Customer Success From Startup to Surf Camp: Expert Insights with David Becerra

Thibaut de Lataillade: Welcome to Let’s Talk Customer Success. I’m Thibaut and I’m here with Dave Becerra. Dave spent years helping software companies not just get customers, but keep them and turn them into huge fans. So I’m really excited to dive into his experience today to speak customer success.

Thibaut de Lataillade: Let’s start with maybe your background. Can you tell us more about you, Dave?

Dave Becerra: Yeah, sure. Thanks for having me, first. Excited to talk about this topic with you. But yeah, myself. So my name’s David Becerra to begin with. I’ve had a very varied and diverse career, I guess I should say, and how I got into customer success. But initially, I co-founded a data visualization mobile BI company slash product. This was like late two thousands. And I did that for quite an amount of time, for about eight or nine years, and rode the waves of a typical startup, from launching a new product in a market to venture capital funding to growing teams and expanding internationally, all the good and bad times that you have typically in a startup environment.

Dave Becerra: From there, we were lucky and fortunate enough to be acquired. And so we moved, the product and the team moved on into a larger organization, large global software company called SAP. So that’s when I had my official transition into customer success. Before that, in the startup, you just wear many hats. So I realized I’d actually been doing customer success for a while. I just didn’t really – we didn’t really call it that. It was just, in the startup, you’re like I said, wearing a lot of different hats.

Dave Becerra: When I moved over to SAP, that actually became the moment I had more of a traditional customer success management role. I moved over to Europe. I’m originally from the US. I started managing accounts here. I was an individual contributor for maybe three to four years, managing large enterprise customers across Europe, different regions, mainly focused on analytics. That was my background, coming from analytics and business intelligence.

Dave Becerra: So I was focused on customers who were deploying these sort of enterprise analytics across the organization. Did that for a few years. That turned into a really nice opportunity at this company to build – really helped build what at that time was called, I guess it’s called the same now, but a digital slash low-touch customer success organization. Very common now. I think at that time, it was still very new within the organization, but essentially was how to create a successful customer success model that didn’t require you to just scale with headcount, right? Was how to use data signals, automation, how you could go from having one CSM that was managing maybe 10 to 20 accounts, but how could they manage 60 to 70.

Dave Becerra: Especially these long-tail customers who maybe made a small investment upfront, right? They weren’t like the big ARR customers from day one, but they had potential for growth. And so how you grew those customers and identified them and helped grow them at scale, in a sense. So that was a project that lasted a few years, and I got to build and manage and run a team, which was a great experience for me. It was a strange sensation because it felt like we were operating like a scale-up, because it was a brand new organization we built from scratch. But we had the resources around us in a larger organization. So that was a really great experience to see how to build something again within a large organization.

Dave Becerra: So I did that for a few years. And eventually ended up taking some personal time after that. That had been a long run from startup to moving into these other roles in customer success. Took some time off for myself. Did a bit of traveling, a bit of surfing, which is something I’ve been doing since I was quite young, so I wanted to spend a little more time doing those things.

Dave Becerra: And eventually that landed me, through happenstance – I thought I was gonna come back and then get back into customer success right away and continue my career that way. And I ended up managing a surf and wellness retreat in Indonesia. So I jumped into hospitality, unplanned, but ended up doing that for two years, of which that just finished a few months ago.

Dave Becerra: But that was a really cool experience for me, and interesting to see how much my background in customer experience and customer success was very related to what you do in hospitality. In a way, it was customer success, but just more intense, right? It was face-to-face people experiences pretty much six, seven days a week, sometimes 24/7. But a very rewarding experience, I would say, after spending so many years in tech, to then actually get to spend time with real people and be part of their experience.

Thibaut de Lataillade: Fantastic. Thanks for that intro. That gives a lot of context already, and we’re gonna come back to some of these experiences that you’ve mentioned. But first, let’s start with the basics. How would you explain customer success to someone who’s never heard about it?

Dave Becerra: That’s a really good question, because I have to explain it a lot to a lot of people that don’t know what it is. Ultimately, customer success is really about deriving business outcomes, right? For a customer. And I guess that’s regardless if you’re in software, you’re in hospitality. But in software, we would say business outcomes or value realization. That’s probably not a word that you would say to someone in hospitality – “value realization.” But ultimately, underneath all that is you want customers to feel like they want to come back, right? That they had a great experience, that they’re – in their eyes – getting great value for what they paid or what they invested in. And if it’s in the context of software, it could even be hospitality, but that they’re getting the outcomes they expected from the investment.

Dave Becerra: So I guess you could call it ROI, you could call it outcomes. But that they’re getting that from what they were able to put in, which is time, monetary value, that they put into this project or whatever it is, that they’re deriving those outcomes.

Thibaut de Lataillade: Very clear. And what do people usually misunderstand about customer success?

Dave Becerra: Yeah, that’s very common. Whether surprisingly, even in the SaaS industry, it’s still something you have to explain a lot, either to customers or even within your – I’ve been in organizations where you have to even explain your role and what it is you do, because it’s one of these roles that touches so many different – it’s great cross-training. I think it’s probably one of the best cross-training fields of study, in a work environment you can have, because you are so cross-functional. You’re working with support, product, sales, you’re talking business with a customer. You’re in some cases speaking with marketing. You’re really touching so many different parts of the business, which is great.

Dave Becerra: I think that also is part of the challenge and one of the things that’s mostly either undervalued or maybe misinterpreted, which is when everything goes wrong, right? And there’s just a mess somewhere in aisle four, they’re like, “That’s your job to go fix it.” So I think that’s something that’s very misinterpreted – that our job is just to fix everything. Whereas what we’re really doing is making sure that we’re being proactive and making sure we’re driving outcomes that the customer’s looking for. But it’s very often mixed with a combination like, “Are you sales? Are you support?” Somewhere in between there is usually what I see that people are very confused about, and where the misconceptions lie.

Thibaut de Lataillade: And where do you see the good customer success managers or leaders coming from? Is it more from sales, from product, or from support?

Dave Becerra: It could be from any of those, right? I think it’s just someone that comes across with the right mindset. I’ve seen some people come in from product that could be really good at customer success because they understand the product so well. I think coming from sales is a big – I’m seeing especially a trend now as companies and teams are getting leaner, and AI is automating a lot of the processes – being able to have that commercial acumen to have a discovery call. To really be able to speak to – in the case of hospitality, if I’m selling hospitality software, I really should understand the business of who’s buying and the decision makers. Not even just the technical side of implementing this product, but the problems it’s solving, the ROI they’re getting from it.

Dave Becerra: So having – I think coming from a sales background, I’ve seen, gives you the best sort of base. Everything else you can learn. You can learn product stuff, you can learn a few different things. But if you’ve got a good base in discovery and having conversations, and asking good questions, which you tend to do a lot in sales, then I think you can be very successful in customer success as well.

Thibaut de Lataillade: All right. So let’s now try to jump into the customer lifecycle and where customer success plays a role. So what does winning look like for you, for a software customer?

Dave Becerra: Yeah, I think ultimately, at least internally, if we’re selling the software – maybe I’ll talk about what success looks like as us, working in a software company, and then maybe for the customer. If I’m a CSM or managing a CSM team, for us, success ultimately – you’re measured, and we’ll probably get into a discussion about metrics – but having a solid net revenue retention number is the benchmark that every SaaS company tries to get to. So operating at maybe 120, 130% of net revenue retention – again, if I’m looking at it from the lens of “I’m a software vendor and what does good look like?” – that’s the gold standard, right? To be able to get to those numbers of net revenue retention.

Dave Becerra: I’ll say those numbers mainly because what that means is if we’re operating at 120% of NRR, that basically means if my sales are flat for the next year, we’re still growing at a 20% rate just from our base, right? I think any company would love that. So I would consider that success from that perspective.

Thibaut de Lataillade: Just before we dive into the customer perspective, tell me more about these other 20%. Where is the growth coming from? Is it from new things that you’re able to sell, new seats, new services?

Dave Becerra: Yeah, it would be expansion, either an upsell or cross-sell of more seats or maybe it’s a cross-sell of different products within the product line. But all just coming from our existing base. And that should be driven by – in the best customer success organizations, they’re revenue-influenced or revenue-driven. So even if they’re not the ones necessarily closing the deal, because there’s sometimes a lot of overlap with account management and sales, but the fact that they’re able to really influence or discover that deal or be a large part of it, not just necessarily taking orders, but doing that discovery and pushing for that.

Dave Becerra: The best customer success managers and teams are able to manage that and to drive that. And that, again, seeing more and more of the importance of that in companies as they’re growing, especially now. There’s a massive trend right now of new sales lagging a little bit, right? Because there are a lot of different reasons – macroeconomic reasons, AI, there’s more time being taken to make decisions because of all the changes that are happening so rapidly right now. More than ever it’s been more important to ask, “How much can we grow with our existing customer base?”

Dave Becerra: So the better you do that, the better the unit economics work, the better your valuation’s gonna be as a company. And ultimately, the more success and bigger seat at the table you’re gonna have within the customer success organization.

Thibaut de Lataillade: And so now if you put your customer hat on, what does winning look like for a customer?

Dave Becerra: Yeah. I’d say it feels more like a partnership than it is anything else, right? If I’m – and I’ve used many other software tools as well, so I’ve been a customer of different SaaS or recurring revenue products. And for me, winning looks like I feel supported the entire time, that there’s someone at the other end, right? It’s not just a fully data-driven application, but there’s a human on the other side who has had a conversation with me, who understands the goals that I’m trying to reach and my outcomes. And ultimately, it just feels like they’re guiding me towards those resolutions. And we’re always talking about the impact on my business, right?

Dave Becerra: And they understand my business, my challenges. Often what happens – and it’s a problem we all fall into, and it’s certainly a challenge I’ve fallen into as well – but when we think from a software perspective, we think in our metrics, our timelines, this is success for us. But companies operate on whole different timelines. And so really being able to step into the shoes of the customer – when I feel someone really understands my business and has a good conversation with what challenges I’m trying to solve, then I feel like I’m supported. And it just makes a lot of sense, right?

Dave Becerra: We bought this software for a reason. We didn’t just buy it because we didn’t do research. But when they really feel like they’re not driving their agenda, but they’re really on board with what my agenda and my goals are, that’s when I’ve felt like everything happens naturally. The renewal, the expansion, whatever it may be. But we’re partnering more than we are – I would say, feeling like I’ve been sold something.

Thibaut de Lataillade: And where do software companies usually fail first?

Dave Becerra: I’d say an area that I felt like – in my experience, from what I’ve seen – the thing in customer success is you can do everything right and still not get it right. That’s something you always have to keep in mind. It’s totally normal. You’re not gonna always renew a hundred percent of your customer base, even if things look good.

Dave Becerra: So you can do everything right and still lose a customer. But I definitely think there’s some things that if you don’t do right, you’re really doing yourself a disservice to make sure that customer renews. And I think one of the ones that I’ve learned a few different times through my different experiences is that initial – you wanna call it time to value. It’s onboarding. It’s like the transition from sales over to CS into time to value. I would say that’s the great metric. The TTV, sometimes they call it. Is how long from that time when they buy this software, when they have momentum, are you getting to that value point where they can realize some value.

Dave Becerra: It doesn’t have to be the full gamut, whether it’s a go-live or whatever that initial project is. But essentially you’re not losing momentum. I think when you miss that – and we’ve certainly missed it at different times – but when the momentum breaks and then the project stalls and then it gets pushed, you’re really setting yourself up for more work later on and really having to undo all of that.

Dave Becerra: One of the best sort of metaphors or visualizations I’ve had to describe it, that I think works well – in great organizations that I’ve been a part of, where sales and customer success have this really nice transition and handoff, it’s almost like the relay race in the Olympics, right? The hundred meters, whatever it is, one guy’s running and then the other guy already starts running and there’s zero momentum loss when he passes the baton and then keeps running. And I feel like that’s how you wanna operate ideally – the customer doesn’t feel any transition from a deal was closed and then now you’re gonna meet this person, and you don’t lose the momentum.

Dave Becerra: If you’re running the hundred-meter race and you stop or you drop the baton, it breaks all the momentum. And it really sometimes can – I don’t wanna say set you up for failure, but you’re starting off on a bad foot. And that can really make it challenging to get things where you wanna get to. So that’s one area that I feel, if you do it well, you’re setting yourself up for better things later on.

Thibaut de Lataillade: So does it mean that, if you go back to your analogy of this race, does the customer success manager start running with the salesperson before the deal is closed?

Dave Becerra: Yeah, I think the best organizations – and of course it gets very challenging as you scale, and the bigger the company, you have to have processes very optimized to do it. But I think the best organizations understand that you have to have that transition, right? The same way from marketing, it goes to sales, closes the deal, and then it moves over to us. The customer shouldn’t really feel like they’re just moving from one place to another. It feels like one seamless transition. But yeah, absolutely. There should be a lot of collaboration between sales and CS – we’re already getting a heads-up on use cases and the who’s who, and we’re not losing time on trying to do all that stuff.

Thibaut de Lataillade: Can you tell me about the best onboarding experience that you’ve ever either seen as a customer or built as a provider?

Dave Becerra: I’m biased to say that maybe we did something really good at – we were at our startup called Roambi. And it wasn’t because we were so brilliant. It’s because we were actually doing it really wrong and we’re like, we have to fix it. But it’s very related to this time to value and this onboarding process, right? Where I think we were selling products, sometimes to big customers, and there was that initial real excitement around our product. We had a really nice visual product that people fell in love with, and they wanted to get something built, see it with their data, and present it to their executives or their leadership team.

Dave Becerra: But we often found that one metric we tracked was how long it took to publish one of these visualizations, right? And the longer it took, the more the momentum went down and the more it shifted, and ultimately it just didn’t really become sticky. And we found that we were churning a lot of customers when we didn’t have a visualization built within the first 30 days. That became our goal.

Dave Becerra: So one of the things that we turned around was we made it mandatory to have what we called an activation package, where we would partner with one of our product experts, consultants, services people, who would be part of every deal. And it was like, you had to buy it. And we even commissioned some of our salespeople to sell it as well. Even though we lost a little bit more margin on it, we knew that the long tail of that would be that the product would go live faster. It would get into their hands. They would see and feel their visualization and be able to show it around.

Dave Becerra: And that was that point where, again, we didn’t – that didn’t confirm a hundred percent the renewal, but we passed the baton as smoothly as we could. And that really helped. We saw a pretty big reduction in early churn. I would say 10 or 15% of churn went down after we were starting to sell those packages. So we’ll tip our hat to say that we didn’t do it right initially, but we learned from it and did it right the second time.

Thibaut de Lataillade: And on that experience, what was the most challenging part? Was it changing the culture of the company, or putting the right processes, the tools?

Dave Becerra: Sure. We specifically started as an on-prem company, so we went through this dual – we almost had what was almost like two parallel companies, looking back on it now. We started selling on-premise. We had a small cloud product. But eventually, our goal – and one of the reasons we were able to secure funding and had these great projections – is we had a great initial on-prem product and great logos, and we were growing. But we also wanted to grow our cloud products and move companies over to a subscription model. And just the unit economics of SaaS, which are so great – if we could take that same growth that we were having on-prem and apply it to cloud, we would have a company that we’d be really happy with.

Dave Becerra: But there were a lot of challenges. Everything specifically from on-prem to cloud – it’s two different worlds almost that you’re selling through. Making that transition, how you incentivize sales – that was a big thing. How we have CS working with our sales team. But we didn’t even have a CS team originally. I think we just had support. That’s all we needed. So we actually created a customer success team. I think we called it Customer for Life originally. Maybe that was an early ode to Salesforce, because I think that’s how they began as well.

Dave Becerra: But yeah, it really took a big change in terms of how we operated. When you’re working in sales and you’re looking to make the most commission possible, you’re looking at how to close big deals and sell everything upfront, the more seats the better. We move over to SaaS. People are just buying what they need, and they can buy as they go. So there is a big shift in how we keep salespeople incentivized to sell the right way, not just sell shelfware. And even think about should there be penalties for selling shelfware? Should there be penalties for selling bad deals? Because that can really kill a company. That can really be hidden in a lot of new sales. But if it’s coming out the other end, you’re losing money on every sale. So it can really be deceptive.

Dave Becerra: Going back to your question, it was a big challenge, a cultural challenge more than anything, to switch from an on-prem to a cloud customer. Which is why so many companies are one or the other. Trying to do both is really a difficult exercise. And we didn’t really fully survive – we never reached the same success, you would say, of selling in one model versus selling and expanding and renewing in a whole different one. It really changed the game.

Dave Becerra: And in a way, it’s really good that it works that way. Because in subscription, you can’t hide behind the metrics, right? In the old world of on-prem, you could sell a big deal, have a maintenance contract, and on paper everything looks good. But when you’re every year being evaluated – am I using this, am I getting value out of this, do I need to downsell a few seats – it really gives much better insight into the valuation of a product and of a company. So there’s a reason why SaaS products and SaaS companies were valued so high, as the unit economics can be just tracked so perfectly, especially when it comes to churn, retention, and growth.

Thibaut de Lataillade: So can you tell me a story about how you’ve managed to turn a dissatisfied customer into a satisfied one, and eventually into an advocate for your products?

Dave Becerra: Yeah. And I’ll say it’s funny. I feel like it’s actually easier to turn a dissatisfied customer into a proponent, because if they’re dissatisfied and they’re angry – I don’t want – it’s not a good thing, but it means that they’re trying to use the product. And we’ll probably talk about it later, but the secret killers, the people that are just silent – yeah, “everything’s okay” – and they don’t really care. Those are the ones that are really hard to turn around.

Dave Becerra: We either have people that are advocates from day one, or you have people who really struggle. But they’re loud enough that you can do something about it. So I recall a few times – and I still think about our director of support. His name was AJ, AJ Duty, great guy. And he was just so good at turning around customers like that. It was almost like one of these things we built our ethos and support around, turning these angry customers into some of our best advocates. Because honestly, we saw that as just a big opportunity.

Dave Becerra: So just being able to spend time with them, listen to them, what’s the issue, and being able to resolve it – in a way has, for us at least, in our experience at the startup, and maybe we had the luxury of being a small company so you could do a lot of these things, but they became some of our best advocates. That started off as not very good. They were not having a good implementation or whatever it was. But again, the signal for us and for me keeps being – I think it’s good if you have people opening a lot of tickets, or being loud and telling you that they’re not happy with it. Because that’s an opportunity to go change it. And most people wanna change it, right? They’re being that way because they want help. They want support. They’re just looking for it. If you’re just quiet and off radar, that to me – that’s a bit more concerning and harder to engage with.

Thibaut de Lataillade: So you’ve mentioned tickets, and you’ve mentioned how to keep track and follow the usage for your different customers. I guess it’s a good time to start talking about tools now. I’d like to get your feedback on tools that work for you.

Dave Becerra: Yeah, sure. I can talk about a few. And I guess maybe I’ll start by saying tools can be great. There’s a lot of tools, and there’s more tools now, gosh, than ever. So it’s really hard to evaluate even which are the best. But I’ll say that my experience generally, before I go into specifics, it’s really how well you implement the tool that can really make the difference. Because you see a lot of features and functionality, but it really comes down to the details of how your organization operates and whether the tool can adapt to that.

Dave Becerra: I’ll give you an example. We were still a startup and we were using Salesforce both for sales and for post-sales. And we were nimble and small enough to be able to create custom fields. And it worked for us in customer success. Salesforce was enough for what we needed, in combination with another marketing tool called Marketo, which helped us with customer marketing and customer lifetime marketing initiatives. So it covered a lot of our bases.

Dave Becerra: As we get into bigger organizations, I worked at SAP where we’re using other tools like Totango, which is a CS platform built just for customer success. Because it’s just such a massive organization, and those tools can work. But again, I’ve had experiences where if they’re not implemented correctly, or maybe they work for certain use cases, but a lot of the times when you end up having to ask, “Can you export this into Excel?” – that means there’s something off with the tool, right? That’s a marker. If you’re going from there into Excel, something’s not working. But pretty common across a lot of different tools.

Dave Becerra: So for CS CRM, we used Salesforce. I’ve had some use cases with Totango. Some were good, some not so good. But I think we had very specific needs on how it was implemented that didn’t really work for us. That’s on the CRM side.

Dave Becerra: One of the tools I can recall that actually helped us a lot in customer success was a tool called Mixpanel, which really helped on getting analytics and insight into specific usage and product features. So we could actually see what features were being activated and things like that. Because data can be deceiving. Sometimes you look at data and it can tell you – you can interpret one story, and you can even have processes based on that story. And that’s not even what’s happening behind the scenes.

Dave Becerra: When we were running the scale organization, we relied heavily on data and we just didn’t have it. We didn’t have usage data or which product features were being adopted. We were doing a lot of things, having high activity, but it’s really hard to tie that and correlate that to an outcome of a renewal or of churn. Because X, Y, Z.

Dave Becerra: But we spent a good amount of time implementing Mixpanel, and that gave our CSMs and everyone a much better insight into which specific features and usage the customers were using. And that just drove better decisions, more contextual decisions that helped us really identify risk early, but also identify upsell and cross-sell opportunities as well. And that actually led to – we were able to quantify it – a 10% reduction in churn over a few years after we implemented that. So we really went from zero to having some insight. And in CS, whether it’s scale or not, data – you really need access to good data to be able to scale your organization and make the right calls on a day-to-day basis.

Dave Becerra: For support, I remember we were big users of Zendesk. That was years ago, though. I think now there’s so many different support tools. But they were the de facto – they were still growing at that time, and obviously they’re one of the biggest players in the space. But for me, I wasn’t working in support, but in CS you had to sometimes know your way around Zendesk just to navigate. I always found it as a very easy product to use, easy to understand, and I remember their support was great. They were actually really good at helping us implement and use their tools.

Thibaut de Lataillade: And if you think about these different tools, what’s the one feature that’s had disproportionate impact on your success?

Dave Becerra: Yeah, it’d have to probably be Mixpanel. The analytics and the usage was so critical that it had an impact. We quantified the impact, but it changed the way we approach customers. It changed our day-to-day, our workflows, and just actually gave us insight into what type of conversations and who we needed to reach out to. Especially in the scale organization where you’ve got 60 to 80 customers – you can’t just go one by one. You have to have signals telling you, “Hey, this is important, this is coming up, this is a conversation or something that needs to happen sooner than later.”

Dave Becerra: So I think Mixpanel is probably the one where I saw the biggest change, at least from where we were, which was like – we knew that they bought the software, we knew how many seats were being used, but in terms of usage and utilization, we had zero visibility. And so that was – we were going from zero, so it was probably a big reason why we felt the biggest impact. We really were operating almost blindly to having at least some visualization of what was going on.

Thibaut de Lataillade: So it helped you to detect wrong behaviors of customers or wrong usage of the tool? And then how do you engage with the customers on that? Do you regularly organize customer success reviews with them?

Dave Becerra: Yeah. It was a combination. We had our high-touch team. We had this low-touch team, which was what I was looking after. And then we had a full digital team as well, where everything was automated. Because you had some customers that were very low ARR. They were buying from a digital store. So we had a combination of different models of touch.

Dave Becerra: But that data we could then use was really useful for our digital customers, right? Because we could automate these things. Again, it would be better to have a human touch, but in reality, you’re not always gonna be able to have a human talk to every single customer. That really helped at least guide customers in a certain direction. If they were not using feature X, which we knew was a big activation key that would drive more adoption and usage, we could cluster all those customers in one cohort and have information, or marketing could send out a message about that specific feature. Or, “Hey, there’s a webinar about this feature – you’re not using this.” So it really helped have more data-driven automation and communication to that customer base.

Dave Becerra: But it also helped even in our segment or even in the high-touch segment, because it gave – maybe even if the customers weren’t receiving that on their own – it gave CSMs that insight to have a human interaction, but contextually around, “Gee, I see you’re not using this product feature. Did you know this or that? Why don’t we set up a call next week so we can dive into it a little bit more?” So it was being able to combine data but also with the human touch, that really helped in those higher-touch segments as well.

Thibaut de Lataillade: All right. We’ve covered already quite a lot on software and how customer success can have an impact, and also the tools that you’ve been using. And I’d like to spend more time on your surf camp experience, which is so different from the corporate world. How did you start there, but also how have you been experiencing managing a very different business – hospitality, probably without the right set of tools?

Dave Becerra: Yeah. Where can I begin on that one? Again, it was an unplanned deviation from where I thought I would be, but through happenstance, an opportunity came up and I jumped on it. I had never managed a hospitality business. I’ve been surfing my whole life, so I know what that is, and I could say I know enough about it to help others and teach others. But as far as running a full hospitality business, that was a new leap for me.

Dave Becerra: But I felt like I’ll just figure it out as I go. I jumped straight into the deep end. And yeah, it was like maybe one or two weeks of onboarding before the other general manager was there. And I saw how things operated. Got an idea of how the business runs, what are the key metrics.

Dave Becerra: But my focus a lot was on the guest experience. A lot of the operational stuff that was going on – this specific retreat had been in operation for a while, so it was managing, making sure that just stayed the pace. But really how to improve the guest experience, and managing a cross-cultural team, right? I was the only – this was based in Indonesia, and I was managing a full staff of Indonesians. And I didn’t speak any Indonesian at the time, still only speak a little bit. There was a lot of how to build trust with a brand new team and how to rally us all behind one goal of making this a great experience for our guests.

Dave Becerra: Looking back – I mean, we didn’t really have any tools or processes. Like I said, the thing was running. But we just didn’t really have any metrics, right? We weren’t looking at how many customers are return customers, what’s the onboarding experience like?

Dave Becerra: So we started with some basic stuff. Like you mentioned tools – we didn’t have tools. We didn’t even have a reservation system. Everything was done via WhatsApp, email, Instagram. Very manual. So it did make things very tough. In fact, I can recall a few times where someone showed up and was looking for a room, and we had double-booked a room because all of this was through emails and very prone to manual error.

Dave Becerra: So it’s funny, going from working in SaaS, in software, from VCs, from Silicon Valley – the most technology-driven environments that I had come from – to basically being like, “Yeah, all this is done manually and with zero process.” So the good news is there was a lot that we could build on. And being that I’ve always been close enough to technology to know there’s a lot of tools that can help, we were able to implement a few things. In fact, I began implementing a reservation system so that everything could be managed properly. And that was a huge reduction in time and money, right? We’re paying someone else to manage all this stuff via email. And yeah, it just made things a whole lot cleaner and easier.

Dave Becerra: I learned a lot about onboarding too, right? I took all these experiences from customer success and morphed them or adapted them to what customer success felt like in this specific surf retreat and surf hotel.

Dave Becerra: And one of the things that I learned, which helped a lot, was this concept of – I don’t call it over-communication. People showed up to the hotel and they’re here for a week-long experience. They don’t wanna think, right? They don’t want to think about what’s coming next or am I supposed to do something this afternoon.

Dave Becerra: So we implemented this really nice setup. Everyone would arrive on a Saturday. We would have a pizza night, right? We order pizzas for everybody. I’d give an overview of what the week was gonna look like. “Here’s what to expect.” Also a little bit of “expect the unexpected,” because this is also Indonesia, things go wrong. It’s part of the journey. But “here’s generally what you can expect. 80% is gonna happen. And we might have some deviations.” Again, this is surfing, right? You’re dealing with weather, with the ocean, sometimes it rains, sometimes you wake up and there’s a flat tire, the road is flooded. So you have to be a little bit adaptable.

Dave Becerra: But even just setting that tone from the beginning – “Guys, this is part of the adventure. This is why you’re here. We’re gonna do all these cool things, and if something goes wrong, we’re gonna call a last-minute change and do it a different way.”

Thibaut de Lataillade: This is the activation service that you were mentioning earlier in software.

Dave Becerra: Exactly. This is the activation service and just prepping for it, right? I think expectations are really important in anything in life. And being able to set the expectations from day one – “Here’s what’s gonna happen, or what we think is gonna happen, or what you can expect from us” – I could tell that people, I just received less questions. That was a metric I had. Otherwise I’d be getting WhatsApps in the middle of the night – “What’s happening here, what are we doing there?”

Dave Becerra: And so we just created – let’s knock it all out on day one. Everyone gets together. It also gives an opportunity for them to all meet each other and have a bonding experience. So what we found is the faster that moment happened – and this is similar to what we talked about in software – that moment of activation, or moment of value, for us was if we have 20 people come in a week, the faster we get to them bonding with each other and having this moment of “oh cool, you’re from here, you do this for work” – and they exchange Instagrams – that’s where we really felt the week started rolling a lot easier. It was like breaking the ice for them to just connect and relax. “You’re on vacation, you don’t have to worry about anything.”

Dave Becerra: So that’s why we created that pizza night. We go over everything, pizza, everyone has a good time, and it just sets the tone for the week. It becomes this icebreaker environment where people just get in, pizza, relax, “Here’s what’s gonna happen.” It’s all good. Whereas before, if we weren’t doing that, people check in, they go to their rooms, maybe they get a WhatsApp at night. There’s trepidation, right? People just come in and are like, “Oh, what’s happening tomorrow? What can I expect?”

Dave Becerra: So it gave us a really good opportunity to do that. And we measured it, right? We started implementing customer feedback forms. What worked, what areas can we improve on? But that activation – yeah, if you want to call it the activation service and the onboarding – that really helped. Not just from the feedback that we got, but I could sense it too. I was just getting less questions throughout the week. People were more expecting the unexpected than they were before.

Thibaut de Lataillade: So if you look back at that experience, what are the learnings that you had from the surf camp that you would apply to software? What did you learn that is a good learning for how SaaS companies are managing their customers?

Dave Becerra: Yeah. I think there’s a lot of crossover between both, and it’s not necessarily new things. I would take from what I learned at the surf camp that are novel for SaaS. But what I mean is they’re actually really similar – it’s more the importance of it, right? Like the onboarding, the activation. Clearly something that you have to do. The time to value, the time to that moment where – whether it’s an activation or whatever product you’re selling – where that first value is realized. That’s one thing that going back into SaaS now is critical: how we identify that point, how we make sure we get there, and how we measure it. So we’re making sure that’s a metric that we’re aspiring to – this time to value.

Dave Becerra: Something else that became really apparent in the surf camp – and this was something I learned more in customer success, but it gave me validation to know that it works both ways – was being able to say no to customers, right? And this goes back to what we talked about earlier, about what’s the biggest misconception about customer success. And many times people just think it’s “make your customer happy.” And happiness doesn’t always equal renewal or expansion or outcome. It’s something really easy we can fall into. And a lot of us get into customer success because we genuinely are empathic people, or we want to help others and we really enjoy that process.

Dave Becerra: But you have to have that ability to draw the boundary and draw the lines and not let them drive your agenda. You’re building that trust to drive the agenda for them. And this is something I did at the surf camp constantly, right? Because I was in charge of an experience every week, week after week, for a group of 30 people. I had to make decisions on what I think is best for them at their surf level – what I think is fun but also safe, but also where they’re gonna learn. And I always thought if I could hit those three things, that’s how I see it. And if they have an off day, I’m looking at the entire week, right? I’m looking at the totality.

Dave Becerra: So many times I had to push back on them as well. You have to do it in a way that’s very friendly and non-threatening. Same way you do in SaaS with customers. But if in SaaS, if you let customers drive the agenda or you’re always saying yes from day one or always being available 24/7, you set yourself up for failure in a way.

Dave Becerra: And probably the last one I’ll mention – again, not a new concept, but it was really fun seeing how both all of these things existed in both worlds. For me, it was like I was living parallel lives. But the concept of advocates, right? Advocates are so important. And the amount of times we had someone come to the surf camp – “Yeah, I’ve heard about this through a friend. My friend told me this was a great experience.” And we started measuring that. Actually, let’s start measuring our return customers, and create some sort of loyalty, because we had people coming back but we had no loyalty programs installed.

Dave Becerra: We had this one guy who celebrated his 70th birthday with us. He comes every year, for five years. He came straight, celebrated his 70th birthday, was surfing with us every year. That’s true loyalty, right? And he became one of our biggest advocates. And being able to identify who those people are, who those guests are, and how much we’re working with them and how much we value them – we actually started, before I left, we created this whole loyalty program. And we actually built tools around customer loyalty, right? So if you’re a return customer, you get a discount. And so we actually started building and helped build a lot of these email automation and customer loyalty programs so that we could make sure we’re getting more return customers.

Dave Becerra: And that actually became a metric that we looked at – are we increasing our customer loyalty? Same thing for SaaS, right? If you’re getting more of these return customers, they’re gonna be your best salespeople, more so than you, more so than anybody else. These concepts, they cross over – onboarding and activation, setting boundaries with customers and building that trust so that you’re the ones guiding them, and this concept of advocacy and loyalty. I just thought they work well in both, and it just reiterated the fact they’re as important in hospitality as they are in SaaS.

Thibaut de Lataillade: So it was very human-centric and direct relationship with your customers, but you’ve tried to also put some processes to follow up and continue the experience before and after the surf camp moment. How would you automate all that process now, with different resources, budget, tools, or agents?

Dave Becerra: Are you talking about the surf retreat specifically? Yeah. I’d do a few different things. For starters, which is a project I’m working on now – I’m still doing it remotely, but I’m implementing this for them – the reservation system is, for me, almost akin to the ERP or the CRM. That’s the foundation, right? That’s where all the data lives, where I know who’s coming in and when. Having a reservation system, number one – again, I’m building it now, but the time I was there, it was still WhatsApps and things like that. But that would be day one critical, right? You can’t run a business without having this automation.

Dave Becerra: From there, I would say it’s probably twofold. Two things I would build on top of that engine. One is more related to marketing. So we spent a lot of time and we actually even hired these marketing teams to help us build Instagram following, create posts, things like that. But we didn’t really have the attribution that we wanted, so we didn’t have the visibility. We knew that when we published stuff, things were going well, but we couldn’t really say it was to this demographic when we sent this marketing campaign to maybe an area in Asia. And that worked out really well.

Dave Becerra: So really optimizing marketing, which is typically – I grew up surfing my whole life, and a lot of surf camps, they’re lifestyle-oriented companies. They don’t always run on the latest tools. It’s a lifestyle that you wanna live more so than running a business. But I would go back and start looking at, “Okay, if we’re spending 5K a month, where do we want to double down? Do we even need to be spending that much on these ads? What are we getting back from them? Which reservations are directly coming from these ads?” So just like we do in SaaS – where’s our marketing budget going? That’s probably one of the biggest opportunities I’d see in a lot of these surf camps. You spend money on acquiring customers, but you really have to optimize what’s working and what’s not, and whether it’s really driving reservations.

Dave Becerra: And then on the other end is what we talked about – customer loyalty. Again, not much of that exists. Some maybe bigger retreats and surf camps have those tools, but it’s keeping people in the loop, right? So helping build – I’m currently helping them build newsletters and getting people in the loop, automating some of this. Like I know when customer X leaves, in two days they’re gonna get this curated email that reminds them to review us on Google, that they have a 10% discount when they come back, that if they refer someone else, they also get loyalty points.

Dave Becerra: So again, creating this customer-for-life loop. So we’re not just about getting people in and out, but how do I actually build more of a community that people want to come back to and tell their friends about? And treat it more like a SaaS business, right? It’s not just selling. It’s like, how are we keeping and growing our customer base? And investing in tools to do that. Those are the three components that I would, and I’m currently helping build, because that’s something that they didn’t have in the past. Critical points for a business.

Thibaut de Lataillade: And do you find end-to-end tools that are able to manage all these processes? Or do you build it yourself with best-of-breed, or leverage AI and AI agents?

Dave Becerra: It’s a combination. I don’t think there’s one tool that can do everything. I think there’s some great tools out there that have APIs and you can really easily connect different products, from payment to reservations to attribution from marketing – where reservations are coming from – to email automation like Mailchimp. So currently I’m using different tools and different software, and it’s really tying all of them together to have an end-to-end outcome and process.

Dave Becerra: You mentioned AI, and AI is – it’s everywhere in a sense. It can be leveraged in many different aspects. Currently it’s helping more in creating copy and more admin-related tasks than it is on fully automating reservations and all these other tools. But it’s there, and we’re using it a little bit. But we’re still trying to figure out how to use it at scale or fully automate some of these agents as it relates to the surf camp.

Thibaut de Lataillade: You’ve been on your island for the last two years or so, which is the time where AI started to surge and become everyone’s focus. How do you see the potential it will have for SaaS companies and the rest of the industry?

Dave Becerra: Yeah, it was – you’re right. It was a culture shock. I’d been out of the loop. I knew some of this stuff existed, but I wasn’t really using it that much day-to-day. And I got back and was testing out different tools, and I was like, “Wow, this has evolved quite a bit in the last few years.” And still evolving every day.

Dave Becerra: It’s been a massive jump, right? And I think most companies and people I talk to in my circles – everyone’s still trying to figure out how to properly leverage it at scale. But it’s all these little – initially it’s just tackling admin tasks, right? So in the context of customer success, it’s great. I think a lot of this administrative time and functions where you used to have to take notes on a call and then upload them into Salesforce, and maybe 10% of your time was in administrative doings – that can really be shrunk down with a nice process. Where even as we speak right now, we probably have an AI note-taker summarizing our call and all the key points, and you can automate that to go to Notion or to go to HubSpot, right into your CRM.

Dave Becerra: The ability to have just better visibility into an account – to look at it from a SaaS perspective, where now if any department has a conversation with a customer and it’s just being automated, translated by AI and put into – automatically being uploaded into a CRM – you’ve really got automated information and full information that doesn’t rely on manual time and manual production anymore. So that’s the first bit – getting rid of admin stuff.

Dave Becerra: But it’s evolving so much now that you can really start using it in – I’ve seen as much as people creating their own QBR decks, right? Or you can even upload a big data set and say, “Where do I need to focus today on these customers?” And it can tell you based on all these things. So it’s really changing the landscape quickly.

Dave Becerra: I haven’t seen – I’m not really aware of large, in-production, at-scale deployments of AI in CS specifically, although I know they’re all being worked on. But I’ve seen a lot of individuals just using it – whether it’s crafting an email, creating a QBR deck, or helping you run your day-to-day. And in some cases, I’ve seen some use cases or read articles about people using it to self-manage themselves. I saw an article about this concept of CSMs almost self-managing, and that even the role of a manager, these mid-level roles – not that they’re going away completely, but today they’re there, tomorrow it’s like maybe you’re just a player-coach. Because you don’t really need a full-time manager. And a few years from now, you never know. It could be fully automated.

Dave Becerra: It’s interesting. It can be seen as scary, depending on what perspective you look at it from. One thing I think we can’t deny – we can’t predict where it’s gonna go, but we can’t deny that it’s definitely automating a lot of things. And in a way, it’s allowing more time for the important, strategic, human touch, which always still needs to be there – whether you’re selling software or even just renewing and expanding. That’s a relationship-based dynamic that’s always gonna exist. AI can just give you more time to do more of that, right?

Dave Becerra: So it’s really also separating and segmenting out – are you really being strategic in your accounts, or are you just being more administrative? It can really strengthen you in a way, but it’s taking away a lot of these menial tasks that are being done daily.

Thibaut de Lataillade: We’ve seen a lot of perspectives and opinions on how AI is gonna impact the SaaS industry and SaaS vendors. What’s your perspective on that?

Dave Becerra: Yeah, I’m glad you brought that up because there’s a lot of things you can read. The “SaaS apocalypse,” right? If you want to go all the way to one extreme, that SaaS is dead. I wouldn’t go to that extreme, or at least not now. But one thing that’s undeniable, that’s affecting companies today, is the licensing model. And that’s something that you notice – traditional SaaS was all seat-based, selling seats, right? If I’m selling more seats, that’s directly tied to my valuation. So if your company’s growing, I’m gonna sell you more seats.

Dave Becerra: But that’s exactly the opposite of what’s happening, right? The bigger trend we’re seeing is companies are being leaner because of this massive transformation of AI. You can do more with less. It’s not necessarily that seat-based pricing is going out, but it’s not really helping the multiples – these sort of multiples on sales and on earnings that SaaS companies have had in the past. Right now, it’s almost table stakes. This is just the bare minimum now. And this more usage-based, adoption-based metric is becoming the norm.

Dave Becerra: There’s some companies out there I know, like Snowflake, and I even see ServiceNow trying to move to more of these usage-based metrics. And those will continue to get higher multiples, higher valuations. So that’s something that’s impacting today. That’s changing just in the past few months. You’ve seen companies trying to switch over, or at least move more of their new product lines to be more usage-based. And that really changes a lot of the unit economics, but also how traditional software has been sold.

Dave Becerra: If it goes full “SaaS apocalypse” and it’s all gonna go altogether, I don’t know. I think it definitely makes it more challenging for maybe these small niche vendors who traditionally with a very niche SaaS product, but a very thin line, could just slip in there. And at a department level, I think nowadays if it’s not enough value or not robust enough, you could probably build it with AI, and you’re probably not gonna sell as much as you used to.

Dave Becerra: But I think if you’re an ERP vendor or a CRM vendor and you’ve got years of deep products that have been tried and tested – like a CRM, you want to be able to trust it – I don’t think a company like Salesforce or HubSpot is just gonna disappear overnight. That’s just me. But crazier things have happened. I think the value’s really gonna be in how you can use AI on top of and across all these different products, right? If you have ERP, CRM, all these tools – what’s the glue that puts all that together and lets them talk to each other? I think that’s where the AI opportunity really lies – sitting a layer on top of those. But those tools have almost become just foundational.

Thibaut de Lataillade: Do you see any other game-changer things that are now powered by AI in the customer success environment?

Dave Becerra: Customer success environment, game changers. The closest thing I’ve seen to a game changer is – you are removing a lot of what the CSM actually has to do. The daily job is starting to change, and some tools are getting to the point where they can really drive enough insight and tell you what to do, right? They’re telling you, “This is what you need to do today,” based on what they see in usage drops or whatever. It’s narrating your day-to-day as opposed to you driving it.

Dave Becerra: And that just begs the question – how much, if that goes at that pace, is AI gonna be able to automate? Maybe it’s 50% of the job, is it gonna be 60 or 70% tomorrow? I don’t know. I haven’t seen it fully automated in CS. I think for now, the best I’ve seen is just automating a lot of these admin tasks. But more to come, probably in the coming years.

Thibaut de Lataillade: Thanks a lot, David. It was super interesting to discuss, a pleasure, and great to get your insights and your perspective on customer success. Thanks a lot, and we’ll continue to stay in touch.

Dave Becerra: Great talking. Thanks, Thibaut. Take care.