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Josh Schachter 0:00
Hey everybody and welcome to [Un]churned this episode. I’m Josh Schachter. I’m the CEO and founder of UpdateAI. You might know my guest, I think you we’ll I think you do. Jay Nathan is here with us today. Jay is the Executive Vice President. He runs the business unit of corporate markets at higher logic and is their chief customer officer. He is also the CO the co founder, excuse me of gain, grow and retain. And he has a wealth of experience in leadership at other growth companies within CSX as well, Jay, thanks so much. I really appreciate your being on the

Jay Nathan 0:43
show with us today. Thanks, Josh. I’m glad to be here doing this finally with you.

Josh Schachter 0:48
Finally made it happen. So the name of the podcast is unchained. Obviously, it’s it’s indifference to to churn rate or retention. key metric for us in the Customer Success world. But unsure it also is raw, right? It’s raw, it’s real. And I want to start out with the conversation. We’re just getting a glimpse of, of jet. So rapid fire questions here. We’ll go for a couple minutes. Where were you raised? And where do you live now?

Jay Nathan 1:22
I was raised in a town called High Point North Carolina. And it’s interesting. I’ve never lived outside of the Carolinas. I travel a lot outside the Carolinas but never lived outside. And I live now in Charleston, right outside of Charleston, South Carolina in a little town called Mount Pleasant. So, Carolina.

Josh Schachter 1:41
Okay, what’s your favorite Carolina cuisine? In that case?

Jay Nathan 1:43
No barbecue barbecue with Eastern North Carolina style barbecue sauce. And so if you know, you know, but that’s like vinegar based crushed red pepper. very tangy. That’s my that’s my favorite in South Carolina.

Josh Schachter 2:01
I like the grouper that they have out there.

Jay Nathan 2:03
Oh, well, that would have been the more sophisticated.

Josh Schachter 2:09
All right. How many siblings do you have? And what number are you?

Jay Nathan 2:13
I am the oldest of three. But there’s an interesting story there. My brother and I grew up together. And then many, many years after my brother and I ran out the house, my parents decided to adopt another sibling. So we have a younger sister who is 17 and a half. So I have a much younger sister. I won’t say how old I am. But she’s much younger than me. My parents are crazy.

Josh Schachter 2:43
That’s great. That’s great. What was your first job?

Jay Nathan 2:47
My first job was actually working for my parents. They had they had retail stores in like shopping centers and malls when I was young. And think like confession, consent, not confessions, that’s a different thing. Concessions like popcorn, candy, gifts, all that kind of stuff. So I worked in their stores from the from the time I was very, very young, sort of grew up learning about business from that entrepreneurial perspective. And then I had, you know, between then and now I’ve had just dozens of other jobs that are some of which are interesting, some of which are not, but that was my first job. Yeah.

Josh Schachter 3:25
And what time do you go to bed?

Jay Nathan 3:28
Ah, this is an ever evolving thing for me. I’ve heard it said that every hour of sleep before midnight counts as to give her that?

Josh Schachter 3:40
I haven’t but it makes sense. Yeah. So I’ve been trying

Jay Nathan 3:43
to get a bed a little earlier here lately. If I can get to bed by 10 o’clock. That’s good. But my kids are teenagers. So they’re up till one two in the morning maybe later sometimes. So there’s this balance between getting myself taken care of and also making sure that everybody else is on track so but trying to get an earlier these days just a little bit.

Josh Schachter 4:06
A little home security you may not actually know exactly when the time they go to bed. Yeah, exactly. Last question here outside. So customer success. This This podcast is all about building relationships is really the foundation right as we know it of, of customer retention and growth and outside of your family members. What’s the relationship that you cherish the most?

Jay Nathan 4:32
Oh, that’s a great question. I have I feel like I have so many relationships, you know, across the customer success community, my colleagues at work my family, of course, as you mentioned, but I got I’ve got one really good I’ve got a bunch of good friends from college. But there’s one person that I’ve stayed in touch with for the whole time and of course we’ve gotten in and out of being in touch at times but um here lately, he and I have, I’m helping him a little bit with his startup that he’s working on your minds via you and a lot of ways. And it’s just a really, really great friend. He was my first roommate out of college, you and I were fraternity brothers back in college. We lived together for a couple of years out of college, you know, he was in my wedding, it was just he just a really, really good friend 20 some plus years. So got a couple of those kinds of folks. But he’s, he’s one of the ones it’s just one of my best friends. So

Josh Schachter 5:32
you’ve, you’ve been in the CS world and the SAS world for quite a while you’ve held several leadership positions. And I’m looking off of your your background here. You are Director of Product Management at Blackbaud, if I’m pronouncing that correctly, yeah, that’s right. VP, VP of services support snag. SVP of CES, people matter, I believe was associated with snag rain focus. And now of course, leading a business, you have a wealth of experience in leadership positions. And you have a purview to many different leaders and connectivity to many different leaders in customer success. So what I think we’d all be interested in learning from EJ is, from your point of view, what makes most effective leadership in customer success today?

Jay Nathan 6:28
Yeah, it’s a great question. And I actually don’t think it differs a lot between customer success or sales or product management, whatever function you’re in is leadership principles apply. And, you know, I’ve had a number of leadership roles, but I could tell you with very concrete certainty that I am still learning every single day, just ask the people that I work with, they will tell you, I’m still learning every single day, and we all are. So you know, maybe the the first principle of leadership would be, just realize that you don’t have all the answers. And that inquiry is probably the smartest thing that you could do as a leader lead with questions, not answers. And even as I say those words, I know, I don’t always do it. Right. So that’s one area that I consistently try to try to work hard at getting better at, I think is a

Josh Schachter 7:27
dive into that a little bit. So lead with questions not answered. So you’re referring to communication with your team, right to interactions with with the folks that work for you? Can you give an example of how that manifests in in your team?

Jay Nathan 7:40
Yeah, well, I would say it manifests for your team and for your colleagues, your peers, you know, even even your superiors. When you ask questions, instead of give answers, it actually allows people to take ownership of their own problems. And I’ve learned this, you know, through the years, and again, like, I’m always having to work at this because my personality is not that my personality is I’ve got an idea in my head, I might even have an answer, I might have some experience. But when I put those things out there in that sort of in an imperative sort of way, instead of asking a question, it transfers ownership from the person that I’m working with to me, and then I have more things sticking to me, because I might appear to sound like I have an answer. But what I really want is to empower the person that I’m that I’m talking to. So and again, you know, I’m coming to you as a person who’s constantly working on this not somebody who has this figured out. But I’ve you know, I’ve had so many discussions Neil’s than Yeah, I don’t know if you know him. He and I have spent a lot of time together. And we’ve talked a lot about this. This concept is book covers it. You know, there’s a great book by John Maxwell, there’s another book by a guy named Michael skinnier, called the Coaching Habit. Just all about asking questions and using inquiry as a method to to get to the right place. And yet not try to take ownership over everything or not inadvertently take ownership over everything so that you’re empowering the people around you instead of building yourself up in that process is

Josh Schachter 9:22
the Coaching Habit, the book about how to conduct one on ones with with your with your team.

Jay Nathan 9:29
Yeah, that’s that’s covered in there for certain, but it’s also it’s much more broad than that just because anybody can be a coach to anyone else. People ask me for advice all the time. And the reality is, I don’t know how to solve, you know, update AI’s specific problems. You’re in the middle of it all day, right? But what I can do is ask you questions that help illuminate different areas of thought for you, you have the answers somewhere in your head. If I can ask you the right question. You can find them and then you have complete agency and ownership over solving that problem.

Josh Schachter 10:03
Now you’re reminding me that I was in school with professors that that when you ask them a question, they just say it depends. And here’s a heuristic that you can apply, but I’m not going to give you the answer.

Jay Nathan 10:12
So Socratic method, right?

Josh Schachter 10:15
It’s the academic method. I think it’s the Coaching Habit, I could be mistaken. But either way, I’ll share this, something that I’ve picked up from that book or another was one on ones how to conduct one on ones with the folks that you work with. And I remember actually wrote this down on a post it and put it on my desktop monitor, so I wouldn’t forget it. And so finally, I was able to ingrain it was able to to i, it ingrained itself upon me, I suppose. And so we’re always starting out with just how’s it going? asking them a question, but how they’re doing? Right, they’re always going to respond is good. Okay, but no, no, really? How is it going? Like, what’s really going on? How are you? And then always falling off? Or ending the conversation with? What can I do to help you? Right, where can I unblock you? What do you need from me? Because I think, likely, at your level of leadership, you have a larger responsibility. And I do too, to a smaller scope and scale, but you find yourself just becoming a air traffic controller in many ways. And like your primary intention is to unblock folks and let them do their best work and get yourself or get others out of their way.

Jay Nathan 11:43
100%. I mean, that is the job of a manager or senior leader is if you could do all this stuff yourself, then you would be doing it right. But the reality is, when you’re trying to scale a business, you have to empower and enable others, you have to make good people decisions all the time, but the right people in the right positions, because you don’t have all the skills you need. Even if you did, you don’t have enough time in the day to do the work. So putting the right people in the right positions, and then helping them move, move obstacles, right and prioritize. That’s the other thing. And again, I’m coming to you from a place of severe imperfection. I’m trying to zation in particular, because I want to do everything fast and all at once. It’s my nature. But if you can prioritize and help people prioritize and stay connected to the business priorities, then that gives them the clarity, they need to act again, with agency without you having to tell them what to do or prioritize for them. Right. Yeah.

Josh Schachter 12:47
Yeah. It’s about it’s about Yeah.

Jay Nathan 12:51
And I was just gonna say that, that book that that question, how can I help you? It’s also a very empowering question. Right? You’re not taking the task from you. What you need for me to support what does support look like is another way to frame it. Right. Right. Yeah, with a little Brene Brown. Definitely don’t look like her she’s.

Josh Schachter 13:17
Yeah, you know, I’ll go back to the, to the, to the one on one for a second. And I remember I years ago, I’m not going to be able to share too much. But years ago, I was conducting a one on one with somebody that worked on my team started out the conversation with you know, how’s it going? And this this person was was very quiet by nature a little younger. And so it’s okay, it’s okay. And it’s okay. How is it going really outgoing? And next thing, you know, there were waterfalls of tears, because there had been some inappropriate misconduct in in in the office, which, you know, then triggered a whole a whole series of things. Sure. But it’s, I think it’s really just by sitting there and being present with your team, you know, like your pencils down your phone away. This case, maybe we’re all working remotely, but yeah, and reiterating the question and showing that you really care. And it strikes me that you are that empathetic type of leader that does just in the conversations that I’ve had with you, you are always present. That is very important to be a leader.

Jay Nathan 14:22
It’s the, it’s the one thing that you can do, that doesn’t require you to have the right words, or you can just listen and be present, multitask, like just be here. And it’s even more important now, to your point role. Many of us working remotely. Higher Logic is now a remote first company, like full stop, remote verse, we close all of our offices down. And so this is this is really critical. It’s a really critical thing and it takes work takes work and it takes time. But yeah, now the flip side of leadership on this is, you know, there’s there’s an empathetic piece, there’s less sending in a collaborative piece to it. The one of the areas that I’m working on, and I, this is just a recent real revelation for me is I’m working on being more directive when I should be directive. At the same time, this is why leadership is so freaking hard. Because on one hand, it’s, it’s all situational, right? On one hand, it’s you need to be collaborative, and you need to, you know, bring other people along. But there are situations in business where you do need to be directive. And you need to practice that, you know, at times, you know, when it’s not, in the heat of the moment, or a delicate situation, you need to practice those things, to see what they feel like and get accustomed to doing that kind of motion as a leader as well. So, leadership is a lifelong journey, man. And I’ve just, yeah, there’s always so much to learn. And so let’s just figure it out. And it will constantly be changing, because the people you interact with are changing all the time.

Josh Schachter 16:01
There’s another great book, welcome to the unchained book, talk with Josh after and we could do this weekly,

we could do this, you know. So I think it was Aashna Patel, who had a CS book club, about a year ago, but anyway, so growth mindset is my holy bible of literature, right, by Carol Dweck. And, and, and the iris, obviously, that having a growth mindset, you’re always learning you’re everybody is, is vulnerable to flaws. And the irony is that I think as you get more mature and you become a better leader, then you understand that better. You know that you’re not perfect. And then I think the other thing, the other book, is radical candor. Yeah, I don’t know if you’ve read that one. Yeah. Right. We’re being empathetic, and but also being candid, and truthful and directed when you need to be directed. My own background was, I used to be overly coarse, I’m still overly coarse. I used to be overly overly directive. You know, I, my background is in product management. I’m the Product Owner, I’m the product manager, you know, like, I get to lay down the marching orders. And that helped me back then I learned from those lessons read that growth mindset develop. But I actually realized, like, I think I actually developed a little bit of a neuroses almost a source from that where I felt like I had to be too passive to compensate. And so now, I think I’m back in a good place, which is more of an equilibrium where it’s somewhere in the middle. What did your journey look like? I mean, you’re talking about that you’re actively working on being more directive? What, what has that process look for you

Jay Nathan 17:57
in the past? Well, it’s it’s not been a long journey, yet. We did a management off site meeting a couple of weeks ago, and we did a, an assessment on on your profile. On your, your conflict profile, basically, is what it says. So when you get into conflict, are you collaborative? Are you directive? Are you do you avoid it? Or do you just acquiesce to the other side? Like what is your what is your style? It’s not saying, Hey, this is not behavior necessarily. It’s just what do you what is your propensity to do this. And as I looked at my results, my my directedness was very, very low, my collaborative is very, very high. And I think that’s sort of like the, the high empathy side of me, always wants to create, not necessarily harmony, but always wants to bring everybody along together, but sometimes, that it takes time and energy to bring people along, right, you have to acknowledge that. And so the drawback, you know, assessments always tell you like, what you’re with the good things about your personality, and then we’re that creates risk for you. The risk that that creates is that you spend way too much time bringing people along, and not enough time just moving things forward. Period. And so it’s it really has I can be directive. I mean, just let me ask my kids, right. Some people have felt maybe directed that I’ve worked with in my in my career, but the I guess the I wouldn’t even say it’s been a long journey. But what I’ve started to practice doing is just being directive outside of the moments of conflict, just practice. What does it feel like? Again, back to that concept? Like, it’s very clear what needs to happen, you know, we don’t really need to collaborate on this. I need to pick the things that we should spend that time and energy on. And there’s other things that it just is what it is, and so it’s got The clear answer, that answer is, you know, been proven over the past couple of decades that that’s the right answer. So we should just do that and go, and it’s teaching somebody and move on. So I think for me, it’s like practicing those things outside of a conflict, if that makes any sense. And now I’m giving you bits and pieces of a framework there. But that was an interesting, it’s always interesting to see those kind of profiles on yourself.

Josh Schachter 20:27
It is, yeah, I mean, it’s, it’s, it’s part, part enriching, part bullshit. Part Part, you know, just the the spawning of us have a different industry to promote that. But, but no, no, I do enjoy those. Especially when they tell me the things that I want to hear.

Jay Nathan 20:50
But if you’re not careful, they can become self fulfilling prophecies, too. So you can’t define yourself, by reading these reports. Everybody does. But

Josh Schachter 20:58
usually, they also, they also coincided with just a moment, I mean, they are a moment of reflection, and make arrests, even more important thing is what is said, but just the process, right? It’s the journey, not the whatever. So, and I really like your your tip there of finding your moments when you’re not in conflict to assert yourself and like anything, it’s a muscle that you build. That’s right. And, you know, when, for my own experience, like, I know, there’s times when I’ve come across too passive, and then I want to redo in that conversation, right or too aggressive, you know, but when you when you you’re able to assert yourself, but also show also feel and have the other person feel that you care. And that came from a good place. No, but you I feel like a million bucks. When when I have that moment.

Jay Nathan 21:44
In 10 matters. It matters more than what you say it’s where you’re coming from. Right. And does the person on the other end know that you care first?

Josh Schachter 21:54
Yeah, and finding credit anyways, to show that, you know, when at any point, right, just to show that you care, so that you have that, that that care capital built up? That’s right,

Jay Nathan 22:04
you build it up a bank account? Yeah, that’s right. It’s same with your family as it is with your your colleagues.

Josh Schachter 22:10
Yeah, I mean, this will, this will come across poorly. Again, I’m still working on the courses. But I look for those moments where I can show I care. So like, you know, I have a colleague, you know, is sick, or something, you know, happens or whatever. And, of course, like your heart goes after them, and you want them to do well. And that is like the first priority. But I also view it. I don’t know, Jay, if this comes up terribly, I view it as an opportunity of using an opportunity to show that I care to build that capital, right? Somebody is COVID on your team and you buy them go on Amazon, you buy them a care package, I view that as you know, of course, I want them to recover fully and be fine, but But you view it as an opportunity to really kind of insert that into your culture and your own leadership style. So that’s, that’s just me.

Jay Nathan 22:59
Yeah. Okay, I’m gonna give you another book that I’m literally in the middle of reading right now. Have you ever read setting the table? By Danny Meyer?

Josh Schachter 23:07
I’ve read leaders eat last but no, not starting today. Okay,

Jay Nathan 23:10
let’s say Danny Meyer’s, the guy who founded Shake Shack and a bunch of other restaurants in New York City, in fact, so. But he talks about the difference between service and hospitality services, doing all the things that you have to do, you have to decant wine, you have to clear the table, you have to present the menu, you have to do all the things right. And same thing in in SAS, like we have, you have to go through the implementation process, you have to handle cases, you have to have to do all these things that’s service. But hospitality is the little things that you do to help people feel like they’re part of something bigger and have an experience that they’re that they’re warm and excited about. So what you’re talking about is hospitality. In a way, I’ve really latched on to this book, by the way, so I love it. Maybe a bridge too far. But

Josh Schachter 23:59
we’ll have to keep it in the show notes for the podcast. We’ll put all the links to all the books and I’ll sign affiliate program before I do that.

Jay Nathan 24:08
That’d be great. Oh, yeah, that was one of my, my first jobs out. So I mean, you could say that my parents business was a hospitality business to some degree, right. But I waited tables, I I waited tables a lot. I was bartender at one point in college as well. So yes, I spent a lot of time in hospitality.

Josh Schachter 24:33
i We both work in customer success. And I wonder the percentage of CS professionals that have worked in service and hospitality.

Jay Nathan 24:40
I think it’s high. Yeah, I think it’s high. Yeah. Yep. Good training there. The

Josh Schachter 24:46
there’s a few other attributes of leadership that you had touched on a few moments ago. You talked about prioritization. I missed that that’s that’s a great point. Right. So you’re, you’re you’re making sure the trains arrive on time and take off on time but you’re you’re also prioritizing those trains and cars, whatever. And you’re also setting the vision. And you’re reiterating that vision again and again and again, to make sure that they’re going those trains are going in the right direction. And that can be really difficult to do. What is the current? Because visions can change, they evolve, just they they have their own growth mindset. What’s the current vision of Higher Logic? And how have you gone about how are you instilling that within your business unit?

Jay Nathan 25:32
Yeah, very good question in, you know, one of the things as a leader of any team, but especially the bigger your teams get, and the more broad they get, you just have to gear yourself up for the fact that part of your job is repetition. You have to continuously remind people of what the vision is, and bring it back to him. Because the reality is people do not understand the first time you tell them something, I can’t, I can’t stand it when people tell me that they’ve told people something. It’s like, Well, did they? Did they get it? Did they hear you? Do they? Were they listening? And did they hear and have they internalize it. So that’s our goal. As leaders, you have to have a strong vision, but you also have to communicate it constantly and in different ways to hit it from different angles. And our vision for our the business unit that I run, is, we want to create awareness in the market of what customer community is in drive people to adopt it, like many industries, there are people who understand the value of what a customer community is. And there are people who don’t yet understand the value because they’ve not experienced it. So how do we go educate them on what the value of customer community is how it works, so that we can get them off the bench and get them into the market. Obviously, we want them to buy our technology, but we want them to reap the benefits of it. So that’s a big focus area for us in terms of our visuals, is creating world class customer experiences led digitally, right, and scaled digitally. So that the companies we serve can grow faster, they can engage their customers in a deeper way. And everybody wins that model. So that’s our vision.

Josh Schachter 27:18
To go deeper with that, what’s the value of customer community community? What’s How does it how does it play out customer communicates

Jay Nathan 27:24
connection, it’s a deeper connection between your customers in the in the, I’ll say the brand, the business, right? One of the challenges I see consistently with customer success teams is that the customer relationship hinges almost entirely on a customer success manager relationship with the individuals within the customer. Right? The relationship is not deep enough, because it feels like the CSM cares. And they do, but it’s just not enough, the company has to care and the customer has to feel that. So whether that’s being able to submit my product feedback ideas into a community where the product management team is going to be reviewing them on a regular basis, right? Whether it’s having the ability to go ask the community people of my peers that use the same products, hey, tell me what you’re doing in this instance, because I’m I feel like I don’t know what to do next. And this particular business process or problem that I’m trying to solve, or searching Google for an answer to a product problem, and finding a community where somebody’s gonna answer that question, so I actually get an answer to my question. I’m always happy to pick up the phone and call support. But hell, if I could do a Google search and find the answer I’m looking for, that’s a little bit better, right? So community supports in those ways. And if you do those things, if you enable your customer base to work together as a community, with your team, then you build advocacy, that’s the real prize for a SaaS company, update AI, Higher Logic, we all need to have people telling our story for us in the more supportive, the more connected they feel to our brand, and that they’re a part of it, that they’re helping build something here, the more they’re gonna get tell our story, which is a virtuous cycle and a flywheel effect that money just can’t buy.

Josh Schachter 29:20
So I sign up for for Higher Logic, or I engage with higher logic. I put the one line snippet of code into my site, create a sub domain couple of forum topics. And I’m good. I’ve created a community. What does it take? What does it take to really get a community? A flywheel of a community going?

Jay Nathan 29:41
Yeah, it’s a little it’s a great question. And, you know, we part part of my learning process, and this was the game brewery tank community. Right? Gang routine is a customer success. Community for Customer Success leaders is what we call it and it’s really about creating that that initial set of connections between people. So I would tell you, the first thing we did when we built the ganger retain community is not launch an online forum. That was a hub of the community started the community started by the, in the conversations we were having on LinkedIn, in the people that we met on LinkedIn and started to interact with on LinkedIn. Then it moved to a call, we had a weekly call, I think you were probably on a couple of those in the early days. We call it office hours. And yeah, we tell people on LinkedIn, hey, let’s, let’s all meet up live. And we’ll jump on a zoom call. And before we knew it, we had 150 to 150 people on these calls every single week with some of the brightest minds in customer success sharing ideas, and we were learning how to facilitate that. But and then what would spin off of that was other relationships. People would hear me say something or they hear Boaz say something or they hear Ziv pellet, say something and or you say something. And they’d be like, Hey, I heard you say such and such, Josh, can I contact you offline and sort of pick your brain on that thing, and then all of a sudden, all these relationships start springing up. So it’s really, it’s not a digital thing. It’s a human connection thing. And if you can identify the the common problems that a group of people with a common set of goals and maybe challenges have, then you’re on the on the track to creating community. And then, of course, it manifests in all kinds of ways digitally, once you once you have built that, but you can throw up digital community and turn it on. And if you build it, they probably won’t come. Unless there’s a good reason for them to engage, get value from the other people that are in that community.