What Rigid Tech Teaches Us About Building Smarter Hospitality Systems
I want to tell you a story. One that changed how I think about the hospitality tech stack, forever. Back when I was Head of Marketing at a startup treehouse resort, I was tasked with building and managing the tech stack that kept everything from “search” to “stay” humming across the whole property. That meant CRM, PMS, housekeeping/maintenance tools for a tiny team that needed to move fast and with full confidence when a guest asked, “would it be possible to get an early check‑in?”
I learned some hard lessons in those early days of building and looking back, here’s what I’d do differently if I were starting over today.
The mistake I made: letting the software shape our business
In that role, our PMS did handle a few key functions well like preventing double bookings and automating pre and post-booking messaging. But as we started to grow, its limitations became impossible to ignore.
Instead of our software serving the needs of our business, we found ourselves reshaping our workflows just to fit what the software could (or couldn’t) do. Every time the PMS fell short, we had to bolt on another tool just to plug the gap.
And here’s the real cost: disconnected systems meant disconnected data.
When we tried to answer basic questions like “Which five states do most of our guests come from?” or “What’s our rebooking rate?”—we came up empty. From a professional standpoint, it was embarrassing. Even worse? Our tech stack was costing nearly $30,000 a year. With that kind of investment, those should have been easy questions to answer.
So what did I do?
I started shopping around.
Five sales calls later, I had my answer: not one of the PMS providers I spoke with offered an open API.
Not one.
The only system that did? The very one we were already using, and honestly, not in love with. But at least it gave us something the others didn’t: the ability to connect. The irony was hard to miss. Despite its clunky interface, this PMS gave us the one thing we needed to grow with confidence—open accessibility to our own data.
What blew my mind even more was how often I heard the same vague reassurance from vendors: “That’s a feature we’re working on—it should be available soon.”
Here’s the truth: “in the works” doesn’t mean it’s coming. It’s a stalling tactic. Because once software companies offer open APIs, they lose some of the control, they no longer hold all the keys. Much like OTAs, these systems are built to create dependence. Not enablement.
So here’s the question I started asking myself and still ask today:
When will the hospitality industry stop giving away control of our businesses in exchange for short-term convenience that hurts us in the long run?
We’re already down that road and the industry is feeling the consequences. Operators are waking up to the fact that their control has shifted away from their in-house teams. Visibility gaps stretch from search to stay. Lead generation, booking, remarketing, guest communication—all fragmented across expensive software solutions. And yet somehow, it’s harder than ever to get a clear view of what’s actually happening in your business.
So I took matters into my own hands.
We stuck with the PMS that offered an open API, and instead of waiting for new features, we built layers around it. We made the tech flex to our needs—not the other way around.
That’s when I brought in my now-CTO, Charles Groce, and we started solving real business problems with custom solutions.
One example: Our leadership team wanted to implement a weekly bonus system for housekeepers, tied to guest satisfaction. Housekeeping is one of the most critical roles in hospitality and also one of the highest-turnover. We wanted to fix that by recognizing and rewarding great work.
The challenge? Making it fair, trackable, and efficient with a small team.
So we built a system that integrated our PMS, CRM, and housekeeping platform. Within two hours of check-out, guests received a short survey—timed perfectly for that moment when they’re scrolling their phones on the drive home, still glowing from a great weekend.
Once submitted, the system automatically matched the survey to the housekeeper who cleaned that specific room. Every week, our GM reviewed the results to determine who qualified for their bonus based on cleanliness ratings.
It wasn’t just fair—it was fast, accurate, and scalable.
No delays. No guesswork. And no repeat issues slipping through the cracks.
We were breaking down tech walls that had been holding us back from answering simple, mission-critical questions.
But those walls don’t just slow you down. They come with a price: extra fees, long delays, and the all-too-familiar “sorry, the system can’t do that” from your vendor for features that should be table stakes in a $900+ monthly subscription.
So you add another tool. Then another. And before long, you’re staring at a tangled tech stack that looks robust on paper but is exhausting to manage in practice. And worse, you still can’t make sense of all the data coming out of it.
That experience forced me to rethink everything about how we use tech in hospitality.
And if I were starting over today, knowing what I know now? I’d build from a completely different foundation—one designed for clarity, connection, and growth.
The Real Cost of Rigid Property Management Systems
When you’re new in the short‑term rental or boutique resort world, a “one‑and‑done” PMS feels like gold.
No double bookings? Check. Stripe integrated? Check. Automated emails? Done. You’re sold.
Then real business happens.
Suddenly you need things like:
Bonuses tied to guest survey scores for housekeeping staff
Door codes that auto‑update based on check‑in times
Text alerts for last‑minute bookings
Custom workflows for upsells that don’t trigger at midnight
Those things aren’t exotic. They’re modern hospitality operations. That’s when it hit me full‑force: I am building a business on someone else’s rigid framework. And the cost to fix it often exceeds the cost of building smarter from scratch.
In fact, industry sources reinforce this idea: integration and flexibility are no longer optional, they’re foundational.
If your PMS locks you into workflows rather than adapts to them, you’re paying hidden costs: lost time, manual workarounds, frustrated staff, and compromised guest experience.
The Power of Open APIs and Modular Systems
One of the best decisions we made—even if we didn’t fully appreciate it at the time—was choosing a PMS with open API.
Because of that one decision we were able to:
Build a bonus system for housekeeping based on real‑time feedback
Trigger door‑code resets via SMS when a last‑minute booking came through
Schedule text‑based check‑in/out summaries for operations staff
Build reward‑based referral programs
Remarketing to past guests via text or email
Why did this work?
Because we owned the integration layer. We didn’t wait for vendor feature releases. We built what we needed. The shift in hospitality tech clearly leans this way: modern PMS solutions are increasingly acting as orchestration layers—not isolated monoliths.
Open APIs + clean data flow = ability to automate, personalize, and scale without being shackled to the vendor’s roadmap.
If I Were Starting Over Today—Here’s How I’d Do It
Let’s imagine I’m back at square one. Early‑stage, lean team, high ambitions. What would I do differently?
1. Define your business model first
Before picking software, I’d map how the business needs to run: guest journey, upsells, check‑in/out, housekeeping logic, referral system, etc.
That means asking questions like:
What are our guest touchpoints?
What workflows require automation?
Where are our bottlenecks?
Where do we expect growth and what tech constraints might that impose?
Industry advice: define workflows before selecting your PMS. When you start with the end in mind, you choose tech that supports your business—rather than bending the business to serve the tech.
2. Ask about the API first
If the software doesn’t offer an open API (or at least a robust integration layer) it’s a no for me.
That single question will filter out a lot of inflexible systems.
Because once you’re live and trying to pivot or add a workflow, a closed system becomes a drag.
3. Map your full customer & operations journey (with pencil and paper)
Old‑school but powerful: take the time to draw out every step—from discovery, to first booking to post‑stay.
Every hand‑off, every manual step, every inefficiency.
Because if you don’t see your bottlenecks, your tech stack will replicate them.
By mapping everything on paper you visualize where automation matters, where integration matters, and where you can improve.
4. Treat marketing and operations as one system
Your CRM and your PMS should talk. Marketing isn’t an afterthought—it’s woven through the guest experience.
Upsells, referrals, stay extensions, reviews—all of that needs logic. If your CRM is siloed from your operations stack you’re leaving money and experience on the table.
5. Choose modular, flexible systems over “everything in one”
We often hear the pitch: “We’ll do everything for you in one system!” Sounds great… until you hit a use‑case they didn’t build for you. Today, many tech leaders argue that best‑of‑breed + open architecture beats monoliths—especially for flexibility and agility. You don’t need to reject one‑stop platforms entirely—but you do need to make sure they don’t trap you in tomorrow’s problems.
Rethink the Foundation Before You Scale
Here’s a truth: Rigid tech will keep you small.
When you’re getting started, yes, “simple” feels right. But simple can also mean “shallow”. As you scale, expand, or deepen your guest experience, that same “simple” system can become your anchor and it will hold you back.
The mindset shift is this: Your tech stack should serve your business model—not trap it.
When you start with that mindset, everything else becomes negotiable: your tools, your processes, your automations.
But your standards? Non‑negotiable.
If I were going back and building again, I’d build not for where we were, but for where we knew we were going. And I’d build the tech stack that could grow with us—flowing with the business model, not fighting it.
Don’t Scale the Mess—Audit It First
If I wasn’t starting over and wanted to know how my current system was stunting growth, I’d kick everything off with one rigorous piece of work: a 360° property audit.
Here’s what that audit would include:
A full tech inventory: what systems are in place, how they talk (or don’t), where gaps are.
A workflow map: guest journey, operations journey, marketing/upsell flows.
A data flows map: which systems own what data, how it moves, where it leaks or duplicates.
A bottleneck analysis: manual steps, repetitive tasks, guest or staff pain‑points.
A scalability check: if we added another 50 rooms/day or another property, what breaks?
Why this audit? Because you can’t fix what you don’t see. A 360° audit gives you the clarity to choose tech that truly aligns, to automate where it counts, and to build your stack to serve your business.
So here’s what I’m inviting you to do: if you recognize the tech‑frustration, the mis‑shaped workflows, the data‑silos—let’s talk. I offer a 360° Property Audit designed specifically for hospitality operators who want to build smarter, not just bigger.
We’ll map where you are, define where you’re going, and build the tech blueprint to get you there.
Ready to stop letting software dictate your strategy—and start letting the strategy dictate the software? Book your audit and let’s build your stack that serves you.
Here’s the core lesson: Rigid tech pretends to solve all your problems upfront. But once you start layering in real business challenges, you hit walls.