In every entrepreneurial journey, there are familiar stages—ideation, prototype, beta release, product launch, product-market fit, and, if all goes well, scaling toward maturity. Each stage brings its own set of challenges, and each requires a different kind of leadership, decision-making, and adaptability.
At Lake, we’ve recently passed a pivotal milestone: product-market fit. We’ve built a niche platform—an online travel agency (OTA) specifically for vacation rental property managers—and the response has been overwhelmingly positive. We now face a compelling operational challenge: onboarding a backlog of more than 10,000 vacation rental properties. It’s a good problem to have, but a problem nonetheless.
Listening at Scale
In our first 18 months, we committed ourselves to an intensive customer discovery process. We hosted dozens of Zoom and Google Meet calls, answered our toll-free hotline, met property managers for coffee, and showed up at major industry conferences—not just as attendees, but as sponsors. The recurring theme in those early conversations? Listen, learn, and serve well.
This effort laid the groundwork for our early product design decisions and validated that we were on to something. But as with many startups chasing product-market fit, we made some trade-offs—technical shortcuts, speed-over-scalability decisions, MVP-level infrastructure. Now, with sharper market insight and increasing customer demand, it’s time to revisit and rebuild.
Today, I want to share three of those technical “speed bumps” and how we’re addressing them as we transition from early-stage hustle to scalable growth.
1. Property Management System (PMS) Integrations: The Backbone of Automation
Most professional property managers rely on a PMS to coordinate listings, bookings, calendars, and guest communications. To truly serve this audience, integration is non-negotiable. We’re now building near-real-time synchronization with platforms like Hostaway and Hostfully. This means not just ingesting data but doing so with speed, accuracy, and minimal friction.
Lesson: MVP integrations won’t hold up when you’re scaling. “Good enough” quickly becomes “not good enough” when your customers depend on automation.
2. Length-of-Stay Pricing: A New Layer of Complexity
Modern pricing strategies in vacation rentals are dynamic—far more nuanced than flat nightly rates. Property managers expect platforms to handle pricing that flexes based on length of stay, number of guests, seasonality, day of the week, and even booking window.
We discovered that for any given day, there could be 40+ price variations for a single property. That’s a massive computational and data challenge, especially when multiplied across thousands of properties.
Lesson: The more sophisticated your customer, the more sophisticated your pricing engine needs to be.
3. Photo Management: Toilets on the Home Page (Yes, Really)
Photos sell properties. But when we imported images from PMS systems, we occasionally encountered what I jokingly call the “toilets on the home page” phenomenon. That is, a bathroom photo—featuring a very prominent toilet—accidentally appearing as the featured image on a listing. Not ideal.
Beyond image ordering, we’re managing sheer volume: the average property has 30+ photos, and each image is stored in up to 8 size variations for mobile, desktop, search results, listing pages, booking emails, and more. That’s roughly 240 images per listing. Multiply by 10,000 listings, and we’re looking at over 2.4 million images hosted.
To handle this, we’re transitioning from WordPress’s media library to Amazon S3, a move that will offer the scale, speed, and reliability we now require.
Lesson: What seems like a minor UX issue (image order) often points to deeper infrastructure needs.
Building in Public
There are many more technical hurdles—each with its own blend of frustration and reward. But these are the kinds of problems that signal you’re building something people actually want.
As we navigate this next chapter, I plan to share more of our behind-the-scenes journey. If you’re interested in these kinds of updates, let me know in the comments. I’d love to hear from others who are scaling software platforms and wrestling with the same kinds of speed bumps.
Because if there’s one thing I’ve learned, it’s that growth doesn’t eliminate challenges—it just changes their shape.