216. Why Every CSM Needs Commercial Skills in the Next 18 Months ft. Jon Johnson (Gainsight)

I think especially when we’re looking at, like, defensibility, like, with these jobs, specifically as CSMs, and I know that there’s a massive amount of CSMs in the marketplace that are going like, what is my job gonna look like? Get a hold of the money as soon as you can. And I don’t mean that, like, in an— maybe it is aggressive, but, like, that’s how we justify the jobs. It’s accountable. It’s accountable.

Jon Johnson:
And, and if you don’t have the soft skills to negotiate and work through that, that’s where you start right now. If you’re not there in the next 18 months, you will be forced there in 18 months. And it’s going to be a difficult conversation.

Josh Schachter [Host]:
You’re listening to Unchurned, brought to you by the Gainsight Podcast Network. Subscribe to our Substack at unchurned.gainsight.com, where we go deep on every episode, like how one post-sales team at Cloudbeds built over 150 AI agents. That story and more at unchurned.gainsight.com.

Jon Johnson:
Dude, this is so much better than our bedrooms when we started this thing.

Josh Schachter [Host]:
I mean, legit, right? I know, it’s great.

Josh Schachter [Host]:
It’s a great experience.

Josh Schachter [Host]:
Okay.

Josh Schachter [Host]:
Hey everybody. Did you fart? No. Can that go in the blooper reel?

Jon Johnson:
No.

Josh Schachter [Host]:
I heard a squeak. I did that for social media.

Jon Johnson:
So happy to be here. Yeah, yeah.

Josh Schachter [Host]:
Hey, everybody. Welcome to this week’s episode of Unchurned. I’m your host, Josh Schachter, Senior Vice President of Strategy and Go-to-Market Development. That’s the 3rd time that I’ve had to do this first intro line because the laughs have already started between my very special guest today in studio in New York, Jon Johnson, Strategic Principal Customer Success Manager.

Jon Johnson:
What do titles mean anymore? Is that it? Principal Customer Success Manager on the strategic team.

Josh Schachter [Host]:
Okay.

Jon Johnson:
Yeah. Okay. Yeah. You had it a little backwards. It all counts.

Josh Schachter [Host]:
I usually have it all backwards.

Jon Johnson:
Yeah, it’s true.

Josh Schachter [Host]:
Well, welcome, John. This is great. You and, and our former co-host.

Jon Johnson:
Yes.

Josh Schachter [Host]:
Of Unchurned.

Jon Johnson:
It is nice to be back.

Josh Schachter [Host]:
OG. You were always the favorite. Literally the fan favorite.

Jon Johnson:
I’ve heard that. Yes.

Josh Schachter [Host]:
I mean, like, we would be at Pulse. This is like before we— I would— you and I were part of Gainsight and we’d be at Pulse and people would come up to me and be like, oh, you know, John’s our favorite. Like, yeah, thanks.

Jon Johnson:
Fuck you. I, I would Venmo them after they said that.

Josh Schachter [Host]:
No, no, no, no, no, no. You have an aura. You’re You’re funnier. You’re more articulate. You know more about customer success.

Jon Johnson:
That is true.

Josh Schachter [Host]:
I’m better at the negs.

Jon Johnson:
Yes. And being late to the podcast studio.

Josh Schachter [Host]:
Yeah. Well, don’t even get me started on tardiness. But outside of that, I think you’re better in everything.

Jon Johnson:
All right. I’ll take that. We have that on film. We do. Yeah.

Josh Schachter [Host]:
And that’s it. That’s it, folks. That’s how we— so cool. We’re going to talk about customer success, your role in customer success, what you do at Gainsight, customer success, the future of customer success, All things customer success and poetry.

Jon Johnson:
And poetry, which is very tied closely to my belief in customer success.

Josh Schachter [Host]:
Yeah, we’re going to get a little bit into the human John element here. So for those listening, if you want to, I’d recommend skipping the last 20 minutes. So what’s your role at Gainsight? We know the title now.

Jon Johnson:
Yeah.

Josh Schachter [Host]:
Let’s back up. What do you do at Gainsight?

Jon Johnson:
Yeah, so our strat team encompasses the largest of the large. Not just enterprise accounts, these are global multinational brands that have entrusted Gainsight to run their revenue motions. My job is less order taker, QBR support question, and more program management. It’s really looking at the entirety of what our customers are doing within our software and within their ecosystem and trying as hard as I possibly can to map as many outcomes as we can Yeah. To the 8, sometimes 9 figures that people are paying.

Josh Schachter [Host]:
There’s a lot of pressure on that.

Jon Johnson:
There is a lot of pressure, yeah.

Josh Schachter [Host]:
What are some of the outcomes that you’re mapping?

Jon Johnson:
I mean, right now, the biggest focus is what are we doing with AI and how do we map to an outcome that is gonna change in 3 to 6 weeks or months or even, right? I mean, in the past, it’s been something that says, hey, in, Q1, we’re expecting this roadmap feature and it will tie to this outcome, but things are happening so much more, I guess, quicker, faster, with more energy that that needle is moving on a daily basis. So what it really comes down to is we say being the human in the loop, but it really is being in seat and aware of all of the planets that are circling around the account that you’re in and making sure that everybody has as close to an understanding. We use the word alignment a lot in the past, and that’s, that’s going to continue, but I, I, that’s not really what it comes down to. It’s just understanding where everything will come into alignment.

Josh Schachter [Host]:
Yeah.

Jon Johnson:
As things move, because they will, and they’ll ebb and flow.

Josh Schachter [Host]:
You’re kind of the control tower or the centripetal force.

Jon Johnson:
I, I’ve used the term, uh, cruise ship director You would be more

Josh Schachter [Host]:
of a cruise ship director.

Jon Johnson:
Yeah, yeah, yeah, and with the buttons, and the pins, and the drink tickets. And just coming off of Pulse, I will say that was also my role in London last week with my customers.

Josh Schachter [Host]:
Yeah, that sounds like a great way to get customer success a seat at the table is to start referring to us as the cruise ship directors.

Jon Johnson:
Yeah, absolutely. Like, I’ll bring you a coffee and a renewal form.

Josh Schachter [Host]:
People have called you the greatest customer success manager of all time. What do you do differently, John? We’re not taking any cuts here, so you better talk.

Jon Johnson:
Okay. Thank you. I’ve had enough coffee for that. I

Josh Schachter [Host]:
said, by the way, I said you— you did. I said you all the questions except for that one.

Jon Johnson:
Except for that one. Yeah, man, I think, I think the heart of it is there is an empathetic nature that I carry with me. And I think it does come from a lot of like my artistry and my background as like an individual. But when we’re working in these large-scale organizations, a lot of times people just feel like a number. Even CCOs, even CFOs, even the highest principal that you can meet in a GM, in a go-to-market strategy who’s got a title that changes every 6 weeks, right? Um, that’s still a person. It’s still somebody who’s gotta take care of the kids on the weekend and has a soccer game. And when I come back down to like the heart of what I love most about this industry, it is that I get to sit in a room and I get to understand this person. And I think if we can continually bring it back to the fact that we’re not just moving zeros and ones, and it’s not just the MCPs and the CLIs and the agents, but that it’s It’s driving towards what an individual needs in order to find value and to be found valuable.

Jon Johnson:
Mm-hmm. I think this is the thing that adds like a little bit of a superpower is we talk about corporate and enterprise value all of the time. But again, that CFO that’s sitting on a board needs to feel valuable. And if we can connect those 2 things to the, here’s the $10 million that you spend and we’re gonna get this growth and we’ll find this package, But that person did a good job and made something better for them. And if we can center on that, it gets us into that trust that we have to have when we go into this, we’ll say, headless future that is going to be a little bit more autonomous. It’s going to be a little bit more probably convoluted at times, and there’s going to be a lot more motion. There’s probably going to be new titles every 6 weeks. There’s probably going to be new strategies every quarter rather than every year.

Jon Johnson:
So if we, if we lose that part that I’m a human being, and yes, I’ve got all these agents and these automations, and so does my customer, but we’re still 2 people that have a goal, that have a number, that have an outcome that they need to match, um, we’re going to get into that greatest of all times.

Josh Schachter [Host]:
So truly human-led. I mean, you love the human element. I do. We’re going to get into your poetry book. It’s all— I mean, there’s nothing more human than that, except the fact that you wrote it all with Claude, but

Jon Johnson:
I want to be very clear that I did not.

Josh Schachter [Host]:
I saw an em dash. I saw an em dash.

Jon Johnson:
And I will own my em dashes, and I will— I have been writing my em dashes since college in the early 2000s.

Josh Schachter [Host]:
Okay. Wow. Wow.

Jon Johnson:
Yeah.

Josh Schachter [Host]:
Okay. Yeah. You’re a human guy. Yes. You’re very, very human. You cry, you laugh. I do. You’re very emotional.

Josh Schachter [Host]:
Some might say too much. I agree with that. No, I was just— I’m just joshing you. I don’t know where I’m going. So you love that, the human element. How do you make the customer the hero? Because that’s what I heard in your superpower.

Jon Johnson:
Yeah, I think it comes down to— I’m going to use the word that you hate— is alignment. Like, what matters—

Josh Schachter [Host]:
Use a different word. Can you find a different word to use than alignment? Because alignment makes it sound so corporate. And you are too human for that.

Jon Johnson:
Yeah. Synergy? I went more corporate. No. centered. I’m gonna say centered. Okay. What’s important to an individual and what does somebody take value in? For me, it’s a lot about beauty and music. Like, I’ve taken you to concerts.

Jon Johnson:
The last time I was up in New York, we went to an emo show in New York, and like, that is me bleeding into this relationship that I care about with you, right? So finding those moments with an individual at the executive level is more than just talking about weather or Goals. Yeah.

Josh Schachter [Host]:
You ready for a human moment?

Jon Johnson:
I— oh gosh, yes.

Josh Schachter [Host]:
I thought we had discussed this, but we—

Josh Schachter [Host]:
I guess we didn’t. You asked me about my hat when I came in.

Jon Johnson:
Yes. Yeah.

Josh Schachter [Host]:
We’re pregnant.

Jon Johnson:
What is this? What?

Josh Schachter [Host]:
No, there’s no— this is— you’re not being punked.

Jon Johnson:
When did you—

Josh Schachter [Host]:
my wife Jess and I, who you know—

Jon Johnson:
I do.

Josh Schachter [Host]:
We’re, we’re due in mid-April with our first baby girl, so I had to buy the Girl Dad Company hat.

Jon Johnson:
I am so pleased. I am so pleased, Josh.

Josh Schachter [Host]:
So I know you are such a human person.

Jon Johnson:
Yeah, and I have 3 kids.

Josh Schachter [Host]:
And you have 3 kids, and you’ve got a girl.

Jon Johnson:
I am a girl dad, yes. My youngest.

Josh Schachter [Host]:
We’re not gonna divert this episode into all about girl dads’ tips and formulas, but I’m gonna need some of those from you.

Jon Johnson:
Yeah, but you’re also gonna be great.

Josh Schachter [Host]:
Thank you.

Jon Johnson:
You are.

Josh Schachter [Host]:
Thank you, yeah. Knock on wood.

Jon Johnson:
Yeah.

Josh Schachter [Host]:
Um, you, you’ve done the CS thing now for, for how many years?

Jon Johnson:
15 years.

Josh Schachter [Host]:
15 years?

Jon Johnson:
Yeah.

Josh Schachter [Host]:
And you’ve been part of true startups?

Jon Johnson:
True startups.

Josh Schachter [Host]:
Like, what’s the smallest startup that you’ve been part of?

Jon Johnson:
Oh man, I had to go way back. Um, I would say Zinnier was a construction startup. Um, I think I was employee Under 40 in the US. I was first of on the CS team. I got to hire a global CS organization from zero.

Josh Schachter [Host]:
OK. And then you’ve done scale-ups?

Jon Johnson:
I’ve done scale-ups.

Josh Schachter [Host]:
What’s a scale-up you’ve done?

Jon Johnson:
Scale-up would be Invoca. We were just starting to— it was actually my first CS job, is when we were just starting to develop the CS model of what revenue retention looked like.

Josh Schachter [Host]:
And now you’re doing— PE enterprise.

Jon Johnson:
Yeah. At Gainsight. And I’ve actually been in the space for about 10 years. So before Gainsight— actually, it’s— I have to do the math. So 7 years, because numbers are important. This is my second, I guess, PE-owned organization on this strategic enterprise side, kind of working with these global multinational organizations.

Josh Schachter [Host]:
How do they all differ? That’s a very open-ended question.

Jon Johnson:
Yeah. Well, I mean, it’s— stakeholder management is the thing that I always come down to. Like, people talk about numbers and they talk about teams. When you get up to this level, it’s less meeting with like a senior customer success manager or a senior manager of to talk about deployment and usage, and it’s, hey, I’ve got 4,000 CSMs and I need to build a dashboard that’s going to be communicative to everybody. So we spend— I spend most of my time in what I call requirements gathering. Hmm. And this is just validation before we deliver, because these are such large numbers. We’re talking about thousands of CSMs across the globe that work for the company that I manage.

Jon Johnson:
And it’s so different than, hey, here’s 4 CSMs, and I’m just going to build them a widget, and they’re going to get rolling, right? So it takes time. It takes— And

Josh Schachter [Host]:
you’re saying when you work for the more SMBs, the startups, the scale-ups, it’s smaller companies. Not only is your client—

Jon Johnson:
Well, and the nimbleness is the word that I would say you have with that, is that you can throw things at the wall, and if they don’t work, Next week you have a meeting and you try something differently. When you’re in these global organizations, you need approvals, you need— there’s people call it red tape, but it’s also just validation because we’re talking about thousands of people that have very different scopes and very different jobs.

Josh Schachter [Host]:
For somebody new in their career, what’s the better place to start?

Jon Johnson:
Oh man, um, this would be really hard if I didn’t have the foundational understanding of what customer success is, if I didn’t have like the lapse in me in that SMB to mid-market. I generally think enterprise in general is a more interesting space because we have bigger numbers, there’s budgets, you get to run executive meetings in a very different way. Yeah. So like, that’s always gonna be like where I think the power of these roles are. And even as we get further into like the AI future, I think that’s where the seats are going to be more than on the SMB. and, you know, scale-ups or true startup side.

Josh Schachter [Host]:
How is the role changing from what you’ve observed, let’s say over this year, 2026?

Jon Johnson:
Yeah, well, they keep like giving us revenue and taking revenue away, and like it is just this constant like pendulum swing of that. But more so now, the biggest change that I’ve seen is the necessity to be at the at the highest point, the most executive level that you can. And when I remember starting out in some of my early CSM jobs, like just senior CSM or even just a basic CSM, it was like if I talked to a CCO, it was once a year in an EBR and they did not know my name. Today, because we have so much automation, because we have so much tooling that solves some of these like entry-level problems, Mm-hmm. I’m spending almost all of my time at the executive level. So the higher that we are up, as being that cruise ship director in those executive spaces—

Josh Schachter [Host]:
Stop calling it a cruise ship director, dude. Let’s do like, you know— Flight attendant. Like heart surgeon or something.

Jon Johnson:
Heart surgeon. I know, but we’re not saving lives here, man.

Josh Schachter [Host]:
No, that’s true. But so is that— and that’s because AI has helped you, as they say, eliminate the busywork and be more strategic, or that’s for other reasons?

Jon Johnson:
I’m gonna— I have a little bit of a sour— I’m gonna say forced me to. I don’t know that it has helped me.

Josh Schachter [Host]:
Oh, because you like the busy work?

Jon Johnson:
Um, no, I don’t. Um, but what I do like is the, the way that these tools connect dots. It allows me to not have to be on every single meeting. And, you know, we have a great, uh, relationship with Notion, and our notes get thrown into a public data share so that my technical team can be on a call that I’m not on, and I can query their notes, and I can get context much quicker without having to set up 5 other meetings like I used to have. That’s what’s empowering it, is that I don’t have to be everywhere at all times. I am informed, and I’m gonna have the context that I need, but I don’t have to sit in every single meeting that I used to. There’s been meetings that we’ve all sat in as CSMs where an engineer is just gonna go as deep as they can and you’re lost, right? You don’t even know where to start. You don’t know where to begin.

Jon Johnson:
Now with all of these tools and this access that we have, I’m able to not worry about that. I’m able to just observe and digest and then work through it when I need to rather than just on that call. Yeah, and be present on that call rather than scribbling my little notes that I’m not gonna be able to read.

Josh Schachter [Host]:
I love the fact that like it still comes back to, you know, you know me from the Update AI days. Yeah. The conversational intelligence note-taker that we built. And still, when you ask somebody their favorite AI use case, they still go back to meeting notes. It’s like the classic canonical thing.

Jon Johnson:
Well, I mean, it’s the same. Like, we ran, we ran in, uh, in-person meetings in London last week, and I had Notion running in those rooms too. Like, that function of not having to scribble out what a specific KPI is and what a follow-up is and to just be present makes that I don’t have to have a 2-hour meeting. I can have a 45-minute meeting, right? It’s brilliant. And the way that we are able to connect all of these tools to be able to automate things into our timeline and automate things into Copilot and to kind of guide customers along when a word is spoken, not just when a CTA is closed.

Josh Schachter [Host]:
Within Gainsight, within RCS. So the role is— I’m hearing a lot from leaders, these 3 branches, pillars of where the role is going. And depending on where you are, that’s already kind of embedded within it. But commercial instincts, strategic work guidance, and technical abilities. Commercial, strategic, technical.

Jon Johnson:
Absolutely.

Josh Schachter [Host]:
Are those— is that how you would characterize where the role is going more as well?

Jon Johnson:
Yeah, I completely agree. And I’m seeing that too. That’s a lot of the programs that we’re building right now follow under those 3 pillars very specifically.

Josh Schachter [Host]:
Which do you think will be the most impactful? Let’s look a year now or a year and a half.

Jon Johnson:
I would like to take, uh, an eraser to the technical side. Um, I think, uh, the idea that we can become technical, uh, takes a lot of time. And if we’re doing— if we’re doing more, if we have more— let’s say I go from $10 million to $20 million in, in what I manage over the next 18 months, the technical acumen needed to meet that is going to be wasted on me, right? So, if we can diminish that side, I think that’s where we’re going is that the technical side is understanding is important. You have to be able to speak the language. You’ve got to have that like native industry, which is what I’m going to say rather than, hey, this is how Amazon works. It’s just, no, this is what e-commerce is, right? So, that industry experience, I think, is going to expand.

Josh Schachter [Host]:
It’s a little more on the strategic.

Jon Johnson:
It is, yeah. And the technical side, I would hope, comes down. That doesn’t mean we can’t solve technical problems, but we’re getting into this deployment model, right, where I will have technical resources that I can deploy following an FDE motion or any of these other motions that we have, whether it’s an agent that I can deploy for a very specific thing. Right. That’s the process that I want to follow, and I’m more interested in refining that process so that we’re getting the right information over to our technical teams, that we’re capturing the right requirements, that we’re not causing more work to just kind of be punted between teams, which is usually what happens.

Josh Schachter [Host]:
You said commercial, they keep giving it, taking it, giving it, taking it away. I mean, that’s, it’s what you hear, like the industry overall. So what’s the deal with commercial?

Jon Johnson:
I want the money. I’ve always wanted the money. Like, we’ve talked about this a number of times on this podcast. Like, I want the money. I think especially when we’re looking at like defensibility, like with these jobs, Specifically as CSMs, and I know that there’s a massive amount of CSMs in the marketplace that are going like, what is my job going to look like? Get a hold of the money as soon as you can. And I don’t mean that like in— maybe it is aggressive, but like, that’s how we justify our jobs. It’s accountable. It’s accountable.

Jon Johnson:
And, and if you don’t have the soft skills to negotiate and work through that, that’s where you start right now. If you’re not there in the next 18 months, you will be forced there in 18 months, and it’s going to be a difficult conversation. So I have always been an advocate for wanting more of the revenue. I love my sales partners. I’ve got incredible account executives. But also, I want them into the greenfield. That’s the most important thing for them to do is how do they keep growing? And if they’re spending all their time on my lawn, their lawn’s not going to get the water that it needs.

Josh Schachter [Host]:
And as we go for— and Chuck, our CEO, says that we’re going from this SaaS economy to this agentic economy, which means that consumption and usage-based and ultimately outcome-based pricing becomes more predominant.

Josh Schachter [Host]:
And the consumption-based pricing, I mean, that’s perfect for CS, right? Like, then it’s completely aligned, to use your terminology, with encouraging adoption. Synergistic. Synergistic with adoption and the commercials of, well, if you adopt, you use more, you get charged more. So it’s one of those things where it’s going to give CS that seat at the table, as we call it, the CCO, that boardroom seat at the table. But it will take some folks having to acclimate that haven’t been commercial before.

Jon Johnson:
Well, like that term seat at the table is always— it’s an interesting one for me because—

Josh Schachter [Host]:
Feels condescending.

Jon Johnson:
It does. When I used to come— when I was coming up, it really felt like I was like, I’m going to have a microphone and everybody’s going to listen to me. And it’s like, no.

Josh Schachter [Host]:
And look at you now. You’re on a podcast with a microphone.

Josh Schachter [Host]:
Everybody’s listening to you.

Jon Johnson:
Absolutely. No, it means there’s a spotlight on you.

Josh Schachter [Host]:
Yeah.

Jon Johnson:
And I think if, if we’re going to continue to grow in any career, you need a spotlight on you occasionally and you need something that will bring you into the spotlight so that people can see your customers, your bosses, your organization can see like the actual effort and the outcomes that you’re tracking. And it can’t just be a Kanban board hidden behind a login that nobody can see. Like, it’s got to be visible. And those are the seats that we’re talking about. So we’re getting into this model where CSMs have actual dollars that are tied to their actual days. And then we can track, just like we’re tracking in our new consumption model, against a goal. I am doing X with Y.

Josh Schachter [Host]:
Yeah. And then it’s not, well, how do you know the value of the CSM, of whether the renewal was because of them or because of market conditions or because—

Jon Johnson:
Yeah, the product— because then it doesn’t matter. Then the person that is— Whether it’s the CSM did a really good job or the market grew, the seat is the value and the management of that seat is the thing that you’re bringing in. So you can— then you can paint whatever you want. That’s where the storytelling of a CSM comes in of like, the market increased and with our consumption price and that also meant that we managed 10% more revenue, so that means growth, right? Like, and I identified that and here’s the story that I’m going to tell to my customers and to my executives.

Josh Schachter [Host]:
I think it is both the scariest and most exciting time for CS, and with more of an emphasis on exciting than scary.

Jon Johnson:
Yeah, it depends on the day, but yeah.

Josh Schachter [Host]:
Well, there’s this convergence of roles. Des Traynor, one of the founders of Intercom, talks about convergence of the different customer roles and things like that. So there is the consolidation of, obviously, the tech stacks and whatnot, but also the people stuff too. And but again, getting closer to those outcomes, being able to be more commercial, focus more on the strategic, it’s incredibly exciting right now for customer success managers.

Jon Johnson:
I agree. I spend a lot of time in that mind space of the excitement. And we spend a lot of time— the only flip side to that is at Gainsight specifically, we work with CSMs. So when I go on site and when I meet with my customers, I’m meeting with CSMs. They’re asking the same questions that I’m asking. And that’s a very fulfilling place to be in because the answer isn’t one thing. It’s let’s just keep having the conversation, and that’s where the answer comes from.

Josh Schachter [Host]:
True or false? Oh. In 18 months, the majority of B2B SaaS software will be headless.

Jon Johnson:
False.

Josh Schachter [Host]:
Headless?

Jon Johnson:
Yeah, I know. I saw the question. False.

Josh Schachter [Host]:
And just to be clear so everybody knows what headless is, I mean, it’s something that we’re fully leaned into with CS and our platform at Gainsight, but it’s basically— We give you the data, the structure of the data, and you do what you need to do wherever you need to do it, whether it’s Claude, OpenAI, Salesforce.

Jon Johnson:
I’m going to put an asterisk on it, but I’m still going to say false. And, but I think this is really important. I think there will be elements that are headless, but I think in my space, in the strategic enterprise space, I do not see that horizon. I see it in a much longer horizon. What I do see is in the SMB, the mid-market, even some of the, like, the light scale-ups, they’re really pushing for a headless experience. And I’m all for it. I really am. That’s a playground that we get to solve a lot of problems in.

Jon Johnson:
That’s going to take a while for it to, like, matriculate up into these big strategic enterprise organizations. And it just comes down to security and access and data and and the speed at which large-scale global enterprises move.

Josh Schachter [Host]:
It’s interesting. We were both in London the other week for our Pulse Europe. And I was at the CXO Summit as well with some leaders. And I polled people— actually, you were there. You were in the front row of the crowd on the stage there doing the Unchurned with Emma and Sean.

Jon Johnson:
Yep.

Josh Schachter [Host]:
By the way, thank you. Thank you. Because that little gaggle right there is the only thing that I could hear on stage.

Jon Johnson:
Those were all my customers. Those were all my CSMs from SAP.

Josh Schachter [Host]:
No, no, you.

Jon Johnson:
Oh, just me?

Josh Schachter [Host]:
Yeah, yeah, you’ve got— see that right there? You’ve got a very loud laugh.

Jon Johnson:
Yeah, I do.

Josh Schachter [Host]:
I envy that.

Jon Johnson:
Yeah.

Josh Schachter [Host]:
Oh. Well, I mean, it’s probably annoying at times, but it’s— you’re very fun-loving. And that’s all I could hear on stage. Good. Over in Europe, it’s a much more— and in London, it’s a much more reserved audience, right? So you don’t get the feedback with my corny jokes that I don’t know if they’re like, you know, like on the edge and they’re going to work or not. I get nothing. No response from the crowd except for my buddy, John Johnson—

Jon Johnson:
In the front row, baby.

Josh Schachter [Host]:
Gaggling.

Jon Johnson:
Yep.

Josh Schachter [Host]:
Cackling, gagging? Cackling.

Jon Johnson:
More of a cackle. Cackling? I think it was more of a cackle.

Josh Schachter [Host]:
Whenever I attempted to be humorous. And that meant a lot to me.

Jon Johnson:
Which you do often, so—

Josh Schachter [Host]:
Attempt, yes. So it was interesting, though. I asked that question to folks that were more on the front lines and frontline managers of, like, will SaaS be headless within 18 months? You know, folks that were ICs and frontline managers, they were actually more favorable towards, yes, it will be headless. Then you ask the CCOs, the VPs, and they’re like, no, no, no, it will not be headless, because they need the dashboards.

Jon Johnson:
They do. Yeah. Well, and here’s where I think there’s— I like to say fault— like, one of the things that I believe in my core is this thing that my dad said to me when I was growing up is firm beliefs loosely held. And this is one of those things that I believe firmly. I do not believe that in 18 months we’re going to be in this utopian headless thing, but I do think that there is a ton of opportunity for us to build that ecosystem. And I’m really excited to see the delta between those frontline folks that are just like, give me all the tools and give me all the access, and the executives that are like, no, no, I need traditional dashboards. I think that’s where we are at as a company, especially at Gainsight. I think that’s— that is our market as CSMs, is to figure out how this fits in that space and then help it coalesce as we move through this cycle of people saying yes and no and maybe and any of that stuff.

Jon Johnson:
So—

Josh Schachter [Host]:
You are an anxious person.

Jon Johnson:
Yes.

Josh Schachter [Host]:
I am an anxious person. Yeah.

Jon Johnson:
Yeah, yeah, yeah.

Josh Schachter [Host]:
Uh, AI is amazing.

Jon Johnson:
It is, yeah.

Josh Schachter [Host]:
It also sucks.

Jon Johnson:
Oh, it does.

Josh Schachter [Host]:
Is it— is AI making you more anxious?

Jon Johnson:
It used to. Um, I struggled with where do I start, and that led to a lot of fear. That led to a lot of that, like, I just don’t know what to do. I’ve gotten into a pretty good habit, um, over the last 6 months since— it’s been about 7 months since I’ve joined Gainsight, and This is kind of my first job where my company has said, here’s unlimited tokens, here’s Claude, we’re gonna connect everything for you.

Josh Schachter [Host]:
Yeah, it’s great how they’ve really opened those gates.

Jon Johnson:
Yeah, and I am pretty hesitant about AI. Like, as an artist, as somebody who creates every day, like, the generative AI thing of Suno making songs that, like, sound like a frickin’ radio banger in 30 seconds when I spend thousands of dollars on my studio and, like, bleeding hard onto poetry and people can just, like, put a prompt— like, I have an opinion about that.

Josh Schachter [Host]:
Yeah.

Jon Johnson:
We live in a different space.

Josh Schachter [Host]:
Then you got some assholes that are writing books that have like their entire system of their book like completely AI-pilled. Yeah. And like—

Jon Johnson:
Yeah, but we can tell. I come back— the biggest thing for me was if I want a human to read this or interact with this, I’m going to make sure a human creates it. And that started a pretty cool path for me. The biggest anxiety for me has always just been email fatigue, like Slack and email. We have— every company that I’ve ever talked to, whether it’s Teams, your internal chat tool and your internal inbox is— it is cacophonous in its noise and its power over your life.

Josh Schachter [Host]:
I love that word.

Jon Johnson:
It’s a great one.

Josh Schachter [Host]:
It’s like one of the best words.

Jon Johnson:
Thank you.

Josh Schachter [Host]:
It sounds like what it means.

Jon Johnson:
Yeah.

Josh Schachter [Host]:
Yeah, yeah. There’s a word for that too, right? But like, yeah.

Jon Johnson:
So, I generally, I actually have not— on Monday morning, I open up my cloud console first before I open my email, before I open my Slack. And I go, hey, what’s the most important thing for me to do? Do you really? Yeah, yeah, yeah. Like, and by that, I mean, like, there’s parameters. So, it’s like, is there an escalate? I’ve got a couple escalations that I’m working through right now. So, it’s like very specific things. And because I have anxiety, because I’m an elder millennial, because I have ADHD and all these other definitions floating around in my head. I’ll read an email and then somebody will Slack me and then my kids will scream and then I’m mowing the lawn somehow. Like, I just kind of go down these paths and what these tools have allowed me to do is say, I’m gonna focus on this one thing and I’m gonna let my little alien crawl through all of my emails and my Google Docs and my Slack.

Jon Johnson:
I’m gonna gather everything that I can and I’m gonna condense it and I’m gonna generate what I need to out of it so that I can take an action and then I get a frickin’ check a box box. And there have been moments that have taken hours out of my day just to check that box because I had to dig and dig and dig. And what email was this? And when was that meeting? And what was the follow-up? And this CTA here and that CTA here. And right now it’s just, okay, what’s next? What’s there? And then the next one is, oh, this email, you missed this email 18 days ago. It’s still sitting unresponded. Oh shit, let me take care of that, right? And then you do it and And that anxiety goes away. It’s insane how being proactive reduces your anxiety. I’m going to say that again.

Jon Johnson:
Being proactive reduces that anxiety, and that gets us into these high-powered CSM roles. Well,

Josh Schachter [Host]:
it’s a good point though. Being proactive also in like in using AI to its fullest, in creating the skills that— because you could sit there and just be prompting reactively. Ugh, it’s gross. Like you were very— I have the skills that you have too, like the daily brief and stuff like that, but I don’t have the discipline to actually use them.

Jon Johnson:
Yeah, well, this is the thing is that like most people when they’re getting these tools are focusing on the output. It’s just like, oh, what can it give me? 100% of my brainpower goes into the input because that little alien that’s inside of these tools, however it works, like it needs to know what’s inside of my brain. And if I don’t put it in there, it won’t.

Josh Schachter [Host]:
And you need to garden it and nurture it.

Jon Johnson:
You do.

Josh Schachter [Host]:
Uh, okay, let’s go to the, the creator side of Jon. You’re a wonderful musician. Thank you. You’re, um, I have one of your songs, uh, geez, what’s the name of it?

Josh Schachter [Host]:
It’s on my like list on Spotify. I keep playing it over and over again.

Jon Johnson:
I think you’re the only one that listens to it.

Josh Schachter [Host]:
I, I mean, I should have teed this up, uh, beforehand.

Jon Johnson:
We’ll put it in the show notes.

Josh Schachter [Host]:
We’ll put it in the show notes.

Josh Schachter [Host]:
Uh, I know we’re, we’re low on time here. What’s it called, the song that I love?

Jon Johnson:
Is it the one that I just released?

Josh Schachter [Host]:
When did you release a new song?

Jon Johnson:
I don’t know, a couple months ago.

Josh Schachter [Host]:
Uh, where is it? No, it’s the one—

Josh Schachter [Host]:
come on, I’ve sent this to you, screenshots of—

Jon Johnson:
There’s— I’ve put out a ton of them and my brain is also blank right now. Is it Way You Move? Is it—

Josh Schachter [Host]:
No, no, no, whatever. I like your music.

Jon Johnson:
Thanks, man.

Josh Schachter [Host]:
Uh, what’s your— what’s your handle on Spotify?

Jon Johnson:
It’s, uh, Wild Coast is the name of the band. Wild Coast. Just Wild Coast.

Josh Schachter [Host]:
And now—

Jon Johnson:
oh my God,

Josh Schachter [Host]:
John The multi-time author, because you’ve published before.

Jon Johnson:
I have.

Josh Schachter [Host]:
This is your latest book of poetry.

Jon Johnson:
It’s not even out yet. This is the advanced reader copy.

Josh Schachter [Host]:
Yep.

Josh Schachter [Host]:
And I’m an advanced reader.

Jon Johnson:
You are, yeah, because I’m an advanced reader of your book, so I felt like it was—

Josh Schachter [Host]:
Well, thank you. And I read it. I’ve read parts of it. I haven’t read the whole thing, but it’s beautiful. Caterwall.

Jon Johnson:
Caterwall.

Josh Schachter [Host]:
Potato, potato.

Jon Johnson:
I mean, you have to speak English when you read English.

Josh Schachter [Host]:
Did I say I’m an advanced reader?

Jon Johnson:
The first page. Spells it out how to say it.

Josh Schachter [Host]:
Yeah, I skipped that one.

Jon Johnson:
Caterwaul.

Josh Schachter [Host]:
Caterwaul. What is caterwaul? It’s a book of poetry. What is caterwaul?

Jon Johnson:
It’s a book of poetry. Well, a lot of it is kind of tied to my anxiety. So caterwaul is just like, the best way that I could describe that is like, if you’re like in New York and you hear a bunch of cats fighting in the back in an alley, that’s a caterwaul. Caterwauling down the street, like cacophonous, using that word again. So a lot of these, pieces are written through processing the very loud brain that I have, which empowers a lot of my day job, but it also like kills me after when I have to have a comedown crash.

Josh Schachter [Host]:
I love it. So it’s basically what I hear

Josh Schachter [Host]:
every night when I go to bed in New York on the first floor of my building.

Jon Johnson:
Yeah.

Josh Schachter [Host]:
You write some beautiful stuff here. You write this thing about like how to— how I read a poem.

Jon Johnson:
Yeah.

Josh Schachter [Host]:
And one of the paragraphs that sat with me was, you wrote, someone sat with a feeling long enough to chase it into language. They then wrote it down, crossed it out, cursed their troubled brain, wrote it again, shaped it and reshaped it until it was true. A person handed you a piece from the interior of their life, which is lovely. The whole thing is just lovely.

Jon Johnson:
Yeah.

Josh Schachter [Host]:
That’s beautiful. That is lovely.

Jon Johnson:
Yeah, it’s my favorite thing.

Josh Schachter [Host]:
Is that a poem right there? That’s just you, right?

Jon Johnson:
I mean, it’s me writing. I write poetically. You can read my emails and be like, dude, enough similes.

Josh Schachter [Host]:
Yeah.

Josh Schachter [Host]:
So, so what? Pick one here.

Jon Johnson:
Yeah, I’m going to read. I’m going to read Holy Hands because this is my favorite one. There are only 10 copies.

Josh Schachter [Host]:
Holy Hands or Holding Hands?

Jon Johnson:
Holy.

Josh Schachter [Host]:
This is where we’re supposed to hold hands as you read it?

Jon Johnson:
Holy. Our hands are holy. Yeah, it’s okay. All right. And this, this ties pretty well into everything that we’ve talked about, actually. nothing about AI. It says— this is called Holy Hands, and I’m doing this on a freaking podcast. This is wild.

Jon Johnson:
Your hands don’t belong in holy places. They belong on steering wheels at midnight. They belong on the back of a neck in a parking lot where the lights have been broken so long the city forgot they were ever on. I was taught that holy meant set apart, consecrated, unreachable by the ordinary. But I have seen your hands peel an orange at 2 a.m. like it’s the most patient thing a person can do. All that care for something that was ever only going to disappear. Tell me that is not a kind of worship.

Jon Johnson:
Tell me the congregation has ever been that quiet, that still, that sure of what it was doing. Your hands don’t belong behind stained glass. They belong in the actual world where the coffee goes cold and someone has to decide whether it’s still worth drinking. The church taught me that holy was a place you entered into. I think holy I think holy is what happens when something ordinary refuses to apologize for how much it matters.

Josh Schachter [Host]:
I think holy— repeat that last line.

Jon Johnson:
I think holy is what happens when something ordinary refuses to apologize for how much it matters.

Josh Schachter [Host]:
That’s awesome, man.

Jon Johnson:
Yeah.

Josh Schachter [Host]:
That’s obviously a personal poem for you that goes back to your background growing up very religious. Yes.

Jon Johnson:
Deconstructed is the word.

Josh Schachter [Host]:
That’s the word. Okay. Deconstructed. Tell us about that one.

Jon Johnson:
Yeah, I think a lot of my life has been painted with this idea of holiness. I was raised evangelical Christian, and I still hold a lot of very personal beliefs, but I definitely, like, stepped out of that world and I had to redefine these words. What does holiness mean? Like, I still believe in beauty. I still believe in grace. I still believe in these things. And a lot of the last probably 4 years of my life, has been redefining. I used to think that I would— when I changed, I couldn’t be what I was before. And I don’t think that that’s true anymore.

Jon Johnson:
I think very much a part of who I am is who I have always been. And how do we embrace that? That’s this acceptance. That’s this model of, of like true understanding. And most of my writing has been through the lens of I need to understand myself. And I’m grateful that people like what I, what I write and people buy my books and I get to go and speak and, and read in public and things like that. I really, really love that because there is this connective tissue that I really do connect back to, like a really great meeting that we do at work when you see a human being for who they are. And there’s no greater way that we can do that than just by like opening up the interior of our life and welcoming people in. And I think that’s, that’s what I want to do with my career.

Jon Johnson:
It’s what I want to do with the rest of my life. And I’m really grateful that specifically customer success is built around human beings that actually like and understand creativeness, that I get to walk into these meetings buttoned up with my, with my tie and my slacks, but then also with my heart. And like, like, that’s the core of it. And I think what I love the most about— just to tie it back to the people that pay both of us— is that, that, that is like, that is ever-present in every Pulse event that we do. In every CXO that we do and the dinners that we do, it is centered around the human beings.

Josh Schachter [Host]:
So we’re going to end this thing poetically.

Jon Johnson:
Okay.

Josh Schachter [Host]:
In honor of Caterwall.

Jon Johnson:
Caterwall.

Josh Schachter [Host]:
Not Caterwall.

Jon Johnson:
Caterwall, whatever.

Josh Schachter [Host]:
Cater buy it on Amazon.

Jon Johnson:
Yeah, Cater buy it.

Josh Schachter [Host]:
Lightning round called John’s Favorite Things.

Jon Johnson:
Oh gosh. Quick, first thing. Okay, yep.

Josh Schachter [Host]:
Favorite CS podcast host?

Jon Johnson:
Oh, Christy Faltruzzo.

Josh Schachter [Host]:
Oh, that’s—

Jon Johnson:
that was such a— that was such an internal niche joke.

Josh Schachter [Host]:
Favorite New Yorker?

Jon Johnson:
Oh, Josh Schachter, hands down.

Josh Schachter [Host]:
Favorite aspiring nonfiction author?

Jon Johnson:
Oh, Josh Schachter.

Josh Schachter [Host]:
Favorite Gainsight marketing leader?

Jon Johnson:
Oh, Emily Singer.

Josh Schachter [Host]:
We’re gonna keep going. Favorite CS podcast host?

Jon Johnson:
Josh Schachter.

Josh Schachter [Host]:
Favorite Gainsight marketing leader?

Jon Johnson:
I think Josh Schachter.

Josh Schachter [Host]:
Nailed it. Nailed it. Done. Your lightning round is over. Thank you so much for being here. My good buddy, Jon Johnson.

Jon Johnson:
I love you, buddy.

Josh Schachter [Host]:
Does all the things. You always impress me so much, man. Thank you for coming up to New York and thank you for being on the program.

Jon Johnson:
Of course. Thank you so much.