Digital CS, Done The Hard Way w/ Madelyn DePrey Global VP of Customer Success @ Aircall

We took 70% of our logos and we moved them to this pool. It was challenging and it still is challenging. And in retrospect, we should have really gone back to the acquisition stage and really understood what types of customers are we bringing in? What is the lead source?

How do they go through the funnel of engagement? And then how do we make sure that the handoff and the expectation set in the sales process is consistent instead of a broken experience? Welcome to Customer Unsuccess, the podcast where we cut out the noise and talk with real leaders about their hardest lessons in customer success and other go-to-market motions. I'm your host, Joe DeGrande, and in each episode, we're going to unpack real challenges from real leaders.

Failed tech implementations, a strategy that didn't yield results for difficult customers. More importantly, we're going to take those lessons learned and share them with you so that way you can avoid those same mistakes with your team. So if you're in customer success, sales, or other go-to-market motions, stick around to hear from the best. Now let's dig into it.

This episode of Customer Unsuccess, I talked with Madeline Dupree. She's the global VP of customer success at AirCall. And she pulls back the curtain on AirCall's shift to a digital CS motion, moving a huge SMB segment from named CSMs to a pulled proactive model. And what went sideways when expectations set by sales didn't match the post-sales reality.

I really enjoyed this conversation. I hope you do too. Now let's dive in. So uh let's let's kick this off.

Let's do it. Awesome. So, Madeline, thank you so much for coming on the Customer Unsuccess podcast. Thank you, Joe.

It's great to be here. And I I love talking about unsuccessful aspects of my career and my life. So I'm really humbled and honored to have some therapy together. Let's do this.

Yeah, definitely like almost like they're starting to become like the therapy sessions, and you know, they're very humbling. Um, and also, you know, for the audience, if you're not familiar with Madeline, she's the global VP of customer success at AirCall. Um, but yeah, I think when it comes to these stories, right, like we all got them, right? I think that's the main thing.

And especially considering I always mention this quite a bit about hey, like we never went for school for customer success or post-sales. And I don't, to be honest with you, I still don't think you can, right? I think there's obviously tons of resources out there, but I guess it's always trial and error, as far as what I found out, and you're kind of learning from the best. Um, but you know, I know today we're talking a lot about uh digital CS or Tech Touch, scaled CS, and I know which is one of my favorite topics, obviously, but I'm always curious to hear the challenges there because it's still very prevalent.

Obviously, A is AI is getting thrown in the mix, and I do feel that a lot of people are intimidated by it as well. So it's always good to hear the stories and challenges that come with it. But I guess tell me uh tell me what's going on as far as your experience, you know, doing it at aircall. Sure.

Thanks, Joe. I I think um, you know, full transparency, we're we're still figuring it out. So I'm not here to tell you a wrapped-up story with a bow about how we solved all our problems. It's it's a work in progress, and quite frankly, it absolutely should be a work in progress because guess what?

Your your customer needs are a work in progress. Though the world we live in is a work in progress, the economy, so so we're still figuring it out. So um, yeah, uh, and and again, thanks for the opportunity to chat about it. So a little a little bit of context.

So I'm at AirCall. We're we're a communications platform. Uh we we lead with AI, so uh an excellent tool to help you uh you know be the voice for your sales and support teams, but also very much with AI at the center of empowering better communications. Um and so AirCall, we're we're largely an SMB business.

Uh I I've got a global team here. We're a company that's uh based all over the world, and that's candidly my favorite part of my job, but that means that our customers are all over the world. And um, for the most part, uh we we serve the small SMBs. We help the little guys act like big uh successful complex organizations with our tools.

And uh in terms of digital success and our transformation, about a year and a half ago, uh we kind of looked at our spend and and as most companies did, wanted to become more efficient. Um, and I looked at within our base, uh, about 70% of our customers are uh sub-10 seats. So we're talking sub-3K CVs, small accounts, um who tend to, you know, need have a lot of needs because while they're small, we are uh and maybe what they spend seems uh you know small in uh in terms of uh our total PL.

There, it it there's it's a big uh amount on on their budget line. And so it's important that we can cater to their needs, uh, even though there are there are a bunch of them and and maybe small in the individual level in our base, we're a big spend for them. And so um, so of that small segment, which is 70% of our logos, we made a decision to uh pretty uh abruptly uh change course uh pretty effectively in terms of how we serve these customers. So these customers historically needed a named CSM, they needed a human-led onboarding experience, and um that was great, and that was sort of our a differentiator and a superpower.

And we wanted to uh we looked at the fact that we had um uh you know a level of coverage that wasn't optimal. Uh, and the team was reactive and we were catering to these customers' needs. Um, mostly the loudest uh customers got the most, um, and we needed to take a step back and really shift to be able to support them at scale. And so we decided to pivot from having a named CSM model to putting these customers into a pool of CSMs.

And so we we developed a digital customer success strategy, and I had to do a lot of it internal education about what that is. And I have to say I love the customer success community because you can talk to so many folks within the business and get ideas, and and I learned so much from what other companies were doing. And uh we did we established a digital customer success team and a strategy. So primarily we took existing CSMs, we sold them on this new role, which was going to be less of you have a bunch of customers and you're responsible for all of them, and more of you're part of a team supporting these customers proactively at scale, and we're gonna make sure that these customers get what they need in a way that's gonna feel like a lot more care because we'll be more proactive and leverage automations, but your role is gonna change a little bit.

So we took these customers, we moved them into a pool, and uh we focused on proactive motions, so leveraging customer journey mapping, doing outbounding, emails, uh gain sight PX for in-product communication, uh, and uh making sure we were looking at both uh adoption triggers in the product, but also time-based triggers. So what stage of the journey they're at, and engaging with these customers at scale, but not saying, hey, I'm your name CSM, here's my phone number and give me a call, but rather saying, here's a way to get in touch with us.

A pool, a team of people are here to support you, right? Sure. We made this change. So we took we took 70% of our logos and we moved them to this pool.

We have a new team and a new way of operating. And um it it was challenging and it still is challenging. And I and I think the reason that um one of the key challenges that I I can kind of look back upon that we could have done better is um, or opportunities is uh we we sort of took the customer journey and we changed it pretty radically, starting after signature. So after that initial signature.

And in retrospect, what we should have done is we should have really gone back to the acquisition stage at the top of the funnel and really understood what types of customers are we bringing in? What is the lead source? How do they go through the funnel of engagement? And then how do we make sure that the handoff and the expectation set in the sales process is consistent instead of a broken experience?

Because Joe, our sales team was still having to offer a pretty high-touch experience to transition these accounts, and then it felt pretty broken when it came into the post-sales experience. And so that's where we had to really change course. And I'll I'll pause there. I said a lot, but that's kind of what I want to geek out with you about today.

100%. No, I love this. Um, it's it's really interesting because um you brought up a very touchy word, at least from my perspective, is the rapid change. I think a lot of people um actually they go in there and they think, hey, I'm just going to implement a bunch of stuff and just turn it on and flick a switch.

And unfortunately, with again, goes back to what you were saying, if they already have these expectations that they've experienced prior, even sometimes I've seen teams where they're migrating people into this post-sales model after the fact, as opposed to just from the new business side, they're already used to it. So now you're just you're going from one end to the one end of the spectrum to the other. That's a pretty big change. Um, so I'm curious though, on that new business piece, right?

So when we're talking about how it should start at you know the top of the funnel, tell me more about that and what you mean. Sure. So uh and and by the way, I I do roll up into go-to-market. So I sit in a in a go-to-market org and and my team does own upsell expansion and and renewal.

And so, you know, uh, especially more upmarket. So we're talking about digital, but more up market, I sit in uh these these meetings with my sales counterparts, and I I feel like that's actually a superpower that I, as a CS leader, uh have developed a deeper understanding of the customer acquisition and the science of sales and how we can apply that successfully to post sales. And so, what I mean in this context is when customers come to us, when however they find us or however we find them, that is their initial impression.

And it's so important that whatever that looks like, whatever their draw is, why they're looking for a phone system, why they're looking for a voice AI, whatever they're needing, that they that expectation that we're setting in the very initial kind of insight stage, and whether it's outbounding or inbounding of leads, whatever that is, that needs to inform everything we do from getting them to sign a contract to getting them through a trial to then being a customer and retaining.

And I think the more we go back to that very, very early stage, a lot of CS and sales leaders focus on the handoff, the handshake from I sold a contract to CS, you need to go even earlier than that. And you need to understand how customers come into your funnel and how they become customers and what that looks like, the channels they come from and the expectations they have. And so specifically, they come through, they're engaging with our marketing resources, they're maybe even talking to SDRs or BDRs, whatever that looks like, or leveraging us a free trial experience.

And then there's a salesperson that comes into play that might be guiding them in a very high-touch way through that trial period, which is what we were doing. We were getting on a call, we were actually configuring the system for them, having multiple follow-up and touch points, even though they're smaller accounts. We were still putting a lot of effort into that stage of the funnel to make sure they converted because we don't want to risk any drop in conversion, which is great.

But one, is that sustainable for the size of accounts we're talking about? And two, let's make sure that whatever expectation we set, we can we can uphold throughout the journey. And so this is where we've had to kind of change course. And and and my sales counterparts are fully on board with this.

Of course, we want to be spending more time on the larger accounts or understanding of these smaller accounts, how much do they really need and how can we make them feel super valued, but do it in a scalable way? Um, and so that's what we've done. We've kind of gone back and we've re-uh-aligned as an entire organization on what is the experience from that very early insight stage to moving through the sales process to trialing the product, and how do we set an expectation that they're going to get what they need to be successful, but do that at scale.

And um, in terms of you know what I what I mentioned, where we still had to have, you know, uh sales individuals reaching out and engaging with smaller accounts to make sure that this as the trial successfully converted, that is such an indicator that something is not working in a product-led way to make the trial conversion possible without human intervention. And actually, that's you know, a lot of what we're doing in the digital side to make sure that they can figure out how to manage themselves and we can do webinar content and one-to-many, but we also have to do that in the sales process.

And if they're not converting Cessway through a trial, that is such a strong indication that they're not going to be successful after they trial and once they're a customer. And so now we've gone back in heavy partnership with the product team. We've looked at every single behavior point. What do they need?

Why did they come to us? What are the three things that they need to do in order to successfully convert and move from a free trial to a paid subscription? And then how do we make sure that we re-emphasize that value throughout the customer journey? And that's the that's the very thing we're doing.

So it's kind of fun. It's it's things like in the trial, can we ask them questions like what they're looking for, what their use case is? Do that in an automated way instead of having someone call them and embed that into their entire customer journey back to kind of what are their success metrics, why did they come to us, and how do we reiterate on that? So that's the shift that that we've been undertaking over the last several months.

I love it. This is it's awesome. And it's it's actually a really it's a really good point, right? Because that sales process, it's at least it sounds like at the time, or maybe it's still going on, or you're working towards a better solution going forward, but it it is very hands-on.

So like once you start to one, again, it's you're also doing that in terms of it's very resource-intensive, right, when it comes to people and you know, teams and so on. But also two, it the the flip side of it is it has an impact on that customer. It gives them essentially that wrong expectation of like, hey, I'm gonna always have this available to me. Um, it's you brought up a really interesting thing I want to actually dive into a little bit more, is that data piece, right?

When it comes to like digital CS, um, tech touch, scaled CS, whatever everybody's defining it now today, uh, you need data to launch automation, whether that's ext internal facing, external facing, whether you're prompting up task communications, right? You brought something up that's interesting about like tracking use cases in the beginning of that funnel during a product. I guess like tell me, tell me more about that and how you're tracking and like how that helped. I'm just curious.

Yes. So um the first thing I'll say is your data house is never going to be fully in order. And don't completely wait for that to be the case to extract. Agreed.

Right. So this is something I'm constantly learning and reminding myself of. You know, we could analyze to death and ask for an army of data scientists and yada, yada, yada. But at the end of the day, what are the insights you have?

What are maybe three key insights you need to have that you don't have? And then hang your hat on those and try and try and execute so that you can kind of move the needle and learn and evolve the experience for your customers. So um, you know, in terms of your question about kind of what are some of the key data points? Um, well, uh, we uh what we found is when we had uh a sales-led motion, so when there was an actual account executive engaging with the customer, the the data hygiene wasn't great.

It actually wasn't so so we did a couple things. One, we introduced a self um kind of uh survey type function so the customer can self uh acknowledge who they are, their company size, their use case, uh select from a short drop-down of goals. We introduce some of those things into the trial. Now you need to be very careful when you're making any changes to a trial because especially in SMB magnitude of scale, any small tweak could have an impact on your growth numbers.

And so you have to A-B test, you have to be careful, you can't introduce another stage where there could be drop-off, abandoned shopping cart, et cetera. So kind of fun CX stuff that you kind of need to be aware of, especially in a growth motion in terms of trial conversions. So we were cautious and tried to err on the side of simplification. So that that's all fine and dandy.

But even, and that was that was we got some of the key indicators that we honestly weren't always as strong when they were written down by an SDR or an AE. So that's good. But that nurture piece is also so important. And and and what there are there are so many tools and automations and uh AI functionality you can use in order to do that.

So one of the things we're doing, uh a very specific data point, is when we think about these smaller accounts, they're we're trying to kind of separate those that are very much maintenance. They're the SMBs, they're small businesses, we're gonna support them, we're gonna make them very successful at scale. But then there's also accounts that come in at this size that have a lot of potential. And we're trying to carve those out and we're calling them high potential or purchasing power accounts.

And so we've introduced a lead scoring mechanism, again, kind of taking the science of sales and applying that to post-sales, where when customers come in and um we look at a series of criteria. So one that back to what they might have self-administered in the in their setup as I'm a company of this size, or I'm using you for a sales use case, but my support team is using something else. Like so, some of those self-subscribed indicators we we leverage. We also use tools like Clay and Apollo for data enrichment to be able to grab insights like company size, number of employees on LinkedIn, the CEO contact information, all those great nuggets in order to create a lead-scoring model that says accounts today in this digital segment are at this stage, but the potential is actually a flag that they can be, that they have a lot of growth.

And so with this enrichment and also the customers giving us such information, now we're able to pull out these high potential accounts and build a model where we can actually put more resources, put more human capital, leverage a success BDR to call into these customers and encourage them to grow and scale with us. And so that's one of the data points that I'm really excited about that we've been able to make sure that we we are uh leveraging and nurturing. Love it. I think it's so funny because I bring up Apollo and Clay a couple times, and you're definitely one of the first on the podcast.

And I mean, I guarantee we're probably what, I don't know, you know, 15 episodes in, but I talk with a lot of leaders and it's I'm shocked on it's it's starting to come up more, but you're the first I've actually spoken to, and this has come up, and I think it's so powerful because you know, you bring up a lot the science of sales and applying it to CS. And I think a lot of people are, you know, they're starting to see like, hey, to get out of this, you know, this catch-all function, right, and be more revenue focused, you need to take it into account the like the science of sales, right?

What are those actual signals that indicates that there's an opportunity for, well, one, also churn or renewal, you know, depending on what spectrum they're looking at there, but also two, that expansion, right? Is there high growth in employees? Are there leadership changes, right? Like has your main point of contact left?

All those tools can identify that. And and then, of course, once you have it automated, brought into your systems automatically, and then launching plays on it, that's how you scale. Um, so there's a lot of yeah, go ahead. And and I I love that you say that.

And again, back to you know, the benefits of having been part of a GoToMarket orga, it's controversial. And I I I actually think we've we've maybe swayed too far in that direction. We need to get back a little bit to like adoption and gross retention and those really important pieces. But at the same time, I do think a lot of customer success folks have not had the great opportunity to benefit from a deep understanding of all of the motions that have worked at the top of the final and in the acquisition stage that we should absolutely be applying to post sales.

Yes. And and honestly, the more as CS leaders, the more time you spend with your sales counterparts and just sit and look at all of the resources we put into acquiring new customers, the better equipped you will be to apply that to post sales across digital, but across all segments. Uh you know, a good example is we we buy leads for the sales teams. We physically buy them leads.

We have marketing engines that work on this. We also then do campaigns and then we have BDRs and SDRs, and then we have sellers. There's so you think of all of those layers that go into acquiring a customer. What if you can take a lot of that that's working so well and apply that into the expansion motion?

And it's not just expansion, it's gross retention as well. Multi-threading is a good example. That is how you save accounts, right? That's a right into sales tactic.

So I could kick out about this uh all day. I love it. I and I I talk about multi-threading a lot, quite a bit. And it's um, I actually got pushed an ad, I I can't remember the company, but they said it was I don't know what they were advertising, but the point is they were interviewing someone at a conference.

Like, what's the number one reason reason accounts churn? And they're like, because you're not multi-threaded. And it's so true because that one champion that might just be like the biggest fan of your product, you don't know what's happening behind the scenes if they did adequate selling across that org, that's it. It could be deal over.

Um, but yeah, I think when it comes down to it, a lot of those same principles and adoption, a lot of those same principles apply, but adoption and like health scoring, right? Sure, is it an element of it, but it's not a full indication of renewal. I've seen in time and time I've tons of conversations, even in my own experience, where health score is like just all the way up to the right, but then they just they just shock you, and then all of a sudden a you know six-figure, seven-figure deal is just churned.

So 100%. And like health score, it's kind of arbitrary. Like that's yes, but you know what I mean. Like it's like what is truly behind the science of that, and what are some of the other indicators?

It it kind of goes back to too in the beginning, right, when we're talking about like digital CS or just customer success in general, any go-to market motion, you're always iterating, right? And I think like it's only as good as how quickly you iterate, it's only as good as how well you're actually identifying and listening to your customers' needs, right? I I see a lot of companies fall into the trap where they're just dictating a health score based on what you know, obviously, if they're just doing a very you know quantitative analysis or just what they think is success, just like they some companies dictate, hey, what actually uh is in terms of you know their metric for identifying time to value, right?

Like how long it took and what is that value metric. But I know we could go on and on, but uh, I guess like I'm curious now, you know, kind of going back into you know digital spital customer success space, right? And we're talking about you know, in the beginning, about hey, it starts at the beginning of the funnel, right? And understanding that customer experience.

I'm curious about like, you know, what are the what were the downstream impacts once you've made some of those changes down online, right? I guess like what were some examples of like, hey, here were some challenges, like customers being upset and so on, then how did that shift as far as like once you start to make those changes? Absolutely. I think I think the biggest thing that I already kind of alluded to is the partnering on product strategy.

So partnering with your sales team on where are some of the drop-off points, where are some of the early indicators that are going to have a lasting effect on the customer's ability to self-serve and be autonomous in their success in your product. And so um, by joining forces with the more go-to-market, top-of-funnel acquisition stage, we then were going in double duty on actually, I know this might be less sexy to build a way for customers to more easily do this thing, like onboarding versus building really cool flashing UI features, but actually they're not even gonna get to those features if we don't do that.

And so, you know, I that's that was one of the biggest benefits was how do we actually partner on product strategy and double down on the ROI of investments in order to not just retain customers, but actually acquire them. And so that that was one of the biggest pivotal changes. The other is just expectation setting. And and and you know, you we we talk a lot as CS leaders about you you map a customer journey, but you need to map it at the very beginning of the journey because there's a lot of little nuggets of how the customer comes to you or what or what questions they ask or what they need, or how you sell the services you offer, that then you can create consistency to throughout the journey.

But as we're mapping, we also identified some other friction points, like, you know, they needed to get in touch with this team, but that was delayed. So how do we go about that? And and what did that look like? And how do we work backwards from there and and all of those things?

So um that was also helpful to kind of identify those friction points that we maybe looked over. That now when we look at the entire journey, they really can came to light in a much more meaningful way. Love it. No, it's it's actually um it's a good point, right?

You could kind of end up in your own silo if you're not working across different stakeholders in the organization, and then you could just totally miss out on all those opportunities. Um, I I do when I talk to people, there's always this constant uh battle for lack of a better phrase of how to navigate those cross-functional relationships. I'm I'm I'm curious as far as like, you know, if you were to tell like the audience now, like what are some of some tips on how to navigate that?

Um like what would you tell them like as far as navigating between sales and product if if they're dealing with any sort of like roadblocks, so to speak? You have to get alignment on OKRs and KPIs. You have to. And it and if if that is not the case, manage up, uh, right.

So you the the the understanding was the business of that that has been so well done in my organization is we have one growth number. And that growth number comes from both the customers and the net new sales. And that I know a lot of companies have that constant friction of net new sales versus expansion. Sure.

We've been good about saying both things are so equally important. And actually, when you look at the scale of what we can do on the expansion side with a base of the size of our customer base versus in you know what we can bring in in a quarter, maybe it's even greater, right? But you have to kind of create those synergies. Uh and so that that's number one.

But same thing on the product side, right? I I've in in my career, the the most success I've had working with product individuals is making sure we have shared KPIs. So, a good example is right now we have a big work stream on improving the customer onboarding experience. It's so critical, and that's gotta be very product led.

And so, guess what? I got with our chief product officer and I said, What is this PM's KPI going to be this quarter on this initiative? Let's agree, it's going to be first six month retention, right? It's not the first one month, it's the first six months.

So we're creating a lasting stickiness. She's measured on that. She maybe even has a quarterly objective and maybe a quarterly commission tied to that. That's the same as my team's objectives and initiatives and incentives.

So now you create that alignment. And so, as leaders, as CS leaders, even at the IC level, making sure one, you understand the KPIs of your counterparts and build empathy on that. So you know how to ask them for things and you can kind of sell to them on when you're recreating an ask. But two, that you're advocating for cohesion in those KPIs and OKRs across the organization.

Love it. Yeah, I think um it's a really important piece in terms of KPI alignment or if it's if it's an OKR or whatever it might be, but having kind of everybody bought in on the same metric or or just even rolling up to the overall like macro level metric that you're you're working towards is going to be key for success. And then everyone, there's it's no one's competing against each other, right? I think like one of the challenges I've seen with a lot of organizations, right?

It's and I'm sure you have seen it too, is new business, it's just sales, you know, sell at all costs just to hit that revenue number. And that could have a downstream impact for your team, right? And customer success post-sales, because maybe not the ideal fit customer is coming across your desk, and it could have an impact on those on those churn numbers. I mean, I sure hope that that's less and less the case, right?

Because you talk to investors, you talk to, I just got off with a board member this morning. Yeah, that the net retention number is the number, right? And and if there is both the net retention, but also the churn. And if they're seeing erosion of churn, that's an indication that you're selling to the wrong ICP, right?

So I hope that's less and less the case that there's such friction points. Now, look, we're we're all we're in SaaS. There's there's this pressure to show big numbers and there's there's funding rounds and all this, but so of course the friction point's not going away completely. But I think we've made so much progress in terms of how investors and operators and public markets think about the actual success of a business, not just at that one number, but actually the blended true outcome and health of the business.

So hopefully that's changing. Yeah, no, Dev, I'm I'm hoping it's changing too. I mean, it's um, you know, hopefully we can get to a place where it is more settled, but you're 100% right. I think um, yeah, you have those two metrics to work against, right?

NRR, net revenue retention, and then kind of if it's renewal rate, GRR, etc., um, to make sure to kind of do a proper evaluation of the book. Um I mean, you know, thinking back now on the overall, like when we're talking about digital CS, I guess like if we were to kind of wrap it up in the bow in terms of like key takeaways here of like the learning lessons, if it's like, hey, you know, I you've done this already now, yeah, Madeline. For I I don't remember I don't remember you telling me like as far as when it started and the entire journey, but like if you were like telling somebody, hey, like here are the key takeaways as far as like what to avoid and what I did wrong, like how would you kind of summise?

Sure. I would say think holistically about the entire customer journey. Start at the beginning. Um, truly deeply take the time to understand your sales process because that's when digital needs to start to be successful and educate the the those counterparts in the business on what that looks like.

So that's that would be number one. I would say don't to go too quickly, uh, test, iterate. Uh, one of the things that That we kind of pivoted to is we our APAC region uh is really great about testing and experimenting. And so we actually had them lead the pack in some of the bigger changes so we could learn and document in a smaller market and then bring that globally, right?

So that's that's another key lesson. Um, and then finally, make sure that you don't wait for perfection in terms of data reliability that you you execute and you go and you take some risks, but it's a well-contained risk and calculated so that you can roll it back if you have to, I would say. Yeah. That'd be my guess.

Yeah, yeah. No, I I love it. You're 100% right. I think um, yeah, starting starting small, especially when you're dealing, you know, going back to your you know, your book size around 70% of the logos, that could have a substantial impact, any small change.

So you definitely have to be cautious. Um, and then focusing on those testing grounds, I think. So you mentioned you said you were testing, you use like a test segment at the APAC market to test out a particular journey. Yep.

Fantastic. I mean, doing that just could kind of help build a business case of seeing how it could roll out. Obviously, it's less of an impact in terms of if things go wrong. I mean, with automation, any sort of strategy, things can go wrong, and being knowledge, you know, knowledgeable of that.

Um, I guess in terms of now, we're talking about digital CS, we're talking about customer success as a whole. I'm curious where I again, my experience is all just experience, right? I was just kind of thrown into it, just learning and as I go. But I'm curious as far as like your background, is there anything that you recommend like people checking out?

You mentioned communities and earlier people within the network, but are there any particular books or courses? I'm always curious to hear what people are like, you know, learning other than like traditional education. I love that question, and I always take notes when I listen to that at the end of podcasts. I'm so glad you asked me.

So I am I am a huge podcast consumer. I take the subway, I live in New York City, and I run every morning, and the podcasts are always in my ear. So um, I my favorite is grit, um, which is Kleiner Perkins, and um, it brings in leaders uh and talks about not just you know their the their biggest triumphs, but also just like you, some of their some of their mistakes and learnings, both in their personal and professional life. And I I have found it to be a very human look at the complexity of being leaders, and I could not recommend it more.

It's an hour or so a week about Brit uh Kleiner Perkins. The other thing I would say uh from a book perspective is I'm gonna go back to a really old favorite. So I um with the rise of AI, we're we're doing so much automation. And honestly, it's what we set Latercon, it's great, but that human touch is still so important, and I would argue it's much more important than ever after COVID and with AI.

And um, I come from hospitality. So before I was in tech, I was in hospitality. And there's uh Danny Meyer, who's the founder of Shake Shack. Before that, he found some founded some of the best restaurants in New York City, and he wrote a book called Setting the Table, which is about bringing the art of hospitality into the workspace.

Uh, and as a customer success leader, I encourage my team, even though we are SMB and we're doing things at scale, to take a step back and really bring that art of anticipating your needs of your customers, being service-oriented, um, and going above and beyond in certain uh uh time in order to serve the needs of your customers. So that's what Danny Meyer wrote about in setting the table. Couldn't recommend it more. That's awesome.

I I actually love that because um I actually I talked, I'm actually kind of a foodie myself and I like going out. I have a couple of friends in like the industry. We always talk about like the synergies of like the work I do, like in you know, in CS and we do, um, and then like the restaurant industry when it comes down to expectation setting. I actually uh talked to him recently about how uh expectation setting from the beginning, right?

Like if you have like a new customer coming in and you give this grand old experience, right? Like you have this the table ready, like the bottle of wine that you know already set at the table and so on. But then he mentioned kind of similar what we're talking about in digital CS, right? Okay, well, how is that individual's experience gonna be the next time and then the next time and down the road?

And then what does that look like you know, for retention, right? If there's any sort of slip up, you know, because again, you you're setting a bar pretty high. What happens? Is that customer gonna churn?

Are they gonna go somewhere else? So it's I I like that. I'm gonna have to, and that was Danny Meyer. Danny Meyer, I love that.

Yeah, and my husband's been in the restaurant industry for 25 years in New York City, and and and while we're in such different fields and he he's never opened a MacBook, uh uh he uh his stories and what he brings home are so similar to what we navigate in customer success. So it's really it's really true. I love that you said that, absolutely. 100%.

And I think also, too, like it's it comes down to people, right? I think like people um, you know, when they they talk about customer as customer, right? It's just like a it's just a it's just a you know a definition of you know, the person that you're working with at a company, they purchase a product, but in reality, it is an individual, it's a person, right? They're people, and that's why there's so much synergy.

Um, you know, I always like reminding people of that because you know, sometimes and I have to remind myself, you know, you get caught up and you don't realize that you're talking to people and trying to figure out what makes people tick um as well, you know, in terms of getting the problem solved. So absolutely. Love it. Good stuff.

And then I guess like, you know, Madeline, to wrap things up, like where where can everybody find you and learn more? Oh, thanks. I mean, I'm on LinkedIn, like we all are. So Madeline DePray on LinkedIn.

Um, but I'm I'm in New York. We've got an office in New York, we've got offices all over the world too. So love connecting with global uh SaaS community. Um and again, it's it's such an honor to be here.

But yes, I'm LinkedIn, like you can find me at Ericall uh as well. Um, and uh yes, such a such a pleasure. Thank you, Joe. Awesome.

No, absolutely love it. We'll definitely put all that in the show notes. Thanks so much for coming on, man. I'd really appreciate this conversation.

Thanks for doing this good work. It's so important. Really, really enjoy your content. So thank you.

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