Beyond SOPs: The Strategic Path to Scaling Your STR Business

Tips to scale your short-term rental business, whether your are a property manager, host or other business - grab insights here to help grow your biz

My business has been growing in an unexpected and delightful way: small property management and co-hosting business founders who have plateaued and are looking to scale. Having been engaged by several such founders as a coach/consultant to help them navigate what it takes to grow a business, I thought I’d share some insights with you from those engagements in order to help you think about your own journey and trajectory for your vacation rental property management or hosting small business.

The Small Business Challenge: “Doing It All” Syndrome

Before diving into strategies, let me share a common theme from the founders I work with: a feeling of being stretched too thin. According to the U.S. Small Business Administration, nearly 20% of small businesses fail within the first year, and by year five, that number rises to 50%. While the reasons vary, one consistent theme emerges, often referred to in business literature as “a crisis of leadership.” This refers to the founder’s difficulty transitioning from a hands-on doer to a strategic leader. Most of my clients come to me with some version of, “I’m doing everything, and I can’t keep doing it all.”

Take one founder I worked with - she built her property management business from scratch and was managing a portfolio of 15 homes. While she mostly loved her work, she was stuck in a cycle of late-night guest communications, scheduling cleaners, and juggling owner expectations. It was clear, however, that she was the bottleneck to growth. Despite hiring help, she couldn’t let go of certain tasks, fearing mistakes or a drop in service quality. And, she was exhausted.

For property management and STR hosting entrepreneurs, letting go of parts of the business is key to enjoying the “freedom” of running your own business. Yet, founders often find this step to be a significant challenge—financially, operationally, or emotionally. Sound familiar?

In the early stages of a business, the founder’s skills and interests shape the operations. However, as the business grows, gaps inevitably appear in areas that haven’t received the same level of attention. Whether it’s financial management, operational systems, or guest experience, these weak points—areas the founder isn’t as confident or interested in—are real barriers to growth. Recognizing and addressing these gaps is the first step to scaling.

The Path to Scaling Starts with an Audit

In every engagement with STR business founders looking to grow, I start with a strategic audit and visioning exercise. This process is as much about uncovering operational gaps as it is about getting me up to speed in order to help the Founder.

Another Founder focuses on delivering exceptional guest experiences. When asked what energized him,he llit up as he described meeting with property owners and pitching his services. His biggest frustration? The never-ending admin tasks that kept him from growing his portfolio.

Through the audit, we identified tasks that could be outsourced or automated, freeing up time for activities that energized him and aligned with his growth goals. This clarity allowed us to design a strategy that balanced his operational needs with his personal strengths and ambitions.

The Case of Misplaced Priorities

Many founders come to me with a specific goal they believe will solve their growth challenges. Often, they’re convinced that creating Standard Operating Procedures (SOPs) for every aspect of their business or ramping up social media posting will unlock the next level of success. While these can be helpful, they’re rarely the true bottleneck.

Consider another client who was adamant about needing SOPs for every process in order to scale. However, during our sessions, she admitted her property management system (PMS) was not serving her businesses needs, requiring significant manual input. The real issue wasn’t a lack of SOPs but a lack of adequate systems. Once we prioritized transitioning to a modern PMS, we started the work to key in on SOP that would be helpful for the tasks we earmarked for delegating.

Some other common bottlenecks I encounter include:

Founder time-blindness: Many founders struggle to delegate tasks, keeping them tied to day-to-day operations and unable to focus on growth and unaware of how much time they truly are spending on tasks best delegated to others. This often results in reactive, rather than proactive, management and often a blindness to their own role in limiting the company's growth.
Boundary setting: Founders who make themselves available 24/7 risk burnout and neglect activities critical to growth. Establishing boundaries—like setting owner expectations or carving out strategic time—is essential.
Inadequate systems: Outdated or inefficient systems can create significant barriers. Whether it’s a PMS, accounting software, or a lead nurturing process, addressing these foundational issues first is key to supporting strategic growth.
Team composition: Founders frequently patch together support based on budget constraints. However, inadequate training or mismatched roles can limit the effectiveness of these hires and ultimately serve as a barrier to growth.

Scaling isn’t just about adding processes or people. It’s about identifying true bottlenecks and addressing them systematically. Having functional systems in place is foundational to sustainable growth.

The Blueprint for Efficient Scaling

For Small Business Founders

Efficiently scaling a property management business requires a thoughtful approach that prevents burnout while building a sustainable operation. Here are five key strategies:

1. Manage Your Energy, Not Just Your Time

Time management often gets all the attention, but energy management is equally, if not more, important for founders. Scaling a business requires strategic thinking, problem-solving, and creativity—all of which depend on high-quality energy.

Focus on your passions: Passion stems from energy. Building a business around what energizes you and delegating tasks that feel heavy or draining leads to greater success and happiness. Intentionality in business growth means honing in on was energizes you and planning to delegate those things that do not.
Take advantage of the flow state: Engaging in energizing, challenging activities can spill over into other areas of your life, increasing productivity and motivation.
Balance activities: Mix high-energy, rewarding tasks with less enjoyable but necessary tasks. For example, balance a slogging project like transitioning accounting systems with energizing business development activities.

2. Get Clear on Your Goals

Scaling without a clear vision is like building a house without a blueprint. Set goals that align with your vision and motivations, ensuring they support your business’s growth.

Most Founders initially tell me the goal is to grow the number of properties managed, but the vision for the company is typically a financial goal as well as a company value, such as high-touch boutique brand or family-friend accessible homes. We typically are refining the goal to incorporate both the financial goal as well as the business vision.

Focus on your why: Start with clarity about why you started your business and what you hope to achieve. Avoid setting goals based on external expectations; this is your business.
Tie goals to the vision: Ensure your goals align with your ultimate vision. For example, if your vision is financial freedom, set revenue-focused goals rather than arbitrary property count targets.
Be realistic: Limit yourself to one major project per quarter and prioritize tasks to maintain focus and efficiency.

Most founders resist this idea, so allow me to expand. We are only capable of doing so much on top of the day to day grind. We are MORE effective when we laser focus, so carve out time for one major project/goal per quarter, and if needed, track a couple of others as part of the day to day prioritization - just adding them to the mix. This typically allows us to make progress across multiple goals while ensuring our biggest priority is executed on.

3. Commit to a Plan: Plan Your Work and Work Your Plan

One of my favorite quotes is to Plan Your Work and Work Your Plan. I still struggle to this day with this but I’ve developed my “work your plan” muscles with time. A written plan with clear milestones and metrics is the real road to progress. Use tools like Trello or Asana to stay organized and schedule dedicated time for project work. Regularly review and reflect on your plan, adapting as needed. I put the link to my plan in every task and appointment I schedule related to it so its always right there.

Plan for shiny object syndrome: We are wired for novelty and easily distracted by new opportunities. Develop boundaries for evaluating these ideas and have a strategy to beat distractions.
- A strategy I personally use is to maintain an Idea List; this is a list of links and ideas to courses, software, programs, and even events that I might like to consider investing time, money or both into. I’m a sucker for a good sales pitch and I’m occasionally convinced that the “quick fix” is real. Instead, I now have boundaries (mine are time and money) that dictate if I can invest in something now, or if I evaluate the opportunity in context of my goals, current and potential future projects and opportunities. I (usually) work hard to make an informed vs influenced decision in order to avoid distraction.

All that to say, I DID buy new software at a Black Friday sale that is as yet sitting on my Idea List - I’m hoping to invest the time next quarter. Ha.

4. Hire Strategically

Hiring is a significant decision for small businesses. A lean hiring strategy should align with your business’s growth phase:

Phase 1: Hire for tasks: Start with economical hires to offload routine tasks, such as guest communication or property inspections. The key here is to free up the Founder to focus on activities that support the vision and goals.
Phase 2: Hire for expertise: Invest in experts who can design and implement new business activities.. This strategy is key for expanding business activities, and the success of this lies in hiring right so the Founder doesn’t find themself even busier managing and taking on tasks. The expert should have the experience and capability to design and execute with only high level oversight and direction. While these hires are investments, investing in the right expert will support the businesses growth without constraining the Founder’s time.
Phase 3: Hire for management: Mid-tier hires are costly and best suited for larger businesses as they typically also require more resources and oversight, making the cost to value relationship appropriate only for companies with strong - and sufficient, cash flow. These hires are typically handling increasing complexity and coordination roles and not taking on as much task work.

5. Step Out of the Daily Grind Routinely

Stepping away from daily operations allows founders to focus on strategic growth.

Schedule CEO time: Dedicate regular time for goal setting, financial reviews, and market analysis. Put it on the calendar as a nonnegotiable.
Empower your team: Train team members to handle routine issues, creating clear escalation paths for emergencies.
Seek external input: Join mastermind groups, hire a coach, or network with peers for fresh insights.

Avoiding Burnout While Scaling

Burnout is a real risk when balancing current operations with growth initiatives. Celebrate small wins, set boundaries, and invest in support systems to maintain your energy and focus.

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Scaling your property management business is a rewarding journey that requires careful planning, strong leadership, and a commitment to sustainable growth. By managing your energy, setting clear goals, creating a practical plan, building a team, and stepping out of daily operations, you can build a scalable business that thrives without burning out.

Remember, every scaling journey is unique. The most important step is to start—whether that means refining your systems, hiring your first team member, or clarifying your vision. Growth is a process, and with the right strategies, you can navigate it successfully while maintaining the passion and energy that inspired you to begin.

Interested in learning more about Scaling Your Property Management Business? Grab The Scale Up Blueprint for your STR Property Management Business for fresh ideas and insights to help you grow your business!

Hey Boss! I'm Kate, owner/founder of The CEO Host. If you are interested in taking a leap into short-term rentals - or struggling with your existing business, my goal - passion, and career, is to help YOU succeed. I've coached hundreds of folks getting started, 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!

Categories: : propertymanagement, small business