Why Most STR VAs “Fail” (And What Hosts Get Wrong)
If you’ve ever hired a virtual assistant for your short-term rental business and thought, “Well… that didn’t work,” you’re not alone.
I hear this all the time from STR owners:
- “My VA is not working well.”
- “They needed way too much hand-holding.”
- “I thought hiring a VA would give me my time back.”
Most STR hosts don’t struggle because VAs are unreliable or unskilled. They struggle because the hiring and training process is broken from the start.
I’ve hired, trained, and managed teams across marketing, sales, customer service and product development throughout my career. And here’s the uncomfortable truth:
👉 When a VA “fails,” it’s usually not the VA. It’s the structure (or lack of one) behind them.
Here are the three most common mistakes STR hosts make, and why the last one is the real deal-breaker.
Mistake #1: Hiring a “Superperson”
Many STR owners start their VA search with a wish list like this:
- Guest messaging
- Calendar management
- Pricing updates
- Listing optimization
- Vendor coordination
- Marketing tasks
- Basic bookkeeping
All in one role. For one hourly rate.
Even if you are a super-operator, that doesn’t mean you have the time, systems, or clarity to train someone else to master all of this.
When you hire for “everything,” two things usually happen:
- The VA is overwhelmed by competing priorities.
- You’re disappointed when they’re strong in some areas but average or underperform in others.
This isn’t a talent problem. It’s a role design problem.
Mistake #2: Weak or Copy-Paste Job Descriptions
Many hosts either:
- Copy a VA job description from another host, or
- Ask ChatGPT to write one without doing the upfront strategic thinking
The result? A generic role that attracts misaligned candidates.
Strong VA hires don’t start with a job post.They start with self-awareness.
If you don’t understand:
- What drains your energy
- What you’re genuinely good at
- Where you need real operational support
You’ll attract candidates who look great on paper but don’t fit your business or working style.
And even if you avoid Mistakes #1 and #2, your VA will still struggle without the next piece.
This is exactly what I help STR hosts fix when hiring and training VAs.
Mistake #3: No Solid Training or Onboarding Plan
(The Real Reason STR VAs “Fail”)
This is the biggest and most damaging mistake I see.
Here’s the pattern:
- You hire a great VA
- You’re busy (W2, life, running the STR)
- Training becomes rushed, reactive, or nonexistent
- SOPs are incomplete or live only in your head
The VA is expected to “figure it out,” ask questions you haven’t made space for, and somehow know what to prioritize.
Even a rockstar VA cannot succeed without a clear onboarding plan.
Effective training is not dumping everything at once. It looks like:
- Bite-sized responsibilities
- Weekly ramp-ups
- Clear expectations and feedback
- Space for questions and course correction
When a VA doesn’t succeed because training never happened, that’s on the owner or host, not the VA.
So… Why Do Most STR VAs “Fail”?
Because most hosts:
- Hire reactively instead of strategically
- Skip real role clarity
- Don’t invest in structured, phased training
VAs don’t fail. Processes do.
When structure and training are done right, VAs don’t just help save you lots of time, they become one of the highest-leverage parts of your STR operation.
How I Help STR Hosts Get This Right
If hiring a VA hasn’t worked out before—or you’re unsure how to even get started—you’re not alone.
As an STR host, your time is incredibly valuable. The last thing you want is to invest time and money into hiring a VA, only to find yourself still responding to guests, still solving the same problems, and still carrying the business in your head.
The issue usually isn’t the VA.It’s that no one ever showed you how to train and support them with a structured, right-sized hiring and training plan that actually fits your STR business—and how to hand work off in a way that truly sticks.
That’s the work I do with STR owners every day: helping them move from constant involvement to real, reliable automation and delegation.
Ready for your STR to feel less heavy and more sustainable?
👉 Explore my Rockstar VA Hiring & Training Program.
👉 Book a free discovery call to see if this approach is right for you.