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LEARN with Jon Herstein, Chief Customer Officer, Box

In the B2B world, people don't buy products because they like you. They buy products because they think they will solve a problem in their business and generate ROI. 

In our latest episode of LEARN, guest Jon Herstein, Chief Customer Officer at Box, shares how customer success (CS) teams must create a delightful experience for customers while providing real business value and solving real business problems.

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“In SaaS, switching costs are much easier. And so there's a lot more worth that has to happen on the customer success side too, again, ensure value high, high-value use cases, etc. So a lot of what we do is focus on doing our best to measure customer health. And you can think of health from a vendor's perspective as a value from a customer's perspective. So if I believe, you, as a customer, are deriving great value from Box, I will give you a high health score. If I think you're not deriving great value, you will have a low health score. So the battle for us is less about, we've gotta fend off these competitors all the time. Really, if you think about it proactively, our job is just to deliver as much value as we possibly can.”

Tune in to hear Jon discuss: 

  • His three-part framework for an effective CS program
  • The importance of positioning yourself as part of the product ecosystem for customers
  • How to scale CS and pivot to an automated-first system

Discover how customer success teams can create a remarkable customer journey, driving real business value and solving crucial business challenges. 


00:00 - Intro

05:00 - From consulting to full-time at Box

10:00 - Delivering delight & value to customers

13:57 - Category creation

16:58 - Renewals & scaling CS

21:37 - Automating CS & 3 part framework

28:29 - Rapid-fire segment


Jon Herstein


Podcast Recommendation:

Ted Blosser 



Jon Herstein: Because of the nature of STAs as a platform, it's much easier to switch than it used to be. I'm old enough to have been around in on-premise mainframe, you know, software deployments, huge upfront investment. So a customer was incentivized to stick around on that platform for a long time, and the vendor was not then an incentive to do anything pure special. In SaaS, switching costs are much easier. And so there's a lot more worth that has to happen on the customer success side too, again, ensure value high, you know, high-value use cases,etc. So a lot of what we do is focus on doing our best to measure customer health. And you can think of health from a vendor's perspective as a value from a customer's perspective. So if I believe you as a customer are deriving great value from Box, I will give you a high health score. If I think you're not deriving great value, you will have a low health score. So the battle for us is less about, we've gotta fend off these competitors all the time. Really, if you think about it proactively, our job is just to deliver as much value as we possibly can.

Ted Blosser: Hi, I'm Ted Blosser, CEO and Co-Founder of WorkRamp, where we're redefining the corporate learning space with the world's first all-in-one learning cloud for employee and customer learning. Welcome to the Learn podcast, where we learn from the biggest leaders in SaaS and hear what makes them successful. Hope you enjoy the show. We are delighted to have our guest, Jon Herstein, Chief Customer Officer at Box. Jon and I worked together back in the day at Box, so I'm so delighted to have him on the show. Thanks for joining, Jon.

Jon Herstein: Absolutely, Ted; thanks for having me on, and it's great to see you again.

Ted Blosser: Well, let's jump into it. Let's start with your background. Give us a, let's say, a Cliff Notes summary on your career, and then we will actually spend some of our time and your deep dive into your time at Box. And also maybe one interesting fact, many people may not know about you.

Jon Herstein: Okay. sure. So I spent most of my career in consulting. So, I came outta college with a computer science background, worked for a company, that used to be called Anderson Consulting, now Accenture, you would know it. And then worked for a software company called Informatica, then one called NetSuite, and now here at Bach. So I'm a little unusual in that I tend to spend a lot of time at one company. And I think my average tenure in companies now is seven or eight years. So although I've been working for 30-plus years, I've only worked for four companies, which is, as you know, quite unusual in Tech. Mo, as I said, most of my career was in Consulting Box was the first role I had that it really expanded on my consulting background to look more comprehensively at all of what we now call customer success. So at Box, where I've been for the past 12 years, customer success comprises our CSMs, our customer success managers, our consulting organization, and our support team, as well as a couple of other miscellaneous things, but that's kind of the core of what I'm responsible for here at boxing.

Ted Blosser: And before we jump into your time at Boxing, I'd love to share some of our stories. What was that? What was that tipping point that changed you from consulting over into, I don't know if you call the Dark side, but, let's say, working at an actual company versus consulting? For one? Well yeah, it's a great point.

Jon Herstein: Working in consulting was all very different. You know, Accenture was a pure-play consulting company, right? So we were just kind of going in doing work for clients and coming out, and you're right, it's very different, right? When you're responsible for the decisions you make in living with them versus you're a consultant, you fly in, make some recommendations, and leave, and it's someone else's problem to solve. And you never really get to see those outcomes. You never really get to see whether your decisions or recommendations panned out, right? And actually, one of the things I learned from one of my bosses at Box was that you should be in a role long enough to live with the consequences of the decisions you make in that role, right? And if you're bouncing from year to year to different things, you always, it always, you always look back and think you were super successful, but you don't actually know.

So maybe I've been a little extreme on that, or I meant companies too long; I don't know. But it's been great and a great time at Box. But you know,, the other two software companies I worked for before Box were consulting teams inside of a software company implementing our software for customers, and was able to kind of take that experience. That's what started the conversation with Box. Cuz Box was starting to get into enterprise as you'll recall it. And we were starting to have higher expectations from customers around, well, okay, we bought the software, but now what do we do? Right? And with smaller customers, it was like, oh, well, Box is easy. You just turn it on; you start using it, it's no problem. But when you're in the enterprise, you have to think about things like, well, what about security and user management and content migration? And it becomes a consulting engagement. And so I first started engaging with Box around this consulting conversation, but then my boss, who was our COO at the time said, well, we've also got a support team, and we've got these folks that we call client service associates. Like, why don't you take all that together and, and sort of run it. I didn't think I was interviewing for that job. I thought I was interviewing for a consulting job. And it turned into this like, why don't you go run customer success Box.

Ted Blosser: Well, I'll, I'll date ourselves a little bit. So when we met, I think it was 2011. Yeah, it almost feels like yesterday. And so I wanted you to share a story with the audience where, and I'll tip the audience off a little bit. It was a story about you introducing yourself to the company. I was in the lunchroom, I think I was sitting towards the back, and I was like, who's this guy John coming in? Yeah. And you tell this story around this barbershop experience. I literally haven't forgotten it to this day. Tell us a little bit about the story. Yeah. if you still agree with the story, yes. I think give the audience some background, to the story. Cuz again, if it got etched in my head, I wanted to get etched in everyone listening's, head, head as well, in terms of how you think about customer success.

Jon Herstein: Yeah, it, it is a, it is kind of a memorable story for me too. I went out to Cincinnati, Ohio; it was my first customer visit at Box. So it was, I dunno, within a few that I was at Box, and there was a, a team, I think a CSM and a, a sales rep going out to see this customer. And they were one of our first enterprise customers. It was kind of a big deal, probably one of our biggest customers at the time. And it was my first customer visit, so I was really looking forward to it. And I realized a day or so before the trip that, like my hair was sort of outta control and wasn't super professional, and I just thought I needed to get a haircut, but with the travel and everything, I didn't have time.

So I landed in Cincinnati and started, and I was using Yelp at the time, so you know, sort of looking for, you know, the best barber I could find, the best-rated barber in Cincinnati. And I found this barbershop, and they had a really funny name I don't remember now, but it was something like, you know, the King's Barber or something about Royal Barber or something like that. So it was sort of fancy, but you go there, and it's not fancy at all. And it was just sort of an experience of being in this barbershop. And this guy was like an Elvis impersonator, and he'd been in movies, and so he had this whole backstory. His son was working in the shop, I think it was summertime, and his son was like offered me a shoe shine. Like there was just this whole experience that was going on.

But what really stuck out to me in the story that I told at Box was when he was all done cutting my hair, and you know, the, there's that moment, that reveal moment, right? Where they, you look in the mirror, and they hold the, the mirror of the back of your head. You can kind of see what it looks like. And he said to me, is this the best haircut you've ever received? Or something, something along those lines. And it was such a direct question, and I don't know if it was or not, but you kind of felt to compelled to say yes, he had this, the script. And then he said, well that's, that's good because if you said no, I wasn't gonna charge you for this for the haircut. And what the reason why it really stood out to me from the standpoint of my job and why I related to the box was that our mindset around customer service, I wanted it to be that, right?

Which was, to create the best experience we could for our customers. And it's funny when I I I told you the story of how I started at Box, it was really a consulting conversation. There was no job description because no one was doing that job at Box. And so the day I started, my boss handed me basically a half page written, you know, a job description and basically said, here's what your job is, go do it. And effectively, what it said was, that your job is to delight our customers. And so my mantra, you'll probably remember this, Ted, for the first couple years I was at Box, was all about customer delight. And that story was a story of customer delight. Like, was this a delightful experience for you? But in the vein of your podcast, which is all about learning, I would say to you and your audience that I think I learned that that was a little too simplistic, right?

This idea of customer delight. And what I mean by that, and what I say quite often, is that delight is important, but it's insufficient right in the sense that it's not enough just to delight your customers. Your customers can love working with you. They can think you're a great partner; they can think you've got great people, great values, and all that. But at the end of the day, people buy software or products in general, or services in general, because they believe it will provide some business benefit to them, right? If it's, if we're talking about b2b, right? B2C is obviously a completely different world, but in the world of b2b, people don't buy products because they like you, right? They buy products because they think they will solve a problem in their business and generate some ROI. And so you have to couple delight in creating a delightful experience with your customer, for your customer with providing real business value, solving real business problems.

And so it felt, you know, now when I look back on, it felt like just too simplistic to say our job's delight customers, we should have happy customers. And there's even been some customer success organizations who call their team like, you know, the customer happiness team or whatever. It's like; it's really not about happiness. And sometimes you have to tell your customers things they don't want to hear to give them more value, right? In the interest of getting more out of your product. And so your job isn't always to make customers happy; it's to ensure you deliver value to them. So anyway, long story, but that's a learning that I've had over the years about, you know, the difference between delight and value, and both are important.

Ted Blosser: When did that shift happen in your mind? Was it like a trend where a churn was ticking up, and you're like, you know what, it's just like smaller away through this churn reduction, right? Like, that's not gonna solve things. At what point did it hit you on the head where it's like, you know what, we actually need to move from just a delight focus to, a value focus? And how's that been going since?

Jon Herstein: I honestly don't know if there was a lightning bolt moment where it was like blindingly obvious that, you know, I'd been wrong the whole time. I think it was more of a gradual transition. And, and part of it had to do with the fact that, and again, you'll recall this, but early on, our go-to-market model was a viral model, right? It was all about free users inside of companies using Box at some point saying, oh, this is really helpful. Now I'm gonna, I'm gonna hand over my credit card and buy a few licenses for my team. And then that starts to grow, giving us the right to go have a conversation with the c I O about going bigger, right? That was the go-to-market model for Box for many, many years. And in that world where it's a delightful product and easy to use, and people get value from it very easily, you didn't have to think as much about value in user adoption because it happened organically.

Like it was a very, very viable product. But what you learn in particular as you move from SMB and our free user base into the enterprise, cause things don't happen like that in the enterprise, right? And I'm sure you've learned this yourself, right? As you know, getting people to do something different in a company is hard, right? It's, it's about user behavior, behavior modification, and change management. And you have to do more than just have a product that people like, right? Again, you have to solve a business problem for them that's compelling enough that users will do something different than what they used to do, right? And so I think it's; it occurred over time as it worked with more and more enterprise companies, and we saw that just having a high adoption rate wasn't sufficient in all cases to prevent churn.

Sometimes you'd have really high adoption, and customers would churn anyway. And like, well, why is that? And sometimes it comes down to, well, their use cases weren't that compelling, right? There weren't beeping up; there weren't deep integrations to where they're rating value. So, I think it was gradual learning because our customer base changed. Our product changed. I think it's some extent the market changed too. Back then, people, SaaS was kind of fun and, you know, it was easy, and you could just sign up and try it. If you didn't like it, you could sign up for something else and try something else. And now enterprise, right? So it's a very different sales model.

Ted Blosser: So yeah. Yeah. Think of one of the e I remember when, when we were, when we were going out in the early days, Dropbox was the easiest product in the category to use, but easy to churn off of it to a box, to a Microsoft office because the business value proposition we would give would be much higher, right? It wasn't about the usage of Dropbox, which was probably through the roof; it was more about the value provided. Let me talk about, let me talk about a really interesting topic that I think you were really well-positioned to comment on. And I call it kind of Cs in the midst of huge competition. What's hard in the space is that when you come up with things like renewals, you have some very good options out there. You have Microsoft Office, which has an embedded OneDrive product. You have Dropbox, you have Gdrive, which Google can provide in their, in their app suite. How do you run a successful renewal CS org every day when every single renewal, I'm assuming not, maybe not every single one, but you probably have to address the elephant in the room of, Hey, why stay on the best of breed platform product versus going to a bundled product? Walk us through how you, how you run a team in admits tough competition like that.

Jon Herstein: Yeah, for sure. Listen, I think every business, unless you're in some, you know, category creation you know, kind of and, and you actually wrote a LinkedIn post I think about a category creation, right? Just this, just this week. I think that’s…

Ted Blosser: Redefinition, redefinition.

Jon Herstein: Redefinition, civic creation. Unless you're in that world where you're creating something new, like you're gonna have competitors, right? So like, I think everyone deals with this; every CS organization deals with it. And again, in SaaS, because of the nature of the SaaS of SaaS as a platform, it's a lot easier to switch than it used to be, right? If you think about, and I won't go in the whole long story about this, but I'm old enough to have been around in like on-premise mainframe, you know, software deployments, huge upfront investment. So a customer was incented to stick around on that platform for a long time and the vendor was not that incented to do anything really special. In SaaS switching costs are much easier. And so there's a lot more worth that has to happen on the customer success side to ensure high value, high-value use cases, etc.

So a lot of what we do is focus on doing our best to measure customer health. And we've got a whole bunch, a whole framework for how we measure that. And you can think of health from a vendor's perspective as a value from a customer's perspective. So if I believe you as a customer are deriving great value from Box, I will give you a high health score. If I think you're not deriving great value, you will have a low health score. And so that's kind of the way we think about it. So the battle for us is less about, we've gotta fend off these competitors all the time. Really, if you think about it proactively, our job is to deliver as much value as possible, which goes back to some of the conversations we're having around delight. Like that might not always mean just making the customer happy.

It might mean pushing the customer, and challenging the customer to do more, right? And, one of the things we've done from a licensing perspective is bundle more capability into our core product from a licensed perspective. So now the customer has access to digital signature through box sign collaboration through box canvas is coming to GA soon security features through box shield, but the customer has to do work to get those things up and running. So a lot of the work we have to do in CS, and it's not just CSMs, it's consulting and support, it challenges the customer to say, you're doing really basic stuff, you're not getting all the value you could and think about it, that's a tough conversation, right?

Ted Blosser: Yeah. Because if I go to you and say, you’ve done your job poorly.

Jon Herstein: Yeah, you're, you're not doing your job well, oh, and by the way, you're paying too much for what you're using and that, you know, that gets part, the customers say, oh, well, we'll go look for something cheaper. No, no, no, that's not the point. The point is you have access to all these capabilities, let's figure out how to maximize them. So a lot of our working customer success is less about like worrying about competition, not they're there, trust me, it's more though about how do you get the customer to get the most value they can from what they're already you know, spending right with you. Cuz they have access to science features.

Ted Blosser: Let me, let me deep dive into this a little bit further. So I'm gonna take a hypothetical customer. Let's say you have customer Acme Corp. Yep. They're doing really well.

Jon Herstein: Those guys, great customer.

Ted Blosser: AC Acme is the best, AC

Jon Herstein: Amazing. Yes.

Ted Blosser: They're doing great things with the product, with high product usage. They're showing that they're getting value. So in your QBR, they’re saying, Hey, we're checking the boxes for the use cases we want to satisfy. Then when you come closer to renewal and having those hard conversations, is your philosophy be proactive in saying, Hey, are you looking at the competition? Are you looking at other vendors or is your philosophy more around, Hey, we keep blinders on and what we can control, and we kind of roll into renewal and into the next, the next term? And just assuming things are all fine, what's your, what's like, if we have to get a little more tactical? What's your advice there?

Jon Herstein: Yeah, I would not; I would not be complacent. Particularly when you're dealing with these sweet kinds of vendors, right? Because here's, here's the reality. If we take Microsoft as an example, in a sense, you could say we compete with Microsoft, we don't directly compete with Microsoft because w we don't have the breadth of products they have, right? We don't have a productivity suite. You know, we don't have a you know, active directory tool, right? That's not what we do. We're a content platform. And the argument would be, well, you know, office 365 also has a content platform in OneDrive, so why wouldn't we just use that cuz we're already paying for it. We have to make that argument every day. What's the added value of using Vox, etc. But the reality is it's not just a competitive situation; it's really a coexist situation.

Every one of our customers is also a Microsoft customer or a Google customer or both, right? So it's not a question of like, my CSM is trying to convince a customer not to use Microsoft. That's never gonna happen, right? Or not use Google. That's never gonna happen. It's more about how do we position ourselves as part of the ecosystem for the customer and why there's a value-added in using us plus those other products as opposed to us instead of those other products. That makes sense. So yeah, we have to be proactive because otherwise, if we assume everything's fine and even sometimes, you know, usage looks good, and we talked about this earlier, but just because usage is good if the, the use cases are low value, really basic veins, it doesn't matter how high your adoption is. If they could quickly say, oh, we can just take those use cases and re-platform them, it's a little work to do migration but not that big of a deal. That's a problem. You must look for high-value, deeply embedded, highly integrated use cases. And that's the benefit we think of having a platform is that we have the capability to deeply integrate into other things.

Ted Blosser: Yeah, to regurgitate what you're saying is like understanding the customer's tech stack and whether you are competing against a bundle player or not, if you understand the tech stack and you're deeply integrated into their tech stack, you can just position, Hey, we are the best choice in this part of your tech stack. We understand your business. Let's let's leave us put for the next renewal. So that's great. That's great advice. Let me actually switch topics just a little bit. I don't think I’ve told you this whole story too, but I'm curious to get your opinion. It's gonna be around scaled CS here in a second. But, so when I was at Box, I remember when I was a product manager, this time it's 2014 I think, and Aaron, Aaron Levy, the CEO for those of you who don't know, would rush into the room and say, oh, I just love self-serve, I love our SMBs, they're a great funnel for us.

Let's go build like 10 things for SMB. And so all of the PMs would look at each other and say, oh, okay, let's give us some s and b focus features. And then I remember once I started a work ramp, I think that was 2018, I was running our, I think our series a pitch deck by him late 2018. And at that time, ServiceNow was just crushing it, and he's like, oh geez, I wish we just had only Enterprise <laugh>. And, and it was, it was just funny how every year it would almost shift with Aaron where, where he would almost see that the grass is green on the other side, where I think our service now had like 97% gross. Like in one quarter, they did 151 million deal. So he was just really envying them. I bring up this whole story because Box is one of the few SaaS providers that can scale the whole spectrum from your premium three-person account or even single-person account to Fortune 100 companies that use box. And so you have this hard dilemma where you also have to control cost of goods sold, your gross margins. A lot of that falls under your team. So you're probably an expense line item that Dylan Smith, the CFO doesn't love at points, right? If he wants high gross margins, how do you, how do you view Scaled Cs now? How do you, has that evolved over time with the company? But give us your point of view on scaled CS in the Box world.

Jon Herstein: Yeah, well I think for a business like ours, it's absolutely essential, right? To have that. I mean, and just to give people some perspective, Box now has a hundred, probably around 120,000 customers in total, sort of sort of paying enterprises, everything, as you said. What we think of free customers as different, cuz those are really individual users with free accounts. But if you think about our lowest paid account, it's three seats. It typically in a business and it goes up to customers who have, you know, tens of thousands or in a couple cases, hundreds of thousands of, of users. So from a CS perspective, you're spot on. That's a really hard problem to solve because, you know, I think CSMs have been around long enough that companies know how to solve for very high-value, very high-touch customers, right? You play very experienced, very senior, maybe director-level CSM on that account, and you say, go do everything you can, right?

To make this customer happy and successful, etc. You can't do that for a hundred thousand companies, right? It's just impossible, right? You just couldn’t scale the business, to your point; from a margin and hiring perspective, it's impossible. So, and I think, you know, what, what have we learned about that? You know, initially, you think about, oh well, how do we have a pool model? We're a CSM now, instead of having 10 or 15 or 20 accounts now, we have a hundred or 150 at some point; it doesn't matter how many accounts you have in your pool, because you're never gonna talk to all of them. So you have to pivot to an not a human first engagement model. You have to pivot to a programmatic or automated first model and then figure out where the touchpoints are where it's actually really essential to have a human.

So it's not to say you're gonna have a pure digital engagement or relationship with a customer but think of it a digital-first and then you sprinkle into that, okay, when is a human required? And maybe it's, you know, you build early warning systems to identify where they may be risk in account, okay, now have a human reach out or automate a bunch of outreach to the customer when you finally get them engaged. Now have a human have the conversation. AI obviously will take us much further down this road than we've been already. But even things like scheduling software, like just think about you've got a really small company, and you're just trying to get them to talk to you for 30 minutes, 30-minute consultation, talk about their value, just getting that meeting scheduled right, could involve a lot of back and forth human, you know, touch.

We'll automate that, right? And then get it to the point where the customer says, yes, I'm happy to meet you. I'll meet with you next Tuesday. Great. Put a human on that call. So it's sort of figuring out how to segment, and you'll hear a lot about segmentation. You know, you've got segmentation on the sales side. How do you segment on the CS side to align with sales, but also think about different strata of customers based on what they're spending, what their strategic value is. So a lot of the work in CS in terms of planning is what your segmentation model looks like? How many resources do you allocate to each of these different segments? What do you think about ratios? What do you think about cost? And then the hard part really is not just the planning, but it's how do you then go execute, right?

How you engage well with a hundred thousand customers digitally, and hey, for better or for worse, that's not just a CS problem, it's a marketing problem, it's a product problem, it's a CS problem, and to do it well. And frankly, we're still learning. All of those teams have to work really well together. What do you do in the product? What do you do through email? What do you do maybe through social? What does support do when there's inbound requests from those customers? And I think it's one of the most interesting areas of customer success is how do you do CS at scale really, really well. And what I would say to people who are, if any of your audience is in customer success, if you're in scale and you sometimes feel like, oh, the enterprise customers get all the love, you know, the wind notices, you know, are all about the big customers. This is actually the more interesting area I think of customer success because the future's gonna be digital-first, right? And if you are building those skills now, even though it doesn't feel quite as sexy as some of the big enterprise logos and brands you have, this is actually, I think, where many of the interesting actions will be going forward.

Ted Blosser: Do you push the envelope every quarter, every half year, every year to say, Hey, can we automate more? What's the cadence there? And have you ever gotten to a point where it's like, Hey, you actually may be automated too much or too fast? Walk me through just a few minutes before we get to the lightning fire around here. How would you recommend people look at scale Cs in pushing the envelope a little bit?

Jon Herstein: I don't think we at Vox have reached a point where we, where I'd say we've automated too much, I think where if, if there's an area where we're not doing it as well if we'd like to, it's just more around the coordination of all those different groups that I talked about. So what are we, what are we showing to end users in-app to help them with the initial onboarding process? What sort of nurture do we do with them via email, coming maybe from the marketing team over time to get them engaged in new products and features? Like that's a really big thing in SaaS. You constantly introduce all these new capabilities in your product, and they magically appear on your platform. Well, how do you get the customer actually to use those things, right? And so a lot of that is, is nurtured.

It's like, how do you make them aware of it in the product? How do you get them to try it? How do you get them to use it? And so a lot of our focus is actually around that. And again, working with product and marketing, on those pieces. But yeah, I think every quarter you should be looking at, particularly as your customer base grows and the diversity of your customer base grows, you have to constantly be looking about what is the best way to engage with this set of customers. And so for some of them, it's not gonna be digital-first, right? There's some, like, we're doing very, very well in the public sector space. Government clients, want high touch, right? They, they're that, that's not digital, that's not a digital space, right? So it's figuring out the right model for the right set of customers and aligning your resources to those.

Ted Blosser: Hopefully, you're not putting the d o d in your skill CS segment, right? Right.

Jon Herstein: I think this is another area of sort of learning on that theme is that I don't think people CS leadership think about this as an either-or, like a customer's either a digital customer or it's a, you know, it's a CSM you know, named account sort of a, a customer. You actually have to do both. And what you have to think about is some customers that are digital only, some customers that are digital first with, again, human contact where it's appropriate, and other customers that will be digital, like digitally enabled, but maybe human first. So think about your highest-value million-dollar customers. They want a relationship with a customer success manager, an account manager, and a renewable manager, right? The technical account manager. Whatever, the high-touch resources are. But you should support all of that with the same sort of digital resources that your mass customers get, right? You should have a great support site, a great community site great resources that are sent outbound to customers to tell 'em about new features and capabilities. Don't assume your c s m's gonna do all that, you know, themselves. So it's, it's not one or the other. And I think for too long we probably thought it was like, oh, we digital customers and we have, you know, human customers and it's, it's not that black and white.

Ted Blosser: That's a great framework. We should publish something around that three-part framework. But that's a great way to look at things. John, this has been an awesome conversation. I will close us with a two-minute, what we call learn rapid fire round. That 30 minutes went by fast. I can talk to you for three hours, John, it's been so long. This is long. But okay, so this is our LEARN rapid-fire round; I'll give you a quick question. Give me a one and two-line answer for each. These are all learning related to the theme of the podcast. So the first question is, who have you learned the most from in life?

Jon Herstein: One thing I would say is I think you actually learn a lot from people who are very different from you. So if I think about my various bosses, I've been lucky to have a few bosses for many years. I've only had two bosses at Box in 12 years. And stylistically, they are very different people from me, right? And so they challenge you in different ways. Sometimes, you butt heads a little bit because you don't see things in quite the same way, but you also grow because they're making you uncomfortable about how you approach things. And so think about learning, not just from people who already agree with you already do things your way, but actually do things in a different way. And at first, it may be super uncomfortable, but I learned a ton from my current boss.

Ted Blosser: I love that answer. Okay, next one. What is one podcast book blog you've learned the most from, or even that you're, it's hot on your list right now that you wanna recommend?

Jon Herstein: Yeah, I mean, I don't know if I'm a, it's a great podcast person in terms of like, I'll gonna listen to this one for now and obviously, but like from a learning perspective, I do it more as, as sort of distraction or like maybe blend a little bit of like personal interest and, and business. So the All-in Podcast, I dunno if people know that one; it's pretty well known, but on, the one hand, you can find it fairly annoying because it's a bunch of really rich people talking about things. But on the other hand, pretty interesting perspective on everything from politics to technology to science, economics, etc, global political things. So that, that one's kind of interesting. But anything I would say, and maybe a little bit of a lesson from, my career, is learning from others, trying to do the same thing you're trying to do, right? So not so much a podcast, but networking with other people outside of your company who are trying to accomplish the same things you're trying to accomplish. And so, some of the best things I've learned about customer success were from other CS leaders that don't even look at Box.

Ted Blosser: I love that. I love that. And you're right, I think Olin podcast it's, I'm spouting out facts from the podcast, but you're right at the same time you're like, who? These four guys have made billions of dollars and have Heavy debates.

Jon Herstein: They're a very different perspective than I do.

Ted Blosser: Alright, one topic. If you were, let's say, if you retire ahead all the time in the world you would wanna learn about in the future, it could be anything.

Jon Herstein: Yeah, this one's easy, actually. I am sort of, I'm, a geek about woodworking, and I, I would love to build things with my hands in my retirement. And so I watch a lot, like a ridiculous amount of YouTube videos of just a few woodworkers that I follow on techniques and tools, and yeah, it's a weird obsession.

Ted Blosser: Should have brought something on the show. That would've been great.

Jon Herstein: Yeah, we're moving soon. I'm gonna have a little more space after we move, so check back with me a year, and I'll maybe I'll, I'll have made something.

Ted Blosser: Last one, one big piece of career advice for anyone who wants to get to the top of the mountain like you have; what's your biggest piece of career advice?

Jon Herstein: I would go back to the networking thing. And probably, one thing I didn't do early enough in my career was that networking. What I mean by that is not so much from a standpoint of like, okay, I'm gonna climb and use my network to climb, but it's more, when you're inside of a company, your perspective can be a little bit shrouded by the company's perspective, right? And so, for the first three companies I worked for, everyone I learned from was those I worked with at the same company, right? And when I got into the job at cus at Box, I'd never run a customer success team before. I'd never run support before. I'd never had a team called CSM. And so, almost outta necessity, I had to go find people.

And the Gainsight community was a great, great community for me, but just meeting other customer success leaders, many of whom, if you think about the early 2000 tens were also learning how to customer success teams, we weren't the first ones to do it, but we're relatively early.

And you know, what, what are you finding conversations around? Like how do you do compensation? How do you measure your CSMs? What's the job definition for a CSM? None of us really knew, right? So that networking was critical to me being successful in this role because I could just go ask other people who weren't, you know, they, they didn't have any attachment to, you know, box or, or you know, well, we what decisions we were gonna make, but they were helpful to me in, in, in Build Down. I could name a ton of people on that, but I would say to people don't; it's never too early to start that. And that networking comes in handy when you're hiring people, doing things like reference checking. When you're trying to hire someone, you're looking for someone, you reach out to your network and like, who do you know? It's an amazing thing. And it's never too soon to start building that.

Ted Blosser: John, that's great advice and a great way to wrap up an awesome session. So John, thanks so much again for joining us. The audience, I'm sure, is gonna love everything that you shared here, and I'll hope, hope to see you again soon here. Let's not make it three or four years until we catch out next. Yes, that's true.

Jon Herstein: Well, Ted, we love what you’re doing at WorkRamp. Appreciate you having me on the show.

Ted Blosser: Best of luck. All right, thanks, Jon. Talk soon. Thank you, everyone, for joining. We hope you enjoyed the episode. And remember, always be learning.