Is this the future of personalization?

Growth by Seeking Wisdom podcast

On this episode of #Growth, host Matt Bilotti sits down with Greg Skloot, President & COO of Crystal, to discuss a whole new level of personalization. We all know we’re targeted online based on past browsing history and offers are often personalized with our name and sometimes location. But are we on the cusp of a whole new level of personalization? One that takes into account personality type and how we might want to be interacted with? Greg and Matt discuss the future of personalization on this episode. Be sure to tune in.

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Full Transcript

Matt Bilotti: Hello and welcome to another episode of #Growth. I’m your host, Matt Bilotti, and today I am super excited to dive deep into the topic of personalization. And today, to talk through that, I have a guest that’s an expert in this space and also a good friend of mine, Greg Skloot who is the president of a company called Crystal. Greg, thanks for joining us today.

Greg Skloot: Matt, absolutely. Thank you so much for having me. And as I promised I will try to avoid any embarrassing stories about you from college.

Matt: That sounds perfect. Outside of us hanging out in college, you want to give a quick rundown of your background for the folks listening?

Greg: I would be happy to. So as Matt mentioned, I’m the president of a tech company called Crystal. We’re an app that can tell you anyone’s personality based on analyzing text online. So we think a lot about personality. And prior to that, I’ve done a bunch of cool entrepreneurial growth type of ventures. Most recently I was the VP of growth at a tech company called Netpulse out of San Francisco that was just acquired last year. So excited to be here and talk about growth and personalization.

Matt: Absolutely. And let’s go ahead and dive right in. So one of the things that we were talking about before we jumped on here was that most of the personalization that happens today is very much based on role. And I’m sure when a lot of listeners hear topic of personalization, you know they’re thinking, “Of course I personalized,” right? Like, “I have to personalize my emails, they have people’s names, they have their job titles, it has the types of info that they want.” But it really seems like we’re on the cusp of this new level of personalization. Do you want to tell us about what you see that being and what we’re ready beginning to move towards?

Greg: Absolutely. So a good way I like to think about it is historically we’ve focused on the what. So when I think about the what in personalization, it’s I have a database of contacts that I’m going to be running growth experiment on, maybe I’m sending them some emails. It’s at this point, industry standard, I’d call it table stakes that of course I’m customizing based on variables I have in their contact record. But in addition, I’m probably writing a couple of different versions of that email based on persona or job title. I’m going to test that separate types of content to those different people and they’re going to be getting a what. So what I’m talking about is going to be highly personalized and relevant to their role within the organization.

That’s just expected at this point. So that’s the what. And I think overall, marketers are doing a pretty good job with that. Where things are starting to get interesting is that there’s now some new technology that’s made it possible to more deeply personalize the how. And when I say the how, I’m talking about how we actually talk to a contact, how we deliver that customized content. So this is where when I think of how, I’m thinking of how can I talk to them in a way that resonates with their personality? I’m saying stuff that’s relevant to them, but can I say it in a way that will appeal to them as a unique person? And that’s the personality component of personalization that I think we’re just on the cusp on and which is so exciting.

Matt: Interesting. So it’s not just about, “This person likes sports, this person likes sailing, and so let me mention those types of things,” but it’s about their personality. Can you give us a little bit more of a definition of exactly what you mean by personality in a way that people can kind of walk away with?

Greg: Yeah, absolutely. I mean, let’s take you and I. So Matt and I have been friends since college and when we met in college, it kind of just felt like our personalities clicked. And to give a couple examples, Matt and I are both very direct. We can be very blunt. We were very straight forward. We’re very fast paced. If I do something that Matt doesn’t like, you better believe I’m going to hear about it. He’s going to say something. And for some people that would probably would make it so Matt doesn’t get along with them. But for me, because of this similarity in our personalities, we actually get along really well. And of course we never really thought about labeling that. It’s just, “Oh, I like Matt, Matt likes me, we get along.”

But the reason that we get along so well is because of these shared personality traits. So when I say personality, I’m thinking about behaviors, motivations, and a communication style that a person typically exhibits and prefers. So being blunt, being direct, being detail oriented, being big picture, stuff like that. A good way to think about it is with a framework called DiSC, and this is a quick tangent, but so important in the world of personalities. So DiSC is a framework. It’s been around for about a hundred years, since the early 1900s, and it basically says similar to Myers-Briggs or Enneagram, if you’ve explored those, DiSC says that there’s four different core personality types, D for dominant, I for imaginative, C for conscientious, and S for stabilizing. D, I S, and C.

Not surprising, our friend Matt and myself are the D personality type, the dominant, direct, blunt, straightforward type. And each of these different personality types have specific traits associated with them and specific preferences. And the idea is once I understand Matt’s personality type, I can use it to predict how Matt will behave and what I can do to communicate with Matt in a way that he’ll appreciate. So that’s the core premise, is understanding someone’s behaviors and motivations, and we could use a framework like DiSC, or any way of categorizing personality types to know “Okay, Matt’s a D type, so I’m going to communicate in a certain way and it’s going to be different than the I personality type, because Matt and that person are different.” So that’s what I’m thinking generally when I say personality.

Matt: Got it. And being in my direct fashion, I’m just going to go ahead ask my next question here. Email is something that most people connect personalization to. What can be different about sending emails or writing emails tomorrow than what people are doing today to personalize when they’re taking personality into account?

Greg: Email, it’s good you bring it up because email is such a good example of where there’s tremendous opportunity. Right now, for better or worse, it’s kind of a blessing and a curse. Usage of email, particularly in growth and marketing has just exploded, and the result is if I’m a buyer, call me a B to B buyer, I am just getting bombarded with email after email, LinkedIn message after LinkedIn message. And of course, they’re all sent with some sort of system that makes it look like they’re completely written manually. They have my name in it. It looks like someone wrote it and I’m just getting tons of these every day. And as a result, because there’s just so many, I’m, not surprisingly, just being accustomed to I have to become more skeptical on being accustomed to tuning those out.

So the bad news is if we just send emails with the status quo of, “I’ll customize the what and then I’ll blast this out to a thousand people on my list,” the response rate’s just going to get lower and lower. Where deeper personalization comes in, we can really start to change the game on email. So for example, let’s take Matt’s personality, this direct, blunt, straightforward, fast-paced, not surprisingly, if I sent Matt a really long email that had all this great detail about my product and links to five case studies and two attachments that go into a lot more depth on how it works, I’m giving him all the information he needs to make a decision. Matt, I mean, what are you going to do with that email?

Matt: It’s too much. I have so many other things to do, I can’t read that email. I’m just going to move on.

Greg: He’s moving on. I’m going to lose. Even though I put all the work into making that email good, I’m going to lose with Matt. Now what’s frustrating is let’s say I sent that to another personality type, the C in DiSC. This is the conscientious, analytical, detailed-oriented, loves to dive deep into solving complex problems and figure out how things work. That person really appreciates detail. When that person reads that long email where I accounted for all these details and giving them all this stuff to research, she’s thinking to herself, “Oh wow, this guy kind of has his stuff together. Thank you for actually including the detail.” A completely different response than Matt had. So if I understood Matt’s personality and this other prospect’s personality, I could not only send them different whats based on their role and job title, but I could frame my email very differently and personalize it in a way that’s going to appeal to them.

So tactically how that comes into play. The length, the length should vary significantly. For personality types like Matt, much shorter. I should use bulleted lists. I should use bolds and italicize and underlining, show him the bottom line of what I’m talking about. For a personality type that’s more detailed-oriented, I should include more attachments, more links, more references. For the personality type of the I in DiSC, that’s more social oriented, relationship building, creative, flexible. That’s one where I might want to include a bunch of references to other people that are in their space that they might know they have used the product. Matt’s going to care a lot less about those references. So I can mix and match these different components and quickly build an email that’s deeply targeted and customized to how Matt likes to communicate.

And I can take that further down to the greeting in the email, the subject line, the call to action at the end, even how I sign my name. At this point, we now have some really good data on the way I sign off an email can greatly vary in how different personality types respond to it. So making those kind of tweaks now, I think of it as it’s a personality revolution. We’re right at the cusp where so few people are doing this. It’s such a tremendous opportunity to make the email standout and ultimately be read.

Matt: It’s funny because I think there’s a lot of people that think email is a dead channel because there’s just no way to stand out, you could try all these different things. And I think about myself as a potential buyer, a consumer, a lead, whatever you want to call me, it would actually be quite a breath of fresh air for me to get a couple emails that like speak to me the way that I want to be spoken to and not just all this noise. That is the way to stand out.

And every now and then there’s an email that connects with me, and as I think about it more, it’s because they hit perfectly on the way that I want to read the email. Not even as much about the content, but it’s just written in the way that’s different than all the others because this one sounds like something that I just, I have time for it and I have a moment to read. So I think that’s pretty awesome. So let’s go to other channels, right? So email is an easier starting point, but there’s so many other channels that can use this type of personalization. I mean things that come to mind are things like websites and meetings and phone calls and ABM, account based marketing outreach. Can we talk about one of those?

Greg: Yeah, account based marketing’s such a great example. So let’s say I’m running an account based marketing growth campaign. I have a set of contacts within an account that I’m trying to do outreach to and I have some targeted content for each of them. Let’s say I’ve seen this a bunch being on the buyer’s side, certain people in the account, typically C-level people are getting something in the mail. It’s some sort of free giveaway. I just got a mail is a jar, and I’m not making this up, a jar of barbecue sauce from a software company in Austin, Texas looking to get our business, and it was clever.

But so here’s the interesting thing. Needless to say, it’s a lot of work to be mailing jars of barbecue sauce all over the country. I’m actually, I’m quite surprised that the jar didn’t crack, but nonetheless the barbecue sauce came through well. As we think about personalization, take this as an example. Matt and I, now, despite the fact that we both share a love for barbecue, we probably are going to be less enticed to buy just because we got that barbecue sauce.

At the end of the day, Matt and I’s personality type is much more comes down to, “Give me the bottom line, give me the price that makes sense. Make sure that the use case works for my team.” I’m not going to buy just because you made a good impression on me. I’m really going to buy because of these nitty gritty details. But there’s other personality types where the impression you make is a lot different, and of course it counts in both for all personalities, but it’s weighed a lot more. So my business partner, for example, Drew. He is the I personality in DiSC, the imaginative, creative, big idea, big picture, relationship person. He really appreciated that barbecue sauce. He actually wanted me to go in and look up this person’s company because he sent the barbecue sauce.

It’s just interesting how the barbecue sauce had a completely different impact on he and I. So as we think about that, why not only send the barbecue sauce to the personality types that are like Drew and don’t waste the marketing dollars on the person like me? Instead, send me something or focus on me with content or specifics around the things I really care about based on my personality. And I think Matt, you said something important earlier where there’s this phrase going around that email is dead, which of course we know is not true, but I think maybe to expand on that and coming into ABM too, it’s the spray and pray marketing and growth tactics, that’s what’s dying, right?

When we think about spray and pray email where I get a list, I have their role or their persona, I’m going to load them into my email marketing system. I’m going to send a blast to 5 thousand people that’s roughly the same. That’s what’s just yielding worse and worse results. Personalized emails, as you send an email that actually feels like it speaks to you, an ABM campaign that sends something in the mail that speaks to me, that’s not dead. For better or worse, the mass amount of marketing and growth that we’ve all been doing has just raised the bar. Now, we have to personalize at a deeper level. Our tried and true tactics of email or gift mailing are far from gone, but we have to take the personalization aspect in them to another level. And I think that’s what we’re really thinking about when we think about this personalization based on personality.

Matt: Yeah, and I think the cool thing about it all is when you tie it together, it’s not just about increasing your connection rates, it’s about saving yourself a lot of time from reaching out to people in ways that they’re not going to answer, but it’s also like a true ROI thing, right? You’re talking about ABM campaigns. Those can add up fast, right? Like a thousand barbecue sauce jars being shipped to all different parts of the country like that. That stuff gets expensive and so it really is like a true ROI decision to be personalizing at this sort of level.

Greg: Yeah, very true.

Matt: That’s great. And I think, when I think about all this personalization stuff, this to me feels like one of these moments where now is the time to act on it. Because there’s not many other people personalizing at this level. There will be a world 10 years from now, at 5, 10 years from now where everyone’s personalizing this way and you need to start thinking about other tactics or other ways to connect with people. Right now, this is something that no one else is really doing and so it can truly give you a competitive advantage. And so for all the listeners out there, I would totally implore you to start thinking about personality based personalization because now is definitely the time to do it. Greg, would you agree?

Greg: It’s very true. I think we’re on the cusp of what we’re calling a personality revolution where historically, personality has been a thing that we think about more in social settings and it’s often sitting just beneath the surface. Coming back to Matt and I’s relationship in college, we became friends and it just felt like we clicked. We didn’t really think about why we just decided, “Oh yeah, I like Matt. We get along well.” In the B to C … In the C to C context and we’re friends, that’s all we need.

But we can start to take that clicking and apply it in the B to B context. It’s something that historically has just really not been done. And particularly with advances around AI, we call it personality AI, we can now use publicly available online data to predict someone’s personality. Without me having to get to know Matt as a friend, I could use a system to be able to actually predict at volume Matt’s most likely to be this D personality. So when I make my first cold outreach to him, let me personalize my communication style to appeal to him. And that is, it’s just a new frontier. I think we’re on the cusp of something really exciting with it.

Matt: This is great. And if there are listeners out there that want to reach out to you with more questions or whatever it might be, what is the best place to do so?

Greg: Absolutely. Well feel free to visit my company’s website,, K-N-O-W-S, and feel free to email me directly. It’s a I’d be happy to chat with anybody.

Matt: And you got a personal blog, right?

Greg: I do. So it’s my last name, Skloot, Lots of marketing and growth articles on there and also other ways to contact me. So yeah, always happy to talk. I can talk about growth all day long. So if that’s your jam, feel free to shoot me an email.

Matt: And if you’re going to do that, take the tips from this podcast and do not send Greg a long, not to say not a thoughtful email. It can be thoughtful, but don’t waste his time.

Greg: Very well said and good free advice.

Matt: Cool. Well Greg, thank you again so much for joining today. For everyone listening out there, I appreciate you tuning in. Feel free to send any feedback, questions, suggested speakers, suggested topics, whatever it might be, my way. My email’s And in true seeking wisdom fashion, five or six stars only for reviews. And thank you again, really appreciate it. And Greg, thanks for joining.

Greg: Absolutely. Thanks for having me.

Matt: All right, take care.