Key takeaways
- Land and expand needs an owner. Most early-stage companies have an expansion strategy on paper — very few have anyone actually running the expand part.
- Referenceable customers reveal the gap. Michael's pivotal moment wasn't support tickets — it was sales asking for references and having none because customers weren't adopting.
- Prove it with a quarter and a territory. A Midwest experiment turned nearly half of revenue from existing logos — twice — before leadership gave him a blank check to build CS across North America.
- Renewals are harder when success looks like silence. In cybersecurity, the product works best when nothing happens — CS has to connect value to budget recovery, compliance overhead, and risk avoided.
- CS and product are converging. The teams that win put customer success managers in the room with product so expectations match reality before anything ships.
Why this matters now
Michael Su noticed the expansion gap in 2008 as a sales engineer at a 40-person startup where nobody was calling anything customer success yet. Leadership told him to stop going back to existing customers. He kept going.
One quarter in the Midwest, nearly half of revenue came from existing logos. He ran the same play on the West Coast with the same result. What followed was a 15-year career built around one question: how do you align what your company needs to grow with what your customer actually needs to succeed?
Today Michael leads customer success at Astrix Security — but what sets him apart is building this function from scratch repeatedly inside companies that didn't know they needed it yet.
What to do next
- Audit your expand motion. If nobody owns expansion after the sale, you're leaving revenue and references on the table.
- Run a bounded experiment. Pick a segment, set a quarter, and prove adoption and expansion before asking for headcount.
- Reframe renewals around risk avoided. When your product works in the background, tie value to what would break without you — not login frequency.
- Subscribe to Scaling Trust on YouTube for more conversations like this: youtube.com/@ScalingTrust
Full transcript
I know the bottom line, the end goal, the outcome is added revenue. However, what I'm really doing, I don't see myself as a salesperson, right? Like, if the results that they're actually buying more, they're spending more money, great, fantastic. Also, let's turn into a KPI because we want to drive that behavior. But really, what I'm doing is I feel like I'm just doing the right thing. Like in fact if I were to close a customer or when I was closing customers when I was a sales engineer and I was asked to just leave them alone and go move on to the next deal it felt wrong like as a person as a human being like they put their trust in me like I was the one that asked them about their problems and everything what are the issues that we're trying to solve for. I find this beautiful thing I put it all together and say all right I'm out of here. Most early stage companies have a land and expand strategy. However, very few have anyone actually running the expand part. And that is the gap our guest today, Michael Su, noticed early in his career as a sales engineer at Cyber Arc. And instead of moving on to the next deal like he was supposed to, he kept going back to his existing customers. Leadership actually told him to stop. So, he kept going and eventually he turned that instinct into a business case. He ran an experiment in the Midwest for just one quarter and came back with nearly half of the business revenue from existing logos. So he got handed a blank check to build Cyber Arc's customer success function from the ground up. That was in 2008.
And honestly, no one was calling it customer success yet. SaaS hadn't quite reached his prime. Our guest today, Michael Su, is a customer success leader with over 15 years of experience helping cyber security and SaaS companies drive customer adoption, retention, and growth. He currently serves as the director of customer success and asterisk security, where he leads customer strategy and works closely with enterprise security teams to deliver measurable business outcomes. But what sets Michael apart isn't just his tenure, 15 years. it's that he's built this function from scratch repeatedly inside of companies that didn't know they even needed it yet. His lens has always been the expansion problem. And you'll hear him discuss how he took the question of how do you align what the company needs to grow with what your customer actually needs to succeed.
And in his case in cyber security, it can often mean building a renewal conversation around a product that works best when no one even notices it. It means connecting security investment to other initiatives like budget recovery or talent reallocation or even unlocking projects an executive has had on the back burner for years. In this episode, Michael talks about how we built the case for CS inside of an organization that thought there was no gap to fill.
We talk about what breaks first when you are scaling something that you've invented on the fly. And we talk about how to measure success when you're striving for zero. We wrap today's conversation with why he believes the line between CS and product is disappearing and what teams need to do to be ready when it does. Let's jump in.
Michael, welcome to the show. Thank you so much for making time to be here. It's it's great to have you.
Thanks for having me. I'm excited. I I'm happy to talk about the things that I love. You know, just for context, you started at uh Cyber Arc in 2008, I believe it was. And you were saying like, hey, it was a 40 person startup. Nobody was really calling anything customer success at that time. SaaS wasn't even particularly like a huge thing at that time. Most stuff was on prim or in like private deployments. Um, but you were actually kind of silently building this customer success function maybe before that was the popular thing to do. When did you realize that this what is now known as customer success or scaled success or digital success or all the titles when did you realize that there was a gap within your organization back then that nobody was really filling even though you were in a a different role by title?
Yeah. No. Um great question and excited to answer that one because like how I got into it like it's I ask everybody the same things like how did you even get into customer success? How did you even know about it? And here I am. It's like how did I even get the idea to even create this thing? So, how did I know that there was a problem to even solve for? Right? And that was an interesting conversation in itself, but maybe we'll get into later. But I think it was when I was asked for referenceable customers.
It was a startup company. It was a growing company. Sales was trying to close more logos. And so, I had the sales team marketing. I was like, "Hey, Mike, we need customers to give us a good case study. Give us a reference.
We're trying to close more deals. We need to put them in front of prospects." And I'm over here it's like uh we don't really have any. So so that's that was like problem number one. It was like uh that we should probably solve for that you know. So I think that was the trick that's the do from that point on it was a domino effect. It was like all right we need referenceable customers. We need customers who are willing to say good things uh which is going to help us with the the top of funnel uh effort the the marketing motions closing more deals sales. Um, you probably know this, but I think, well, we talked about this before, but I was a sales engineer. And so, I felt my own pains because as being in sales myself, I'm like, "Oh, great. I can use my own customers as my own references." And I had the same problem for myself. So, there it was. Problem to solve for.
Oh my gosh. You know, it's like I would think that in the journey of customer success, it' be like, "Ah, we had these product things." Or, "Oh, we had support tickets." Or like, "Oh, we had these things." But it's interesting that your story starts at the other end of the journey. Yours was in the the sales the upfront belief building trust building right sizing solution like kind of the other end of the spectrum where a lot of folks probably are coming maybe out of product or out of you know some other function within the organization.
They're coming into success. You came from the sales side. That's that's probably uncommon. So, not to say that we didn't have those other problems. Like, it's just that if I had to pick one pivotal point, that would be it. Like, we definitely had our fair share of trying to not say problems or issues, but uh you know, things that we had to deal with when it comes to supporting our customers. Okay? You know, support gives their answer. That might not be the answer the customers wanted to hear. uh you know, especially if there was an upsell opportunity on the table, we're working with them and support just like no, we can't do this or you know, the timelines don't quite match up to the speed of the sales motion in which case, okay, maybe I do need to jump in. We need to have some kind of a catalyst to get these tickets out of the way so that we can move forward with that opportunity that we're all working towards.
Yeah. Yeah. So we definitely have it from the support end, the services, professional services enablement, but yeah, like for me the pivotal point was uh top of funnel revenue always about revenue.
Ain't that the truth? And I think that's the I think that's the t-shirt for this episode.
Um I guess so you needed you needed referenceable customers, I guess. Walk me through what that was like to say, okay, here's the problem I'm trying to solve. here are the possible motions I could do. Here are the possible ways I could go out to these customers. What was it like to pitch leadership? What did you have to sell them on in order to get buy in?
Oh, the whole entire thing. They when talking to leadership, they thought it it was crazy. It was like, "All right, what gap are you talking about?" Because I came in like, "Guys, we have a gap. We have a problem to solve for." And they said, "We have pre-sales, we have post sales. There is there is no gap. Like, it's seamless.
I'm like, is it though? Like it's seamless. Yes. Like the customer has no gap in terms of uh you know um you know in their journey, right? Uh you know they've always been handheld all the way from pre-sales all the way through to post sales. However, there were problems there. Uh first of all, not being a referenceable customer. They were shelfware. Uh you know, we found out that customers weren't really using it.
customers didn't know how to use the product in a in rare situations. Some customers didn't even know they owned the product. It's like, okay, this is a problem.
Um, and then also we were always preaching, okay, we're a land and expand. Let's just close that deal. Let's just get them in the door and then we'll grow them from there. So, there was that pre-sales. Yes, let's get them in the door. And then post sales, they were responsible for implementing what they had bought, supporting what they had bought. there was no one there actively working on expansion that everybody dreamt about. It's like we're going to land and expand, but nobody was working on the expansion aspect of it.
And so that's problem number one. And so from a revenues point of view, I was pitching to the leadership team, hey, we're leaving a lot of money on the table. Like, I'll bet you I can turn that 5K customer to a 50K customer. I'm going to turn that 50k customer in by next year it's going to be a 500k. let's I'm just going to keep adding zeros to that t the total contract value of this customer. Uh and they they were skeptical. They're like, "Okay, are you sure? Sounds amazing, Mike. Okay." And then to appease the the marketing folks.
Okay. Well, you guys have been asking for references. You've been asking for case studies, testimonials, and the answer has been like, "No, we don't have anyone." Well, I'm going to create them.
I'm going to create you customers that first of all, they've been customers.
They use the product. They know what the problem is. They are solving something that we actually know. Uh you know we have an exact defined success plan and here's how we got there. And so marketing is like yeah that would be amazing. We need that. So from the marketing side, the financial side um it wasn't much of revenue and churn or retention rates as you said back in 2008 or 2010. It was you know it was all onrem perpetual licenses. So there was no concern. Uh and I feel like customer success as an industry in the introduction of SaaS that's when customer success really blossomed because now we're selling to the same customers year after year where in the beginning that wasn't the case. Everybody was happy.
There was no churn but there were definitely issues that that went along with it.
So you pitched to leadership back in 2008. Hey, I want to I want to create this function or I want to run this this experiment here with the team and I want to here's my goals. And you had financial goals, you had some marketing goals, you had expansion goals uh for existing accounts, things like that. How did that play out? How did how did that roll out in practice? Were you given, you know, just like a segment of the market? Was it your existing accounts?
Like how did that play out? So after pitching this to leadership, there was a big smirk on everybody's face. They're like, "All right, Mike. Well, prove it.
You're telling me you're going to increase revenues. Marketing is going to be happy. You're going to save the world. Prove it. We're going to give you the Midwest. You know, we have a handful of customers out there. Go do your experiment. Let's see what happens." So, I had a quarter. Okay, great. In one quarter, uh, we came back with a very large percentage. Um I think it was like 40% maybe 60% of our revenues came from existing logos. Um and revenue was coming from either upsells, cross sales, services, trainings. Um all of it all the things that would not have come in if I did not actually actively work on it. Uh you know, so proving that out that's when the leadership said, "Okay, beginner's luck. Let's just chalk it up to some to something else, right?
Go do it in the West Coast. let's see what happens over there. It's it's a bigger market. It might be a little bit tougher. And I came back with the exact same number. It was very consistent. So that's when they said, "Okay, you've got the formula down. Go take on North America." And that's when they gave me kind of an open checkbook to build out my team. And so we started repeating this process. We found that process. We found the rhythm. We found what we needed to do, which to be honest, it wasn't that much because we weren't doing very much to begin with. and we were able to repeat that process in the northeast, the southeast down in Tola and generated all this extra revenue. I know I'm talking about revenue and it's all about money, but it's not really the case. It was really helping the customers, you know, it was more about making sure that they're seeing value.
Uh, you know, truly adopting. And those are like the common up-to-date customer success buzzwords, but back in 2010, those were not the buzzwords. Nobody was talking about stickiness and adoption.
um when we really should have been because those are the ones that we we we we created those we created those customers that truly appreciated us and used us and now they are lifers. Uh so now churn that wasn't even an issue. They were they were green with ingrained with us. They they loved us uh not only from a sticky uh point of view but also from the support level. um you know they know that we were almost their safety net. We were an extension of their team.
Um and so they truly appreciated that and they grew with us.
Yeah, it's a it's an interesting thing like the title customer success. I know there's multiple disciplines that roll under that title and um depending on who you listen to on LinkedIn, there's different agreements as to which title is right. But this idea around like advisory, like trusted advisory, being that being that person for that account or for that customer or organization, I think is something that keeps coming back up from folks like yourself that seems like your teams are winning. And uh there was I'm reading a book right now um from Jay Abraham and he had he has a note about um using terminology around like clients versus customers and things like that. And um he said a client the definition of that is someone that's under your protection and a customer is someone that receives a service or a good. And so if we think about the role that terminology plays in our language and things like having clients a book of business um where folks are under our protection like we're we're we're acting in their best interest and our businesses are profiting as a result but we're always acting in the interest of the customer.
I think that's something that you've said in in a number of different ways already on this show, but I think that's something that speaks so true maybe to the intent or to the type of people that really excel. It's like I'm acting in their behalf. As you said, we're we're adding value. We're bringing new things to their organization and they love it.
As a result, our business happens to make a lot more money. You know, that that's a really interesting positioning.
Yeah, 100%. Um and I know the bottom line, the end goal, the outcome is added revenue. However, what I'm really doing, I don't see myself as a salesperson, right? Like, if the result is that they're actually buying more and they're spending more money, great, fantastic.
Also, let's turn into a KPI because we want to drive that behavior. But really, what I'm doing is I feel like I'm just doing the right thing. Like, in fact, if I were to close a customer or when I was closing customers, when I was a sales engineer and I was asked to just leave them alone and go move on to the next deal, it felt wrong. like as a person, as a human being, like they put their trust in me. Like I was the one that asked them about their problems and everything. What are the issues that we're trying to solve for? I find this beautiful thing. I put it all together and say, "All right, I'm out of here." That next.
Yeah. If it's like it did not sit well with me. It felt dirty. Uh and so that's why I kept coming back to the existing customers. It's like no, like you put your trust in me. Like we have many conversations. Are you using it? Like I know you're working with a professional services team to get them get onboarded.
How is everything going? All those follow-ups. I like money aside, adoption aside, I needed to make sure that they that they took my word for it and they're not disappointed. Like I had my own personal brand to protect, right?
You know, my own image. It's like Mike said something. Did Mike follow through?
And the answer was yes, absolutely.
And the end results they adopted. They were sticky. They bought more. They integrated with us. They told their friends. They became references. And so it was just a win-win-win situation.
Wow. I guess I'm curious. It seemed like the playbook just worked in each region.
Was there anything that broke down?
Anything you had to invent along the way?
So many things broke down and invent along the way. First of all, everything needed to be invented along the way. Uh, I can tell you that when I first started doing this, like just in the Midwest, right? When I had my little experiment that the leadership gave me, I was winging it. Like, it's not like I came in with this plan. It's like, all right, step one, I'm going to do this. Step two, I'm going to do that. It was like, hey, let's just try this thing. It really was an experiment. It's like, all right, you know what? I'm going to start pinging these guys uh once a week, once a twice um a month. Um maybe we should have these like a quarterly meetings.
Maybe we'll invite their leadership to make sure that they know what's going on as well. Oh, they call it executive business reviews now. Yes. You know, but we invented all of these kind of things, right? And there were a lot of things that did not work. Maybe there were things that were a waste of time. Um one of one example is I used to go out and visit customers, right? It's like, okay, let's let's let's do this. And this again, it was all on prem, so it was kind of remote stuff wasn't really a thing. So totally I'm gonna go out there. I'm gonna see them. I want to look them in the eyes. I want to shake their hands. I want to do this one by one. Did it work?
Yes. Was it time consuming? Very much so. I have a book of business of 50 customers. Can I reach all 50 customers in a week? No. That was impossible. And so you know what it was? It was more about how do I streamline it now? How do I do this at scale? how do I repeat what I'm doing with this customer multiple times? And so that came up that that's when I came up with this idea of having user forums. Um it's like, hey, let's just get them all in the room at the same time and let's just do it once and get them talking to each other as well.
So creating this on uh you know in-person buzz uh with customers in your own backyard. I think those were the actual terms that uh that I was using or pitching to them to say, "Hey guys, like you're not alone in this. Like all these uh things that you're using with our product, I'm sure you have a lot of questions. I can answer them.
Absolutely. I can tell you what other customers are doing, but you can hear it directly from another customer in your industry or in your region. Have lunch with them." Uh there was one time that I was uh in my taxi. This is before the days of Uber. in my taxi on my way back to the airport because my user forum had ended. We did like a two-hour lunch and questions. It It was great. They would not let me go. It just kept going. Um and I wasn't even the one talking. They were just talking amongst themselves.
And I was like, "Guys, I got to have a flight to catch, but you guys keep going." And so, mission accomplished.
First of all, it was doing it at scale, but it also drove an additional buzz. It made it that much stronger for them to hear the same thing that I would say but from each other and turning them all into champions. It was amazing when you have one champion who would advocate for a product and then another champion advocating for the same product compete against each other because now they're going to say, "No, I'm the stronger advocate versus the other." And so now we have a room full of everybody trying to be the strongest advocate for you.
So, it was absolutely mind-blowing and I I I can't believe I waited so long to do it.
Oh, that's cool. That's cool. You know, this idea of bringing people together, I think, is really timely uh as more and more folks want to get back to human connection. And I think your strategy around doing that then I think is going to play out really well again now. um for especially for brands that don't have any sort of in-person interaction, there's always the concern like there's plenty of concerns or my competitors don't want to talk, you know, share things with each other or not. But I think the reality is is your competitors are probably going to coffee with each other anyway. Like just because they're under different logos doesn't mean they're not they're not people and they're trying to do better things. And so it's like uh I'm always an advocate for bringing people together and I think that's coming back in vogue again in a way that it probably hasn't been since you know 2018 1920 something like that you know 100%. And I think creating that local buzz uh does a lot too because at the end of the day who is signing the checks, who's making the decision? It's just down to humans, human behavior. And if everyone around you is using one product, and you don't want to be the only one who's not, right? Um it it's it sounds silly. It sounds very hokey, but it's very true.
And also to know that I have a support system. like all these folks around me, like I know these people even if they're not in the same neighborhood. Let's say they're on the on the opposite end of the coast. I know them. I can pick up the phone or I can send them a Zoom invite or whatever, however way they want to communicate. But there's that buzz. Uh you don't want to be that one outlier that's like, "Oh, I'm using that other product. There's no support system there. I'm not cool anymore." You know, that's true. That's true. Oh my gosh.
You've operated in cyber for most of your career, correct? I believe it's mostly been cyber security software, right?
Yes. About 15 years in cyber security.
Oh my gosh. Yeah. And I think like um I think about those folks, the practitioners, right? Like if there's an industry, I think about the ones where like folks are really like tight-knit and stick together. It's like the cyber folks are pretty niched down. Like they they're their own their own universe of people at times. But I think that brings some like interesting and difficult challenges as well too because when I think about cyber security software, I think about like it's not necessarily potentially maybe like daily activity or daily login or like all the stuff you might think about with like tracking customer health scores. Like cyber security actually can look almost the inverse like the less they're in there potentially maybe the better it is you know for the business. So um so it brings some challenges right. So how do you build like that relationship? How do you think about customer health scores or renewals particularly in products where sometimes you actually want the users doing a lot less in there on a particular basis you know like how do you think about that in in in your world?
That is so true right and also within cyber security I guess it depends on where you are in cyber security. Uh if you are the authentication app then I'm using that all day every day. Uh but for things where if it's anomaly detections right if something is happening then we will tell you it's like oh yeah no news is good news right uh but the risk behind that is now now going back to the person who signs the check the decision maker when it comes time for renewal they might not even know you exist they'll be like wait who who is this Mike never heard of him and it's like because our product works so well like we we work so well and that's why you don't know me, right? It's like going to the doctors or anything like that. It's like I never want to see you ever again and that can happen to your point. And so what do we do about that?
Right. And that's that's always a difficult conversation to have or different it's difficult to create the metrics or the KPIs. How do we measure success when we're striving for zero?
And it's a little bit of the opposite really. Uh because we have to think about what would happen if we weren't here to help you today, right? If we think back the last seven months, assuming you're starting your renewal process early like you're supposed to, the last seven months, uh if we weren't helping you, if we weren't securing your environment, what would it look like today? What would your attack surface look like? How many times would you have been breached?
You've been in the media how many times?
Zero. Guess why? It's because of us, right? And I like to bring up examples and it's not to like do any kind of scare tactics or anything like that.
It's just just sharing industry news. I do this very often.
I share similar breaches uh or breaches that we directly protect. And I share with my existing customers like, "Guys, have you seen this? Good thing you use us, huh?" Yeah. Like that. Uh, you know, I I would say in a more professional way, but essentially it's like, yeah, if you didn't use us, that could have been you in the news. That could have been you last month. And you know what? Next month is going to be someone else. And also, have you noticed that all of those guys, they're not using my software, you know, coincidence? I think not.
So, there's that, but then there's also the amount of work and time that goes into it. So, let's say they're like, "Well, without you, before you showed up in our lives, Mike, we we weren't breached. We didn't have a problem. We rotated our secrets every 90 days. We did the right thing. We got our uh PCI compliance. Everything is fine." It's like, okay, no, that's great. I'm happy that you never got breached from a security point standpoint. That's fantastic. But how many hours did it take to rotate all of your secrets? how many hours did it take to make sure that you stayed compliant? And that's when they're like, oh yeah, we had to hire X number of teams and everything or we needed to there was a lot of work and overhead around doing what software can do for us, right? And that's the whole idea around software. And now in today's world, AI, right? And we s we hear about AI taking over or replacing jobs.
Security, same thing. I can hire a security guard to stand at my front door all day long or I can just buy a deadbolt. You know, it's like, okay, I can save a lot of money. I don't need to have uh three security guards at my front door, back door, and my my sliding door at the kitchen. There's this thing called a lock. And very similar idea.
So, now that we have security software in place, you can reduce the number of your staff. Reducing the number of your staff means now you have budget uh or you know remaining budget and with that budget now you can actually do that other project that you unrelated project that you've been putting on the back burner for three years because you didn't have the money for it. Well, I just found you some budget. I found you the budget to proceed with that project and that project now is going to unlock other things that's actually going to fit in with the overall company's business model. So you uh Mr. you know, executive sponsor, whoever it is that I'm working with, you're gonna look like a champion just because you're using my software, right? So, it's just about connecting these little dots.
Yeah.
So, good. You blend sales like perspective and just like not not like persuasiveness, but some of that, right?
Like you just do such a n you're so natural at like blending those two sides of the conversation together to kind of extend the runway. It's no wonder you were successful literally in every region that you went to. Um, it makes sense.
Well, thank you. But it's because I truly believe in it. Again, sales is just the outcome. I'm truly trying to help my customers. That's really all I'm doing. I just I'm just trying to do the right thing. Uh, number one, from a value perspective, they spent a lot of money. I want to make sure that they see value in it and they're doing it. But then also, if I put my security analyst hat on, Yeah. I want to make sure that the world is protected. Um, you know, if you see my actual build, I I do not look like a superhero, but I would love to be. I can be one from here behind this behind the keyboard. And this is the way I wear a cape. This is the reason why I got into cyber security, by the way, because I wanted to protect the world. This is how I can contribute. And so, I want to make sure that they lock those doors. It's imagine if you bought locks for all of your doors, but you didn't turn the knob.
Yeah. No, that doesn't help. And that's customer success.
So good, Mike. Oh my gosh. So good. So good. You may have already given us this answer, but it was something that was really top of mind because I think this this concept goes beyond cyber security industry. I think it's this idea of like we haven't really had a problem, therefore we don't really need your software anymore. And it sounds like from one of your examples, you got really creative. It seems like in staying in the loop with your customers, maybe it's slightly counterintuitive for success professionals to do what you did, which was here are relevant news, industry, market signals, here's things that are happening and I need to make sure proactively that my customers are aware of them and like why this is in their interest. like that idea of closing the loop. I don't know how many folks that would wear a CS hat would think of that as uh as as something to do, but it seems like that was one way that you overcame this like you haven't heard from us. No breaches, no nothing there, but you still need us because, you know, and you like injected yourself back into the conversation. How did you come up with that? Is that just something that you were like, "Oh, so and so might want to see this." Or was there like a was there a strategy or approach to that?
Yeah, you know what? This um actually reminds me of when I'm building my teams or when when I'm just like in hiring mode.
I need someone who's going to be able to empathize with a customer. Not to say that I'm looking for myself. Like I'm going to hire people just like me. Like they they even say like if you hire a room full of yourself then, you know, it's like what's the point of that, right? It's like I want people who are smarter than me, better than me. But going back to empathy, I think that is going to be the key word. The reason why I don't take no for an answer and I'm going to close every deal is because I I truly want them to do the right thing.
It's like no. Like you live in a bad neighborhood. Dead boat is not enough.
You're going to need to put it in a chain. Please just listen to here are reports about your area. You How can you live? Like I can't sleep at night because knowing that you're not putting a chain on your door, right?
Hypothetically speaking, obviously. Of course. Yeah, but I think it it's empathy. It's like if I were you, this is what I would do for myself. And I and the reason why I brought up recruiting and hiring is because I feel that a lot of new or even tenure customer success managers, they see the task in front of them. It's like, okay. And everybody defines customer success wildly different by the way. So if we talk about everything from the customer journeys perspective, my job is to get these five things installed. Got it. I'm installing those five things. Done. My job is to make sure they don't fail and if they do to fix it. Got it. Number two broke. I'm going to go in. I'm going to fix it.
It's operational now. Done.
In my eyes, I that doesn't sound like a like what value did you add here? you know, it's no, it's more of my job is to make sure that they are secured or maybe my job is to make sure that they see what they defined as value. And so, it takes a level of curiosity to understand why did you spend all this money on this product? Uh what are we trying to achieve here? And without asking questions, you'll never know.
And I know a lot of people say it's like, oh, right, it's all about talking to the right person. Sometimes it's not right talking to the right one person.
Maybe there's two people, three people.
Maybe it's a collective group. Maybe it's a person in an entirely different department that's actually driving this.
And again, it's understanding where does this team fall in the entire business model. I can install these five things, make sure they work, and that's going to solve this one person's problem. It might even solve his team's problem. But does this that one team is part of a department? Does it how does that connect to that entire department?
Yeah.
And those are the questions. Those are the things. And through asking a lot of questions, being really curious and truly understanding or empathizing with them, I might uncover the fact that you're you asked me to install these five things. You only need two of them.
Sorry. Uh sorry sales folks. Return the other three. Get your money back. Cuz with these two deploy in the right way, you're going to achieve what you're trying to go for. That's what you're going for. And by the way, uh you also left that back door open. And then then we get into the whole upsell and opportunity expansion conversions. Another door you got to go.
But wait, there's more, right? So at the end of the day, we're not trying to contract. Obviously, we're going to grow the contract value, but I'm growing it in the way that makes sense. I'm not going to sell you something just for the sake of selling it. I'm going to sell it because I truly believe in it. Like I have a personal mantra that I have my myself. Every company I've ever worked at, I need to believe in the product. And I think that's what makes it easier for me. Um and not to say that this job is easy by any means. It's the the hardest thing I've ever done. Um it makes it easier or makes it feel less like work because I believe in the product. I truly believe in every single product that I've ever worked with and never sold because I empathize. I put myself on the other side. If I have my own company, would I buy this product? Yes. When I'm out interviewing for jobs and companies, like there might be three companies that are they're direct competitors with each other. I feel like I'm a company picking the vendor, right? I'm putting them through a PO or demos. It's like, huh, which one do I which one would I pick personally? Uh, and the one that I pick and goes back to being the advocate and competing to be the loudest advocate for that company. That's me inside and I'm turning it onto the customers.
No, that's cool. Well, I I guess speaking of you being your own company, you did that for a while, right? You stepped out. You were a consultant, a CS consultant and adviser for for a time. I believe I was a consultant for a couple of years. Yes. a little over two years I think.
What did you learn as being on the outside of companies consulting on CS?
This is my day-to-day now. Uh what advantage did that give you that maybe being on the inside didn't? I know there's pros and cons to both of live journeys, but I'm curious what you saw how that how that applied to your customers and and your current employers and things like that.
Yeah. So first I I'll say that uh as a consultant I was working with allsiz companies from startups, larger companies, companies that already had a customer success motion, some that had none. And the one commonality I can say is that I was not the only one who was lost.
Like I said earlier, I was winging it in the Midwest like let's see what happens.
Let's try this. Let's try that. they were all in the same boat. It was like, "Oh my goodness, great." Like I felt like less of a of a fool, right? It's like, "Okay, we're all in this together.
We're all doing the same thing. We're all thinking the same thing and we can all learn from each other." A lot of times as I'm consulting them, I'm learning from them as well. Like it's it's all about exchanging information amongst each other. And so, you know, if one thing that I was always brought in to do was help them with like their journeys, right? Like h like how how do I take a customer and just walk them through this journey? Like how do I take them to success? Mike, go figure it out. We've tried so many different ways. And so then I start asking my probing questions. I like, okay, well, what do you do currently? Well, what does the segmentation look like? Who are the customers? How much time do you spend with them? And a lot of the times they would say uh I don't know. We don't we we never measured it. We just go uh especially the early stage startups it's like um customer says they need something let's just do it. It's like okay very reactive right and we we all heard like okay reactive versus proactive so I'm not even going to go there. However it really does start with segmentation and segmentation needs to be revenue based 100%. uh it does not make sense for you to spend the same amount of time on a customer spending this much versus a customer spending this little.
Yeah. If if you're spending if you're doing your white glove service to all of your customers, you're losing money down here. And I get it for early stage startup companies, maybe there's a product limitation. Maybe there's no selfserving aspect to it. So, okay, product, go do your job, right? Make it more self- serving. But I've worked with clients, not customers, clients that did not have a that that did have a self-serving model and yet their problem was that their CSM still had to have this hightouch model and they couldn't get out of it. Why? Why? Why, Mike? Why why can't we break out of this? And because well, first of it goes back to segmentation. Well, why how do we segment your customers?
It's revenue based, yes, but what are the complexities? Like, maybe we're segmenting the wrong way. Maybe we need to create multiple tiers or groups, first of all, based on revenue, of course, that's the obvious one. But there's going to be some customers that are more complex than others. Some that would require more time than others.
Maybe we're trying to push a self-serving model on customers who are just not equipped for that or the other way around. So, you know what? Let's slice it and dice it in a way that makes sense for the customers for what they want. Let's meet them where they are.
There are going to be customers that will raise their hand every other minute and say, "Wait, what's this? Wait, what's that? This is broken. I have a thousand feature requests every single day." versus the opposite end of the spectrum where you're going to have customers that are going to say, "You know what? Leave me alone. I got the manual. I'm just going to do it. I'll let you know if I have questions." And they're not shrugging you off. They're That's just how they work. Who goes to the bank today? You go to the ATM. You want to self-s serve. But those are the scary customers because now we don't know what they're doing.
Yep. Did did you find that any sort of relationship between the dollar amount customers are spending with you and the more touches you had to have on on the account to keep it healthy?
Broad strokes. I know it always depends.
Yeah, definitely depends. But yeah, if I was looking at broad strokes and if I were to plot it out on a graph, I think so. I think there's a direct correlation there. Usually the customers that spend more money are the complex ones and usually the complex ones are going to be the ones that require a higher touch model.
I was also thinking about your work as a consultant and I'm curious were there any false positives?
Were there any things that that companies mentioned like we've got to do this otherwise people will leave? and you you kind of came in and brought a new perspective to it and realized like you're burning a lot of cycles on this and it's maybe not needed. Maybe that isn't the trigger to retention or expansion or whatever the outcome was that that you're thinking it is.
I've seen that more than more than once um where and this is usually uh early stage startups where the two co-founders like the company is their baby and they want to be so there for their customers which is amazing every time there's a new product release or an update like no we need this personal touch I want to be there to deliver the news or have a customer success manager deliver the news every single step of the Hey, that's great. I I love your charisma, but that's not scalable. You're burning a lot of time here, right? And so newsletters or inapp communications, banners, we have so many things to deliver the same the same value, the same touch points, the same journey without burning so many hours, right?
And so I think it goes back to streamlining efficiencies and not to say that hey we're going to send you a newsletter and never talk to you ever again. Uh and so if I'm talking to like a lower touch digital touch customer, I'm not going to have my weekly cadence meetings. I'm not going to have my executive business reviews twice a year or three times a year. But monthly newsletters, everything you need to know, it's right there. Maybe I'll have a bi-weekly email check-in, maybe a quarterly meeting, right? And so, like, there are things that you can take from your entire your large your main customer journey and trim it down a little bit and deliver the same customer journey. It's just a reduced version of it that at the end of it uses far less hours.
I like what you just said there though because I think about that in productization, right? like you got the width and you've got the depth of the product. How deep do we go in every single step of this problem that we're solving. What you just described is something I personally haven't thought of before where it's like let's take the same energy, maybe even the same delivery mechanism or the same modality and let's just dial back the frequency.
We're not going to tell you no, you don't get it at all, but we're just going to to make it sustainable, make it scalable, make it something we can afford to do by dialing back the frequency. And that's a that's an interesting lever. I haven't I haven't thought of that before. That's great.
That's awesome.
Yeah. So dialing down the frequency but also at the same time we're talking about dials dialing up a little bit on the product side because now if the product and all products have some kind of a dashboard but imagine if there was a dashboard that had a constant executive business report view every single time you're logged in and so we're force feeding them all the value all the stuff all the things that they're getting from your software every single time they log in. Well, guess what? Now we can eliminate an EBR while still delivering an EBR, right?
Yeah. Yep. So, you're like, actually, the frequency of that goes up. Just the the format in which you get it dows back. That's awesome.
Correct.
Awesome. And I love it. You and I were talking when we first met about the role of CS in a world where things are becoming more and more integrated, automated. thinking about even simple things like the handoffs from product development teams to knowledge base and documentation teams and tech writers like the role that AI is playing right now in this transformation of of the business and you said something really interesting has stuck with me since we first met which was that customer success and product are heading toward each other and and you actually see a world where like that line could potentially disappear like it's it's getting thinner and thinner but CS and product Could you share more about that with our audience? Like I thought it was really interesting this this concept of CS and product merging over time potentially becoming one really strong function together. Why is that happening and what would have to be true of the CS team for that to happen in the future?
Yeah, great. No, I love that. So, first of all, CS exists after a project is already there, right? So product is there it's built it's sold now we have paying customers now we bring in CS so now once there's a relationship between product and CS products team is to cater to the existing customers what do they want what do they need let's build on that now who better to understand what the customer actually wants than the customer success manager so in my experience all the best product managers are the ones who used to work directly with the customers who had a direct pulse on the customers who understood what they needed uh who are keeping in check the the the real expectation versus reality, right? You see all those funny memes and they're always wildly off, but product married to customer success can match that to say like this is what they're expecting. This is that's exactly what we're building and and so yes, I see that a lot.
Furthermore, I would say that product is dependent on how the customers actually use it. Product can say, "Well, we have this vision. We're going to build this machine. We're going to throw it out into the the world. This is how they're going to use it." And customers are like, "No, no." Like, like it it does work that way, but we actually found an alternative use for what you build. we love it and we're using it this way and we're still seeing a ton of value in it. And so if we can deliver that back to product and product is like wait really that's how they're using it. That's that's actually what they wanted to do with it. Let's lean into it. Let's make it even easier.
Let's not make it like a a workaround to take this product and do something else with it. Let's actually make it that way. And again, who better to deliver the news than a CS product management, right? And and so in my eyes, they definitely go hand in hand. They are partners in crime.
Yeah, I love that. I I used to work as a business analyst and so my job was obviously gathering lots of requirements from customers and things like that to go back to product teams with. And I think about that role and how at the time, you know, perspective or I guess hindsight's 2020 really what that was was an iteration of of client success in a way where to your point we're not we're not having to predict the future, shake the crystal ball, hope we see the right answer. It's, you know, we're really involving customers in that process. And I I agree with you. I think that the vision of the future with CS and product really married at the hip versus sometimes at odds with each other. Sometimes I feel like the organizations I've been a part of, you know, you have power dynamics that are interesting to navigate sometimes, but seeing those roles blend in and actually becoming either part of the the sprint and the development pods and functions and things in new ways or maybe even like learning the vocabulary kind of like the tool set and the vocabulary of the engineering team that maybe they've never had to learn before. It's like understanding how those handoffs can happen. Um, I think ultimately to your point, it's getting the voice of the customer as close to the person building the thing as humanly possible. And sometimes having an extra team member that has unique skill sets or has unique ways of communicating or has unique ways of asking questions and extracting that information out um, sometimes is facilitated better. And so having that little team put together around your accounts is is really important. That's cool.
That's cool.
100%. No, I even have an example of that. Um, there was one time I won't name what company I was working with at the time, but product was working on this huge project. It was they were very excited and so I started floating that idea around with my existing customers.
Nobody wanted it. I was like, "Hey, if we have this thing, would would you be excited about it? Would you use it?" 10 out of 10, nobody wanted it really. So, I went back to product and said, "Guys, scrap that project." like please like spend the time spend all that time on these are the things these are the things that they want um you know so it's it's it's it's amazing which is why they definitely need to be married at the hip and which is why I'm seeing more and more product teams leaning on the CS team and and vice versa CS leaning on product and which is why that that line is getting thinner and thinner to the point where it's just non-existent.
Yeah. If a CS leader wanted to like CSM or or an executive wants to build more influence at the product layer, especially like maybe new to the organization or things like that, like where do they start? How do CST members begin to build that rapport? How do they get involved or integrated with the product team? What advice would you have?
The easy advice that everybody says like, "Oh, well, let's meet weekly.
Let's just throw another meeting on the calendar." I would Yes, sure. We should do that. Any ways I would urge uh I I implore the product team to be with the customers. Join them. Listen. Uh it's one thing for me to say I can talk to the customer and I will advocate for them and bring it to the product team and vice versa. I want them to hear it from from each other. Um for so many reasons. Uh the product team will also have their own follow-up questions and they can hear it directly from the customer. But the product team can truly empathize and understand ah they're asking for this because of that and without it here are the ramifications. And so it's it just it just hits a little bit differently. They feel what I would feel and there's no way for me to convey the customer's emotions over a Slack message or even just a meeting with them. Uh and so I think that's my one piece of advice.
Join the customer meetings. I love it.
You You are really good um picking this up and really big on empathy with other folks. Like even just our pre-in you had such a great way of building rapport and like doing that. And as you've spoken throughout the different obstacles, it seems like if there's one word that comes through all of your answers, it's usually like empathy for the customer. I think that that's a maybe a superpower that you have, which is which is really theme. I try to stay consistent.
you're like, "If nothing else, I'm I'm at least consistent there." I'm thinking about as we as we wrap up our time here, thank you for spending some some of your Friday afternoon with me. For someone who's maybe early in their CS career, maybe an earlier stage company that's very new at building out this sort of function. They've been in logo acquisition mode and now they're like, "Oh, we got to keep these logos around." What is the thing that they might get wrong first? like what is the big stumbling block that early teams or early companies have when they're building out a CS function? What would be your advice there?
I think it's a little it's a combination of a lot of the things that I was saying earlier. So, this is a great way to wrap up the show. This is the summary. Here it is.
It's the expectation of what you built like this is how they're going to use it versus like they're not using it that way at all. They love it, but not for that. they they're going to love bits and pieces of it in certain ways. And so the advice would be roll with it. Be flexible. Meet them where they are.
Understand why did they team up? Why did they decide to buy your product? Are they did they buy the whole thing? Yes.
But maybe it's just that one thing.
That's the one thing that they really wanted. And so if I go into a deployment or I'm working as customer success and I start harping about these other things and they're like, "We only wanted that one thing. There's a misalignment there.
Right there. Right. So, really, you got to empathize. There's that word again.
You got to empathize with the customer and truly understand why. What are we doing here, guys? Why are we at this table today? What are we doing? Ah, that's the one thing you need. Let's work on that. Let's focus on that. Let's double down. Let's not ignore the other things. Well, do it. But now I understand what your focus is. So, that's advice number one. The other thing is ex or lack of a journey. Uh everybody has this idea. Okay, day zero we're going to have this kickoff meeting. Tomorrow we're going to have we're going to start our cadence meetings. Yeah. And then by next week we'll be in production and then by the end of the month you you'll be doing all these cool things with it. That doesn't always work that way. In a perfect world, yes. During a uh POV, during the pre-sale cycle, sure. But in production, in a real live uh scenario, you're going to have to pull in someone else. You need to involve other teams. There's going to be um I don't know other other uh per permissions and security uh measures that we need to take into place. So and so was on vacation that week. Okay. There's a lot of things that go at play uh that that that's in play here. And so that one month dream, it's like, oh yeah, it should take about a month. In reality, it might take longer.
And so, it's not CS's fault. And I'm gonna say that on behalf of all CSMs in the world here. It's not our fault, guys. Please back off. It's not our fault. We're doing what we can. There's a lot of things that is just outside of our control. And that's how we have to learn. This is how we learn what is the true customer experience, the true customer journey, a realistic customer journey, if you will. Because one month is not realistic. Maybe it's three, maybe it's four, depending on what we've been seeing. So, let's collect data.
I love it. We've got a couple of punchlines there, Mike. Excellent.
Excellent conversation. Thank you so much again for sharing your Friday with me. I'm sure that anyone that gets a chance to hear some of this. They're going to get a chance to dive into your genius and uh and your experience and uh just how much you care about making the teams you work with successful. So, thank you for sharing your insights with me today.
No, thank you. really looking forward to any other shows. So, this would be great. This would be fantastic. No, but thank you so much. It's been a pleasure.

Founder, CEO
Matt Tidwell is a strategist, creator, and founder of ThinkThru, where he helps teams build education-led customer experiences that scale trust and unlock product value. He also co-founded Care Transformation Studio, a platform reshaping how healthcare organizations access expertise and intelligence.
