Scaling a property management business is one of the most challenging phases in any operator’s journey. There’s a critical inflection point around 150-200 properties where everything that got you there stops working and many businesses stall or fail.
At our September GuestyVal event, three top professionals who’ve successfully navigated this journey to become global enterprise leaders shared their hard-won lessons. Moderated by Robin Clifford, Sales Director at Guesty, this session featured Will Creedon (Alloggio, 15 hotels and 3,500 properties across Australia), Kamil Krzyzanowski (Renters.pl, 6,000+ properties across Central and Eastern Europe), and Gonçalo Ribeiro (Altido/Joivy, scaled to 4,000 assets across Europe), who discussed what it really takes to scale — including the painful mistakes they made along the way.
Finding your inflection point
Before you can scale effectively, you need to recognize when your business is ready for that next leap. Each of the three speakers had, at one point, the realization that their business had the potential to grow exponentially if they made the right strategic moves.
Will Creedon’s approach: Break it to understand it
In the early days, Will deliberately tried to push the limits with owners to understand where the fragile points were in those relationships. “By understanding how you can break the very fragile link of goodwill and trust, you know where not to go next time.”
When COVID hit, this knowledge became invaluable. While others panicked, Will’s team had already learned to remove what he called “white noise” — the things that seemed important emotionally but weren’t critical to cash flow, sustainability, or building the right team structure.
Kamil Krzyzanowski’s turning point: Shift to owner acquisition
For Kamil, the turning point was a shift to owner acquisition. After reaching 80 properties and realizing they were among the best local managers, Kamil’s business partner saw a property management company advertising to property owners in London and they decided to follow suit. The shift from spending to attract guests to spending to attract property owners was the decision that propelled their business.
Gonçalo’s merger strategy: Better together
Running separate 100-150 unit companies, Gonçalo Ribeiro and his Altido co-founders realized they needed to join forces. Estimating that the sum of the parts would be better together, they decided to capitalize and build a brand that could actually scale in Europe. Despite the ego challenge of merging, combining forces gave them regulatory safety across multiple geographies and ultimately led to a multimillion-euro exit.
Getting your foundation right: The three critical models
According to Kamil, once you’ve identified your growth opportunity, success hinges on getting three fundamental models aligned before you accelerate.
1. Your mindset model
Having the right mindset is crucial. “If you’re not obsessed with getting new property owners and units, if you only do this on the side, you will never scale, or you’ll scale like a snail.”
2. Your sales team model
Incentivize your sales team by paying them per acquired property with higher compensation the longer the property stays.
3. Your business model with owners
Start with the right commission structure. Kamil initially offered 30% total including OTAs, a model that didn’t generate profits. They shifted to 20% plus OTAs, and now customize pricing based on property type, location, and gross booking value potential.
The contract must allow for flexibility as market conditions change. “You need the option to change your prices or commissions without too many negotiations with property owners in the future.”
The foundation of sustainable growth: Management agreements
With the right models in place, the next critical piece of scaling infrastructure is your management agreements. These contracts aren’t just legal documents — they’re the foundation that determines whether your growth will be sustainable or fragile.
Will emphasized just how critical retention becomes at scale: “For every property you lose, it takes two and a half new properties in the first year to replace that revenue.” Each new property takes time to develop its place, its pricing, and its ability to respond to the algorithms. This makes retention absolutely critical.
When crafting management agreements, you need to be deliberate and understand local practices such as term length. In much of Australia and New Zealand, for example, management agreements run in perpetuity unless terminated, while in other jurisdictions, you need to renew yearly. This means you need to work harder to keep owners happy so they will renew.
Will shares that local commission structures range from 11-25%, with OTA fees on top. The goal is to use OTAs for marketing your properties and, over time, shift to direct bookings, which remove the OTA commissions. That’s straight to the bottom line for owners and for property managers.
The acquisition challenge
The importance of flexible management agreements becomes even more apparent when you start acquiring other companies. You must live with their existing management agreements. “If you interfere with that, you risk losing owners through termination,” Will said. “It’s like you’re buying nothing.”
Structure your business to ingest different types of management agreements across different geographies and property types. “You have to be the water that wears away the rock, not the other way around, because you won’t be able to scale,” he said.
Building your team for scale
Strong agreements and business models mean nothing without the right people to execute them. All three operators emphasized that building a team capable of scaling requires a fundamentally different approach than hiring for early-stage growth.
Gonçalo’s framework: Know your weaknesses
As the founder, the first thing you need to do is to understand your weaknesses and strengths and then start hiring based on filling those gaps, not hiring people like you.
His advice: Don’t rush executive hires, but don’t get too comfortable either. “Hire the person who balances your weaknesses because that will give you back time.”
Will’s hard truth: Not everyone will make it
Will shares that hiring is about finding the right people at the right time to take you to the next stage, and you need to be ruthlessly honest with yourself. This goes for knowing when it’s time to step away and bring someone else in, as well as deciding who is the right person for your business.
You need people who are hungry for disruption and comfortable with change. “You cannot have people who are afraid of change. They will slow you down.”
Learning from mistakes
The road to success is paved with failures, and all three operators shared candid reflections on where they went wrong and the costs of their mistakes. These hard-won lessons provide a roadmap of pitfalls to avoid on your own scaling journey. Here are the key learnings they wanted to share:
Kamil:
- Keep a constant eye on profitability as you grow
- Maintain a healthy work-life balance
- Following acquisitions, identify and keep the people who have relationships with owners
Gonçalo:
- Embrace failure – this is how you innovate and disrupt the market
- When merging companies, do it as fast as possible, building frameworks so you can scale
- Focus on three key goals a year that are connected to your vision
Will:
- Remind your team about the “why” behind decisions
- Accept failure – the faster the better
Practical tools for execution
Theory and strategy only matter if you can execute daily. Here is some tactical advice on how to operationalize these lessons and keep your scaling business on track.
Gonçalo on values and data:
- Values are key. When you have the framework right and your team understands, they won’t need you to follow the script.
- Get your data and KPIs correct. Use them for weekly and monthly business reviews. If you don’t have data, you’re blind — and you can’t make managers accountable.
Kamil on healthy habits:
Kamil was once given the following advice by a cab driver and it has stuck with him: “Be healthy, be lucky, and don’t be lazy.” Maintain your personal and mental well-being so you can lead effectively.
Will on focus and communication:
- Give teams three things to focus on, then incentivize them. What is incentivized is focused on.
- Run daily “blockers calls” – 30 minutes, every department head, identifying what’s blocking the business that day, making decisions and aligning on the big picture.
- Create “translators” who can spread critical information across the organization. You know why you bought that business, why that owner stays—but nobody else does. You need an avenue for that information to spread.
Robin on avoiding universal mistakes:
Guesty’s Robin Clifford brought the conversation full circle by highlighting three mistakes she sees repeatedly across the industry:
- Not understanding contribution margin per property: Know what each property costs versus what it generates. Cut the vanity metric properties that don’t make sense.
- Focusing on the wrong 10%: If 90% of your bookings come from OTAs, why spend all your energy on direct bookings? Optimize your OTA presence: change profile pictures, update text for seasonality, test different approaches.
- Burning money on technology: You’re not a technology company. Leave technology to companies like Guesty whose sole job is to stay ahead and focus on your business expertise.
The path forward
Scaling isn’t about growth at any cost — it’s about sustainable, profitable expansion with the right team, right model, and right focus. The operators who scale successfully aren’t the ones who do everything. They’re the ones who focus relentlessly on owners, build the right team, maintain profitability, and partner strategically for everything else.
The key principles of achieving responsible, successful scale:
- Be ruthlessly honest about your weaknesses and hire to fill gaps
- Fail fast and learn faster
- Focus on contribution margin, not door count
- Let your team understand the “why” behind decisions
- Use data to make managers accountable
- Focus on your USP and partner with tech specialists rather than building in-house
- Remember: you’re managing owners, not just properties