Jaime Carney is another one of those RGP (Really Good People) who have been involved in email deliverability, spam fighting and anti-abuse going back to the turn of the millennium. Most recently as a Senior Deliverability Ops Engineer for Adobe, he's been helping set clients up for deliverability success, and sharing his technical expertise with coworkers and clients along that deliverability journey. With experience at Adobe, Constant Contact, and Lycos, he's really done it all -- from kicking the bad guys off the network, to consulting on inbox success and deliverability, to managing teams that do all of this and more. So allow me today to share with you my conversation with Jaime about his journey from then until now, where he'd like to see things go from here, and of course, we'll probably talk about raisins, too.
You can find his Linkedin profile here. And note that Jaime is actively looking for a new role, so please keep him in mind, if you are hiring!
Jaime, thank you for taking time out of your day to step into the Spam Resource Spotlight! I think a good starting point for these chats is to look back and talk about how you got your start in the email space. Your Linkedin CV says that you got your start as a Network Abuse Specialist for Lycos back in 2000. How did you end up with that job, and what did it entail? And it perhaps can't hurt to remind folks what Lycos was back then, as I imagine not everybody remembers!
During that period, Lycos was a prominent web search engine and portal offering a range of free and paid services. Customers could access email (@lycos.com), web hosting (Tripod and Angelfire), and dating services (Matchmaker). This was before Google existed, and Lycos was a major competitor to Yahoo.
I quickly learned that providing free services attracts a subset of users with malicious intentions. Recognizing this, Lycos established an Abuse desk to address these issues, and they were absolutely right to do so.
In the early days, job opportunities and career fairs were advertised through newspapers or radio. I heard an ad on Boston's local rock and roll radio station, WBCN, about a career fair for various positions at Lycos. Being passionate about the Internet (especially Napster), I decided to attend and see what it was all about.
Given my background and interests, Lycos thought I would be a great fit for their Network Abuse team. Our role was to police the network and remove content that violated our Terms of Service. Unfortunately, there was a lot of it—pornography, piracy, defamation, spam, hacking, and more. This exposed me to the darker side of the Internet.
It was a fascinating experience. After about a year, I became the team manager and regularly collaborated with the FBI (who even awarded me for my dedication and service), various law enforcement agencies, and government bodies, handling subpoenas, warrants, and FISA orders around the time of 9/11. It was an intense introduction to the tech industry, and while the things I witnessed were often unsettling, I developed a thick skin to handle it all.
That led onward toward various roles for email service provider (ESP) Constant Contact. I recall being amazed at the time that for CC, their MTA platform seemed to be Postfix running on Linux. Am I getting that right? Scaling up to manage the huge amount of email volume in that environment, working with folks to keep that huge server farm under control, what was that like? What was the secret to operational success? Tons of customization? A zillion shell scripts to automate and centralize configuration management?
You're right, Al. Constant Contact initially sent all their email via Postfix, and we didn't have any true automation to manage the frequent configuration changes we needed. It was challenging, but thanks to our exceptional mail administrators, we managed to make it work.
Eventually, we implemented Puppet as a change management tool, which allowed us to make changes in a much safer and more reliable manner. Instead of logging into each server to make individual changes, Puppet served as a central hub for changes, which then propagated to all the servers in the farm.
The key to our operational success was having both the deliverability team (Tara N and Jeremy A) and the mail administrators working together as one "MailOps" unit. When changes were necessary, the two teams collaborated directly to ensure everything went smoothly for our customers.
I wish every ESP was organized this way, but not all dreams come true.
You and I have both had something in common -- we've worked both in operational and consultative roles throughout the years. I think it's a good combination of knowledge to have -- being able to understand the hardware and software that creates and servers email messages, while also understanding the strategic best practices around what to send and whom to send it to -- you come to the table with a deeper understanding of the email ecosystem compared to just knowing one side or the other. How has that helped you throughout your career?
Having a 360-degree view is invaluable. Even a simple DNS misconfiguration, such as a mismatch between forward and reverse records, can have a disastrous effect on the customer's experience and reputation. A solid baseline understanding of what's happening under the hood can greatly enhance the consulting experience you're providing to customers who are driving the car.
I'm not extremely technical, but I do have a solid understanding of how email works and how it relates to best practices. Additionally, being able to explain technical concepts in a way that a non-technical audience can understand is a skill everyone should have in their toolkit.
Over the past few years I've been observing a lack of respect for (or a lack of investment in) email operational roles -- hiring managers and leadership who don't seem to understand the practice that is deliverability seem to look for unicorn hires that just don't exist. They want somebody to be an expert deliverability consultant (check), have strong operational/admin or devops expertise (check), but then also be a senior level software engineer (whut). Too much braining for one mind, is my take. I always have felt that while you want an engineer to have some knowledge of email technology, the operations (or even deliverability product management) role is to help inform them of the little technical nooks and crannies associated with deliverability. Like, I don't expect a software engineer to be keeping pace with the evolution of list-unsub. I expect us to bring that to them, and guide them through implementation and upgrade. Anyway, I'm pontificating here. What's your take on the deliverability operational role and where it fits into the email ecosystem?
I completely agree with you, Al. People often assume that having "Engineer" in the title means we're writing Python scripts or working on Machine Learning. In my opinion, we should drop "Engineer" from the title to avoid this confusion. "Delivery Operations" might be a better fit.
From my experience, a deliverability operations role involves understanding the ESP's MTA and being able to explain those details to less technical audiences. That includes both internal stakeholders as well customers. This skill is invaluable for a company that sends email at scale
In interviews with Skyler and others, most agreed with me that raisins ruin everything. What's a food that you think just absolutely ruins everything? (And how do you feel about raisins?)
What the heck did raisins ever do to you? Scratch that, I don't want to know.
I have nothing against raisins, but I see absolutely no need for black olives. THEY RUIN EVERYTHING!
Ha. If you could snap your fingers, get the attention of every email marketer in the world, and impart just a little bit of best practices or deliverability expertise into them, what would you tell them?
Stop trying to force email into our mailboxes and focus on the engaged recipients you do have. Those subscribers will take you to the promised land and improve deliverability. Sending more email is NOT the answer. Be strategic with how you're marketing to your customers, focus on your engaged subscribers and cut bait with folks who aren't interested.
Oh, and always listen to your deliverability consultants!!! They are here to help and guide you towards success! And they all smell nice and fresh too!
I know you're looking for a new role, as the dreaded RIF ended your tenure with Adobe. What would be the perfect future role for you? What do you think you most excel at?
I had a fantastic time at Adobe and carry only great experiences and memories from my time there. Moving forward, the ideal role for me would be with an innovative company where I can collaborate with amazing people and help customers achieve their goals. I'm a people person, and I believe I would be a valuable addition to any team that aims to crush goals and share some laughs along the way.
Jaime, thanks so much for taking the time to share your thoughts and expertise with me and with my readers. I appreciate you!
Jaime Carney is another one of those RGP (Really Good People) who have been involved in email deliverability, spam fighting and anti-abuse going back to the turn of the millennium. Most recently as a Senior Deliverability Ops Engineer for Adobe, he's been helping set clients up for deliverability success, and sharing his technical expertise with coworkers and clients along that deliverability journey. With experience at Adobe, Constant Contact, and Lycos, he's really done it all -- from kicking the bad guys off the network, to consulting on inbox success and deliverability, to managing teams that do all of this and more. So allow me today to share with you my conversation with Jaime about his journey from then until now, where he'd like to see things go from here, and of course, we'll probably talk about raisins, too.
You can find his Linkedin profile here. And note that Jaime is actively looking for a new role, so please keep him in mind, if you are hiring!
Jaime, thank you for taking time out of your day to step into the Spam Resource Spotlight! I think a good starting point for these chats is to look back and talk about how you got your start in the email space. Your Linkedin CV says that you got your start as a Network Abuse Specialist for Lycos back in 2000. How did you end up with that job, and what did it entail? And it perhaps can't hurt to remind folks what Lycos was back then, as I imagine not everybody remembers!
During that period, Lycos was a prominent web search engine and portal offering a range of free and paid services. Customers could access email (@lycos.com), web hosting (Tripod and Angelfire), and dating services (Matchmaker). This was before Google existed, and Lycos was a major competitor to Yahoo.
I quickly learned that providing free services attracts a subset of users with malicious intentions. Recognizing this, Lycos established an Abuse desk to address these issues, and they were absolutely right to do so.
In the early days, job opportunities and career fairs were advertised through newspapers or radio. I heard an ad on Boston's local rock and roll radio station, WBCN, about a career fair for various positions at Lycos. Being passionate about the Internet (especially Napster), I decided to attend and see what it was all about.
Given my background and interests, Lycos thought I would be a great fit for their Network Abuse team. Our role was to police the network and remove content that violated our Terms of Service. Unfortunately, there was a lot of it—pornography, piracy, defamation, spam, hacking, and more. This exposed me to the darker side of the Internet.
It was a fascinating experience. After about a year, I became the team manager and regularly collaborated with the FBI (who even awarded me for my dedication and service), various law enforcement agencies, and government bodies, handling subpoenas, warrants, and FISA orders around the time of 9/11. It was an intense introduction to the tech industry, and while the things I witnessed were often unsettling, I developed a thick skin to handle it all.
That led onward toward various roles for email service provider (ESP) Constant Contact. I recall being amazed at the time that for CC, their MTA platform seemed to be Postfix running on Linux. Am I getting that right? Scaling up to manage the huge amount of email volume in that environment, working with folks to keep that huge server farm under control, what was that like? What was the secret to operational success? Tons of customization? A zillion shell scripts to automate and centralize configuration management?
You're right, Al. Constant Contact initially sent all their email via Postfix, and we didn't have any true automation to manage the frequent configuration changes we needed. It was challenging, but thanks to our exceptional mail administrators, we managed to make it work.
Eventually, we implemented Puppet as a change management tool, which allowed us to make changes in a much safer and more reliable manner. Instead of logging into each server to make individual changes, Puppet served as a central hub for changes, which then propagated to all the servers in the farm.
The key to our operational success was having both the deliverability team (Tara N and Jeremy A) and the mail administrators working together as one "MailOps" unit. When changes were necessary, the two teams collaborated directly to ensure everything went smoothly for our customers.
I wish every ESP was organized this way, but not all dreams come true.
You and I have both had something in common -- we've worked both in operational and consultative roles throughout the years. I think it's a good combination of knowledge to have -- being able to understand the hardware and software that creates and servers email messages, while also understanding the strategic best practices around what to send and whom to send it to -- you come to the table with a deeper understanding of the email ecosystem compared to just knowing one side or the other. How has that helped you throughout your career?
Having a 360-degree view is invaluable. Even a simple DNS misconfiguration, such as a mismatch between forward and reverse records, can have a disastrous effect on the customer's experience and reputation. A solid baseline understanding of what's happening under the hood can greatly enhance the consulting experience you're providing to customers who are driving the car.
I'm not extremely technical, but I do have a solid understanding of how email works and how it relates to best practices. Additionally, being able to explain technical concepts in a way that a non-technical audience can understand is a skill everyone should have in their toolkit.
Over the past few years I've been observing a lack of respect for (or a lack of investment in) email operational roles -- hiring managers and leadership who don't seem to understand the practice that is deliverability seem to look for unicorn hires that just don't exist. They want somebody to be an expert deliverability consultant (check), have strong operational/admin or devops expertise (check), but then also be a senior level software engineer (whut). Too much braining for one mind, is my take. I always have felt that while you want an engineer to have some knowledge of email technology, the operations (or even deliverability product management) role is to help inform them of the little technical nooks and crannies associated with deliverability. Like, I don't expect a software engineer to be keeping pace with the evolution of list-unsub. I expect us to bring that to them, and guide them through implementation and upgrade. Anyway, I'm pontificating here. What's your take on the deliverability operational role and where it fits into the email ecosystem?
I completely agree with you, Al. People often assume that having "Engineer" in the title means we're writing Python scripts or working on Machine Learning. In my opinion, we should drop "Engineer" from the title to avoid this confusion. "Delivery Operations" might be a better fit.
From my experience, a deliverability operations role involves understanding the ESP's MTA and being able to explain those details to less technical audiences. That includes both internal stakeholders as well customers. This skill is invaluable for a company that sends email at scale
In interviews with Skyler and others, most agreed with me that raisins ruin everything. What's a food that you think just absolutely ruins everything? (And how do you feel about raisins?)
What the heck did raisins ever do to you? Scratch that, I don't want to know.
I have nothing against raisins, but I see absolutely no need for black olives. THEY RUIN EVERYTHING!
Ha. If you could snap your fingers, get the attention of every email marketer in the world, and impart just a little bit of best practices or deliverability expertise into them, what would you tell them?
Stop trying to force email into our mailboxes and focus on the engaged recipients you do have. Those subscribers will take you to the promised land and improve deliverability. Sending more email is NOT the answer. Be strategic with how you're marketing to your customers, focus on your engaged subscribers and cut bait with folks who aren't interested.
Oh, and always listen to your deliverability consultants!!! They are here to help and guide you towards success! And they all smell nice and fresh too!
I know you're looking for a new role, as the dreaded RIF ended your tenure with Adobe. What would be the perfect future role for you? What do you think you most excel at?
I had a fantastic time at Adobe and carry only great experiences and memories from my time there. Moving forward, the ideal role for me would be with an innovative company where I can collaborate with amazing people and help customers achieve their goals. I'm a people person, and I believe I would be a valuable addition to any team that aims to crush goals and share some laughs along the way.
Jaime, thanks so much for taking the time to share your thoughts and expertise with me and with my readers. I appreciate you!
Folks, be sure to HIRE JAIME! He's actively looking for employment. Find him on Linkedin here.
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