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Josh Schachter 0:00
I want to welcome our guests this week, the Vice President of CES customer success at Safegraph, Ryan Weisert. Ryan, thanks so much for being on our episode of [Un]churned and really appreciate it,

Ryan 0:19
Josh, thanks very much for having me.

Josh Schachter 0:22
So, we’re gonna get into a bunch of topics today. You and I were talking earlier, and I think you’ve got some really, really interesting ways that you’ve been able to develop talent and help to build your, your customer success teams. I want to start out unsure and our podcast is all about building relationships, I believe fervently that CES is really all about building relationships. And I like to ask all the guests on our show, to think about a relationship describe to us that you’ve really cherished outside of a family member relationship or the domestic partner, can you tell us about a relationship that you’ve really cherished?

Ryan 1:05
Absolutely. So a friend of mine will call him Brian, I don’t know if he wants me to. He and I have been friends for almost 20 years now. And we were introduced, our dads used to work together. But we didn’t know each other as kids, he came to my class at University of California at Santa Barbara. So he was a freshman when I was a junior or a senior. And I got a phone call from my dad one day and said, Hey, show this guy. And I met him for a Jamba Juice. And he seemed like, you know, halfway decent kids. So I invited him to the house for a party, he wiped the floor with my entire house, playing, you know, playing beer pong. And I was like, Okay, this kid’s really excited. So we started calling him the sort of calling him the rookie. And he’s been he’s been, he’s been in one of my best friends ever since. But what I the reason why I cherish the relationship is our brains are both very entrepreneurial people. So when we catch up, whether it’s over zoom, or over drinks, or whatever it is, we do the pleasantries, Hey, how’s the wife, how’s the dog has worked, all those sorts of things we both have, you know, careers that we’re excited about. But inevitably, it’s really just a countdown to we start brainstorming business ideas. Some of them are great. Some of them are not so great. But it’s that’s one of the things that I really love is just somebody who operates at that same wavelength, who brings energy and ideas kind of to the table, we have somebody that I very much, very much cherish that relationship. So that

Josh Schachter 2:34
was what I want to double again, double click into that for a moment. What is it doesn’t you guys have this improvisation. It’s just comes naturally to you. What is it about your persona is about that dynamic between the two of you that allows you to have that rhythm.

Ryan 2:49
I come at things from a almost like more of a people centric mindset, like what would somebody want? What would make somebody’s life easier? What would get somebody excited? And he comes at things from me, finance and numbers and margin? Background. And so I think we, we’ve known each other for so long, like we can speak in shorthand, and we understand what the person likes and doesn’t like and those sorts of things, but coming at it from two different perspectives, but arriving at the same sort of mutual goal of hey, let’s get excited about this. How do we shape you know, how do we shape this up? I think that’s really what’s allowed us to sort of thrive from that. From that standpoint, I

Josh Schachter 3:27
think they call it blanking on the name, but there’s a term for multi intersectional. Well, I’m blanking on it. But when you come from things from different angles, but the diversity of that adds and builds upon it that way, yeah, yeah. All right. So let’s take that that paradigm of a relationship that you have with with quote unquote, Brian, and talk about your relationships in the business world. In your role, leading customer success, there are several relationships that are dear to you. There’s the relationship, probably, laterally and upward with other departments and with with company leadership, there’s the relationship, of course, with the team that you’re working with your team and customer success, and then goes without saying there’s building the relationship with the customer. Let’s pick one and dive into it, of really what you think makes for the most effective building of relationships.

Ryan 4:32
Yeah, absolutely. So I would imagine that a lot of people come in and talk about customers, the importance of the relationship to customers is very critical. The one that I actually enjoy the most is the horizontal relationship with the leaders of other teams. For me, the closest every place that I’ve been and been successful, the closest relationship that I have company wise horizontally with another team leader, specifically the head of product, right So being hyper aligned with the head of product, I think is really, really critical as as VP of Customer Success, I look at it as my job to take the company vision, right, that’s coming down from the executive team or coming down from the CEO, and translate that into a set of priorities for my team. So they’re able to exercise really good judgment, make decisions independently, and really do things with our customers, or just do the kind of work that allows us to progress forward, in terms of where we’re going as a company. To me, it’s hyper in SAS, or data as a service or any of these any of these business models, your company vision is really your product vision as well. And so to me, it’s really hyper critical that how I’m guiding my team and how I want them thinking about where I want them driving customers to type are aligned with where our product team wants our customers to go, right? Where do they want to generate demand for new products? Where do they want to increase adoption on existing products, so we can be hyper aligned, and we can be very, very successful, because then all it really takes is they built, we sell and renew and everybody makes money and everybody’s everybody’s successful. If you’re misaligned there, then we’re pitching things that they’re not going to build right or that they’re not supporting. They’re developing products that we’re not generating demand for everybody gets, everybody gets frustrated. The company does not, does not succeed. So to me, that’s the relationship that I like to that I like to really develop it.

Josh Schachter 6:29
I’ve already said this word, but it’s a sacred relationship, right. Like that relationship, I think you’re referring a lot to the relationship between customer success and product management product groups. I was a product owner for about 15 years. So I certainly have worn both hats and understand that fully, and 100%. Agree. Let’s talk a little bit tactically. What do you do to forge that relationship? At all levels, you know, leadership, the leadership of the teams, and then you know, I see individual contributor to the future contributor?

Ryan 6:59
Absolutely. So first and foremost, you got to hang out, you got to be around right product people aren’t on aren’t necessarily on customer calls, or internal calls all day, they are spending time in deep work mode, thinking up stuff coming up with ideas, right? So first thing you’re doing is you’re just hanging around back in the world, we’re all in the office, the product office was it was just the office that I hung out, right. The reason being is I want to be there sounding normal, right? I want to either myself, my team, or maybe even a select group of customers to be who they go to first they had an inspiration, they’ve shaped it up, they all take a quarterback that idea, right, and it’s gonna go in front of a customer, maybe I want it to be half baked. But I want to create an atmosphere where customer success and our customers by extension can be their sounding board, or they can sort of pressure test ideas to see if they’re worth it to see if they’re worth pursuing. So from a from a sort of leadership standpoint, I’m telling them I’m coming coming through them or not being accountable. Ces will be your sounding board, we will give you instant feedback, you will not have to wait on us if you want customers, we will go get those for you. By bringing that level of accountability to the relationship, you get things from them that you might not otherwise get from an IC to IC fan, whoever’s leading a particular proof of concept or is running with an idea on the product side, making sure that the customers they want to talk to in the CSM and manage those, everybody’s on the same page, this is something we’re going to prioritize this is space within an existing meter. And that new meeting that we’re going to create, that’s really how you how you make that work. And then up upwards, the critical thing is one of the things I look at a company that thinking about joining a company, or I’m advising a company is who builds the business case for new products. Some companies, it’s all profit, they just want all they want unfiltered feedback from customers and prospects in competition. They’re shipping themselves in other places, it’s Hey, go to market teams build the revenue case, right exclusively in a natural world. In a perfect world as both, right? It’s that symbiotic relationship that we talked about, that allows the the revenue teams customer success being one of them, and the product team to sort of CO build these things together, and then take that to leadership to say, Hey, this is what we should spend our time and money and resources on. These are what we need to market so on and so forth. So that’s kind of how I try to stay aligned at the upper leadership level at my level and then at the IC levels.

Josh Schachter 9:23
Saying sounds truly collaborative. It’s one of those things, I kind of feel like I need to see it to believe it. That you’re able to get the you know, the head of product and leadership to really kind of buy into that. But I think what you’re I think from listening to you, one of the approaches you’re taking is one that’s cited by Adam Grant, and I think his book is called Give or take or give and take where it’s all about. You have to give first, build that trust and then you earn the right to have Have you no more of a voice and to make the asks and it sounds to me like what you’re doing is a little bit of servant leadership, where you’re going in you’re, you’re, you’re offering yourself up and your team up saying, Hey, how can we help you? We’re at the frontlines with the customer. Let us serve as your your customer marketing group, in some sense, right customer advocates, let us help you build that out and get for you the feedback. And then now now you’ve got yourself inside of the concentric circles, making product decisions, it sounds to me like that’s a little bit of what you’re applying

Ryan 10:33
100% I mean, product teams need two things, right? They need the access to customer to things from CES, they need access to customers. And they need they need revenue, right, and revenue and adoption. And I look at those as two sides of the same coin. And so all I have to do as a Customer Success leader is make my team and the resources available to me available to them, right, that’s easy enough to do. I’m a firm believer that in tech, you will only go as far as far as your product will take you right. So I have a very vested interest, both from a team success standpoint, a company success standpoint, and the product being great. So making those resources available, makes sense 10 times out of 10. But the other piece is Starbase be accountable for the revenue. If you build this, I will bring you this number of dollars or euros or whatever it is, right. And by bringing that level of accountability, you give them the confidence, right, you overcome the fear that they might build something that nobody buys, because if you don’t sell it, the time is on me. Right? If it doesn’t sell, it’s on me, it’s not on them,

Josh Schachter 11:32
you present you present that those those targets, you actually present to them the numbers and the projections of implications of certain features that you’re advocating for.

Ryan 11:40
100%, right, because if we don’t, I’ve always led teams where we were responsible for upselling in order to upsell new product in order to in order to build right, it’s an easier thing for me to be accountable for because I’m telling them, Hey, I’m going to come deliver the revenue you need to you need to build this thing, because if we don’t deliver that revenue, I’m fired anyways, right, because I haven’t achieved the broader goal in my in my in my role as VP FCS. So I can be out on a limb with them say, Hey, this is what we need to do here on the on the cutting edge, because we need the cutting edge the new the new product in order to deliver the kind of outcomes that kind of growth that companies in this space aspire to.

Josh Schachter 12:21
There’s a vibe that I’m getting from you, Ryan, which is a word to describe the way you work is ownership that you take a lot of ownership and and you know proactivity and ownership of building the relationship and making yourself a servant to the other horizontal functions for the greater good. The ownership of of presenting your ideas to them once you’ve built that trust, but sharing with them the why and the implications and maybe even some of the quant behind it. I really liked that. And then, of course, as as a team leader, you want that ownership to transmit to the folks that work on your team as well. Right. So we’re gonna go 360 with Ryan Weiser, we’ve already gone to the left, right, you know, and kind of up to now let’s go. I hate the word. But let’s go downward a little bit. Right. Let’s talk about building the relationships with the folks that are on your team. What’s the magic there?

Ryan 13:20
For me, I spend more time and effort on personnel development than most people in my experience. There are kind of three, I look at it, as you said, the servant mentality I think that’s that’s, that’s high praise, right? I think that’s what I aspire to. I don’t think I get there every day. But in reality I look at is these people are choosing to spend their, you know, to share their career with me, I want to be as good a steward of that trust as I possibly can. So for me, what I focused on are I focus on getting three things in alignment, right. So what they’re good at what the company needs, and what motivates them, right. If I can get all three of those things in alignment, at one point, I have the right person in the right role, which is something to be very proud of. But if you’re going to be serious about personal development, you have to understand the two of those things are going to evolve no matter what the company needs, and what motivates them will evolve over time. Right? In my position sort of leading CES, I should have as good of you as I need to to understand how what the company needs, who’s going to evolve. What the person with the direct report, or whoever it is, brings to the table is an understanding that include transparency and how what motivates them might evolve over time. When you assume that those two things will change. You can then create a development path hey, here’s what we’re going to add. That will develop your skill set so that you can meet the demand of what the company needs. You can be good at more things, different things that you better at things. So that knowing that what motivates you over time knowing that you’re gonna aspire to different things in your career, we can actually have you on a career path If we’re each step along the way, we have those three things in alignment. That’s how you create a career path for somebody.

Josh Schachter 15:07
Are you I want to make sure I’m understanding you correctly, because I think it’s really insightful. Are you saying that there’s a formula to career path? Which in some ways, which is it’s what? What motivates that person? Plus what the company needs, which, like you said, Those both dynamic and evolving, equals what they’re good at? Or what you what skills you want to develop in them? Am I hearing that correctly? Or how

Ryan 15:31
100%? Correct. It’s a very succinct way to really succinct way to say that.

Josh Schachter 15:36
Got it. Got it. And so sounds like you have to have a lot of that, that improv communication skills that you had, or dynamic that you talked about with your friend, Brian, right, quote, unquote, and where there’s open honesty, trust, they’re bringing to the table, what motivates them, which, frankly, can be a very personal thing. And you’re bringing to the table, the evolution of the company, what they need, which also can be fairly confidential and requires a lot of trust. So how do you build that foundation of trust that you can have this conversation in a really effective way with your reports?

Ryan 16:17
Totally. So you hit the nail on the head, all I really need from a direct report to be successful in order for me to actually have positive impact on the group. And I just need them to be honest with me interesting, right? I need them to be good at their jobs and those sorts of things. But like, in order for that, to get value out of me as their manager, I just need them to be honest with me interesting. That’s a relatively easy thing to bring to the table. But people will only do that we’ll only sort of expose themselves in some way. If they if there’s a clear get right give guests if there’s a clear upside for them. In order to do that upset, it’s really in order to present that upset, it’s not really rocket science, right? Make it really clear to them that you’re invested in getting them in there. Like actual success, right. And they’re not only their professional success, but their personal success as well, right, you’re not trying to work them to death, right? You want them to sort of achieve all the things that they write the by making it really clear, I am going to help you get from point A to point B. And I will also as as the definition of point B or point C or whatever it involves, I’m here for that I’m not closing any doors, I’m not telling you, I’m not putting you to a decision and then making making it so you can never go back on that decision. You make this collaborative? How do we get you to where you want to go? Kind of thing it allows, if I can establish that, then it allows me to be really honest with them, here’s what you’re good at, here’s what you’re not so good at, here’s what we’re going here’s the experiences and the skills that we’re going to add to it, you can get to where you want to go on this step and step by step.

Josh Schachter 17:58
What is your what is your initial intake with a new hire look like? Is this all happen on day one? Does this happen? As a handover from a recruiting machine? Is this something that’s built over the first few months? What does it actually look like for you?

Ryan 18:12
So I’ve inherited I’ve inherited different teams over time. So I’ll give you kind of two answers. I just inherited somebody and the I hired somebody. So when I inherit somebody, it actually does happen on day one, so or day one with them. So the first one on one is like the times I’ve stepped into a new job, I make it really clear to people that are hiring me that like I’m doing people first, then tech, and then customers. We could spend a ton of time on that one too. But the P the reason why people first is so important is that if you’re going to be somebody’s manager, you can’t be their manager, if you’re prioritizing your understanding of the technology, your understanding of the business first, right, I make it really clear, all I really care about today on day one is I want to understand you. And so that first one on one is, is a long time, I’m giving them much the same talk that I am now, they’re not going to tell me everything I need to know in order to get the most out of them on day one. But we’re least establishing that foundation that I want to know these things. I want unabated honesty, I’m always available to them, and we’re going to get them together to where they want to be. So that’s the that’s when you inherit somebody. This the this conversation that we’re having right now I have with people that are so the I’m trying to keep three things in alignment, but on all times they get that whole thing so that they’re coming in knowing that’s the kind of that’s the kind of manager that they’re going to have. And they’re they’re like, I’m getting some of that because I want to understand what motivates a candidate and those sorts of things where they want to go in their career. I wouldn’t hire somebody without that knowledge. So then we can just continue that conversation as they come in

Josh Schachter 19:44
search. What are you looking for in candidates to come join your teams and customer success?

Ryan 19:53
So there’s a bunch of things right and the I’ve listened to this podcast and seen the videos before the one that I really loved and forget the poor sustainment. It talks about intellectual curiosity, or like clap my hands. Right? I need intellectual curiosity. I need somebody who is mentally smart mentally agile can have 20 conversations about 20 things in 20 minutes, right, though all of those are the things that you need. In order to do CES, what I’ve learned about me specifically that I value probably more than anything else, it’s just the, I have neither the time nor the inclination to micromanage anyone, right? There are always so many demands on Customer Success teams time that everybody’s going to sprint a little bit, right. And so optimizing for this is something I have to thank my current current company state graph, and I’m founder, Hoffman, like, this is one of our values, right? We want people with great judgment. And it’s something that’s really resonated with something that’s really resonated with me. So it’s a conversation we have with candidates, right off the bat, right? We talked to them about our values, and we say, hey, we want you to be able to make independent judgment, judgment calls and feel very confident in that, know that you’re not gonna lose your job if you make the wrong call. But we really want people who have good judgment, and are committed to making their judgment better. So one of the questions that I asked in interview cycles, which always throws people for a loop, but I always get really honest answers, is they’re given the spiel about hate without judgment. And I asked them, what’s the last judgement call that you got wrong? And can you walk me through? Right? And inevitably, there’s about a five second pause, right, as they’re thinking about it, and they’re trying to wrap their heads around it, you give them the space to answer Hey, you can tell me at work where you can tell me outside of work, either one is fine. But what it gives you is when they answer that question, it shows you how, like, how serious they’re taking the question, how willing to be vulnerable, they are, right? When people would like the best answers are the ones where it’s like, I made a major mistake. Right? That’s a really scary thing to say that interview. But that’s exactly the kind of person that you want. Because you’re going to make mistakes, you’re not going to be perfect. I make bad calls all the time, right, just as my team format. But the the key is, learn how to like fix it, learn from it, and then make a better call the next time. And that’s how you grow. That’s how you grow. And I trust you, but it’s also how you grow in your it’s very much

Josh Schachter 22:18
by its growth mindset, right? If I can, if I had a penny for every time I’ve invoked that, or a guest is invoke that on his podcast. There’s one book to read ever. It’s growth mindset. But I also like the reference to judgment, that’s something that I haven’t heard before. That I’m sure that is a grown skill. But there’s also a little bit of a Nate aspects of that as well of an innate. Yeah. And I think you’ve articulated that, really, I’ve never really put my my finger on that. But I really like I really liked like, the way that you described that. What percentage of your time in your day as a vice president of customer success do you spend on people?

Ryan 23:06
At least 25% Because typically, I’m at least two one on ones per day. So I would say about a third of my time on people, whether it’s managing relationships up managing relationships with people that work for me, or managing because I also look at, like, I’ve got one on ones with a ton of different people in the world of company, right? So I just bump into people, you know, so I over over index on just kind of cross functional one on ones, but I’m looking at those not just as ketchups not just as like tactical air, we’re doing this, this and this, but also a chance to build that relationship. So I’d say probably about a third.

Josh Schachter 23:42
Yeah, you’re that you’re that funnel and next is a communication all this whole one on ones. So I want to crank the crank the brakes here for a second through a U turn and a little bit of a 180. I know you have an interesting perspective on customer segmentation. What’s the right balance of you know getting to hyper personalization versus more broader strokes? That tell me and tell us a little bit about your philosophy in customer success around segmentation?

Ryan 24:10
customer segmentation as kind of the polar the tension between two polls right? One is is CSM experience and the other is customer experience, right? I find in companies where growth is maximized over everything that we’re they’re maximizing for their maximize maximizing for sort of company profitability and scalability. And you’ll notice that I didn’t mention either of those. I didn’t mention that as either of the two poles right. I feel like that gets in the way of obviously have to be realistic right camp, one CSM for every customer and all those sorts of things. But the in reality if you can optimize for your your CSM experience and optimize for your customers experience, the outcome of that will be so profitable that the company is going to get what they need to out of it. Anyways, that’s Steps, that is my that’s my philosophy. So where, to me a lot of segmentation strategies fall flat is that they don’t really look at the feasibility just on a day to day basis of how like a CSM manages their time, they also don’t look at like the growth path or the just the relative enjoyability of the job. So I’ll give you an example. If you let’s say you’re a relatively high touch, right? So your expectation is that your CSM is going to have monthly meetings with your customers to introduce new introduce new features and drive adoption of those to check in on kind of business processes start to measure risk and opportunity, all these, it’s pretty standard, pretty standard cadence, right? If you’re segmenting at if you’re giving them 40 customers, right? What that amounts to is that they are taking they’re doing to customers call, they’re doing two customer calls a day, if there’s 20 working days in a month. Very straightforward, right. But you see a lot of companies where the expectation is, hey, lots and lots of engagement with our customers, but the customer, the CST has 100. And that’s where you fall short of that feasibility measure. Because now you’re asking them to do something that’s fundamentally impossible. And when that happens, the CSM knows going into the day that they are going to fundamentally fail at what they’re being asked to do. So now all of a sudden, their standards across everything, they do start to slip, they take on a survivor mentality, and they take on a quantity over quality mentality. And they’re just trying to survive and fight fires, and all of these different things. That’s not a functional, right, that’s a recipe for burnout. And if you really look at your customer success managers as a massive part of your customer experience, if that part of the customer experience is heading towards burnout, then your customers are also probably heading towards as well. That’s one side of the equation. The other side of the equation is your customers don’t care how you segment them, right? They don’t care, if you look at them as a good marketer or as an SMB, or as a strategic or an enterprise, right? They want their needs met, they want the promise of whatever it is they’ve invested in data or services or software, whatever it needs to pay off, right. And so that’s where I see like, the best customer success jobs are the ones where the product is awesome, right where the product works. And it’s all kind of right, customer success, it’s a hell of a lot harder when you’re making up for it with consulting or extra support or guidance, or whatever it is for shortcomings of the of the of the call. And that’s where having a real look at what it is that your customers need from the human side of your business, which starts with CES in order to maximize their value or to realize the intended value of their investment. That’s the other piece of it. And so, most people look at customer segmentation. And they start with the bouche, right, they start with here’s a number of revenue, here’s the percentage that we’re allocating towards the s, okay, here’s how we’ll balance that out. When instead, they should look at the calendars and the day to day of their customer success managers, and really getting deep with their customers to understand, Okay, how much time do they actually build the model from there, you maximize your CSMs experience and maximize your customers experience, you’re gonna be in a significantly better places. So

Josh Schachter 28:16
it sounds like for you, proper segmentation is at this intersection of like, what are our capabilities, but but also I’m going to start over. So a little a little notes to to our producer here to cut this out. So it sounds like for you that segmentation is really about understanding what value needs to be delivered, right? It’s almost in the product world, again, I come from the drug world, it’s like, minimum viable product. Now, I don’t want to say you’re always looking for like the minimum threshold or whatever, right? As a product manager, I would argue that I have always in my career, right? What’s the minimum iterative thing, but it’s like, what’s the minimum viable value to deliver to your customers that really, truly satisfies them. And you can build up that model of the resources and people and etc, that you need from there and make sure that it all fits

Ryan 29:16
100% And you have to be honest with yourself, what percentage of that value is coming from the humans and not the it’s coming from the humans. And that’s where it requires a fairly humble company and requires a fairly humble leadership team to adopt this kind of model to say, Hey, this is where we’re we are purveyors of technology. But here’s where here’s where that technology is actually out in the world. And here’s what we’re filming. Here’s where we’re filming.

Josh Schachter 29:42
Ryan, last question for you. On the note of technology, we update AI Of course as a platform, technology platform for customer success. There’s others that are doing other things for the CES community to help help lift it up. Technology or not? What excites you The most about the future of customer success.