Customer Success: Pivot Your Career · 2025-08-14 · 53 min
Key moments - from our scoring
Substance score
44 / 100
Five dimensions, 20 points each
Matthew Rinkert brings seven years of customer success experience across Outreach, Icertis, Trustee, and DocuSign, where he manages enterprise relationships around agreement digitization. The discussion centers on the evolution of customer success from traditional account management to a broader organizational mindset, with particular focus on procurement dynamics, vendor-customer relationships, and multi-departmental collaboration. Matthew explores how successful CS professionals balance renewal ownership with genuine value delivery, drawing parallels between his early consultative selling at Windstream (handling 63+ telecom products) and modern enterprise customer success. Key themes include moving beyond cost-cutting procurement mentalities to relationship-based value creation, the importance of understanding customer OKRs and business outcomes rather than just churn metrics, and embedding CS principles across product, support, professional services, and sales teams. The conversation challenges whether CS should be decoupled from revenue and examines how curiosity about customer business models - whether in telecom, SaaS, or agreement management - creates trusted advisor relationships that drive both retention and expansion.
Traditional account management was primarily revenue-driven with quota ownership of renewals, while modern CS (popularized by Salesforce) decoupled from revenue to focus on success metrics and churn reduction. Matthew notes a recent return to hybrid models where CS owns renewals if they've proven value through business outcomes and multi-threaded relationships.
Rather than compete solely on price, successful CS professionals should demonstrate broader value through tacit knowledge, reduced friction, business outcomes, and additional capabilities - positioning upgrades or staying at current rates as superior to the uncertainty and knowledge loss of switching vendors.
Product decisions impact the entire customer base, so CS must act as a feedback loop, bringing customer insights directly to product teams to ensure platforms remain relevant and innovative while following the 80/20 rule on feature requests.
When CS professionals understand customer business models, industry challenges, and organizational goals, they can have candid conversations, position relevant use cases, and become trusted advisors rather than order-takers, which strengthens retention and expansion.
Matthew and the hosts argue these metrics have limitations - customers can have healthy relationships yet churn due to executive changes, macroeconomic factors, or recency bias (bad product days), so models should account for external variables similar to how sales teams adjust forecasts for market headwinds.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains a few useful operational points (single vs. multi-threaded in enterprise, CS attached during pre-sale implementation, sales owning first renewal) but they're diluted by long stretches of generic relationship platitudes and a wandering procurement intro.
I think that's one mistake that people make in the enterprise is being single threaded
customer success is actually attached during the implementation, whether it's a, uh, system integrator partner or in house professional services
A couple of mildly fresh angles (salesperson responsible for first renewal, CS pre-signature involvement, waiter/gas-station as CS training) but most content recycles standard CS-vs-account-management and AI-won't-replace-us takes heard broadly.
the salesperson's actually responsible for the first renewal
that is customer success. Because they want me to go out that door and come back to Pete's
Guest is a genuine practitioner with real enterprise CS experience at named companies (DocuSign, Outreach, Icertis, Trustee), though at IC/CSM level rather than a scaled leader who's built programs.
Matthew has worked for such companies as Outreach, Icertus and Trustee. Along with his current role with DocuSign
About seven years ago, Matthew pivoted into CS to become a successful enterprise customer success manager
One concrete detailed anecdote (the 50% procurement cut walkaway) and named companies/roles, but most claims stay abstract with few metrics, dollar figures, or measured outcomes.
we're cutting all of our subscription services in half. So if you can't cut it by 50%
the company I work for, Windstream, they sold about upwards of 63 products
Hosts ask reasonable open questions and share their own experiences, but they rarely push back or challenge claims; it's a friendly, agreement-heavy exchange with hosts often answering their own questions at length.
Have you seen that model or what are your thoughts on something like that?
How does that old account manager role vibe with where CS was to where CS is going?
Computed from the transcript - who did the talking, and the words that came up most.
Guest Matthew Rinker, Enterprise Customer Success Manager for DocuSign , joins the Customer Success Pivot Your Career podcast with co-hosts Alex White and David Lokietz. Matthew shares insights from his journey from consumer hardware to SaaS, highlighting the importance of consultative selling, strong customer relationships, and the evolving roles in customer success. Learn what it means to be an Enterprise CSM and the challenges encountered and how to manage these effectively. 01:47 Role of Procurement in Renewals 12:34 Account Management vs. Customer Success 18:55 The Importance of Customer Success Mindset 27:44 Customer Success Models and Strategies 38:50 Enterprise Customer Success Insights 42:52 LinkedIn Tips for Customer Success Professionals 45:31 Alex & David Wrap Up
Transcribed and scored by The B2B Podcast Index.
Speaker A: Foreign.
Speaker B: Welcome to the Customer Success Pivot your Career podcast. I'm Alex White and my co host is David Loketes. Our podcast is focused on people looking to get into CS or move up in CS if you're already in the field. Hey, David, how's it going?
Speaker C: Hey, Alex. It's going great. How are you doing?
Speaker B: I am having a busy but somewhat good day. I've gotten some strategic stuff done. I've gotten some tactical things done. I'll probably be working a few more hours, even though it's getting late in the day, probably more than a few hours. But, hey, it's leading up to my vacation, so to be expected. But, uh, anyway, what's on your mind today?
Speaker C: You know, there's always a lot going through my mind, but in the immediate time, right now, it's all wrapped around procurement. Just the general relationship of renewals. How do vendors and vendor management react to individuals and companies and the expectations?
Speaker B: Yeah, that's a big topic. Now let's get into it.
Speaker C: When you talk about customer success, we talk about renewals, we talk about customer satisfaction. What I found is that depending on the person, they want to just grind and grind and grind. They don't want it to be a symbiotic or they don't want it to be about a relationship and what's fair. So it doesn't matter how large or how small the organization. Sometimes individuals just have to get their point across and win. And it's really a terrible way to operate and build relationships.
Speaker B: It's one of those things that the procurement industry has to change because their goal is they get comped on how much they save on things. And I remember when I was at a big company back at the back in 2016, I was doing renewals, uh, for a short term, trying to get some old contracts back on track. And one company called me and said, we're cutting all of our subscription services in half. So if you can't cut it by 50%, then I'm not interested in renewing. And I had to go back to the salesperson and go to the CEO and say, okay, this is the situation. They had really good rates already. I said, I say that we walk away from it. It's too much overhead for us if they're not willing to pay us for it and we lose them. But I don't think we will. And I contacted them and said, here's the steps we have to do to transition off of our site. And I gave him a plan for how to move to another vendor and he goes, whoa, whoa, uh, what are you doing? And I go, well, you said not to even provide you a quote if you're not going to. If I can't cut it by 50% and I can't do that, so I'm just providing you the steps over the next 30 days. So you have a smooth transition. You don't impact your business. They resigned. And I actually think there was actually a little bump in it because when I came back, I had reduced the bump a little bit, but they were so far below market value.
Speaker A: So.
Speaker B: But anyway, it's interesting. A lot of times you just have to play the procurement game, but it's not necessarily in the best interest of the companies to have a good relationship. And you have to kind of separate that in your brain of the people you work with versus they're told they have to go use procurement.
Speaker C: It's amazing. And I get. Companies are trying to save a nickel. I get it. And there's a lot of overhead and a lot of costs and. But they don't always look at what's the right thing to cut and. Or what are we getting in return for that. When you talk about some of these contracts and again, idea at the enterprise level most of the time, but they don't look at things like tacit knowledge. They don't look at things like reduction in friction. They don't look at things as. And you know about, hey, what are some of the additional things you're able to take on? And they just sit there and look at it from a dollar perspective. And that's like I said earlier, it's. Sometimes individuals just have to win. Okay, I got to cut it by this number. That's what I told my boss. I'm going to look like a shining star. Where the flip side says, I've worked with people that take advantage of who we are, all the things we've brought to the table over the years, and they go to their boss and it's even a bigger win because they're saying, hey, instead of cutting from a dollar down to 70 cents, we're at a dollar ten or even for that dollar, look how much more we're getting. And if we go somewhere else, there's the uncertainty, there's the lack of tacit knowledge.
Speaker B: And, uh, it's tough, right, because what they're trying to do is just get good value for their money. And where I thought there was an interesting model, I'm assuming it's still around, I don't know. But one of the renewals I was doing back this was like eight years ago. One of them was they outsourced their procurement to a company and the goal of it was essentially which made sense at like a large scale thing. So things that were small amounts but a ton of licenses, where people like buy it for the whole company, they get some like video conferencing system or if they do some other thing where there's this commodity that this company knows across all these companies, what the going rate is, then I can say, okay, you don't want to get the one salesperson that just is a stick in the mud. In that sense it makes sense because economies of scale and stuff and work that. But when you start talking about enterprise customers and these custom solutions and stuff like that, it goes out the window. Those models, it's like you got to really understand the business, the experience, how long we've been working together. Is this going to make our company money or not? But they're incented by cutting. Uh, so it's like the company sets itself up to kind of hurt itself in a little bit.
Speaker C: It blows my mind. And hey, we've been doing this a long time. We're this large enterprises organization. Hey, we want you to do this. But oh, by the way, we're sunsetting these four applications. Can we pivot and can you help us with these three things? Short term, there's so many give and takes that could occur. That's just goodwill that you may do that you can help them and you may have enough of an ability to then even help them sunset some things. If you're constantly playing the price game, you're just missing things that may be going on in the shadows that just aren't jumping out at you.
Speaker B: So yeah, and when I'm in a position that I'm getting software from someone, I think about that, right? Because usually I'm working for smaller companies. So it's someone that plays like five roles and part of its procurement and finance and all these different things. So I don't have that structure in place. And I always think about like how do I make my vendor happy to want to work with me? Not how do I get the lowest cost so I can get this little gold star when I get to the quarter that you cut down the costs here. But at the end of the day, they're not going to do anything extra for me. They're not going to return my call real quick. They're not going to do all those things. Instead I'm going to them and saying, hey, why don't I, uh, become a reference for your company or why don't I go do this? Or I'll do a case study with you. I'm looking for ways to not only give them value back that they can go and tout that they receive this, but maybe reduce the price increase a little bit. On me, I like helping my vendors. My vendors are successful using their product. That means I still get to use the product and they continue to enhance it. So I think everybody wins. So we definitely should have a full episode on this and maybe get some procurement people in that might be thinking of this differently and thinking of themselves as part of customer success. With that, let's go to our guest. Today's guest is Matthew Rinker.
Speaker C: Kurt.
Speaker B: Matthew has worked for such companies as Outreach, Icertus and Trustee. Along with his current role with DocuSign, his roles over the years have included sales, business development and strategic partnership development. About seven years ago, Matthew pivoted into CS to become a successful enterprise customer success manager. Welcome to the show, Matthew.
Speaker A: Thank you. David and Alex, thank you for having me.
Speaker B: So, Matthew, to get us started, why don't you provide us some context to your career and how you ended up in customer success?
Speaker A: Yeah, I'll try to do an abbreviated version. And so if we go way back to the start of the career, I started more in kind of hardware, consumer hardware. And so that included a stint within consumer hardware that it would actually sell to big box retailers at one point, the best buys and targets, obviously it has no correlation to what I do today in sas. And there was one point in my career where I made an intentional pivot, being in the San Francisco Bay area to get into the burgeoning software as a service space. So that was probably around the 200910 mark. And at that point I was more traditional sales. I would do full cycle. So anything from the inception of a lead, cultivate my own lead working with marketing. I think we're all familiar with that, to account management to business development. And you mentioned strategic partnerships at one point. And so to get into software as a service, that was the goal. The light at the end of the tunnel. Actually did a time in the telecom industry and so very commoditized. But the company I work for, Windstream, they sold about upwards of 63 products. And I think that's where I really truly learned the value of consultative selling, which we also know bodes well within customer success. So that's where I got the notion of, uh, you're not just selling a widget that goes on A shelf somewhere. But in fact you're selling a service and then what business outcomes are you trying to get out of that? Especially in a highly commoditized industry like telecom. And from there I was able to cultivate a very strong network within the Bay Area as we know. Like it's a very insert community and then also a very giving and sharing community as well. So that meant itself to trustee Data Privacy where I was net new sales. But I always honed in on the account management aspect. So like many sellers you usually retain like a certain percentage. You're able to grow them, cultivate it, get those strategic relationships and really expand the business. Fast forward a couple years. My then girlfriend, now wife and I we moved up to the Pacific Northwest to Seattle and I took on probably my more traditional customer success customer advocacy role at icertis. And that was again it was when customer success was m coming more to the forefront within technology. And from there I've been in some form or fashion in customer success since then. More traditional roles, whether it's you're decoupled from any renewal or ones that you are owning the renewal number. And that's kind of a truncated version of where I've been and where I'm at now.
Speaker C: Matthew, that's a great introduction. Thank you. I'm really there's a lot to unpack with what you just said and currently the work you're doing and customer success. I think it'd be interesting just to go roll back a little bit. And why did you pivot from consumer hardware to the SaaS selling software as a service? It'd be interesting because then we can have a little bit more foundational as to now what you're doing in customer success.
Speaker A: Yeah, absolutely. For consumer hardware there was kind of two lanes for that. So you had the wholesale reseller division and then you had the traditional sell to on the shelf. And with that one it's very specific of the outcomes that the retailers at A channel wants. You know, it's all about very margin driven for the most part. You certainly want to make sure that they expand their categories and then even one of the offerings that I was part of that was the case and the emphasis. But I think for me I wanted to challenge my train of thought and thinking instead of going outside the widget, which widgets we all know that they have a place in the world. But I wanted to really force myself into the idea of the intangible. So as we know whether it's a consultancy like a big four or software as A service, you're not actually holding anything in your hand, but you're working with people below the line and above the line trying to understand what their okrs are, what their business outcomes are. And that really to me was a shift in a mindset and I think for others as well. And so one, it was a personal challenge and also I saw where the industry was going, at least within the Bay Area, which was software as a service and this consultative business outcome approach.
Speaker B: So now that you're in the SaaS area, one of the things that you had talked about was a role of an account manager. And curious to get your take on it. Now that you're in CS and have a successful career now pivoting in there. How does that old account manager role vibe with where CS was to where CS is going? Because there's a lot of talk out there on the podcasts and forums and stuff about is the new CS really an account manager? What's your kind of take on that? Uh, as you played in both those roles?
Speaker A: Yeah, I'll take my take. And then I'm curious about the two of yours as well. So traditional account management, you get X amount of accounts and you're expected to grow on X percentage year over year. And then sometimes you can retain them for 12 to in perpetuity, depending on the relationship. Account management, it was always revenue driven, so you had a certain quota if you will. And I think also too that because you own that renewal, that was some of the relationships with that said client. One thing I liked about it is that you always, you get to establish the relationships again, which I mentioned, folks that are making the decision in terms of budget, the influencers and also the would be stakeholders as well. And I think that a lot of that has carried over. You always want your business decision makers, stakeholders and influencers. I think that transcends both account management and customer success. Then in the last m, I would say 10 years there was like that discipline of uh, decoupling customer success from the revenue and then more being a special team. I'm a big football guy. So you have the special teams that would come in and they're really truly focusing on KPI's success metrics, obviously influencing growth and then decrease in churn. And I think that was the different approach and I know that Salesforce popularized it and then a lot of software companies followed suit. I think what you have now is you have a return to customer success. That that might be the title, but in a lot of cases they might be account management where they own renewal or they're tethered to the revenue and that's either growth or retaining the current book of business. For me personally, uh, I think if you have a good relationship in customer success, there's no reason why you can't own the renewal. Because if you successfully proven the value and business outcomes based on what they're trying to do, again maybe it's multi thread and multi departmental, you get that right to ask for that renewal another three year term. You also get that right to explore other parts of the platform that might be beneficial and then do proper discovery and then be able to add more value to their business and then help them do more with your particular awareness. And I'm curious, the two of you, what you think about it, because there is certain doctrines or disciplines where it should be tied to a revenue or it should be decoupled from it. So I'm curious to two of your thoughts as well.
Speaker C: Matthew. I think that's a great description from account management to customer success. The key differentiator for me and the whole customer success management, because there's a broad span of responsibilities we have and a lot of it is covered, would be covered under management. But now I see us driving more to the customer, how they're using our product, what does success mean for the client? You're really developing a relationship at a different level. You're not. We are always going to be revenue driven, we're always going to be upselling, cross selling. It really is how does the customer achieve proper outcomes and how do they measure it? Because and you talked about okrs a little bit earlier on, but once they're achieving their desired outcomes, you really develop that relationship, that seat at the table or that trusted advisor. There's so many different ways of putting it. And I think that's where customer success management has really taken what we used to call account management, customer service, all that kind of stuff, bundled it together and bringing it to a more effective way of building relationships with our customers. And the other part, I think there's also a greater emphasis across the organization into understanding what is customer success, how is that shared across the organization, what can they do a little bit differently and possibly in product development as well. Alex, your thoughts?
Speaker B: Yeah. Most of my roles in customer success have not been directly tied to uh, the revenue side of it, surprisingly. I always thought it was odd that people would have things like CSAT or NPS as kind of part of their goals because I've had several customers that love me. We did everything the product was Doing what they want and they don't renew.
Speaker A: Yep.
Speaker B: Because a new executive has come in or something else that's happened. There's so many different variables to it. I think it's an interesting, you know, how you manage that and how you manage the percentage of uh, how that churn happened and understand the root cause of that. I think should go into the model of how you measure the churn. I'm actually pushing very heavily to now create as I'm starting to build a team. I'm in a startup and I'm the only one in cs. As I add someone I want to be and I want the other person to both be on revenue things because I think it does create a little bit of a different way that you think about things and it's not just about servicing. It is the continued leaning forward and you don't lean back and I've always been a lean forward. But it makes you think about a little bit more.
Speaker A: One thing. Just playing off of that. I appreciate both of you. You mentioned the csat, uh, and nps. It's interesting you mentioned like you can have a completely healthy customer client and then they do churn. But there's also a recency bias as well. It could be a bad day where there might be an outage or the product is not working. The change management wasn't effective. So I agree that we should revisit that modeling. Just like sales teams revisited, there's macro headwinds. They're probably going to reduce their forecast as well. There's so many factors coming into play and especially publicly traded companies, when they talk to the street, there's different models and different ways of approaching revenue.
Speaker B: Yeah. And as we look at that, I'd get curious because I brought this up on a few of the podcasts is taking customer success as less of a department and more of a mindset within the organization because you are reliant. How have you seen, seen that work or not work? Uh, organizations and how does that impact the churn and stuff if you don't have that mindset?
Speaker A: Yeah, I really like the mindset and that was one thing that I wanted to broach is the interdepartmental aspect of customer success. We all three have had that title for many years, but it is a shift in culture of customer success. So whether you're customer support, looking through this barrage of tickets, what is the business outcome? You can identify patterns. Professional services, when they implement, what is the perceived outcome at the outset of the go live. One thing that I've really partnered strongly with is product throughout my career is actually at one point I went to product school here in San Francisco intending to pivot but I think it's actually made me a very stronger customer success. And the reason being the only reason anyone works at a company in software is because the platform or product has been built. And so one thing that you don't want to do is alienate the vast majority of users doing things in a vacuum. And so I think that's one thing that customer success the onus is upon us to uh, bring product in the frame takes a village to say and ensure that they're hearing that feedback loop directly from customers. And as democratically or democratized as it can be, that's what's building out the platform. You certainly want to be innovative but I think you also need to follow the 8020 rule and it also goes in lines with your sales counterparts. In my role I think it's also you sell a uh, product to a client net new they've never heard of your company before but now you have that relationship. You need to make sure you're not just hitting your quota but during that sales cycle they really understand what's the long term success they want to see in that product. And I think the good salespeople partner with folks like us uh because we'll inherit that they truly understand the client, the problem statements and business outcomes. So I do agree with that mindset and it's a mesh network to make customer success effective in any organization.
Speaker C: I have to uh, believe Matthew that partnering with sales I think is a really good way to tag team with the client especially with the trust that you've developed. And from my perspective I'd like to hear your thoughts on it is the customers actually appreciate having that other layer because throughout the year you're in constant contact with them and you're beginning to learn a little bit more intimately what their problems are. Is that what you're seeing? And I know you deal with customers at an enterprise level and then down to smaller clients as well.
Speaker A: Yep. And also two different roles admin, uh, all the way up to executives. Yeah, I think that customer success you do get the seat at the table and you can have very candid conversations if you understand their business. Business I think that's another aspect you as much as you can try to put yourself in their shoes, their industry, what they're encountering and I, I'm always in the mindset is I'm huge in the business. I've always been enthralled by businesses. So I think that's also what gives me an extra edge. And then if I'm partnering with my counterpart on the sales part, I want to equip them as much as possible, empower them, making them a SME as much as possible because it is teamwork. And I'm also okay with that layup, providing the assist on the court. It doesn't always have to be a customer success win, because even it's the account director, it's ultimately our win.
Speaker B: Yeah, absolutely. Curiosity and being engaged with the customer, just not from an artificial like, hey, we need to this piece and you should do it because everybody else is. It's like, well, what's the value? And I understand your business and maybe that's not the right thing for them. You're not just pushing something to push something. You're curious about their business and then figuring out how it maps to your product and how you can make them better.
Speaker A: Yeah, absolutely. I mean, in my current role, we deal with agreements, so the digitization of it and it impacts every organization from a small coffee shop down the street all the way to the F100. And so you have to understand a bit more about their business and be disciplined. So at some points, I might be a little annoying because I'm always curious about what does this acronym mean? What does this particular document mean? I see this about your industry and I see this about your company, but I also think that makes you more armed to have a point of view and how it marries with your particular platform. And sometimes your platform may not always make sense for their biggest initiative. And yes, you also have to admit that too as well.
Speaker C: I think that being armed is brilliant, especially on one hand. You're in a position not just to understand, but to come to the table and say, have you seen this? Because this is what I'm seeing in the industry. Here's some of the things our customers are rolling out. So you're able to be a little bit more proactive. And since they're already using the product, that relationship, I have to believe that you can be not only forthright, you can be rather assertive and saying, you need to think through this.
Speaker A: Absolutely. I mean, I'm curious to the two of you. There's also an argument for customer success too, that maybe AI can just erode that role. A customer comes and then they ask very challenging or strategic questions, and then some can spit it back, maybe on the website or something like that. I don't think that's the case because I think that there's still that human to human interaction and. But I also think that people that don't come with a point of view or understand the business, again you don't have to understand 100%, but maybe 60%, you're paying attention to their industry, you're paying attention to what they're saying and then you come in with that stronger point of view but also being malleable. They say, I don't agree with that point of view. That's where the human interaction comes in and the kind of complementary nature of it. And that I've heard that time and time again that, that artificial intelligence, not just customer success. And I fundamentally disagree with it. If you're strategic and your relationship minded, that's not going to come about.
Speaker C: No, I think AI is a great tool. It is in the infancy and a lot of what we do with AI right now is just generative. It's Kant based. I think when we get to stronger agentic AI, I think the interaction with people leveraging AI and being able to bounce it back and forth, it's a great tool for you because your customers can sit there and look through the right AI and get things flushed out, but it will trigger a conversation with you. So again, if people believe that AI is going to replace, they're. They're sorely mistaken because there really is that interaction, there is that tacit knowledge, there are the unknowns and things that AI just isn't going to be able to learn completely. So you really are going to always need that type of relationship. My opinion.
Speaker B: Yeah, yeah. And I agree. At the end of the day, people like to talk to people. It's nice to get guidance so you're a little bit more educated when you go into something. But at the end of the day the dynamics of how people interact and one solution for a company might not be the right timing or something based on the dynamics within the company and understanding how things are politically. We never want to be in political companies, but there's always political stuff, stuff in every company. It's just a matter of what degree and those type of things, of talking through that and coming up with unique change management strategies of how you roll something out. Not just oh, you should do this next.
Speaker A: Absolutely.
Speaker B: So one of the things that I find interesting, we talked a little bit about that whole go to market where you have sales and the handing it off to customer success. Have you seen? Because it's unique at my company now because we have a subscription model and there's some customers that actually have something Right away. And they need X number of licenses and others that are subscribing to our service with nothing. And you have to figure out like how does a salesperson get compensated for a zero sale? There's a forecast and all those things. So one of the things I think is unique with our company that we're doing, and I'm curious, curious if you've seen this before, is the salesperson's actually responsible for the first renewal.
Speaker A: Okay.
Speaker B: Then customer success is responsible for it after they're not. The customer success in that first year isn't doing everything that they normally do, but it's a salesperson making sure things are happening and someone that's engaged at a high level that I call into saying we're not moving forward in this area. Can you call the marketing person because we agreed to do X?
Speaker A: Yep.
Speaker B: Have you seen that model or what are your thoughts on something like that?
Speaker A: I have not seen it and actually I was going to talk about something a little later about a different model in customer success. I've not seen it, but I like that model and I could see it could be successful maybe depending on what type of organization or what type of solution because it's. And I've always looked at my sales counterparts that they're always co owners and they want the success. But I do think that one, it puts a bit more onus maybe on the first year and you're still doing your customer success success playbooks to also ensure a successful first year which as we know with Change Management center of Excellence, it's one of the hardest, can be more laborious years to implement something. Yeah.
Speaker B: Uh, so what was the other model that you wanted to talk about?
Speaker A: Yeah, I'm curious your thoughts. I've seen in my role that maybe historically customer success would come day one after the agreement was signed or maybe within the first month. Uh, but then in my career I've seen a lot of it shift even before that day one minus six months depending on the implementation. So customer success is actually attached during the implementation, whether it's a, uh, system integrator partner or in house professional services. Because then you hear the discovery, you see like who's talking about what, who's asking about what, the different Personas. And then you also understand how they're thinking about it, what's their readiness or maturity curve. So I've seen that shift quite a bit. Again, maybe bandwidth excludes that kind of dedication, but I've really been able to form point of views or establish uh, relationships even before that Day one. And it's not every discovery or UAT demo that you're going to attend. It's the key ones and some visibility sprinkled throughout. So curious about that approach.
Speaker C: From my perspective, what I've seen over the years and, and again, with or without the title of customer success manager management, I've seen it where the customer success person, whatever their title, is often brought into a pre sales type of uh, situation for a couple reasons. Number one is just purely to flush out and make sure that there's a good match as to what we're selling. Okay. Sometimes it's to be able to give additional credibility and introduce to the customer the ongoing support, hey, here's who else we're going to have on your account. It begins to give continuity. So when a client signs, they do have a common face, common voice, or at least a group of folks that they start getting accustomed to. Because depending on what you're going to do, there's going to be an onboarding process, then there's going to be potentially a delivery type process and then there's the ongoing management of the relationship, etc. And then from a renewal perspective, they may tag team with the salesperson because the clients understand the salesperson is responsible for new business, for renewals, for the commercial aspect of it and they know that they're going to ask what else can I help you with? When they partner with somebody responsible for customer success management, we have the ability to flesh out at an organic level or grassroots level potential opportunities. So the customer is used to a salesperson asking certain questions. They're also going to get used to us beginning to fill in those gaps or also identify and we can represent internally what the customer pain point or needs are. So that's how I've seen it.
Speaker A: Yeah.
Speaker B: And you hit on a lot of the points that I had as well that the one around the continuity piece because it does give a comfort level that the salesperson is going to walk away. And then I'm like, where is everybody? They actually have a person that's going to be able, they can call up if they're not getting something. Hopefully there's an onboarding or something depending on your product and the complexity of it. So I do definitely agree on that. You start to build that relationship really. So it doesn't, it's like the contract signature is just a check mark type thing, thing but they just continue on seamlessly into actually implementing it. And then the other one that you hit on is the learning about sales because what I've heard out there is people going into CS outside of CS there's a much bigger emphasis on sales backgrounds because CS people don't have that sales kind of background to be able to do that. And I think it's unique but, but I think it's if they start going down that path having some type of sales background. I think even if you're in CS now and say you had a layoff or something, you decided to leave a company for one reason or another and you're having trouble getting into cs, what might be interesting is to say well instead of just forcing this thing into CS and there's so many people I'm um, not getting traction, you may want to think let me take a step back and get a little bit of business background in the sales area and helping generate leads or sell small deals to understand the process and get that under my belt and then go back into CS might be an interesting path for people to consider.
Speaker A: I absolutely agree and I think one thing that from my sales days and actually this is an interesting thing about customer success I don't see as formal training in customer success. Whereas sales you have these different methodologies like I'm of the mindset mindset Challenger Sales and then there's a follow up book called Challenger Customer that I think bodes really well for the customer success or account management discipline. And there's Gap selling, there's Spice, there's Miller Hyman, etc. But it's all about taking your mindset out of that widget. And then even then the discipline is understanding the client as much as you can. So when you do go and then it's a very competitive world, you want to different even if you're in a combination commoditized industry, you've heard it, you've replayed it and you're essentially saying this is the business outcome. So I think having a sales background that I uh think I've gone through five sales trainings in my career with customer success you do get training but I wouldn't say there's formalized like challenger type training that I've seen. I'm curious if you've seen it.
Speaker B: I haven't. It's pretty much you kind of fend for yourself and the sales piece, uh, what we were talking about earlier, sit in on a discovery call, sit on those type of thing, review the notes from that conversation, that's your training. So it's you have to figure it out which in one sense is good because CS learns to be flexible, be a self Motivated person to figure it out. And is probably one of the reasons why CS as a community so open because you don't know everything. So you start reaching out to people in your network saying, hey, I'm being asked to do this and I'm not sure where to go. And getting other feedback and not having that formal CS piece is an interesting gap that I think is out there.
Speaker C: Yeah, I think, um, I align completely with both y'. All. I don't see a lot of it going on. And organizations have a tendency definitely to focus on sales and sales training. What I've seen is you have an offering, a contract, lifecycle management. And what I've seen is that broken into three, four, eight different components where internally organizations will say, hey, this is what we offer as A, this is what we offer as B, so it's more product. And then you get into the organic discussion, okay, how would that be applied? What would be the problem use case? But there really isn't the formal training as to how to close move it forward. So that's where your sales training does help. But when you have at least a defined process or a series of offerings like you do, like you, you deal with your contract. Life cycle management, I think is what you call it, that provides really distinct opportunities to talk to a client. That's where I've seen organizations focus on A or B or C along the journey. But, uh, formally across everything, no poor is a core competency. There are certifications now and organizations are beginning to offer it, but it's always outside of a company that you're working for. And to get them to sponsor you or buy into that training is valuable at this time. Isn't always the highest thing on the priority list. So, Matthew, I really was thinking about you pivoted from hardware to the SaaS model. I think it'd be really interesting to hear from you because we have a lot of younger folks in their just early on in their profession. It would be really helpful or get to get your insights on how they could pivot from their existing role, how they should start thinking about customer success, applying some of the things they're currently doing and how to begin translating into that and preparing themselves.
Speaker A: Yeah, I think we broached on it a little bit that customer success is relatively new, how we think of it today. So all of us have seen some fluidity and providing definitions, playbooks, et cetera. So at the younger generation, I try to have them look introspectively of what they've done. I was a waiter for many Years in college. And I think that's actually where my initial training grounds were for customer success. We'd actually call them a guest when they sat at the table, not a customer. And then we were prepped to learn it was a medium to high end restaurant. So we needed to know a lot about the wine, the food on the table kind of things. There's a lot of expectations that actually were CSAT type approach. And so I hone that to this very day. Treating everyone like they want a delightful experience. And then you have that kind of monetary aspect as well. Or I've seen a lot of teachers come into the field as well. Teaching is an incredible tool and knack that not everyone has. And I would really say, what have they done that has been customer success? Even today I was at a coffee shop, uh, a local Pete's, and I've always been delighted by this location. They even know my particular drink sometimes it varies a little bit. They know my name. They're trying to create a delightful experience. That to me is not customer service, that is customer success. Because they want me to go out that door and come back to Pete's day in, day out. And I think it's just looking at that and looking beyond the four walls of what they might be doing to today. It might not be easy to get into customer success, but most people that really have a delight in their career or role are doing customer success today without even knowing it.
Speaker B: That would be an interesting thing to add to the podcast is asking people what did they do before they were 22 as a job and to see if anyone was able to relate something in that past. As a kid I ran a lawn mowing business.
Speaker C: Yep.
Speaker B: And all I thought about was the money I was making on it. But I needed to make sure that I did all the extra little things to make sure that the customer is happy. You have to really provide a good product, a good service, follow up with them and ask them how it is and really be able to learn that. It's an interesting thing to have people think about and look at back at their past. M so, Matthew, one other thing, maybe before we get to our last question where we talked a little bit about LinkedIn. You're in the enterprise space and there's a lot of people that are thinking of getting into enterprise customer success. Either they're not in customer success and they're trying to get into it and jump right into that role. Some in small medium businesses are fully digital where people pay $15 a month and they don't really talk to them and they have some maybe large customers they deal with. But it's really a transactional type thing. Wondering if you could provide some insight into the what does it take or what things you focus on as an enterprise customer success that would be different from those other roles.
Speaker A: I think you mentioned it, you know, maybe SMB might be a bit more transactional. You might have a bigger swath of accounts. It can be dozens as opposed to honed in 10 or less. I think some people in my career I've seen, whether it's sales or customer success, prefer that kind of like scaled approach to it. And then also too like you might get access to the CEO because you're dealing with a $3 million company versus a $5 billion company. So it's easier and swifter. And a lot of times there's not like a multi stakeholder approach that you might need to take with that versus enterprise. As we know you take a company, let's just say Oracle for example has many different subsidiaries. So if you're selling in enterprise software, they are and successing it, you need to understand the different business units in there that might be incorporated into their motion and rhythm. You also need to understand the various stakeholders like in my world, contract lifecycle management, we're working with sales folks, procurement, legal, finance, HR and some of these. So I think truly understanding business, again it's my curiosity and understanding the business and then the various Personas within that business, what they're trying to achieve. And then also too as much as you can be multi threaded, I think that's one mistake that people make in the enterprise is being single threaded because you might have an uh, admin and admins are great for the day in, day out, the week in week out, et cetera because they own the system. But you also need access to their internal customers. You also need access to the executive sponsor. And again it's not always easily done as we know we have limited bandwidth and unlimited influence. But I think that's the key is maybe more like a ground up approach to an enterprise. One understanding what their business is, you know, the different departments or business units and then the different multi threaded approach to Personas and how each one is motivated with your product and then try
Speaker B: to come to a consensus tying back the whole thing about a sales background and everything. The salespeople know when they go to close a contract, who needs to sign off on it, who's the old what process do you have to go through? Because they have to forecast when that sale is going to end. Uh, so they have to learn that process. And CS goes, oh, it's 30 days from a renewal. Are you ready to sign at the enterprise level? And they're like, well, it's going to take 30 days just to get in front of so and so for them to look at the renewal. You have to understand that and start 120 days in advance and start getting the right thing and get it in the process by this date to get it renewed. So it's one of those things of understanding, just like you had kind of wrapping in that other part.
Speaker A: So that's a good point, the processes involved. And then even with that, uh, maybe 120 day, are there any other things you might need to renew? Like maybe there's compliance or privacy questions as well that may not impact like a small business. And then there also might be multitude of people that own that particular budget versus a smaller as well. And so it could be something where they lost that budget. And now you need to understand, is there elsewhere that your solution can work and can you get that budget?
Speaker C: Matthew, this has been a great session. We really appreciate you jumping in and joining us. I think our listeners are really going to enjoy it, the interaction and your advice. Before we let you go, we do have a tradition. We like to ask our guests to provide a little bit of pearls of wisdom about how they should look at LinkedIn and present themselves to. So if you could just give a few kind of tips or a tip that our listeners might want to grasp a hold of as to how to present them on LinkedIn or things maybe not to do on LinkedIn, we always find that's a great way to end our visit.
Speaker A: Yeah, well, actually, I'll just say maybe it's not, uh, LinkedIn like on your profile per se, but one thing I've always loved about LinkedIn and I've been on LinkedIn, I think 19 years, probably longer than I care to admit, and it's evolved. I mean, some people say it's very Facebook now. I agree that there's a lot of content, but what I like about it is you didn't have content before. I think the three of us remember, whatever it was, this was really just a, uh, bulletin board, more or less. And so with the content, I've seen so many people where I'm like, I really gel with that particular point of view. And historically, mentors were insulated to your physical network. And now you can have mentors within LinkedIn. If you see a thought leader, people are actually more gracious with your time than you would think or even somebody that's. We talked about trying to get into customer success. Now if I'm earlier in my career, I could see these people that are maybe 10 years into customer success at the enterprise level, they want to manifest that they can do a dm, um, and it's a call to action. My name is Bob. I'm looking to break into customer success. This is what I've done historically and I would love 15 minutes of your time. I've been called outreach so many times and where, if and where I can, I try to imbue what wisdom I have. And so I think that's what it is. It is a networking tool. But people don't realize the graciousness that people have on LinkedIn. They think that, oh, I'm nobody. I don't even stand on that same level of them. I've been surprised in my career and I've encouraged people to do the same and they've been surprised. So it's a very giving community.
Speaker B: Thank you, Matthew, for that advice. I absolutely agree with you. The community is open for you to take advantage of it. Don't be shy. Not everyone will reply. But, uh, when I was looking for a job, I would send messages and 90% of the times the person replying, we'd end up meeting for 15 minutes. So definitely recommend that. Well, we appreciate your time and being on the podcast, sharing your experience, experience and thoughts. So again, thank you Matthew for being here and we hope you have a good week and all of that. So thank you.
Speaker A: Yeah, I appreciate the, uh, multi directional dialogue and it's a time well spent. Thank you.
Speaker C: We really appreciate it. It was great to meet you. Well, Alex, that was a great session. What stood out to you?
Speaker B: There's a bunch of things. Let me, I'll come up with a couple and then I'd love to have you add to it. One was that consumer hardware to SaaS and that pivot and being able to go into that. I think everyone that's thinking of getting into CS has to start thinking about what have they done in their past and how does that add to that experience of being a customer success person. We focus a little bit on all the sales and stuff. I'm an honest believer that whatever skills you bring to the table, it's what you do once you get the role, like sit down and if you don't have sales, you go into a, uh, discovery meeting and sit on sales things. You have to do the legwork. You just don't Go well, I don't have sales so I'll be bad at that. You gotta take some action there. So I think hopefully that was some good conversation there. The other one was a strong link to the product manager. I absolutely agree with that comment because I found that you're going to get a lot of requests from customers and a lot of it will be noise like I want this button red to blue. That's something like, yeah, we'll get to that. But there's some really some concrete things there that just make sense to you and you're like, this is something that I need to fight for internally and see how I get a higher priority on it. And I think having that relationship with the product manager will only strengthen that ability to get them to quickly buy into you and what you're doing. Especially if they're getting, they're always getting a lot of requests. A smaller company, it's easier because they're just getting it from fewer people. When you get in a big organization that ah, the technical debt they have, the CEO, special projects, they have the other things that they're already on their list and these contracts are signing for prospects and how do you get your thing in there? So those are some of the things I thought were interesting. How about from your perspective?
Speaker C: I'm in alignment with you. I thought both those were really interesting topics. What I also liked was how he dove into the, his explanation on enterprise customer success, especially around the different, many the various roles, the Personas. It was interesting and I think that ties back to your first statement about really defining who you are and being able to track historically some of your positions. You've had to. What is customer success today and how is it defined? If you think about the different organizations we've been exposed to at the startup, to SaaS, uh, models, to enterprise, each organization has their own terminology and that may not align with what we would think of as customer success verbiage today. How does what you've done in the past relate to the different roles today? So when somebody's looking at your resume or you're talking about your experience, you can actually compare apples to apples. You have to bridge your experience with the way it relates today. It's not like 20 years ago we were in a role that said customer success. However, what did we do about cross selling? What did we do about net promoter scores or how did we evaluate clients? It's really important and I think the way he explained that and helped to bridge that gap was really good.
Speaker B: Yeah. And highlight it. How do you highlight that. Because I was thinking, even in my own career, like, depending on what type of job I want to get, being able to say, some of my strengths are being in a small organization where you have 10,000 things to get done, you have a variety of different customers, and how you manage that workload and how I've been successful in that would get a company in a similar position excited about it. But right now it says, oh, I do this, I do that, and I do that, and it's like, okay, this is. This could be anyone's resume. But talk about really pulling out those highlights and being able to make it relatable to the customer based on what your strengths are. Maybe you don't have everything, but some of those things, I think. Really good point.
Speaker C: Well, on top of that, you know, we talk often about looking for a job or how to promote yourself outside of your organization, but sometimes some of that history, that verbiage is good at promoting yourself internally into your organization. There could be an opportunity that leadership or management or you may be missing out on where you can help the company, you can help your existing customer base. So I think it's good to revisit that and start talking through it and seeing, hey, oh, I've done this in the past.
Speaker B: So, David, speaking of our past, in the podcast I mentioned one of my first jobs was owning my own lawn mowing business. How about you? What did you have that was kind of customer success really early in your life that's impacted you?
Speaker C: Yeah, boy, I can think of several roles, but the one that just jumps out at me. When I first started driving, I went to work at a gas station. And yes, this was long ago when you would have gas attendance that would not only pump your gas, but while you were doing that, you were washing the windows, you were checking the oil. And it was actually, believe it or not, it was a steep learning curve as to what clean windows meant. How to pump the gas properly, check the oil. Because what you're doing is you're getting the customer to come back because it was more competitive back then. Now people are mostly looking, hey, I'm pumping my own gas. I just want to look to see, okay, what's the octane? And am I going to pay a couple cents less per gallon? Back then, it was more around, okay, we're getting full service here. He checked my oil. The windows were clean. Not just the, uh, front window, but the side windows and the mirrors. So, yeah, it was. It was a tough learning lesson. My boss was rather rigid about the quality of that. It's something you would see in like Back to the Future in a movie where you wear the little hat and the uniform. I didn't have to wear a hat, but I did have to wear a uniform.
Speaker B: I think in New Jersey, they still pump your gas. I think it's a law because they didn't want to lose the jobs. In Oregon maybe. Yeah, another state. But I think it's just when I went there last time, when I went back home, they just start pumping the gas and they're getting like three or four cars all going at the same time. They're not cleaning windshields, they're not doing anything. But it's interesting concept because the gas stations I see that still have that service, you pay more for the gas. But to your point, why are you charging for that? Why aren't you creating a service differentiator? Because competition on price is just. Everyone starts to lose at it. Kind of, uh, interesting to bring back those old things to the way it was. Well, that does it for this episode of Customer Success Pivot your career podcast. We hope you enjoyed the episode. Encourage people to subscribe and rate our podcast along with leaving comments wherever you listen and or respond to our LinkedIn post for the episode. We'd love to get your comments until next time. We hope everyone has a great day and we'll talk to you next month.
Speaker C: Have a great vacation. Alex.
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