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How I transitioned from a career in finance to short-term property management

Mariette Williams   

How I transitioned from a career in finance to short-term property management
  • Shannon St. Val pivoted from her job in finance to pursue a career in real estate.
  • She is now the founder and owner of a short-term vacation-rental company.

Shannon St. Val is the founder and owner of Elevate Vacation Rentals, a short-term vacation-rental company based in New York. She left her job in finance to manage short-term rental properties and shares how she started, how she makes money, and the challenges of the industry.

This as-told-to essay is based on a conversation with Shannon St. Val. It has been edited for length and clarity.

My career in property management hasn't been a straight path. My degrees are in finance and real estate, and I graduated in 2008 when the subprime meltdown happened. I thought I would be working in commercial real estate, but then all the real-estate jobs disappeared and I started working in finance.

I worked at Klynveld Peat Marwick Goerdeler, or KPMG, on the consulting side, specializing in financial operations for big banks and broker-dealers, specifically for investment-management firms.

I knew I didn't want to work in finance for too long because the culture was intense. In 2016, I left my job to be my own boss. I took many of my finance and consulting skills and founded my own short-term property management company.

At first, I started managing a few properties for myself, and then when COVID happened, I had to pivot and expand. I decided to take on clients outside New York instead of just managing my own. It's been my dream to return to real estate with property management.

How I find clients

A lot of my early clients came through word of mouth. I had friends, particularly people I met in the finance industry, who had houses in Martha's Vineyard or the Hamptons and would ask, "Hey, you're managing properties. I have a house. Can you manage mine?" Some people will advertise on social media, but I've gotten my business through referrals. If you do good business, people will refer you to their network.

Some property managers who are just starting have found success in cold pitching. This means reaching out to short-term rental owners and saying, "I know you may have a manager, but I'm willing to work for a lower rate for the first year." Then, if you meet their expectations, you can increase the rate.

Some companies can do outbound emails or outbound marketing for you, where you blast local owners or anyone who recently bought a new house in that particular vacation-rental area, advertising your services.

How I earn a living from property management

There are two ways to earn money from managing short-term properties. The first is by working with vacation-rental owners and charging a commission on the nightly rate. I've seen commissions as low as 10% and as high as 30%, but the industry standard is typically 15% to 20%.

I also manage a building. It's a master lease, which means I pay a flat rate and collect rent from each unit as a short-term vacation rental. Some homeowners just want their flat-rate rent and don't want to be involved, so I'll do a short-term rental. You have to be a little more sophisticated in this because if you don't budget and know your expected revenue, you could misprice it and lose a lot of money. With that model, we want to get at least a 25% to 30% return to provide a buffer in slower months.

My typical day

Your typical workday will depend on how many properties you manage. We're managing roughly 30 properties now, so we have a team that handles guest support. I work about eight or nine hours a day, but the job is really 24/7. If there's an emergency, you need to be available.

My typical schedule involves a lot of meetings. We always meet with the cleaning team to discuss maintenance and cleaning issues. We go over that once a week with one of the cleaning companies we work with. In the middle of the day, we'll work on pricing reports for owners, update the listings, and read through guest reviews.

We also schedule property checks and inspections at least once or twice a month, depending on the property. It requires a lot of coordination, so you'll have to get used to talking on the phone frequently, rather than texting or Slacking messages.

The challenges and rewards of property management

Managing properties is time-consuming, especially if you're doing short-term rentals. You have to have 24-hour guest support, and things like cleaning crews and a maintenance person have to be coordinated for each property. The logistics are significantly harder with vacation-rental management versus standard property management.

The most rewarding part of the job is helping my clients or the owners see the untapped value in their homes and helping them earn more money than they would have anticipated. I get thrilled when I double their income. I'm also happy to get a five-star review or feedback that we were super attentive, paid attention to detail, provided great customer service, or resolved an issue quickly.

Advice for transitioning to property management

You have to be very organized, have structured processes, and be good at communicating with multiple stakeholders, including the vendors, owners, and guests. My corporate background helped me a lot because it had so much structure, and I came in with project management and logistical skills. I have a certification through the Project Management Institute, but getting a degree or certification is optional.

To break into the industry, I recommend working for a vacation-rental company before branching out independently. Use the time to learn some of their best practices before you move on. Check out national companies like Vacasa or Host Genius, which usually hire in different markets.

You could also work with a smaller company like mine, where you just reach out and say, "Hey, do you have any roles?" There's always something to be done, and management companies are always looking for good help. Another way to break in is to attend a regional or national vacation-rental management conference to network. Find a conference in your area, and you'll meet a lot of managers in one setting.

What I wish I'd known before starting out

Property management can be very rewarding, but I didn't realize how important it was to overcommunicate. I also didn't know how hard managing so many stakeholders would be. For every property, I usually have between four and seven different people involved. I have the owner, the lawn person, the trash person, the regular maintenance person, the cleaner for that house, and then I have my guest support.

Sometimes, keeping track of who's who can be overwhelming. So if you want to manage a larger portfolio, you need a really good process and team to keep track of everything. You also have to be extremely organized, provide good customer service, and pay close attention to detail.



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