The Ultimate Guide to Launching and Growing Your Successful Short-Term Rental Business

STEP 10: Hiring & Managing a Team

'Finding Talent'
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This page is part 10 of a step-by-step guide to get your business up and running.  There’s no fluff here - just information, help, and suggestions for doing it right - the first time!

Everything in this guide comes from experience.

Not a mere 6 months of experience in running an Airbnb, nor a year of co-hosting.

This is from 25 years of being in the vacation rental business, owning 7 properties and owning a seriously successful property management company with over 180 properties.

Our team have attended and presented at countless conferences and we continue our education by sitting in on hundreds of educational presentations, and still do to this day.  So, we can bring you the learning from all those experts as well.

So, sit back and enjoy the ride…or the read!

Contents of this step:

This step of 'The Ultimate Guide to Launching and Growing your Successful Short-Term Rental Business' is written by vacation rental formula business schools own head of education Heather Bayer.

Most new property managers start their businesses wearing every hat.  While some start off with hiring professional cleaners and maintenance staff, many take on board every role, whether that be troubleshooting the plumbing and doing minor repairs,  managing enquiries and reservations, communicating with guests and owners, keeping the finances up to date, etc, etc.  

There are a multitude of jobs that need doing, but until there is some serious income, most feel that doing it all themselves is the only option.

Over the years I’ve talked to hundreds of property managers on the podcast and a great many of them were managing 10 - 20 homes before they took on their first non-housekeeping staff.

In fact as time has gone by and automated software has made communication, operations and some marketing so much easier, operators have the option of leaving hiring until much later.

The time comes however, when you have to get help and that’s when the challenges start.

This guide prepares you for that time, and if you are already on the hiring roller coaster, will help with some of your questions and issues.

What happens when you take that first step and start your hiring journey

Your employees are the backbone of your business! Their skills, dedication, and how well they fit into your company culture have a huge impact on the quality of service you provide to your clients and guests. So, it's important to hire the right people who not only know what they're doing but also bring a positive vibe to the workplace.

When you bring in talented individuals who truly fit your team, here are some great things that can happen:

Happy guests all around

Skilled employees who genuinely care about customers make a big difference. They know how to create amazing experiences, which leads to fantastic reviews, more repeat bookings, and word-of-mouth referrals from satisfied clients.!

Smooth sailing operations

When you have competent employees, everything runs like clockwork. They communicate well, find efficient ways to get things done, and solve problems like the professionals they are. That means less stress and more streamlined operations.

Teamwork Makes the Dream Work

A true cliche!  When employees share your company's values and fit in with the culture, it creates a work environment where everyone gets along and supports each other. This teamwork boosts productivity and makes everyone happier at work.

Building a Stellar Reputation

When you consistently hire talented folks, your company gains a reputation for being professional, reliable, and providing exceptional service. That kind of reputation attracts more property owners and guests, who want to be part of the awesomeness!

All of the above would happen in an ideal world and hey….who wouldn’t want to be in that enviable place.  Realistically however, simple economics and logistical elements can hinder those goals so we have to work with what we have and what we get.But….there are ways to make it a rewarding and positive process which can help achieve the best outcomes possible under any circumstances.

How to really know your hiring needs

Our first hire filled a huge void in our skillset.

I’d been the front person of our PM company for four years, ably assisted by my husband who got to do the jobs I hated, like talking to upset guests.  There is a greater story in there which culminates in him being banned from ever talking to any guests, ever again, but that’s for another time!

Anyhow, my business partner, Craig, and I had been muddling along as the company grew and by the time we got to 30 properties we knew it was time to expand.

I was no good at bookkeeping, and while Craig was a detail kind of person, it just wasn’t something he enjoyed. He loved building databases and had created a very workable reservation system while I enjoyed the owner facing side, and keeping in touch with happy guests.

So we made a wishlist of the ideal person.

He/she would be a detail oriented person; would know how to use Quickbooks, and have experience of basic accounts.  Some knowledge of customer service would be great and it would be a bonus if there were some marketing skills too.

Looking back, it wasn’t a well thought out list.

Despite that, we found our treasure.

We enlisted the help of our local small business bureau who linked us in with a return to work program running in our area.

Sandra had worked in a bank for 15 years before taking time off with her growing family.  She was enrolled in the back to work course and joined us on a sponsored employee programme which meant the government paid a good proportion of her onboarding and training costs.

If I was doing this again, the process would be more structured as follows:

Step 1: Put a valuation on your time

Are the tasks you are doing worth your time?  Entrepreneurs often do everything because they think it’s an economic decision not to hire anyone in the early stages. But when you consider what you could be doing with the freed up time and find out how valuable that is, your world could change.  James Clear says it very succinctly in his post “The Value of Time: How Much is Your Time Really Worth?”.  It’s a lengthy article and could take some time to really grasp the concepts and do the calculations, but it’s well worth the exercise.

Once you have done this, you can decide what roles can be delegated, and begin to identify the  skills each role would need and how they will fit into the culture of your business.

Step 2: Identifying the skills you need
  • Clearly define the skills and qualifications required for each role in your company. Break down the tasks and functions of each role to understand what skills are necessary.

  • Determine the most important skills and qualifications for successful job performance. Focus on finding people who meet these criteria.

  • Look for industry-specific skills or certifications that are helpful for certain roles.

Each year in our company we hired a seasonal assistant to help out with guest issues.  It was vitally important to find someone who would not be fazed by an angry guest or owner, and who was able to defuse a situation and at times, mediate between two parties.  We found that second-year law students were the best fit, as they often had the right temperament to handle tougher issues.  

Our summer students found the experience to be highly beneficial to their resumés when they started looking for internships on completing their initial law studies.  Their testimonials made it easy for us to find the next student which was an added benefit.

Step 3: Considering cultural fit
  • Think about the culture of your company, including your mission, values, and work environment. Consider things like teamwork, adaptability, customer focus, and innovation.

  • Take into account the work environment - for instance if you have mostly remote staff.

  • When interviewing candidates, assess how well they align with your company's values and culture. Look for shared values, attitudes, and behaviors.

  • Consider candidates who have good interpersonal skills, can work well in a team, and prioritize customer satisfaction, as most roles in our industry involve hospitality and customer service.

The Personality Fit

Psychometric testing can provide valuable insights into a candidate's personality traits, cognitive abilities, and work preferences. There are a number of tests that can be used to identify if your candidate woud be a good fit.

Myers-Briggs Type Indicator (MBTI)

The MBTI assesses personality preferences based on four dichotomies: extraversion/introversion, sensing/intuition, thinking/feeling, and judging/perceiving. This test can help determine how candidates prefer to communicate, make decisions, and approach tasks. For example, an extraverted candidate may excel in roles involving guest interactions or marketing, while an introverted candidate may be better suited for behind-the-scenes tasks like data analysis or property maintenance.

DISC Assessment

The DISC assessment measures four dimensions of behavior: dominance, influence, steadiness, and conscientiousness. It provides insights into how individuals communicate, work in teams, and handle challenges. For a short-term rental company, a candidate who scores high in influence may thrive in roles requiring sales and client relationship management, while a candidate strong in conscientiousness may excel in detail-oriented positions such as accounting or quality control.

Culture Index

Culture Index is a psychometric assessment that measures an individual's work-related behaviors and provides insights into their natural talents, communication style, and approach to problem-solving. It helps identify candidates who are likely to thrive in specific roles and align with the company's culture. For instance, a candidate with high sociability and assertiveness may be suitable for guest services or marketing positions, while a candidate with strong attention to detail and compliance may excel in accounting or regulatory roles.

Cognitive Ability Tests

Cognitive ability tests assess an individual's mental capabilities, such as logical reasoning, numerical reasoning, verbal reasoning, and problem-solving skills. These tests measure a candidate's capacity to learn, adapt, and perform complex tasks, which can be important for roles that require critical thinking and decision-making. For example, a candidate with high numerical reasoning abilities may be well-suited for financial analysis or pricing strategies.

It's important to note that these tests should be administered by qualified professionals and used as one piece of the overall hiring puzzle. Psychometric testing should not be the sole determinant in the hiring decision but rather used in conjunction with other assessments, interviews, and evaluations to gain a holistic understanding of the candidate's fit for the role and the organization.

The second person we hired in our company was someone to do data entry and deal with all the little things that took up time, were important, but go in the way of more strategic and operational tasks.  We used an outsourcing company to find us a VA in the Philippines.  The company used several psychometric tests to help with finding the right candidate, and they shortlisted three applicants.  We chose Hana and she is still with the company after 10 years.  She was perfect for the job, and we attributed that to her being the right personality type for the job, along with the hard skills she was selected for.

Types of Employees for a Growing Property Management Company

It’s challenging at the start to decide who will be of the most benefit to you. There are various types of employees you may need to support your operations and deliver exceptional hospitality-focused services. Here are some key roles to consider:

Guest Services Representatives

Guest services representatives are the primary point of contact for guests, providing them with information, handling inquiries, and addressing any concerns or issues that may arise. These individuals should have exceptional customer service skills, be knowledgeable about the local area, and possess strong communication and problem-solving abilities. Guest services representatives are responsible for delivering a high level of hospitality to ensure guest satisfaction and promote positive reviews.

Sales and Marketing Professionals

Sales and marketing professionals are crucial for attracting property owners and securing bookings. They develop marketing strategies, manage online listings, build relationships with vendors and online platforms, and conduct sales activities to expand the company's client base. They should have strong negotiation skills, marketing expertise, and the ability to identify and seize business opportunities.

Maintenance and Housekeeping Staff

These employees are the cornerstone of your business and  are responsible for ensuring the cleanliness, functionality, and safety of your rental properties. They might handle routine maintenance tasks, address any repairs, and ensure the properties are properly cleaned and stocked for guest arrivals. These employees should possess practical skills, attention to detail, and a proactive approach to maintenance. Housekeeping staff should be diligent, reliable, and capable of maintaining high cleanliness standards. They also need to have an understanding of the hospitality nature of the business.

Financial and Administrative Personnel

They handle financial transactions, budgeting, bookkeeping, and financial reporting. Additionally, they may oversee administrative tasks such as scheduling, record-keeping, and coordinating with property owners. These employees should have strong organizational skills, attention to detail, and proficiency in financial management software.

Revenue Management Specialists

This is a newer role and one that is becoming increasingly important. . They analyze market trends, competitor rates, and historical data to determine the most effective pricing models. By using  revenue management software and tools, they monitor demand patterns, occupancy rates, and seasonal fluctuations to make data-driven decisions. Their goal is to achieve the highest possible occupancy rates and rental income by setting competitive prices, implementing dynamic pricing strategies, and adjusting rates based on market conditions. Additionally, they collaborate with other departments to develop promotional campaigns and pricing packages to attract guests and increase bookings. Overall, the revenue management specialist plays a crucial role in driving profitability and enhancing the financial performance of the short-term rental management company.

Compliance and Legal Professionals

Compliance and legal professionals ensure that your business operates within legal frameworks and adheres to industry regulations. They handle matters such as lease agreements, compliance with safety regulations, data protection, and resolving legal disputes. These employees should have a strong understanding of relevant laws and regulations, excellent problem-solving abilities, and attention to detail.

Remember, the specific roles and number of employees required will depend on the size of your property management company, the number of properties you manage, and the scope of your services. At the start you may look for employees who can take on multiple roles i.e. Sandra, our office manager, was responsible for bookkeeping, compliance, and ensured smooth running of all administrative functions.  She was deeply involved in selecting a new PMS as she had a strong understanding of all the functions.  

Ways to source and manage remote staff

In our business, we regularly outsourced work to specialized experts which allowed us to scale our operations efficiently, and improve flexibility. There can be huge benefits in this if you do it right.

The benefits are in cost-effectiveness, tapping into expertise of professionals who specialize in specific areas, scalability, and in time-saving. Here’s a couple of examples:

  • You could engage a digital marketing agency to develop targeted marketing campaigns, ensuring effective promotion and increased bookings.

  • Outsourcing certain functions, such as accounting, marketing, or customer support, can be cost-effective compared to hiring full-time employees. There are companies dedicated to providing these services for small property management companies.

  • Using a specialised revenue management service

  • Hiring a social media manager to manage an editorial schedule for all the SM channels.

There are a lot of advantages in using a remote staffing strategy.

It allows you to tap into a global talent pool. You can recruit skilled professionals who may not be available locally, bringing diversity and fresh perspectives to your team.

Remote staffing offers flexibility for both employees and employers. It allows individuals to work from their preferred location, promoting work-life balance and potentially attracting highly motivated and experienced professionals.

Expenses associated with office space, utilities, and equipment are reduced. It can also mitigate overhead costs associated with employee benefits, insurance, and other expenses traditionally incurred with on-site employees.

Remote work can lead to increased productivity and employee satisfaction. Without the distractions of a traditional office environment, employees may have fewer interruptions and enjoy a better work-life integration, ultimately leading to higher efficiency.

The pandemic had a positive side in that most people are now comfortable with remote working and are familiar with platforms such as Zoom, Slack, Ring Central, and with collaborative software such as Asana and Monday.  It’s a lot easier to integrate remote staff into this type of culture.

There’s a couple of things we learned from hiring many remote assistants over the years, because we made mistakes along the way.

  • Time zone differences: If you hire remote employees from different time zones, you need to establish clear communication and scheduling protocols to ensure smooth collaboration.

  • Self-motivation and discipline: Remote employees need to be self-motivated and disciplined to manage their work effectively without direct supervision. Consider assessing candidates' ability to work independently during the hiring process.

  • Cultural differences: It’s important to research and understand any differences in work ethic, standards, and practices with workers from other countries. Learning about these differences can mitigate any challenges you might meet.

Onboarding and Training

Onboarding and training are crucial steps in integrating new employees into your business. You have to make sure they understand their roles, responsibilities, and the company's expectations as this will set them up for success.

Take time to develop an effective onboarding and training program at the start. Even if you are just planning on one assistant, this is a worthwhile exercise as you will need it in the future as you expand.

Preparing for Onboarding

Create a comprehensive welcome package that includes essential information about the company, its mission, values, policies, and procedures. Provide an overview of the organizational structure, team members, and any relevant resources or materials.

This can be part of a lengthier staff handbook that includes systems and processes.  We use the Touch Stay platform to create a simple, readable handbook that could be read on any device, and easily accessed.

Workspace setup: Ensure that the new employee's workspace is properly set up and equipped with the necessary tools, technology, and access to required systems or software.  For remote 

Designate a mentor or buddy who can guide the new employee during the onboarding process. The mentor can offer support, answer questions, and provide insights into the company culture.  If this is a first hire, then that person is going to be you, so be aware of the responsibilities of sharing everything they need to be comfortable and happy in the new role.

Onboarding Process:
  • Orientation: Conduct a formal orientation session to introduce new employees to the company's culture, values, and mission. Cover essential information related to HR policies, benefits, workplace safety, and compliance requirements.

  • General industry training: Ensure they have access to industry training that includes the history of the vacation rental business, hospitality philosophy, a glossary of terms (given the multitude of acronyms in this business!), a background in the legal and regulatory aspects of short term rentals, and an understanding of the landscape of the industry (OTA’s, direct booking, etc).

  • Role-specific training: Provide role-specific training to familiarize new employees with their responsibilities, tasks, and performance expectations. This may involve shadowing experienced team members, participating in training sessions, or utilizing online learning platforms.  

  • Introduction to tools and systems: Ensure that new employees receive training on the tools, software, and systems they will be using in their roles. Offer guidance on how to navigate property management software, communication platforms, project management tools, and other relevant technologies.

  • Clear communication channels: Establish effective communication channels for new employees to ask questions, seek clarification, and receive ongoing support. Encourage them to reach out to their manager, mentor, or colleagues when needed.

Consider ongoing training and development, and provide opportunities for ongoing learning and growth through workshops, webinars, conferences, and industry-related courses. 

A well-structured onboarding and training program helps new employees feel welcomed, engaged, and equipped to contribute to your success. This Guide should give you enough material to start you thinking about your hiring strategy.