There are career detours and then there is what David Becerra did. After more than a decade in SaaS – co-founding a startup, surviving an acquisition into SAP, building a scale CS organization from scratch – he went to Indonesia and managed a surf and wellness retreat for two years. No CRM. No Salesforce. No customer health scores. Reservations arrived via WhatsApp. Rooms were occasionally double-booked because the entire operation ran on email and manual spreadsheets. It was, by any SaaS professional’s standards, a technological dark age. And yet, as Becerra explained to Thibaut de Lataillade, the customer success principles he had spent years refining transferred to hospitality with a precision that was almost eerie.
Pizza Night as an Activation Service
The retreat had an onboarding problem that will sound uncomfortably familiar to anyone who has ever watched a SaaS customer stall in their first week. Guests would arrive on Saturday, check into their rooms, and then spend the next 24 to 48 hours in a state of low-grade anxiety. What happens tomorrow? When is the first surf session? Where do I eat? Do I need to bring my own towel to the beach? The questions would arrive via WhatsApp at all hours – midnight, 6 AM, during dinner – because nobody had set expectations, and in the absence of information, people generate anxiety.
Becerra’s solution was so simple it almost reads as a parody of enterprise onboarding best practices, except that it worked. Saturday pizza night. Every guest, every week. Pizzas are ordered. Becerra walks through the week ahead. Sets expectations. Introduces the team. Explains the daily rhythm. Acknowledges that this is Indonesia, that things will go sideways, that the road might flood and the surf might be flat and someone’s motorbike might have a flat tire, and that all of this is part of the adventure.
“The faster we get to them bonding with each other and having this moment of ‘oh cool’ – that’s where we really felt the week started rolling a lot easier.”
The real function of pizza night, beyond the logistical information dump, was social activation. Twenty strangers in a shared space need a catalytic moment to become a group. The pizzas, the casual setting, the shared experience of being new – it broke the ice in a way that individual check-ins never could. Guests exchanged Instagrams. They discovered overlapping interests. The week had a social foundation before the first wave was surfed.
The midnight WhatsApp messages dropped to near zero. Guest feedback scores improved. And the staff, who had been fielding ad-hoc questions around the clock, got their evenings back. The total investment was a stack of pizzas and thirty minutes of Becerra’s time on a Saturday evening. The ROI, measured in reduced anxiety, improved guest satisfaction, and lower operational burden, was disproportionate.
The Boundaries That Nobody Wants to Set
One of the most transferable lessons Becerra brought back from hospitality has nothing to do with onboarding and everything to do with a misconception that plagues CS organizations universally: the belief that customer success means making the customer happy.
It does not. Happiness, as Becerra frames it, is a side effect of outcomes, not a goal in itself. And the path to outcomes frequently requires saying no.
At the surf camp, this played out in the most literal way imaginable. Guests would want to surf a particular break that was too advanced for their level. They would want to change the schedule to accommodate a preference that conflicted with the group’s best interest. They would want more of the thing they already liked at the expense of the thing they actually needed. Becerra had to make decisions about what was fun, what was safe, and what would produce learning – and when those three things conflicted, he had to choose.
The parallel to SaaS is precise. A customer who asks for a custom feature that does not align with their stated business objectives is asking you to say yes to something that will not help them. A customer who wants 24/7 access to their CSM from day one is establishing a dynamic that is unsustainable and will eventually produce resentment on both sides. A customer who insists on driving the agenda for every quarterly review is a customer whose outcomes you are not managing – they are managing you.
Becerra’s formulation is that you build trust in order to drive the agenda for the customer, not to hand the agenda over to them. The trust is what gives you the authority to push back when pushing back is what the customer actually needs. And the surf camp gave him weekly, face-to-face proof that this works: the guests who had the best weeks were the ones who trusted the team to make decisions on their behalf, not the ones who negotiated every detail of the itinerary.
Loyalty Programs Built From Zero
The retreat had no formal loyalty program when Becerra arrived. Guests came back – some of them regularly, year after year – but there was no system to track return visits, no mechanism to reward loyalty, and no automated follow-up after departure. A guest would leave, and the relationship would go dormant until they decided, on their own, to book again.
Becerra saw this through the lens of a SaaS professional looking at a customer base with zero post-sale engagement. The potential was obvious. The infrastructure was absent.
He started measuring return rates. He identified repeat visitors – including one who had been coming back for five years and celebrated his 70th birthday at the camp, which is the hospitality equivalent of a customer who upgrades annually without being asked. He built a post-departure email sequence: two days after checkout, the guest receives a curated email thanking them, asking for a Google review, offering a 10% return discount, and explaining a referral program that rewards advocacy.
None of this was technologically sophisticated. It was Mailchimp and a spreadsheet. But it created a customer-for-life loop where none had existed, and it started generating data about which guests were likely to return, which channels drove the most referrals, and which parts of the experience produced the strongest advocacy.
The broader point, and the one that Becerra brings back to SaaS with conviction, is that advocacy does not happen by accident. You build systems for it. You create the moments that generate it. You measure it. And you invest in it with the same seriousness you invest in acquisition, because a customer who sends their friends is more valuable than any ad campaign, whether you are selling enterprise software or a week of waves in Indonesia.
The Takeaway That Keeps Repeating
The thread running through all of Becerra’s hospitality experience is that customer success is not a SaaS concept that happens to be useful in other industries. It is a human concept that the SaaS industry happened to name first. The mechanics – activate early, set expectations, build trust through boundaries, turn complaints into advocacy, invest in loyalty – are universal. They work because they are about how people make decisions about whether to stay or leave, and people make those decisions the same way whether they are evaluating a subscription to an analytics platform or deciding whether to rebook a surf trip.
The difference between SaaS and hospitality, in Becerra’s experience, is intensity. In hospitality, the feedback is immediate. A guest who has a bad morning tells you at lunch. A guest who has a great week tells you at checkout. The iteration cycles are measured in hours, not quarters. And that speed of feedback, Becerra argues, is something SaaS companies would benefit enormously from emulating – not by running surf camps, but by shortening the distance between the customer’s experience and the organization’s awareness of it.
For the full interview breakdown, see our complete Expert Insight with David Becerra.
Tools Mentioned in the Interview
The following tools and platforms were referenced during this conversation.
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