Skyler, thank you for taking the time to talk to me today! You've come a long way from when I first knew you as a member of the policy compliance team for the Pardot email platform. Was that your start in email? How did you land in this world?
Thank you for interviewing me! I got my start in compliance while I was working at the University of Georgia, somewhat by accident. I worked in student tech support, so it was mostly dealing with network issues on the campus wifi.
I wound up volunteering for a project that boiled down to, "go take this device (that looked like a large, BRIGHT YELLOW golf club, it could not have been goofier), walk around all the dorms, and figure out what dorm rooms have private wifi networks set up, so we can tell them to cut it out and use the main campus wifi". I had SO MUCH FUN with that project. I liked the idea of finding people who were doing the wrong thing (to be fair, usually accidentally!), educating them on why they needed to cut it out, and making the wifi experience better for everyone else.
As fun as it is, waving a wifi-detecting golf club around dorms doesn't quite make a living, so I eventually wound up joining Pardot's support team. During a team meeting, our manager asked if someone wanted to do email deliverability, because we needed more than one person on that team. I had no clue what email deliverability was, but I volunteered anyway because it sounded interesting. I wound up doing dual roles in deliverability and compliance until we needed to scale, then I focused entirely on building out our compliance team. And now, (mumble) years later, here I am!
We've both moved back and forth between deliverability/compliance and product management. What do you think your background in compliance and deliverability does to help inform what you do as a product manager?
I've never been asked this, but wow do I love this question. There's so much I could wax poetic about, but I think the absolute biggest contributor to my success as a product manager has been the concept of not being my job. It's served as the foundation upon which I've built effectively everything else, and I'm so excited to nerd out about it here. Fair warning, I majored in psychology with a particular emphasis on social psychology, and it's one of my favorite ADHD hyperfocus topics. :)
So! The manner in which we identify ourselves is one of the most fascinating and complex topics in psychology. In modern society, we've wrapped a LOT of our identities up in what we do for work. If I ask you, "What do you do", you're more likely to jump to telling me what you do for work versus what your hobbies are. That's totally understandable: you spend SO MUCH time at work, thinking about work, maybe explicitly not thinking about work but in doing that you're paradoxically thinking about it, it's hard to not have it merge with who you define yourself to be.
Now, let me wrap that concept into where I'm going: compliance is not for the faint of heart. It involves telling a lot of angry people no, then telling them no again, then telling some other person no, then justifying why you're saying no, then getting shouted at after you said no, then then, then, ad nauseam. It can be exhausting, isolating work. If you cannot figure out how to untangle the role from the self, it's a recipe for significant mental health problems (you'll never guess how I know that). For the longest time, I didn't untangle the role from my personal identity. At one point, I was talking to a career coach about how "everyone hated me", because I am the one who tells people no. She immediately stopped me and said, "They hate the ROLE, not YOU". I wound up writing that down and sticking it behind my laptop as a reminder that my job is not who I am. I am not Skyler, <job title>. I am Skyler, <long list of other things that make me, me>.
Game. Changer.
That concept, that my job is not who I am, and learning that through the fires of compliance, set me up for a great deal of success in product management. I do not fear "looking stupid" through making a mistake or asking 500 questions of my engineering team, because my job is not who I am. Someone being mad because their request got deprioritized has nothing to do with me as a human. They do not hate Skyler for saying no, they hate that the thing they wanted isn't being done right now. I don't come into a room NEEDING to be the one who is right or the winner in a negotiation, because the focus isn't on protecting my personal identity, the focus is on actually solving an issue.
I think that mindset has been the biggest contributor to our success as an organization, as it's built a massively trusting relationship between me and my engineering team. I don't feel a need to protect my ego on any decisions I make, because my job and my ego have nothing to do with one another. If there's a better call we can make as a team, we make it.
Oh, and I learned some really intensive negotiation tactics and communication skills, which always helps. :)
I love this! It's a great way to get away from the angst of "will they hate me for asking questions" so you can be open and honest about the hunt for knowledge that you need to get the job done!
You've told me a bit about the cool stuff you're working on now over at SocketLabs. Here's your chance to tell the world! What cool things have you been working on?
I feel like Oprah saying "YOU GET A CAR" when I talk about my favorite pieces of the platform. You've got scoring! You've got the ability to filter your data in extremely flexible ways! You've got context as to what's actually going on with your email program so you can actually act on your data instead of trying to sort through it blindly! You've got the ability to look at all of your SendGrid subusers from one place, so you can actually get a sense of the full picture of your infrastructure! You want MailGun data in there? You'll GET MailGun data (soon!).
I think one of the things I'm most proud of with it is how easy it is to set up. If you can copy paste, you can set up Spotlight. There's no need to involve an engineering team at all, and I'm incredibly proud of the work my engineering team put in to make that a reality. It was kind of wild to have built it to be that way, I KNEW it was built that way, and then it was demoed back to me and I briefly panicked to my lead engineer- "did we forget something? How is it this simple?". It's so cool to see what happens when you let engineering do what they do best: solve problems and build interesting stuff.
I don't know if you relate to this, but I feel like being in Product is perpetually being the person who is planning a surprise party. I know SO MUCH cool stuff is coming on top of the cool thing we just built, but I can't tell you because then I'd ruin the party. Is that a common feeling?
Not as much as I wish it was! Sometimes it has been more like ... plan 14 surprise parties, then cancel 13 of them. Then scale the last one back. Now maybe we split a muffin. Sigh. But yeah, when you do actually have the resources to make things happen and you know what is coming, it really is a great feeling!
Alison Gootee and I agreed recently that raisins ruin everything. Do you agree, or are you wrong? If not raisins, what is one foodstuff or ingredient that you believe should simply NOT exist, something you can't believe people knowingly enjoy?
I couldn't possibly agree more. I share a visceral hate of an oatmeal raisin cookie lacking in chocolate chips. I'm making myself angry just thinking about it.
And here's the part of the interview in which I get canceled for my food opinions: I cannot stand tomato ketchup. I love tomatoes, but the second you add sugar to a tomato, it's dead to me. Fascinatingly, ketchup wasn't always made with tomatoes! The original ketchup was made with fish and soybeans. Mushroom ketchup was also a thing for a bit, before Heinz came in with their sugary tomato abomination and dominated the market.
Ha. Ironically, my wife loves ketchup but hates tomatoes. Speaking of Alison, she's quite the master-of-memes. And we've got another friend who is a self proclaimed "margarita enthusiast." What do you do for fun? Dogs? Purple hair? Home repair?
With ADHD comes a whole mess of hobbies that I generally bounce between. Right now, my husband and I are completely gutting and renovating our house, room-by-room. We just passed a waterproofing test on the shower we built (24 hours of water in the shower pan, if the water level doesn't drop, you're good to go!), so now we're ready for tile! We're DIY-ing as much as possible, which has been one heck of a learning experience. In the last year, I've learned how to swap plugs and switches, do drywall, install flooring, remove floor squeaks, deal in basement flood management, it's been….a lot.
Non-drywall-dust-covered hobbies include crocheting, sewing, leatherworking, cross stitching, watching garbage reality TV, and papercrafting. I used to teach laser cutter safety at a makerspace and I loved it, so I've got plans to get a giant laser cutter after the home reno is done. Don't ask me how many ongoing crafty projects I have. :)
So much (too much) of deliverability is based around "tricks" or "hacks" to try and get into an inbox or to stay out of the spam folder. If you could get the attention of every email marketer on earth to try to convince them of one myth they absolutely need to stop perpetuating, what would it be and why?
If 👏the 👏spammers 👏 know 👏 the 👏 hack 👏 it's 👏 not 👏 useful 👏. SPAM TRIGGER WORDS ARE NOT A THING. If there was a magic list of words that guaranteed your email would land in the spam folder, the spammers would simply ✨ also not use those words ✨, rendering the magic list entirely useless. There's a reason the inboxing filters and rules and such are such highly guarded secrets, and it's entirely to prevent spammers from figuring it out. Focus on sending wanted mail to people who have asked for it, that's what is actually key to inboxing.
So go on, use that exclamation point. Use two, even. FREE THE ALLCAPS!
Skyler, thanks so much for your time and words and knowledge and opinions! I appreciate you!
Skyler, thank you for taking the time to talk to me today! You've come a long way from when I first knew you as a member of the policy compliance team for the Pardot email platform. Was that your start in email? How did you land in this world?
Thank you for interviewing me! I got my start in compliance while I was working at the University of Georgia, somewhat by accident. I worked in student tech support, so it was mostly dealing with network issues on the campus wifi.
I wound up volunteering for a project that boiled down to, "go take this device (that looked like a large, BRIGHT YELLOW golf club, it could not have been goofier), walk around all the dorms, and figure out what dorm rooms have private wifi networks set up, so we can tell them to cut it out and use the main campus wifi". I had SO MUCH FUN with that project. I liked the idea of finding people who were doing the wrong thing (to be fair, usually accidentally!), educating them on why they needed to cut it out, and making the wifi experience better for everyone else.
As fun as it is, waving a wifi-detecting golf club around dorms doesn't quite make a living, so I eventually wound up joining Pardot's support team. During a team meeting, our manager asked if someone wanted to do email deliverability, because we needed more than one person on that team. I had no clue what email deliverability was, but I volunteered anyway because it sounded interesting. I wound up doing dual roles in deliverability and compliance until we needed to scale, then I focused entirely on building out our compliance team. And now, (mumble) years later, here I am!
We've both moved back and forth between deliverability/compliance and product management. What do you think your background in compliance and deliverability does to help inform what you do as a product manager?
I've never been asked this, but wow do I love this question. There's so much I could wax poetic about, but I think the absolute biggest contributor to my success as a product manager has been the concept of not being my job. It's served as the foundation upon which I've built effectively everything else, and I'm so excited to nerd out about it here. Fair warning, I majored in psychology with a particular emphasis on social psychology, and it's one of my favorite ADHD hyperfocus topics. :)
So! The manner in which we identify ourselves is one of the most fascinating and complex topics in psychology. In modern society, we've wrapped a LOT of our identities up in what we do for work. If I ask you, "What do you do", you're more likely to jump to telling me what you do for work versus what your hobbies are. That's totally understandable: you spend SO MUCH time at work, thinking about work, maybe explicitly not thinking about work but in doing that you're paradoxically thinking about it, it's hard to not have it merge with who you define yourself to be.
Now, let me wrap that concept into where I'm going: compliance is not for the faint of heart. It involves telling a lot of angry people no, then telling them no again, then telling some other person no, then justifying why you're saying no, then getting shouted at after you said no, then then, then, ad nauseam. It can be exhausting, isolating work. If you cannot figure out how to untangle the role from the self, it's a recipe for significant mental health problems (you'll never guess how I know that). For the longest time, I didn't untangle the role from my personal identity. At one point, I was talking to a career coach about how "everyone hated me", because I am the one who tells people no. She immediately stopped me and said, "They hate the ROLE, not YOU". I wound up writing that down and sticking it behind my laptop as a reminder that my job is not who I am. I am not Skyler, <job title>. I am Skyler, <long list of other things that make me, me>.
Game. Changer.
That concept, that my job is not who I am, and learning that through the fires of compliance, set me up for a great deal of success in product management. I do not fear "looking stupid" through making a mistake or asking 500 questions of my engineering team, because my job is not who I am. Someone being mad because their request got deprioritized has nothing to do with me as a human. They do not hate Skyler for saying no, they hate that the thing they wanted isn't being done right now. I don't come into a room NEEDING to be the one who is right or the winner in a negotiation, because the focus isn't on protecting my personal identity, the focus is on actually solving an issue.
I think that mindset has been the biggest contributor to our success as an organization, as it's built a massively trusting relationship between me and my engineering team. I don't feel a need to protect my ego on any decisions I make, because my job and my ego have nothing to do with one another. If there's a better call we can make as a team, we make it.
Oh, and I learned some really intensive negotiation tactics and communication skills, which always helps. :)
I love this! It's a great way to get away from the angst of "will they hate me for asking questions" so you can be open and honest about the hunt for knowledge that you need to get the job done!
You've told me a bit about the cool stuff you're working on now over at SocketLabs. Here's your chance to tell the world! What cool things have you been working on?
So, most recently, we released Spotlight (https://www.socketlabs.com/hub/spotlight-diagnostics/) , which connects to your SendGrid account and provides actionable insights into your email program.
I feel like Oprah saying "YOU GET A CAR" when I talk about my favorite pieces of the platform. You've got scoring! You've got the ability to filter your data in extremely flexible ways! You've got context as to what's actually going on with your email program so you can actually act on your data instead of trying to sort through it blindly! You've got the ability to look at all of your SendGrid subusers from one place, so you can actually get a sense of the full picture of your infrastructure! You want MailGun data in there? You'll GET MailGun data (soon!).
I think one of the things I'm most proud of with it is how easy it is to set up. If you can copy paste, you can set up Spotlight. There's no need to involve an engineering team at all, and I'm incredibly proud of the work my engineering team put in to make that a reality. It was kind of wild to have built it to be that way, I KNEW it was built that way, and then it was demoed back to me and I briefly panicked to my lead engineer- "did we forget something? How is it this simple?". It's so cool to see what happens when you let engineering do what they do best: solve problems and build interesting stuff.
I don't know if you relate to this, but I feel like being in Product is perpetually being the person who is planning a surprise party. I know SO MUCH cool stuff is coming on top of the cool thing we just built, but I can't tell you because then I'd ruin the party. Is that a common feeling?
Not as much as I wish it was! Sometimes it has been more like ... plan 14 surprise parties, then cancel 13 of them. Then scale the last one back. Now maybe we split a muffin. Sigh. But yeah, when you do actually have the resources to make things happen and you know what is coming, it really is a great feeling!
Alison Gootee and I agreed recently that raisins ruin everything. Do you agree, or are you wrong? If not raisins, what is one foodstuff or ingredient that you believe should simply NOT exist, something you can't believe people knowingly enjoy?
I couldn't possibly agree more. I share a visceral hate of an oatmeal raisin cookie lacking in chocolate chips. I'm making myself angry just thinking about it.
And here's the part of the interview in which I get canceled for my food opinions: I cannot stand tomato ketchup. I love tomatoes, but the second you add sugar to a tomato, it's dead to me. Fascinatingly, ketchup wasn't always made with tomatoes! The original ketchup was made with fish and soybeans. Mushroom ketchup was also a thing for a bit, before Heinz came in with their sugary tomato abomination and dominated the market.
Ha. Ironically, my wife loves ketchup but hates tomatoes. Speaking of Alison, she's quite the master-of-memes. And we've got another friend who is a self proclaimed "margarita enthusiast." What do you do for fun? Dogs? Purple hair? Home repair?
With ADHD comes a whole mess of hobbies that I generally bounce between. Right now, my husband and I are completely gutting and renovating our house, room-by-room. We just passed a waterproofing test on the shower we built (24 hours of water in the shower pan, if the water level doesn't drop, you're good to go!), so now we're ready for tile! We're DIY-ing as much as possible, which has been one heck of a learning experience. In the last year, I've learned how to swap plugs and switches, do drywall, install flooring, remove floor squeaks, deal in basement flood management, it's been….a lot.
Non-drywall-dust-covered hobbies include crocheting, sewing, leatherworking, cross stitching, watching garbage reality TV, and papercrafting. I used to teach laser cutter safety at a makerspace and I loved it, so I've got plans to get a giant laser cutter after the home reno is done. Don't ask me how many ongoing crafty projects I have. :)
So much (too much) of deliverability is based around "tricks" or "hacks" to try and get into an inbox or to stay out of the spam folder. If you could get the attention of every email marketer on earth to try to convince them of one myth they absolutely need to stop perpetuating, what would it be and why?
If 👏the 👏spammers 👏 know 👏 the 👏 hack 👏 it's 👏 not 👏 useful 👏. SPAM TRIGGER WORDS ARE NOT A THING. If there was a magic list of words that guaranteed your email would land in the spam folder, the spammers would simply ✨ also not use those words ✨, rendering the magic list entirely useless. There's a reason the inboxing filters and rules and such are such highly guarded secrets, and it's entirely to prevent spammers from figuring it out. Focus on sending wanted mail to people who have asked for it, that's what is actually key to inboxing.
So go on, use that exclamation point. Use two, even. FREE THE ALLCAPS!
Skyler, thanks so much for your time and words and knowledge and opinions! I appreciate you!
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