Building Strong Relationships With Your Customer Base

with Wes Schifone,

Director of Customer Success, Postman

In this episode, “Podcast Pete” is joined by Wes Schifone, the Director of Customer Success at Postman. From his experience at HubSpot, Datadog, and PagerDuty, Wes talks about rising in the field of customer success and how to build a strong customer base.


Key topics in today’s conversation include:

  • How Wes got into enablement (1:17)
  • Leaving big data for customer success (5:47)
  • Predicting a company’s success (8:29)
  • The wild card of PagerDuty (12:04)
  • Learning how to treat people when in leadership (18:16)
  • Challenges of scale (22:21)
  • Rapid fire round: biggest challenge, favorite leadership moment, 12-month team vision, advice to younger self (26:07)


The SaaS Ramp Podcast explores how tech leaders scale from product adoption to enterprise success. Learn more at


Pete Thornton 0:06
Welcome back to The SaaS ramp podcast. I’m your host, Podcast Pete, on with a familiar face today. This is Wes Schifone, CS Director at Postman. Unicorn turned centaur, as I understand it from meeting him yesterday. Welcome to the show, Wes.

Wes Schifone 0:22
Thanks for having me. Psyched to be here, man.

Pete Thornton 0:24
Yeah, I’m so glad you got to get on live. So the maybe the context is that we do work together at Postman like this is not just getting to know you. But for the audience, like we can definitely dig in and kind of and do the full-on get-to-know-you. What are the things always get in like everybody always wants to know, it’s kind of like how you get to be where you’re at. So for full context, like, like the one thing that struck me about Wes, as soon as I met him, he’s like, is Well, besides his persona. I mean, like, I won’t go there. But it’s just like the Datadog, PagerDuty, HubSpot, like he has been at all of these organizations. And he’s almost like a hypergrowth junkie, like you run this loop for these companies. And like, it is a valuable loop. But it, it comes with the territory. So take as long as you need, I would rudely interrupt, but would you like unpack your story for us?

Wes Schifone 0:43
Yes, I have a bit of a different path than a lot of folks that are a bit different, a couple of different turns throughout my career. I mean, first of all, I’ve been very fortunate to be around very smart people. So I think that’s one of the things is just new see that conviction and some of the founders and the companies that I’ve worked with, you get that vibe from them right away. And postman is definitely one of those companies and visionary and the things that we’re trying to do for our customers. So but more personally, yes, I came up in sales. And now I find myself in customer success. So I started pretty early on at HubSpot. So I’m in the Boston area. And I think there was about 30 or 40 of us when I first joined HubSpot, as a seller as an individual contributor. So I had an opportunity to learn a lot more about sort of the science of selling for folks who aren’t super familiar with HubSpot. They’re a large publicly traded company now. But their roots were on MIT’s campus in the Boston area. So very analytical, super smart sales leaders that I had learned from, at the time, our sales leader was Mark robear. And he graduated from MIT Sloan. And it just kind of taught me the importance of balancing the art of selling with the science of it. So that was a really good experience. The other thing that I didn’t realize at the time, but it definitely influenced the eventual path I would take into the post-sales side and customer success was, we had such an amazing new customer acquisition machine. Right? That it was my first understanding as a seller, will the importance of LTV and the long-term value that a customer gets and what their spend over time and the importance of net retention. And funny story, I know you’re obviously in the enablement and sort of employee development world, Pete. So you’ll probably appreciate this, I was a first-time seller coming out of new hire training. And I think my first day I got like four people that give me their credit card over the phone. And I’m like, This is awesome, right? Three months later, none of them were customers. And I realized the importance of really understanding what value you can offer because no matter how good you are in the SaaS world of acquiring new customers, if you got a leaky bucket, right, and they’re not staying and seeing value, you’re never gonna have the outcome that you’re looking for. So HubSpot was very intentional about building a model that drove the right behaviors, find the best-fit customers, and incentivize sellers to do that effectively. So I can talk more about that later. And then I moved on, kind of stayed down that sales path at HubSpot for a few years, and got presented with the opportunity to start the customer success team at Datadog. Again, very early on there was shoot though 30 or 40 people, only three to five in the Boston office at the time on the sales side. And admittedly, the first time we talked it was we need someone to lead customer success. And I admit, I kind of dismissed it initially. I thought because you’re receptive like Yeah, I thought that’s not selling. I learned more about their model. They were definitely pioneers in the true product lead growth phenomenon that we’ve seen. But you realize the move to first of all subscription based so the move to SAS software kind of changed that I saw that experience at HubSpot. It doesn’t matter if you’re greater than acquiring customers if you can’t keep them. So I understood that pendulum was kind of swinging to the post-sales side in terms of the impact on the revenue in the business. And they really pushed for, you know, early on, we drove a lot of usage-based billing. So a lot of the acquisitions that actually came through on the top of the funnel for new customers, nobody really talked to them. And so the relationships were actually built on The post-sale side. And so it was really interesting to me to kind of see that momentum shift with not only kind of where the money is spent and where that long-term net retention and how the market looks at that now, but also the fact that the best opportunity to build strong relationships with customers comes, ironically, after you sell them. A lot of tastes.

Pete Thornton 5:19
This is a super interesting topic. And for anybody interested in product-led growth, which I think I mean, these days, just such a mainstream topic, but like, the role of customer success, it’s transition maybe over the last six, eight years. Like, what have you seen? Why would somebody who was a successful seller at HubSpot at a successful company even consider taking over like into a customer success?

Wes Schifone 5:47
I think a lot of it has to do with your own personal preference, even to an extent where you’re at in your life, you know, at the time, when the opportunity presented itself at a Datadog and middlee, personally, I was starting a family. And the idea of having a more consistent, you know, the chase in the hunt of that monthly, you know, closing business is really exciting on some, in some on some man. But it can get a little challenging those ebbs and flows, right. As sellers, I remember, you have a great month or a great quarter, and you figured it out right then you have a bad month or a bad quarter. And it’s stressful, and just the upside is high. But the inconsistency could be challenging for people sometimes at that point in their life where I have three young boys now at the time, it was like I need something maybe a little bit more consistent. So I think if folks are at their at that point in their life, considering something that maybe lacks that upside that sellers are, are accustomed to, but makes up for it with some consistency in the lifestyle. That was one thing, admittedly, that initially drew me over. And then the other one was, it’s funny, one of the skills I look for in building a customer success team is this very high level of empathy. And so I joke sometimes with some of my seller, friends that often the best sellers in new business sales, in a way kind of lack that empathy, not as a dig, but it’s like, when you’re I got to sell this month, it’s about me, we got to close this deal. By this month, we got to do this discount, and there’s a there’s, sometimes the best sellers need to be able to remove themselves from that in order to be effective. Whereas if you’re in sales, and you’re feeling a little pressured by that, and you don’t feel like, like you want to keep that relationship after you sell, you don’t want to just move on to the next one. Some people love doing that sales is for you, if you want to keep that relationship and stay. Customer Success, I think is something that people should consider.

Pete Thornton 7:34
I have about seven people to tag with that little timestamp right there. But it’s because they’re— I mean, again, a few on the anthemic side, but they’re a little bit of like say yes, shake my hand.

Wes Schifone 7:44
A little bit of a bulldog, and it’s that’s a good trait, right, like, and that’s, I think, really important. We’ll probably get into it later. But I think just having that self-awareness and understanding what you enjoy doing because even in the early days, you’re going to be a bit more of a generalist in these companies. And you need to be able to do a lot of different things. But I think eventually, if the company is having the success that you hope it does, that focus needs to narrow down on one particular or shorter set of competencies for that role. And if those aren’t things that you find yourself enjoying on a day-to-day basis, you can’t fake it, it will eventually catch up with you.

Pete Thornton 8:18
So moving into HubSpot, that was Boston-based, there were smart people they had like conviction around what they were speaking of. Is there any reason you took that Datadog position, like could you look at Datadog, even with three to four people in the office and already know?

Wes Schifone 8:34
Yeah, if I said I knew at the time that it would have the outcome. I mean, they’re about a $40 billion market cap and a publicly traded company. I didn’t have that understanding. I mean, I definitely got the vibe from Olivier and Alexei, who were the founders that they were on to something. And they were very visionary. And it was definitely different from a HubSpot where our CEO Brian Halligan used to talk about the blue, blue ocean opportunity, right? Like they’re changing the way things are being done, if you maybe I’ll be dating myself a bit here. But there was a time when websites weren’t always used to generate leads. And not every website had a form on it. And so they were really pioneering that concept of inbound marketing. And it just made sense. It was like this new blue ocean, you don’t have direct competitors, you’re just trying to you’re trying to send a call to category creators, right? You’re creating a category Datadog is that was definitely much more of a traditional market that was transitioning from monitoring on-prem infrastructure and just rolled that cloud wave. Everyone’s moving up in patient cloud. So I think in some ways, ignorance was bliss. For me outside looking in, it’s like, that makes sense. They’re focused on monitoring and the cloud. Everyone’s moving to the cloud. Sounds like a good opportunity. But I’d be lying if I said, I knew the potential was there.

Pete Thornton 9:49
So did not see the user base necessarily, or like, like, because coming into postman, you could be like, Oh, I’m the model. I don’t remember the exact right one email, but maybe it was 10 million users at the time developers utilizing.

Wes Schifone 10:01
I think there was a similar level of excitement in that. And this is how you kind of know you’re built for startups when you look at the customer base and think, if you can do that much with that little investment that small of a team, imagine what you can do if, if we put some real juice behind it. And I had a similar feeling with postman where it’s just like this groundswell of adoption and people who love the product, that is a very similar experience for me here is it was a Datadog HubSpot was challenging, customers had to put a lot of work in to get value of the product. But a place like Datadog and Postman it’s so refreshing, because customers really do love using the tool. And that sort of organic business is fueling and can continue to fuel our business as we build out the go-to-market strategy on top of that.

Pete Thornton 10:49
Some of those things like when you say, like, yeah, I was just I was here and stuff like that, like, I would love to be able to, like codify out whatever it is that made your heartbeat and be like, maybe I’ll give this opportunity a chance, maybe I don’t even change rolls into it. Because it’s like, sometimes you’ll notice something, you get a gut reaction, but like, what were those three things?

Wes Schifone 11:05
I think it’s a little bit going with your gut to an extent, right, and being able to, you know, ask yourself about the people that you’d be working with, and not only internally with the customers you’d be working with, right, and talking to people and seeing that community that’s built around the product. So you know, I would, I would, I’ve also, like, had grown in appreciation, or lack thereof for titles. You know, I just want to see on the rocket ship doesn’t really matter to me about owning a certain amount of responsibility. And it’s like, I think sometimes people in their career get caught up. And I need to make this progression in their career and their title. Because I definitely had people saying to me, when I went from sales into customer success, my sales friends were like, What are you doing? Why are you getting into customer success? So you got to be strong and your conviction when you have a feel for where you want to go in your career?

Pete Thornton 11:54
Yep. Okay. And the Datadog obviously did with Datadog did and like, and then you made one more transition, so what was that?

Wes Schifone 12:02
Yeah. The wildcard was PagerDuty. And again, I think it may be comes back a little bit to our own where we’re at in our lives and our personal life. And what’s most important to us at the time, I think, at the time, I was honest with myself, and coming out of the experience, that Datadog that in order to really grow in my career and become more well rounded, I needed to better understand big, traditional enterprise top-down selling. So coincidentally, I went from sales, the customer some sales at HubSpot to customer success, a Datadog. And then the opportunity to PagerDuty was they needed somebody to manage some of the largest customers as the company was going to get going public. So it required it was a selling role, but it required somebody who was strong with customers. And that was an awesome experience to meet for me, because for one on one hand, it was me testing myself. It was mean saying I’m, I’ve been told I can’t do this, I’m in customer success, right? Like I can’t, I can’t close a big deal. And those skills aren’t necessarily transferable. So I took it as an opportunity to see if I could do it. And I had some success there. It was really fun. And I honestly believe, you know, people would reach out to me when I was there and kind of ask, you know, what were some of the things that I had done to be able to have success with the accounts I worked with. And I really felt like it came back to that customer success experience, is really working closely with customers to understand what the value is, build those relationships, and make those introductions to other people in those accounts. And so it was really refreshing for me to kind of prove to myself that I could do it ultimately. And that realistically, those skills across those teams are often very transferable.

Pete Thornton 13:40
What role did leadership play? Not like, like, because you’ve mentioned, like strong leaders in your life, the founder, CEOs, sales leaders at some of these companies, but like, when did that enter the picture for you? Was it by necessity? Or was it by design? Like, were they like, you were like, Hey, I have this job. I’ve got to scale it. So I’m just gonna need some additional people to work with me, or was it like, from the beginning, we want you to build the function a little bit more like Postman?

Wes Schifone 14:03
Yeah. I mean, that’s a good question. In most cases, it was people that I knew coming to me and seeing something in me that I might not have even seen it myself. Right. So particularly when I think of Datadog, a good friend of mine, was on the board there. And he said, We want you to start customer success. And I was like, Why buy me what? And I didn’t even see it in myself. And so trusting in that was really important and helpful. And I’m glad I did. And then even the move to PagerDuty wasn’t necessarily on my radar, but a strong sales leader of somebody that I looked up to kind of saw the writing on the wall where the business is going. And even, you know, I’ve had conversations with even the big companies like AWS, and they say the same thing where the personality or the profile in a lot of ways it’s changing for the sellers that they’re hiring. You know, I’m in the Boston area. So I came up around these massive companies like EMC, who are known for selling big fields on golf courses. Old School traditional selling, right? Yeah. And so a lot of folks that started a company like AWS in this area, are from those big companies that didn’t get that we’re in it for the long run, right? Like we need, the more we engage with the customer, when we sell them, the better value, the more they’re going to spend with us eventually. So even I guess, long story short, it was my sales of sales mentor friend of mine at PagerDuty, and kind of proven through conversations I had with AWS at the time as well was, we need the profile that’s in it for the long run more, we need, I can’t bring in a bulldog, to work with these massive accounts in New York City, as we go public, and worry about potentially not having one of those. And well, we need to kind of play to the strengths of that empathy, and some selling skills. But a little bit more around relationship, if that makes sense. So even look at the model or the evolution of like an AWS sales team, it’s very much gone from old school sellers, to the recognition that they want that profile. Like I challenged them back and said, I’m looking at your entire selling team at AWS in the Boston area, for example, they all worked at EMC. That’s not me. And their response was we actually want a different profile, that profile is not working for us, if that makes sense.

Pete Thornton 16:14
Yeah. Interesting. So you were actually approached like they knew you well enough to actually know that and then your self-awareness and probably ability to communicate that.

Wes Schifone 16:24
Yeah, I think that self-awareness is really, really important. I think it’s, it’s even really important as you continue to grow in the company like leaving that ego side, which is hard. Because I’m I consider myself a very confident person. But at the end of the day, if postman and Datadog and these companies are doing really well, they’re going to bring in people that have a different set of skills that I do that complement me that I can learn from, so I’m going to be hired over. And that’s good. My position in the company, my equity and nothing changes. So embrace that as, and I think sometimes comes back to that title thing, right? Like, if you’re having success, the company is going to grow. And there are more people that are going to be invested in and built around you. And I think sometimes people get too caught up in this is mine, it needs to be mind no matter how big it gets, even if it’s out of their experience or skill set. And just having that self-awareness is so important.

Pete Thornton 17:15
Yeah, yeah, that’s awesome.

Wes Schifone 17:17
Because if you can’t do it, you’ll fail. And then it won’t work out anyways.

Pete Thornton 17:23
Right. Yeah, that’s a good way to look at it like it because you kind of have to, like, look, at worst case scenario. You’re like, yeah, what if then, you know, you’re trying to like project into the future, and these things that are changing all the time very, very rapidly. And yeah, try to find her fit very quickly. So you’re like I have, I have the insight here before we even but I kind of like to go back to the genesis of it. So I know at postman that your team loves you. Like, do they just, they’re like, they love like it. It’s I know. It’s like embarrassing thing. But like I have to kind of like scientifically actually set that as a fact. What about because you’re trying to say like, Hey, can it be learned? Or is it is it? Is it a more natural thing? Is it from your youth or whatever? This is your background, your background, you have an athletic background? I mean, listen, I don’t know what part luck plays in any of this like Shaquille O’Neal comes and crashes your wedding. But as far as leadership goes, what did you lean on? It was probably a gut instinct on how you should treat people or how you should try to align their incentives. What did you lean on before you read 14 management books or whatever?

Wes Schifone 18:29
It’s all experience at the end of the day. When I first became a manager, I think that’s a tough thing. You see, oftentimes, in these fast-growing tech companies, especially as the top performers become managers, that’s not always necessary. Again, it comes back to self-awareness, if you’re really good as an individual contributor, those skill sets might not transfer over to being a good manager. And I early on, I don’t think I was as good as a leader as I need to be. And one of the main things I look at is, is being very direct with people, maybe it’s the Northeast, the Boston in me. Or maybe it’s just the fact that I’m a dad now and I don’t really have time to beat around the bush, I just got to be direct with people. I actually honestly think people appreciate that. When you’re direct, and I think if you combine that with, again, being empathetic to them, and trying to genuinely care, like when we start one on ones, I’m asking how their family is right, we’re not jumping right into numbers, those little things, I feel like, earn me the right to then when I need to, I can be I won’t say a jerk, but I can hold it, you know, you gotta hold people accountable. And I think people take that feedback, even if I’m giving them coaching tips on things, they can do better. I think if you build up that trust, and you show that you care enough, then it allows you to be hold them highly accountable and still not dislike so I’m glad to hear that my team enjoys working with me. But I think that’s really important to kind of build that right? To then if you need You too, just got to be direct with somebody.

Pete Thornton 20:02
Yeah, you made some deposits. You can withdraw from time to time, which is actually still another type of deposit, it’s just a different mechanism. It’s whether you get the upfront “thank you” for it or if it’s like a silent or later on down the road.

Wes Schifone 20:18
And I think knowing being comfortable pushing back also, right, like, especially in a growing company, there’s going to be so many things that we can do better. My job is to filter through some of that, right, you might have five complaints to me in a one on one, I’m going to tell you straight up, we’re gonna have to do a four out of those five, but I got you on that one, I’ll escalate that it’s good feedback. But I think too often, especially young managers, will escalate everything, they don’t know how to push back necessarily on their people, right? And hold them accountable to those things and say, Look, we learn the list of things we need to get to, I want to be straight up with you, we’re not going to be able to get to those things. So we’re gonna roll with it. And the other thing I’ll say is, if you’re very intentional with that, during the hiring process, it makes life a lot easier, like my role in the hiring process. Now more than anything else is that, effectively, we are a massive science experiment. If you don’t like testing new things, if you want some structured process, this is not the place who we’re going to switch it up all the time. So then when they join, it’s kind of like a buyer beware, I told you, though, we’re going to be agile and try different things. And you’re going to help me build that by influencing it participate. If you get uncomfortable with the dynamic environment like that. We’re not the right place.

Pete Thornton 21:35
That’s interesting. That’s a place to hang out. So okay, so we’ve established that you’ve been in all of these growing fast-growing companies, and we’ve just gone through the ones that are like, just household names in tech. Anyway, there are a couple more in there as well, but and now at postman have talked about posting on the podcast before massively growing company, over 20 million developers, just 100% year over year growth in almost any metric you want to measure. And then you find yourself here for the past 18. What challenges of scale-like do you see repeatedly like things that you know, you’re going to come into this organization? And see, even if it’s not brought to you up front? And then and then what things? How can you prepare people for that, as a leader? You kind of mentioned some.

Wes Schifone 22:18
Yeah, that’s a good question. I think, again, it comes back to knowing what you’re getting yourself into, and the pros and cons of everything, like, I’ve worked for companies that have had more business mind, stronger, like brand personalities as our leaders. And in some ways, those can be easier companies to work for because maybe there’s a higher emphasis on operations and kind of back end and kind of building the company from the inside out, which I think relieves some of the stress behind like process and scaling. But then I’ve worked for founders who are visionaries, like in this product, like growth, technical founders, who, when you talk to them, their excitement for the product is so high, and they’re constantly talking about the value their customers get, or the last time they talked to a customer. Those are the signs I’m looking for. And I guess, the one thing is, is that you have to prepare yourself that those visionary technical leaders, they’re so laser-focused on the product, which is great, I would much prefer this over the alternative. Sometimes operationally, things aren’t gonna be as smooth, do I know that our process could improve, and I know our Salesforce instance, could be cleaner, and do I know we could probably invest in different parts of the business, maybe, right, but I don’t even want to distract our found our leaders and our like, that product is so good, and so solid, that I’ll filter out some of that noise and push back on my team. And then make sure that if there are things that are really important, will escalate up, but I think sometimes people who come from those two sales minded or business minded companies can’t always relate to these technical founders, and everything becomes a fire drill, or I lost this deal because of this. And so you want to fix that and you want to change price or something like that. And you’re asking yourself, Is that really what’s best for the business? Or is that what’s best for me at that moment, so that I can hit my arbitrary number, I would much rather deal with the pain of like working through the process and have confidence in the founders and the vision and the product than the opposite.

Pete Thornton 24:28
That whole nugget right there is so really, really helpful because you can see like coming through these new hire programs like you understand their backgrounds, and everybody here is talented and everybody here is smart. We hire really well. And it’s such a beacon for hiring such a lighthouse-like people are attracted to it especially— I mean, we’re later stage now for a start-up, so we get these good people, but depending on their background, they will have different avenues and routes of thinking of things and none of them are actually wrong. It’s just where we’re at in the company.

Wes Schifone 25:03
Totally. Yeah. And it’s funny one of the, one of the lines, I use an interview process from the movie, the breakup where they get an argument about doing the dishes. And the comment is, I want you to want to do the dishes. So when you’re interviewing somebody, and they’re like, No, I want to work for a startup, but they came from a bigger company, and I like I want to work for a startup. And it’s like, well, there’s a lot of different things we have to do, we’re gonna wear a lot of different hats. And it’s like, I’m capable of doing that. You got to embrace it, like, You got to get bored. If you’re not wearing multiple hats. That’s the type of environment and like, I hate the term, but that’s the type of environment you’re gonna be in hypergrowth, whether you want to or not, you’re part of a science experiment. And you’re going to try a bunch of different stuff. And if that’s not cool with you, be careful, because you’re not going to have fun.

Pete Thornton 25:44
Part of the science experiment. Dude, this is such a good outlook on it. I’m telling you, like, not a lot of people have been in like four or five of these types of orders on like others repeating bases. It’s really interesting to hear from me on these. Okay, let’s try this one. Let me try some some some quick answers, like five quick wins in a row. Let’s click quick, but you know, whatever same old thing, biggest challenge from the last six months. We’re talking H1 2022 for any additional context for listening later.

Wes Schifone 26:15
I think this is a general Customer Success challenge that we also have here is maybe it’s because of my background in sales, sales, very straightforward, you have a number, oftentimes this product, lead growth world, we have such organic business, and the things we focus on in customer success is making a customer successful. Right? So I think goal setting is can be really challenging is understanding how you’re measuring people and what their performance is. It’s not as cut and dry black and white as when you’re in sales. So I think continuing to look at, and this is just a challenge in customer success. It’s always, you know, how do you scale your operation? How do you show the best influence or the biggest impact you’re making on the business? Is it net revenue retention? Is it some product consumption or output like case studies or things like that? So it’s really important to continue testing out where you’re having the biggest impact, and not just get locked in on? Well, here’s how we did it another company, it’s purely dollars driven. What’s right for us?

Pete Thornton 27:16
Yeah, yeah, measurement uncertainty. And then, and then the transitions over time, like the new the next wave as you get more data, but you also have different, like, initiatives might be in the future. That is big, and that is more on the customer success side naturally. You’re so involved in the entire portion of the motion, pre and post, and then you have these day-to-day almost interactions with the customer, versus like a motion that leads up to a point in time, there’s such a 360 happening there that always kind of boggles my mind.

Wes Schifone 27:49
You got to be a little bit, you got to be able to do a little bit everything. You got to be able to have those commercial conversations and have some skin in the game from a retention standpoint, want to see that revenue growth? You also have to be able to separate yourself.

Pete Thornton 28:01
Yeah, okay. That’s a good one. Felt that as well. Favorite leadership moment? No timestamp on it whatsoever, just like one of those things where somebody got it, or it was just a good team collaboration or something like that, or whatever it happens to be they could be.

Wes Schifone 28:19
Nice. Yeah, I don’t know if I have one particular story I come back to, but I mean, not to make it purely financial or anything like that. But when I see people who I’ve hired, early stage who had like me, like no idea, you’re gonna have the outcome that we ended up having, when I see how their lives impacted. Or I see them years later, and they have families, and they don’t have as much stress in their life because of that outcome. That to me is really cool, right? Like, we didn’t know, the opportunity that was in front of us when we were working together. But just to see the impact and how it’s changed people’s lives. That to me is like, it sounds tacky, but it makes it all worth it.

Pete Thornton 29:03
You know, it’s awesome. It’s awesome. So that’s a massive amount.

Wes Schifone 29:07
At the time, it’s hard to realize the juice is worth the squeeze. You know what I mean? It’s tough. You’re asking yourself why you go work somewhere else. Not as hard, maybe for bigger salary or something like that, right? But when you see the outcome, make it all worth it. I just met up with a bunch of friends in New York, the other day, we all work together and it’s just like, man, it’s fun. You know?

Pete Thornton 29:30
That’s so good. That meeting right there, maybe it gives a little bit more, maybe it still just an internal thing that you’re sitting with as you’re trying to maybe handle more like day-to-day challenges. Vision for your team over the next 12 months. Like if this could happen, it would just be maybe even miraculous status.

Wes Schifone 29:48
I think we continue that evolution from a team of people who can do a bunch of things really well to a team that’s able to because the businesses are going to require that more narrow focus and kind of play to a shorter list of skills for particularly people on the team. So understanding what that stratification looks like, you’re starting to see it with some of the ways that we’re kind of setting the organization up and recognizing some people are really good at working with massive organizations and doing like a top-down deployment. And other people are really good at managing a bigger number of accounts. But at the end of the day, the responsibility, the ownership that they have with the business is similar, right? If you’re a CSM, who’s managing a small number of accounts that spend $10 million a year with us in total at a time that each individual account, and then you are somebody who’s really good at multitasking and managing maybe a bigger set of accounts, but still for 10 million. Those are different skill sets that have a similar impact on the business. So I’m trying to be intentional about playing to those people’s strengths, but also kind of breaking that traditional mold of if you’re, if you’re handling the big accounts that somehow you’re better than or paid more or anything like that than somebody who’s managing a smaller set. I personally think it’s a different skill set. I don’t believe that one is above the other. They’re both responsible for several are amount of revenue to the business. It’s just each individuals have strengths. That role towards either one is interesting.

Pete Thornton 31:21
It is interesting because it’s always viewed outside looking in. And maybe this is just an old viewpoint of like one is better than another and sometimes Yeah, in that manner. Yeah, like, very different skill sets.

Wes Schifone 31:22
Yeah. And I think we’re seeing that a little bit happen on the sales side as well. And that’s one of the things that I’ve loved about customer success is is not this linear progression. Coming up as a seller, it was always you start inside, you move outside, and then you move up the enterprise of size of the company. I’m trying to break that mold and customer success. I don’t think it has to be that way.

Pete Thornton 31:49
It’s interesting. That’s cool. That’s definitely cool. Okay, awesome. All right, then the finale. So this one’s meant for you. But it’s meant for everybody. So like, so some of our listeners or people who are like looking in and saying like, that sounds like a good gig, I’d like to be at those types of organizations and that type of position. So but the best way to kind of give somebody advice is like, well, if I told myself 10 years ago, like what would the tip Be 10 years ago, you know, for yourself wanting to get where you are today, or just in general like, “Hey young Wes, here’s what’s up.”

Wes Schifone 32:23
Yeah. Well, on one hand, it’s played a long game. You know, and that’s easy to say looking back, but you know, sometimes people might get frustrated by a bad quarter or a bad month. But in the scheme of things, if the company is having success, and the continuing to grow, you continue to execute, then the outcome is worth it. Even if individually, you might be challenged by this commission plan isn’t great, or I feel like I need to get paid more. So that’s one thing on one hand, is just keep that in perspective, but the juice can be worth the squeeze, even if it doesn’t seem like it is at the time. And then, I think the other one is, just be strong in your convictions, right? Like, I think I’m lucky in that I’ve potentially have like, blind confidence at times. So when those friends of mine are saying, You’re crazy, why would you get into customer success, right? Or, I went from a leader to an individual contributor, a PagerDuty, straight up, that like, people were like, Whoa, you’re taking a step back in your career, not I’m confident in myself. And I think I’m gonna have success doing this, that it’s gonna make me better. So I think if you have that level of self-awareness, and you know what you enjoy doing, and you have a shortlist of people that you consider to be mentors and you trust, block out that noise in this, then just go with your gut.

Pete Thornton 33:49
Nice. Yes. That’s fantastic. I only have one follow-up to that. Knowing that, would you have changed anything about your personal or professional growth over the last 10 years based on that advice?

Wes Schifone 34:05
Yeah, definitely. I think I’ve learned now to be more patient. I think at there’s times when you’re like, I know this can be done better. And maybe I didn’t filter as much of those things that I filter now than it used to be. You know what, you’re right, that Salesforce quoting process stinks. So I’m gonna go, I’m gonna go rock salt, ruffle some feathers, make sure it gets fixed. You know, I think in the scheme of things, having that perspective of like, what’s really important, and if everything’s a fire drill, then nothing is then realizing like, I’ve done this enough times now to know it’s, it’s always gonna feel like a shit show. It’s always gonna feel like it’s chaotic, right? Like, we’re always gonna be lagging process-wise, and it’s okay being uncomfortable.

Pete Thornton 34:58
This time that statement came with context and like an example or two, and so, but you hear that all the time. I’m like, “Thanks Instagram me.”

Wes Schifone 35:07
Yeah, was that Instagram me?

Pete Thornton 35:09
Definitely, but like when it gets because it’s so true, so people like to use it. And that with the examples, it makes total sense. Okay, that’s so good. I really appreciate the time. It’s been fantastic on here. Thanks for coming on and just great to work with you. Thanks for the effort and the collaboration, man.

Wes Schifone 35:27
Thanks for everything. All right. Good luck. We’ll talk later.