing. Venue aside, the key is having a group of people -- friends or strangers -- that like to sing along. The quality of the singing isn't nearly as important as the camaraderie (or maybe commiseration?)
Finally, deliverability is one of those practices where an ounce of prevention is often as valuable as (or more so than) a pound of cure. If you could convince every email marketer to take one step, make one change in practices, make one improvement somewhere in their data, practices or configuration, to help inoculate them against future deliverability problems, what would that step be?
I always cheat on these questions a bit because I just can't choose one single practice, so I'll choose something that's a bit of a copout: Listen to the experts.
Email marketers know their business, their audience, their brand better than anyone -- but they usually don't know deliverability. Our corner of the industry exists for a reason; though I do want to clarify that not every piece of expert advice is the best. There has to be some discernment involved, and that can be tricky at times. But if the consensus among people in the know is to follow a certain practice, you're generally going to see better results if you do that thing.
To paraphrase an infamous public official, I'd love to see marketers acknowledge the "unknown unknowns,” the things they don't know they don't know. When we're able to admit we don't know everything, it's so much easier to learn from others with different areas of expertise.
Brad, thanks so much for your time and words and knowledge and opinions! It was great to connect with you today.
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