March 6, 2024

Cracking the Code of Customer Success with Jay Nathan

Alper Yurder interviews Jay Nathan, covering Nathan's software industry journey, leadership insights, and customer success strategies. Nathan shares tips on collaboration, onboarding, and reflects on the future of tech sales.

Meet our guest

Jay Nathan, Head of Growth at Churnkey | Gain Grow Retain

Jay Nathan brings over 20 years of experience in software leadership, having held prominent roles at companies like Blackbaud and Higher Logic. With expertise in SaaS, sales, marketing, and customer success, Jay is a driving force in shaping the industry's future through his insightful contributions and visionary leadership.

Key takeaways

  • Customer success is an organizational capability, not just a team or role.
  • The challenges in customer success include justifying the team's existence and delivering value in a cost-effective way.
  • Advisors play a crucial role in providing guidance, opening doors, and offering support to companies. Establishing the first phase of growth involves prospecting and generating conversations to understand the market and ideal customer personas.
  • Onboarding is a critical stage in reducing churn, and early value demonstration is key.
  • The biggest mistake that leads to churn is a lack of focus on onboarding and activation.
  • The future of tech sales lies in a two-way exchange of value and collaboration between go-to-market teams.

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Watch the highlights

Soccer mishaps and coding adventures

The conversation begins with a glimpse into Jay's childhood in the Carolinas, where he worked in his parents' retail businesses from a young age, fostering an entrepreneurial spirit. Jay shares an unexpected personal story about losing a kidney during a soccer game in high school but bouncing back to continue playing football. 

"My parents were entrepreneurs... I worked in my parents' businesses, which were essentially retail shops in malls... My mom taught me how to count money and give change. I still use some of those tricks today in my day-to-day life and try to teach those to my kids. I was one of the first people in my family to go to college, believe it or not. I went to Appalachian State University in the mountains of North Carolina."

He then delves into his career journey, including his technical background, coding skills, and first job at Blackbaud, a leading software company serving nonprofit organizations. Jay reflects on his nine-year tenure at Blackbaud, where he experienced significant growth, led large teams, and contributed to product launches and acquisitions. The conversation touches on the challenges and triumphs of Jay's leadership journey, offering insights into his approach to business and life.

"I got out of school just as the dot-com bubble was bursting... I found a great job and something that allowed me to get deeper technically, which I wanted to do at the time and learn on time. I taught myself how to code in college and just sort of fell in love with what technology could do back in, you know, during the dot-com era."

Leadership, customer success, and growth

Jay Nathan shares insights into his journey as a leader in the tech industry, reflecting on both the highs and lows. He discusses the challenges of transitioning from an individual contributor to a leadership role, emphasizing the importance of delegation and focusing on coaching and mentoring as a leader. Nathan also delves into the evolving role of customer success in the SaaS industry, highlighting the need for companies to deliver value beyond traditional customer success teams and leverage various channels to support customer needs effectively. 

"And I've heard people joke before that level is the playing field for people who aren't as smart, right? Because you take the smartest people out of what they're really, really good at and you give them a completely different job, which being a people leader is a completely different job than whatever it is you did before to get there.”

Additionally, he provides insights into his current role at Cherokee, where he serves as an advisor turned operational leader, focusing on driving growth through hands-on involvement in prospecting and market exploration to inform strategic marketing initiatives. Throughout the discussion, Nathan emphasizes the importance of aligning with a company's vision, team, and market opportunity, and the value of continuous learning and adaptation in leadership roles.

“Customer success is an organizational capability. It's not necessarily delivered by a thing called a customer success team. So think about your product, think about your go-to-market motion, your selling approach. Think about how you show value after the customers have started using it."

Navigating the complexities of tech sales

In this rapid-fire Q&A session between Alper Yurder and Jay Nathan, they cover essential tips for moving upmarket in the tech industry, emphasizing the critical importance of data security and understanding the complex decision-making processes within larger organizations. They also touch upon the necessity of collaboration between sales and customer success teams, highlighting the value of effective communication and documentation during the handoff process. Jay emphasizes the significance of early retention strategies, stressing the need for proactive customer engagement well before renewal time.

"One of the biggest challenges for technology companies today is data security and privacy. It just is. You can have a beautiful product that meets a need in the enterprise space, but if you don't have your security certifications and you have issues on the data and privacy side of things, you're never going to get it into even mid-market."

The conversation continues with insights into common mistakes that lead to churn, particularly focusing on the importance of thorough onboarding processes to set customers up for success from the beginning. They also briefly discuss the limitations of traditional quarterly business reviews (QBRs), advocating for more dynamic and interactive approaches to account management discussions. Overall, the discussion underscores the importance of adaptability, collaboration, and proactive customer engagement in navigating the complexities of tech sales and customer success.

"The biggest issue that many companies make that leads to churn is onboarding. They don't do a great job of getting their customers onboarded and activated and launched... If you have a churn problem, start at the beginning to look where the seeds of churn were planted, it's usually one of them."

Full episode transcript

Alper Yurder: So today I'm very excited. In the therapy chair we have Jay Nathan who is the head of growth at Churnkey. You know him probably as the guy he has been for over two decades in the space of a go-to-market and client success. But Jay is one of those voices you turn to get the latest and greatest wisdom especially on client success, growth and retention. As I said, he's one of the co-founders of Gain Grown Retain. The incredible community started by some of our previous guests such as Jeff Heckler. And Jay has over 20 years of experience in the software industry, a great career of commercial leadership at companies like HigherLogic, PeopleMatter and Snack. And after that usual very long intro, we'll talk about his success, the joy, the pain and the journey that took him here. Welcome to Sales Therapy Jay. How are you feeling today?

Jay Nathan: I'm feeling great, man. Thanks for having me, Alper. It's good to connect with you.

Alper Yurder: Absolutely, my pleasure. Thanks for being open and joining. Was that an intro that does justice to you? Anything I'm missing? Any medals? Any Olympic wins?

Jay Nathan: That was awesome. That was really good. Any medals? I haven't won any medals since my swimming days back in high school. So no medals to speak of.

Alper Yurder: Okay. We'll talk about that. Okay. Fine. Okay. You have the virtual digital medals, which we'll talk about today. So you touch, I'm glad you touched on the high school because the good therapy starts with childhood and growing up. We love to hear a little bit like, where are you today? Where did you grow up? And I love to hear sometimes people tell me the story from two years to 18. Others confined it to 16. Well, what was growing up like for you? Let's start from there.

Jay Nathan: Oh man, all right, we're going way back. So I grew up in North Carolina. I live in South Carolina now, so I've always been a Carolinas guy. And yeah, I mean, you know, I had a loving family around me. My parents were entrepreneurs, which I think explains a little bit about, you know, where maybe I got that kind of bug from. So I worked in my parents' businesses, which were essentially retail shops and malls.

From the time that I was very young, I remember standing behind a cash register, like standing on a box so that I could actually reach and do what I needed to do. My mom taught me how to count money and give change. I still use some of those tricks today in my day-to-day life and try to teach those to my kids. I was one of the first people in my family to go to college, believe it or not. I went to Appalachian State University in the mountains of North Carolina.

Alper Yurder: And what, counting the money?

Jay Nathan: And when I graduated from there, I went into, actually back in my childhood, I was an athlete growing up. I played football. I swam, like I just mentioned. I played soccer. Here's something I don't ever mention on a podcast. I got hurt in a soccer game once and I had to have surgery three days later to remove a kidney that was basically broken or fractured. So that was my big story as

Jay Nathan: Um, playing soccer and so, you know, I recovered six weeks later. I was back on the field.

Alper Yurder: Clean sucker and kidney removed? Help me out here, how do they connect?

Jay Nathan: Yeah, it actually, I guess, you know, just the goalie hit me in the back with his knee, and it just exploded my kidney. And so it was dicey. Yeah, it was a crazy situation. But, you know, made it through that. And I think, you know, I was back on the field playing much to my parents' chagrin six weeks later after that surgery, although my coach wasn't really happy about it either. But I

Alper Yurder: Crazy crazy.

Jay Nathan: I quit playing soccer after that year and I decided to stick with a little more safe sport which was football. I was the kicker on the football team.

Alper Yurder: Okay, relatively safe, gotcha, fine.

Jay Nathan: American football. Yeah, exactly. Kickers are pretty safe. Kickers are pretty safe. So you know, I always had that sort of athletic drive to win. And I think you know, more than anything that shows up in my day to day, you know, work that I do from a business standpoint. Now, I graduated from Appalachian State and went to work for you know, I like we were talking about the pre show.

I was very technical. I got a business degree, but I taught myself how to code in college and just sort of fell in love with what technology could do back in, you know, during the dot-com era and I got out of school just as the dot-com bubble was bursting. And so there were very few jobs. It was a tough time in the economy, but I ended up getting a job with a big enterprise organization and learned how enterprise technology worked and.

Jay Nathan: You know, I was only at this company for like two years, but it gave me a great foundational knowledge of how, of what big, you know, enterprise B2B tech looks like, um, and so that, that was cool.

Alper Yurder: Okay, well, we'll get there. One thing I realized in my, in my what now 2030 podcast is people skip the kidney and want to rush to the business. And I'm actually stuck at the kidney. I'm going to keep you there for a minute. I mean, not, not necessarily the kidney, but I want to learn a little bit more about that. Um, did that have an effect on your health later on or like how was life after that injury?

Jay Nathan: All right, let's go back to the kidney.

Jay Nathan: No, no. Yeah, I mean, it's been very normal, at least up until now, knock on wood. Yeah, really. So what happens, I mean, the body is an amazing thing. And so you have two kidneys, of course, you have two lungs, you have double of some things. And what happens is your other kidney takes over for the one that is now gone, in my case.

Alper Yurder: Okay good, knock on everything, fine.

Jay Nathan: And what I've been told by the doctors is that my, you know, your original kidney is so, you know, so big, maybe the size of your fist, but my kid, my remaining kidney now is like twice the size. It has compensated for the fact that I don't have two. So.

Alper Yurder: I think that's a nice segue to psychology, overcompensating. You know, when one thing is gone, the other one is overcompensating.

Jay Nathan: Yeah, that's right. That's right. Your body leads the way. But no, I mean, the body is a magnificent creation, right? And so it's very, very cool.

Alper Yurder: Excellent. And other than that, other than that, it wasn't like you started with a pretty normal, straightforward, not eventful childhood. And then, okay, that's, I like that. And then bam, okay. So you, after that, you started, you know, the school, of course, the engineering experience, coding, etc. And during the dot com bubble, is that when you got to your first job?

Jay Nathan: Damn! Thank you.

Jay Nathan: It was actually as it was, yeah, sort of in the middle of it, but I, toward the tail end of it, after it had started to burst, I graduated from school in 2001 and, um, you know, it was, it was sort of messy at that point. But, um, I found a great job and something that allowed me to get deeper technically, which I wanted to do at the time and learn to time. Um, and you know, there's still things that, you know, I recall from those days, which helped shape the way that I think about.

Jay Nathan: the world today. I've been in B2B technology now for over 20 years. And, you know, well, thank you. I appreciate that.

Alper Yurder: Yes, well I can tell you don't look at Jay. To be honest, this will be so weird to say, but you look so much younger than your LinkedIn profile picture. And I'm happy to edit this out if you prefer to, but I think, yeah, when I thought I was going to meet a slightly older looking gentleman and, you know, somebody who looks very much more like me is, I'm not young at all by the way, I'm 38, so yeah. Okay.

Jay Nathan: Oh really? Bye.

Jay Nathan: You're young. You're young. Well, I look older in person. You can't see all the gray from where you sit.

Alper Yurder: Ah, okay. Well, if anyone's watching this, I think they will definitely agree with me. And I had an old friend of mine now, ex-CRO for now, CRO Aviar. And I was like, dude, like you had such a crazy career, like how do you still keep your hair? And he was like, well, the same way that you do. So it's good that we still have our hair on our head. Okay.

Jay Nathan: You can't see the back of my hair either. We'll just leave it at that.

Alper Yurder: Okay, fine. So let's talk about the first role a little bit. Where was this first B2B SaaS tech job? Was it snaggy or was there somewhere before?

Jay Nathan: Well, no, it wasn't actually, this is something you didn't mention in my profile, but I worked for a company called BlackBot for almost nine years. BlackBot is one of the biggest software companies that, really one of the, probably one of the biggest software companies in the country actually, but you would never know them. They serve a vertical market of nonprofit organizations. And today it's a billion dollar a year business. It was back when I joined.

Jay Nathan: In 2005, we were probably 125 million. We had just gone public in 2003. And I remember sitting there in the first couple of days that I was there, first couple of weeks, I saw some all hands presentation. They were showing growth over the past couple of years. And I was like, man, I missed all the growth. Well, we went from 125 to 550 million while I was there.

Jay Nathan: And so I got to, I got to experience so many cool things. I got to be involved. I got to run a large team, which I had never done before. Obviously I got to be involved with acquisitions. Um, I got to help launch new products. I was on a tiger team of people that were launching a new product into a new market. We literally sat with our CEO and all the executives of the company every Friday.

Alper Yurder: Yeah, first time, yeah.

Jay Nathan: having like a cross-functional working team meeting about how to get this thing into the market and do it efficiently. And so just, you know, some days I couldn't believe I was still there because it was eight, you know, it was there five, six, seven, eight, almost nine years. Um, but I have so many fond memories. Yeah. It's certainly today.

Alper Yurder: Yeah, that's a very long time. I guess for anybody listening, like more junior in their career, like what is the average tenure of a CEO now? Like 18 months, whatever, two years. So I think nine years is pretty, pretty massive. By the way, yes, of course I couldn't mention everything in your career because it's just full of too many, too many successful things, but I'm going to dive into some of them now. I'm actually very curious to start with your leadership journey and you already mentioned, you know, the first.

Jay Nathan: Yeah. Exactly.

Alper Yurder: of that, what does it mean to be a leader? And then you continue that story with places like Snag and People Matter. Let's start talking about that period. I always love to hear the highs and I also love to hear the lows. Because one thing is we all share the highs very candidly, but a lot of people listening to this podcast are quite...

earlier in their journey and they look up to people like you as leaders and they think, wow, like this guy, you know, he's very successful, blah, blah. But, you know, it wasn't always that way. You know, the road to success is bumpy. So maybe walk us through a little bit of that journey, like the highs and the lows and on the way up.

Jay Nathan: Yeah, well, I'm still on it. Just to be clear, like we all are, right? I mean, we're all learning constantly. You know, I was thinking when you were talking there, I was thinking about the first, probably first year that I was in leadership, officially in a management role where I had been promoted. And what tends to happen, especially in larger companies, we take the best people, the people who are best at doing whatever it is they do, and we make the managers. And I've heard people joke before that level is the playing field for people who aren't as smart, right? Because you, you take the smartest people out of what they're really, really good at and you give them a completely different job, which being a people leader is a completely different job than whatever it is you did before to get there. Um, but one of the big mistakes that I made, or that was just part of my story when I transitioned into leadership, was that I kept a lot of my individual contributor projects and tasks. at the time, because I didn't want to delegate them to anybody as a new leader. And that stunted my growth as a leader. So I would say that, you know, in a lot of software companies, you see that people get promoted from within, which is awesome, but it can be really hard to make that transition. And that was a tough one for me, for whatever reason, uh, there were some complex projects, but you know, when you're, when you're leading people, you're all of a sudden the person that somebody is most connected with at the company from an employment standpoint. So you really have to be there. You really have to be focused on coaching and mentoring and guiding and being a leader, not being the doer anymore. And so that was an interesting experience for me.

Alper Yurder: I love that. Maybe let's stay on that for a second, because I hear this quite a lot. And, you know, how to let go, how to learn to delegate and how to learn to actually not always have the praise and try to, you know, praise others, etc. Those all come together. I wonder if this holds a bit more true for tech sales and because it's such a high velocity, you know, to the moon and especially the last decade, high growth. Well, I didn't come from sales. Sorry, tech sales.

Alper Yurder: I did many other things before. I wonder if there is a bit more tendency to promote fast and that machine, the cycle has to go on. You had the eight demos, now you have to teach someone else to have the eight demos a day kind of mentality. Does that contribute to that friction?

Jay Nathan: Um, I think so. Now, you know, on the flip side of that, like it's an interesting parallel, an interesting point you bring up because guess what I'm doing at Cherokee now. I've just joined about a month ago. We're a very small company and. I consider myself a BDR at Cherokee. I am doing the job very well, yeah. I mean, you know, you're working in a startup as well, but why am I doing that? Why are you doing that?

Jay Nathan: because it's not because that's the job we're gonna have forever. It's because we need to know the market and the motions better than anybody so that we can design the go-to-market strategy that will eventually scale. I always think about doing things that are effective first and then making them efficient, right? If you try to create an efficient process out of the gates without knowing what works and how it works, then you're destined to fail.

Jay Nathan: And so, you know, I think there is benefit in being able to move in and out of knowing as a leader when you get involved hands on in something and when you need to stay out and delegate it. And that's really more art than science. And I don't always get it right. But there are certain things that you can't afford to not know, you know, depending on the stage and size of the company.

Alper Yurder: Yeah. I think it was the CMO of Jellyfish who wrote that recently. I forgot his name, apologies, but he was mentioning something about the leader getting his hands dirty. And I was like, if you want to sit on your ivory tower, look at your dashboards and tell people to do things. Just never be a founder. Because honestly, I've never worked with Gen Z as much as I have in this past year and a half of building Flohola. And, and, and now I'm, as you say, I'm BDR numero uno, I'm the AE numero uno. So I'm on the ground.

Jay Nathan: Yeah.

Alper Yurder: the work. How does that feel for you though? Like, obviously, you know, CCO at Higher Logic, that huge organization, etc. And now you, me, we're in the trenches doing this again. Like how does that feel?

Jay Nathan: It's fun. I think it's fun. Because now, but the danger in it is that you get stuck in that rut, right? You have to know what you're doing and why you're doing it. If you're just running around being an individual contributor, because that's all you know how to do, that's fine, but you have to know that at some point, you're going to get replaced with somebody who can think and scale on a different level than you can. So, yeah.

Alper Yurder: So what, that's really cool. So I want to get do's and don'ts of this, or like best tips of this. Like what mental notes are you taking on that journey of, now I need to crack this because I'm going to start hiring people. What are those two, three notes you're making along that journey?

Jay Nathan: Yeah. It's funny that you asked that because I literally just wrote up a note about a week ago and sent it to the founders of the company who had graciously given me an opportunity to do this with them. And I told them exactly what I'm doing. Like, here's what I've done. Here's the process. Here's the list that I've pulled in Apollo. Here's the way that I'm trying to figure out if they're qualified before I even try to contact anybody. Here's how I'm networking to get to them.

So it's really, you know, those kinds of notes also from a go-to-market perspective, you have your ideal customers, right? Your target customers, but then inside of those customers, you really have to understand the personas that you're trying, the people that you're trying to talk to. Who has the responsibility or the thing that I'm trying to talk to them, talk to this company about. And so some of the notes that I've taken just to open up the kimono, like we have a pretty... broad product that allows you to do a number of different things with credit card subscribers. Yeah.

Alper Yurder: I was gonna come to that, I was gonna come to that, the broad versus narrow thing, like how are you narrowing things down? I'm very curious.

Jay Nathan: Well, you know, initially it's about, when you're trying, you know this, right? When you're trying to get a meeting with somebody, it's about being relevant to what their problem is. And so I can't go in and pitch our entire platform. I need to know if I'm gonna go talk to the chief product officer, this is the problem that I'm gonna go address with that person or.

Alper Yurder: Yep.

Jay Nathan: If I'm going to talk to somebody on the revenue operations team, this is the problem that rev ops teams usually have. I have a ton of contacts in the customer success world. Sometimes they might be a buyer of our products. Sometimes they won't, but I know what their problem is relative to what I do. Um, and you know, the more of those conversations I have, the more the talk tracks, the more the, um, the, the way that we get their attention, the more ideas for content.

Jay Nathan: that I can put together that I know will resonate with the problems that they have, which we are trying to solve in a systematic way. Yeah, so I just, I think it's a lot of fun.

Alper Yurder: Yeah. I realized I, yeah, back to that. I already caught you twice there because we were talking about the fun of, you know, going back to the, you know, being in the trenches, but because also this is about you also, Jay, I think I realized, you know, there's so many creators, influencers, whatever, but when you write something, it is full of context and data and actual real stories that it makes it so interesting, which is probably why I caught you twice already there.

Jay Nathan: That's right.

Alper Yurder: You mentioned the problems of CS context and network. What are those three, four top challenges of CS people at the moment in your observation?

Jay Nathan: Wow. Well, right now I think there's a lot of, um, there's a lot of scrutiny on customer success teams. And so what's happened in the world is there's no doubt that in a SaaS company, customer success is a requirement, but I'm not talking about a team of people. I'm talking about the outcome. Um, I have a good friend, his name is Dave Jackson. I don't mind promoting him at all.

Jay Nathan: He says that customer success is an organizational capability. It's not necessarily delivered by a thing called a customer success team. So think about your product, think about your go-to-market motion, your selling approach. Think about how you show value after the customers have started using it. Think about how you onboard the customer to get value quickly. That's all part of a comprehensive customer success motion.

Jay Nathan: And what's happened over the past 15 years is that we've had a ton of investment in SaaS companies. Um, a lot, you know, many of your listeners are probably well aware of that. A lot of these companies have not, they've not delivered on the, um, the results that they needed to have the valuations that they had at their last fundraising round, they're upside down, just to say it really simply, right. But with all the fundraising that's happened in the past decade with zero interest rates and plentiful cash, we've built these teams and we've done a lot with humans that should be automated and should be done in different ways through the product, through tooling, and we've thrown people at it. So I would say right now, the biggest challenge that customer success teams have is justifying their own existence relative to the cost scrutiny that's now present in the SaaS industry.

Alper Yurder: Really? I mean that's so interesting. That would be so contrary. I think your train of thought was very much in line with what I had in mind, but now I'm a bit confused. Let me explain. To me...

At the end of the day, you build the best product, but like competition is on product and price. I think like there's a, there's 10, 15 other products that can do what your product does to some level. Right. So then when people ask me things about, okay, I want to do this with Flola. How do I do it? It's more than actually tapping into my knowledge, my best practice. You know, the human. So, okay. If you send a flow like this is gonna, you know, improve your chances of closing. No, no, no. At the end of the day, I'm trying to build that into the product. Right. But it's human knowledge. It's the.

Jay Nathan: Yeah, that's right.

Alper Yurder: And I think that is the element of service, customer service, customer success, whatever. So to me, I see the customer success function, although I started from sales and my first CS colleagues maybe hated me for just being a sales guy. Then I understood what it was. And to me, it's so crucial and fundamental. It's right in the middle. So am I getting this right? Are you saying CS is trying to figure out their role in all this? Or maybe I got it completely wrong.

Jay Nathan: I think you have it right. So, a few things to unpack there. So what you said is absolutely correct. That is what we're trying to do. We're trying to make sure the customer is activated and that they understand how they're going to get value out of this product and how to get more value out of it.

Jay Nathan: My suggestion here is that a CSM is not the only way to accomplish that. Customer success manager, yes, I agree, we have to do that. If customers don't get value, if they don't get onboarded appropriately, if they're not getting coaching and mentoring and guidance along the way, how can we keep them in the long run? But the question is then, how do we deliver that kind of experience to the customer? You have to have a great support team, right?

Jay Nathan: A support team is different. It's more reactive. I have a problem, I'm gonna tell you about it and you're gonna solve it for me. That's what support does. That experience needs to be smooth, fast and seamless. Not delightful. It doesn't, delightful doesn't matter. What matters is low friction for me as a user. Right? Now, what you bring up is a really good point. How do you use our product to do your job better?

Alper Yurder: Mm-hmm. Solve my problem. Yeah, yeah. Low friction, yeah, exactly. So, I'm going to go ahead and close the slides.

Alper Yurder: Get the best value. Yeah. OK.

Jay Nathan: That is really customer success, right? So that can be done in a bunch of different ways. Again, through the product, a lot of these products that are out on the market today have not really been designed for customer success. Can you see the results that the customer is getting even as a CSM or as somebody that's sitting inside of the company that's selling it? How would you coach the customer?

Alper Yurder: Yeah, it's almost like you need another product to coach how to use the product. It's almost like many of those instances. Yeah. Okay. Now. Yeah.

Jay Nathan: Yeah. Or a community or a knowledge base, right? You know, the reality is if you sell a high dollar product, if your ACVs are, you know, 10,000, $20,000 plus, then you could probably afford to spend more time one-to-one with each customer. But if you're selling a product for $2,000 a year, which many people are, right, how do I do that at a cost-effective clip? Well, I hold webinars for my customer community. I

Jay Nathan: You know, publish a knowledge base. I send them emails every week with tips and tricks on how to do things better. I personalize emails that say, hey, here's what your results have been over the past 30 days. And here's some recommendations automatically generated that you could use to improve your results with our product. So I just think there's a lot of different ways to come at it and hiring a team of CSMs isn't always the right answer.

Alper Yurder: Gotcha, okay, now that's more clear. So now my follow-up question to that would be, we'll come to the experience now at Cherokee, et cetera, but before I go to that, I guess as a CCO at HireLogic, like, you know, huge company, blah, like the tools and tricks and methods and strategies that applied there are gonna be, I guess, different from a smaller startup or somebody at their series A or B.

So my question is like, what were some of the issues you were dealing with at that time? What did you learn from there? And to what extent they applied to a smaller organization or do they? That's a long question. I'm aware.

Jay Nathan: Yeah, no, it's a great question. It's a great question. So in, you know, basically like what are the, what are the challenges in a larger organization and how do they relate to those in a smaller organization? Um, a lot, the bigger the organization is, the more work it takes to just create alignment on a day-to-day basis. What is our strategy? What are our plans? What are we focused on? What are the metrics that really matter? There's just a lot of repetition.

And I think that repetition is important in both large and small companies. You have to have a North Star. You have to know what you're pursuing and why. People get a lot more excited if they know they're part of something bigger than just making their next sale or making sure that next renewal happens or having that next call with the customer to drive adoption. So.

Alper Yurder: Of course.

Jay Nathan: So those things apply, but they apply differently because you don't have to have as much rigor in a smaller company as you do in a larger company in terms of how you communicate those things. But the frequency does need to be there. Other than that, I think as you scale and get larger, the processes are just a little bit more heavy because you've got a lot more volume to deal with, frankly, where we might have several hundred customers at Cherokee. We had thousands of customers at HigherLogic

Jay Nathan: different renewal dates and you just have to, you have to run, you know, more robust processes to manage those things. But at the same time, what's really important, and I'll say it in reverse, is that early stage companies do really well, they just move quickly to solve customer problems because they know it's a life and death thing. Larger companies don't do that as well. And I think if you look at companies like HubSpot, they've done a great job of it.

Alper Yurder: Yeah, of course.

Jay Nathan: of it, right? They've created new products. They iterate quickly. They build very smooth user experiences into their products. So they really do move like a small organization, even though they're really, really big these days. So I think you could take good and bad from either and apply it in either direction.

Alper Yurder: Okay. And to close that leadership section, my last question would be then, it sounds like you've got it all figured now. And I know you're in your journey, but it sounds like you've got it figured. I'm going to ask you, how did it feel to have that title for the first time? You know, CCO, Chief Customer Officer.

Jay Nathan: Um, I mean, I don't get hung up on titles that much. Um, I guess it's easy to say, but I mean,

Alper Yurder: Okay. Oh, okay. Let's move on then. No, I'm sure that, I mean, of course we say that, but at the end of the day, I think titles mean something at the end of the day, to me, at least it did in my career.

Jay Nathan: Well, they do. They do. And one of the titles that I was most proud of was being promoted to a director at BlackBod because it was a big organization and that was not a small promotion. So, I guess I was being a little magnanimous by saying I don't care about titles, but where titles are more important is when your customer is looking at you. Like, who am I talking to? Like that's really key, right?

Jay Nathan: Um, and because if a customer needs help or they need to escalate something or, you know, somebody from the company is trying to reach out to the customer and to make a contact that we haven't had before or a prospect, right. Then that title does become more important because it's like, okay, this is an executive reaching out to me from this company, maybe I should listen. Right. Whereas they might have a tendency to disregard people with lesser titles, right, wrong or indifferent, that happens every day.

Alper Yurder: Yeah, I guess it was like, what is it? Yeah. With any heuristic, it signals something to people. It makes it easy to understand. So that's why I think titles at the end of the day, unfortunately, are important and they're a good way to motivate people when you can't throw some money. Okay. Moving on to today, let's talk about some of the more current issues you're dealing with and you know, in your day to day.

Alper Yurder: So you've been an advisor to Cherenki. Can you tell us a little bit about that and then the move from being an advisor to actually being part of the operating team, a leader in the team? How is that experience for you? And why did you make that move? If I can.

Jay Nathan: Yep.

Jay Nathan: Yeah, great question. So, yeah, I joined Cherokee as an advisor back in August of last year. And when you get old like us, Alper, people look at your experience and they look at yours.

Alper Yurder: I don't accept that. I love the pose though. I love the pose for validation and I'm not accepting it.

Jay Nathan: I expected a little push back there. They, um, well, people look at you and say, Hey, like this person's been active in this particular industry. We're trying to grow in that particular industry. Um, in, you know, maybe there's some help that they can provide. So an advisor is really someone who can help open doors, um, for the company. It's someone who can. You know, maybe give some guidance. It's sort of like a board role. It's not a board. I'm not a board member of Cherokee, but.

Jay Nathan: It's like a board role where you can say, you know, from arms length distance, say, Hey, like, here's a way to think about some things. You've probably got advisors in your company. I hope you do. Um, and they're, you know, they're just good outside. You never do right.

Alper Yurder: We don't have enough. I'm sorry to cut you there. We don't have enough. Just a shameless plug there, yeah.

Jay Nathan: You never do. But... So advisors play a really important role in a couple of different facets. I mean, maybe even just a shoulder to cry on for the CEO, right? Or the founder. So, but the reason that I was open to joining as an advisor is because the company built a great product, they have a great team. Oh, look at that little bubble popped up. And...

Jay Nathan: they're in a market that's growing. Those are the three things you really want to look for when you look for a company that you want to be involved with in any way. Do they have a good team? Do they have a great product? And is it a market that's growing? Those are three things to always look for in a career move. And I found all three of those with Cher and Key. And I got really excited about the business that they are in. And I knew that I could add something else to what they were already doing, which is important for me.

And so, you know, I left higher logic in December and, you know, the timing worked out great for me to jump in and start helping these guys on a more operational day-to-day basis. And so that's what I did. I mean, my goal is to help them grow fast enough to, you know, it's sort of a fractional role today, but my goal is to help this thing grow fast enough where this becomes my next full-time gig, because I believe in what they're doing. So.

Alper Yurder: Excellent.

Alper Yurder: Wonderful. So you have full incentives to make it work then. I love that. And in the day to day, you already mentioned you're getting your hands dirty with the go to market, et cetera. By the way, I think everybody would like to pick your go to market notes. If you share them at some point, you know how people are doing these LinkedIn things and you have to comment to get them. Maybe you do want to, but what are you establishing?

Jay Nathan: That's right. Yeah, that's a good idea.

Alper Yurder: I mean, you don't need it, but what are you establishing right now? Like what's that base like once when you feel like, OK, I've established this first phase now onto the next phase.

Jay Nathan: Yeah, it's a good question. So I've been here about a month and what I have been doing is, I think I told you this before the show, but I've become a BDR. I'm prospecting every day. I spend two to three hours a day prospecting. And number one, I'm doing that because we actually don't have much of a marketing motion for mid-market enterprise. Most of what we get today and we're growing very quickly today, even despite this comes inbound with very little marketing. The team has just built a great reputation in the market and people are starting to find us and come inbound. We believe there's an opportunity to take the product that we have today, which is enterprise grade and move up market with it, which is my mandate. And so what I'm doing is going out to the market and trying to generate as many conversations as I can. And figure out

Jay Nathan: Who is it that I'm selling to? Who are the personas? Like what does an ideal customer look like? And so that we can then begin to go create marketing campaigns. We can go create a more robust system. BDR outbound selling program. Like my network is not going to take this company to a hundred million in ARR. It'll get us somewhere to start with, but the goal is to leverage my network and you know, some of the contacts that I'm able to make.

Alper Yurder: What is it that you need?

Jay Nathan: to learn about the market so that we can go tell our story more broadly and in a more scalable way. So that's the first step. That's the first step. The next step is really then to start laying down the first, I guess, marketing tracks. Like what kind of paid attention do we get? What kind of earned attention are we gonna go try to drive? Where do we need to go to play that's not our own media, right? Like where do we go to participate?

Alper Yurder: Okay. So in there, I try, okay, I try, I think I figure the kind of challenges you're going through. So this was your therapy so far where you were sharing with the problems you're trying to solve, right? But now I'm going to put you on the therapist chair. And this is a new section that I'm trying and you know, feel free to answer in your own way. But no matter what, I'm trying to get to like

Jay Nathan: Alright.

Alper Yurder: for my own egoistic reasons, practical tips from leaders. And I think people who are listening to this are enjoying it, and then this goes to our media hub and et cetera. So I'll have a few rapid fire question types if you don't mind. So maybe let's start with that last point that you mentioned, that move from mid market to enterprise, everybody talks about it. In your experience, are there like one or two things that are a must have to go up market? And what are they?

Jay Nathan: Well, you know, I think one of the biggest challenges for technology companies today is data security and privacy. It just is. You can have a beautiful product that meets a need in the enterprise space, but if you don't have your security certifications and you have issues on the data and privacy side of things, you're never going to get it into even mid-market. And by the way, maybe we should do some definitions. I think about...

Jay Nathan: looking at the tech space, SMB typically 200 employees and below, mid market 200 to about a thousand, and then a thousand and up being enterprise, even though a thousand employees is pretty much a small enterprise business. But if you don't have a really strong security stance, it doesn't matter how good your product is, you won't be able to get it in. I think you also need, when you're moving up market, you need people who...

Jay Nathan: Understand a team purchase environment and know that the first person you make contact with is probably not the person who's approving the budget for this purchase. So, you know, it's just a matter of sort of understanding the organizations that you're dealing with and becoming a student of that, right? No matter what industry you could be selling into healthcare, you could be selling into manufacturing or retail or e-commerce or SaaS like we are, and you really need to become a student.

Jay Nathan: of those industries, right? So that you know what the trends are. You know how those organizations typically make decisions. That's just non-negotiable. If you're really going to create a motion that scales.

Alper Yurder: Yeah. I think the first thing that you mentioned was definitely the first thing I would have mentioned. And on that second point around, you know, team selling, definitely you're selling to a panel. And that's kind of my experience has always been like a decade of enterprise sales. That's why I started building Flola. And now I have the startups building to enterprises, sorry, selling to enterprises. And sometimes they come and say, you know, I thought my champion was X.

But then I saw this why appear out of nowhere and engage with the content. And that was actually my champion. That's how it helped. I mean, that's the story of an enterprise sales director or whatever, trying to figure out, you know, the complexities in a deal. And, um, I agree with that. Okay. This next one is you have a whole newsletter and, um,

Jay Nathan: Yeah, that's right. You gotta understand it.

Alper Yurder: And there, you sometimes talk about, you know, CS and sales collaboration. I think that collaboration inherently has a lot of friction and, you know, some of my lead career has been trying to figure out how to remove those frictions. Do you have any sales to client success collaboration slash handoff tips that work like magic, no matter where you go?

Jay Nathan: Hmm. Sales to service handoff tips. You know, there's depending again, depending on the size of the deals, like there's some threshold at which, you know, documenting the value prop and the players, like some of the basics that you capture during a sales process, what is the customer trying to achieve? That's, you have all those conversations during a sale in theory, right? You really have to connect.

Jay Nathan: Salespeople don't have a choice. They've got to connect the product with some kind of tangible value for the customer, or it won't get by the CFO, not in 2024. So those conversations are all being had. The thing that I find missing most often is just a quick summary of those points, right? That alone would make a huge difference to the team that's onboarding the customer, the team that's got to manage the customer in the long run is that. Now,

I think this is also an area where AI is just really, really going to help accelerate that a lot because I mean, we use something called grain today. We record all of our sales calls, we record everything. Like there's no excuse today for not having that summary because it can be done for you without you having to lift a finger to type anything out as a sales rep. So I put that on. Say again.

Alper Yurder: But is a summary enough in itself if you're not having a timeline, a mutual action plan, holding people to account for things? How do you make it actionable then?

Jay Nathan: Oh, you have to have all that. You have to have all that. I'm just talking about the sales to service handoff, right? Which is any of the context, if we just start with context, we'll already be doing better than 80% of the companies out there, right? And so, no, I don't think it's enough to close a deal on its own, but having those summaries and they're pretty good. I have to tell you, I took a transcript of a call the other day. This is before I started using grain a couple of weeks ago.

Jay Nathan: Um, which is a call recording technology. I've been a gong user forever. I love gong, but I took the transcript out of a call directly from zoom and I dropped it into chat GPT and I told chatGPT who I was, what I was trying to do, and I said, please summarize this. Prospect phone call into. Oh, the points. And would it spit out? I shared with my team. There were seven bullet points. I pasted it into Slack and.

Jay Nathan: You know who was most appreciative? There was a ton of product feedback. My CTO was most appreciative. He was like, Oh my God, this is amazing. And I didn't do much to generate that. Right. So there's just so much context that happens in these calls and these interactions and these emails. And if we can easily get that summarized and stored somewhere in the CRM so that we, everybody who needs to touch that client after the fact has access to it. That's a huge win. So to me, just flow of information.

Alper Yurder: Yeah, I love that. Okay. Already a big win. Okay.

Jay Nathan: And it's also a benefit to the customer experience because what are we trying to do Alper? We're trying to take friction out of the customer experience not just in support, but with every interaction. And so if I can read those notes and say, okay, Alper, I'm coming to you, I already understand X, Y and Z about Flowla. Now tell me what else I need to know. Boy, that's a much better experience than starting from zero.

Alper Yurder: Yeah. Builds a relation, builds a relation, credibility adds so much value. Like it makes it much more human. You care about me, et cetera. Okay. This section, I'm going to do really like 30 second answers. Okay. So I'm, I know I'm pushing your limits. I apologize for that. These are specific questions from our users and you can skip it, answer it, do whatever, but in 30 seconds. One, what's the one thing all customer success people love and one thing they don't?

Jay Nathan: That's right. Okay, all right.

Alper Yurder: Maybe you mentioned the good notes already. So you mentioned what they like.

Jay Nathan: All right, one thing they love, I would say, love it when those renewals come through. One thing they don't love is being introduced as an extension of support. We'll just leave it at that.

Alper Yurder: Yeah. Okay. Love it. Love it. Okay. And this one is a good segue to the next question. What signals do you look for that retention to happen like? Or is there a ritual? Is there a time behavior? When does retention become top of mind and what do you do to retain?

Jay Nathan: Well, I'll keep it to 30 seconds. You always have to be thinking about retention in terms of how you sell, because I mean, retention is literally the lifeblood of, besides cash, it's the lifeblood of a subscription business. You have to retain your customers. So thinking about those motions needs to happen very quickly after you start a company. And it's not just about the renewal. It's about showing the value early so that the renewal is a non-issue. It's a non-event.

Alper Yurder: Mm-hmm. But in a big... I mean, I agree with all that, but maybe you had your trip, I don't know, especially in large companies, like three months before, or these things have to be done. Did you have any written processes or anything like that?

Jay Nathan: Yep.

Jay Nathan: Oh yeah, absolutely. So a good process starts at least six months ahead with sending information on the value that the customer's gotten and helping them understand that their renewal is coming up. A lot of companies will even ask the question six months ahead, hey, if your renewal was today, would you be renewing with us? And that's a good way to ask a hard question early so that if you need to make some adjustments, you can do that before it's actually time to go through the renewal. But yeah, I mean, there's some complexity there too that people need to be aware of because typically, a lot of companies, if you're on an invoice kind of basis, there's a point of no return at 90 days, right? You auto renew in a lot of cases, you're sending an invoice 30 days ahead of the renewal date so that it's paid on the renewal date, right? So...

Alper Yurder: Yeah, absolutely.

Jay Nathan: Yes, there's a sequence in an order to... Yep.

Alper Yurder: Little tricks off the yeah, yeah. Yeah. And actually the other question was what's the golden period for retaining existing contracts? Like, you know, and I think you kind of mentioned that. I think, and I need to have you back for all these specific questions. And I'm sorry, I'm making it extra hard with this 30 second, where you're doing great. Last two, the last, the last two. One, one mistake companies can make.

Jay Nathan: We could probably do a whole podcast just on that. There's so much to it. Yeah. Thank you.

Alper Yurder: avoid to make sure that return. Okay, I did a terrible job. Like we'll edit that out. It's my end of day and I think I'm getting tired or we'll keep it in. One giant mistake companies make that leads to churn. That's a better way of asking that question. Well done.

Jay Nathan: The biggest issue that many companies make that leads to churn is onboarding. They don't do a great job of getting their customers onboarded and activated and launched. I used to run a consulting firm, we worked with SaaS companies and that was the number one issue we were working with companies to fix most of the time. If you have a churn problem, start at the beginning to look where the seeds of churn were planted, it's usually one of them.

Alper Yurder: I love that. And the last one, what is a good QBR to sit on? Or do people do QBRs anymore? I don't even know.

Jay Nathan: I was going to say the one you don't have to sit on. I think QBRs are terrible. This, what you and I are doing right now is the way to do a QBR. You have a discussion, right? Send information ahead that shows the performance of the account, that shows the opportunities, and then sit down and have a two-way discussion. Don't show me slides. I will not sit through that. As an executive, I won't do it. So, yeah.

Alper Yurder: I love that. Okay, so we'll, excellent. Let's finish on a good note now, Jay. Is that hope for the world of tech sales?

Jay Nathan: Is there hope? Is that what you asked? Is there hope? Of course. I, I think, yes, I think sales is a highly noble profession. I think we have really tried to over process it and make it into more of a machine than it is probably ready to be in most companies, um, selling something is all about.

Alper Yurder: Hmm. Yeah, that's the question. Is there hope for the world of tech sales?

Jay Nathan: is all about two-way exchange of value, right? It's not about features. It's not about, it's not about, it's just a two-way exchange of value. And I think to sell something, nothing happens until you sell something in a software company. And I'm a customer guy. That's been my remit for the past 20 years, but I've always had great relationships with my sales teams, supportive of the sales teams, because I know where...

Jay Nathan: The dollars come from in a business, right? And I know how they get delivered as well. So it's a healthy push and pull relationship between sales, customer success, marketing, product, all the go-to-market teams have to be working together in a task company to make it work.

Alper Yurder: Yeah. All right, right. You say you're a customer success guy, but now with this new role, you're shifted to the dark side, Jay. You are a go to market slash sales guy. So welcome on board.

Jay Nathan: Well, thank you. I've been doing it for the past couple of years, but I understand that, you know, I've made the shift to the dark side for sure. I'm happy to be straddling the line, I'll tell you that.

Alper Yurder: Yeah, okay. I love that too. As you say, I'm sorry I'm going to have to cut us on time like any good therapist, but this has been an amazing show. You need to come back like when are you coming next week? I'm joking, but definitely in a couple of months. So any closing remarks before we go?

Jay Nathan: Let's do it. No, I appreciate you having me and excited about what you're doing. So keep up the great work and let's stay in touch for sure.

Alper Yurder: Thank you. Excellent. Now that's a wrap on this episode of Sales Therapy. If you enjoy the show, subscribe to us on YouTube and on your favorite podcast platform. Otherwise, see you in the next episode. Bye.

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