Discover how to scale your short-term rental business to $250K+ while working less. Learn key systems, delegation strategies & automation tips!
A few days ago, I sat down for a strategic planning session with a client, who is first and foremost an STR investor who also manages a small portfolio of properties in addition to her own. She came in with one goal:
"I want my STR business to net $250K per year."
Simple, right?
But when I asked how close she was to that goal, she said:
"I made that last year."
So why was she struggling?
"Because I’m working way too much, and I don’t know how to back out"
And that is the real challenge most STR property managers struggle with. Making money isn’t the key issue—it’s keeping that income while removing yourself from the daily chaos.
If that sounds familiar, keep reading. We’re diving into how to systemize your STR business, delegate effectively, and scale sustainably—so you can hit (or exceed) your income goals without being a full-time operator.
One of the biggest mistakes STR owners make? Holding onto too many tasks.
If you’re still handling guest communication, scheduling cleanings, and troubleshooting WiFi at midnight… you’re the bottleneck in your business. I work with so many clients who struggle to let go - in fact, this is such a universal pheromone that it has a name! "The Crisis of Leadership" is the inability to let go - even when hanging on "because no one else can do it like I can" but that means - you can't grow any more.
Before you think about adding more properties, start by auditing your current workload. Ask yourself:
✅ What tasks truly require my expertise?
✅ What tasks could be automated or outsourced?
✅ What am I still doing because I haven’t set up a system for it?
Every high-performing STR business has systems that keep things running smoothly. Without them, you’ll always be stuck in the weeds. Many (many!) of my strategic planning clients are short-term rental business founders who say "It's all in my head, I just haven't had time to write it down". I encourage folks not only to automate their business - but also themselves. Carve out the time on a regular basis not only to capture those things you routinely do - but to carve out time to be intentional with your time. Weekly, monthly, and quarterly "pauses" to get centered and have clarity about how your actions align with your goals is key!
Here are the key systems in a short-term rental management that help streamline operations;
These systems don’t just free up your time—they make your business scalable because it can operate independently of you.
👉 Need some inspiration? Download my free PM Systems Blueprint to grab some insights for systems to help structure your STR business for success.
Many STR owners struggle to delegate because they don’t have systems in place; and then they hire without them in place and get frustrated that their team isn't effective - which in turn takes more of the owners time! The reality it, you have to systemize to some extent in order to have a successful team! If you’re hiring out of desperation instead of strategy, you’ll keep finding yourself back in the trenches.
Here’s how to delegate the right way:
1️⃣ Clarify your roles. Who is responsible for what tasks? Clear descriptions of duties, and hiring for the duties and skills that will be most important is key!
2️⃣ Hire the right people. An admin assistant, VA, or co-host isn’t just a “task doer”—they should take full ownership of their responsibilities.
3️⃣ Have the necessary resources for the team. The right people need tools; document key processes so that anyone can step in and execute without your involvement.
By the end of our session, my Client - looking to continue to support the same or a higher level of revenue with far less involvement in the day-to-day operations, had a much clearer understanding of her business and the steps needed to get where she needed to go. Because she identified she didn't have nor want to figure out how to create SOP's, we'll book another session and work together to get all that set up for her in the key areas she has identified - because growth is also about recognizing the gaps in skills, resources, and personal interests, and identifying how to fill them.
Many clients like the one in this post found themselves owners of management businesses after starting out building an investment portfolio. I commonly get told "it just sort of happened". And they find they are working so hard, they are burning out and don't have systems in place but can't back down because they are executing much of the work themselves. It doesn't have to be like that, and the key truly is getting more systematized. This is often a hard leap - either in feeling like the time is there to devote to putting infrastructure in place, or they've tried and failed to systematize - often selecting a system that doesn't work for how they themselves tend to work, or they simply have no idea how to proceed.
➡️If this is you - lets hop on a call! I do custom consulting for STR business owners and investors, marrying my deep expertise in business management and my passion and experience in short-term rentals to support others in the industry.
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Hey Boss! I'm Kate, owner/founder of The CEO Host. If you are interested in taking a leap into short-term rentals - or have some questions about your existing business, my goal - passion, and career, is to help YOU succeed. I've coached hundreds of folks getting started or looking to optimize, analyzed more deals (and duds) than I could count, completed thousands of hours of education and training, attended conferences... So don't be shy. A good CEO knows to bring in expert help - and that's what I'm here for! Lets HOP ON A CALL and chat!
Your goal: Eliminate or delegate anything that doesn’t drive revenue or require your direct input.
Categories: : Scaling & Business Optimization