Kristen Alessi is a property manager at Draper and Kramer, overseeing the community at Eleven Thirty in Chicago’s South Loop. She joined the firm in 2013 as a property administrator, quickly advanced through promotions and was recently named Accredited Residential Manager of the Year by the Institute of Real Estate Management’s Chicago chapter.
Tell us about your background. Where did you grow up, where did you go to school?
I was born in New Jersey, but spent the majority of my childhood growing up in Northwest Indiana. Valparaiso is a city that provides small town values, but with a big city feel since Chicago is only 35 minutes away. I attended Purdue University, where I earned a bachelor’s degree in hospitality and tourism management with a double emphasis in restaurants and hotels.
When you were young, what did you aspire to be?
Growing up I wanted to be a marine biologist—even going as far as obtaining my PADI Open Water Diver certification and attending research trips in Key Largo during high school. I loved swimming with sharks, sea turtles and ship wrecks.
How did you get your start in the industry?
After college, I started working at Club Quarters Hotels in Chicago as a guest services manager. It was an amazing experience that really jump started my career in this customer service-based industry. A year later I moved on to student housing, working for a subsidiary of DePaul University, before eventually switching gears again and shifting into apartment management. Fast forward to today, and I am a property manager with Draper and Kramer, a real estate services firm that has been in the industry for over 125 years. I started as a property administrator in 2013, and ended up being promoted three times in three years.
Did you have a mentor who helped you get on your feet, or is there someone you turn to now for support?
One of the best things about Draper and Kramer is how close all of the property managers and staff are. We have a group email chain that we all use for support, to bounce ideas off of each other and for comic relief when we need it. It’s great to be able to reach out to a group of people who do what I do every day for other properties. You might think you are dealing with a unique situation, only to find out that two other managers have experienced the same thing—and they provide their ideas and tips on how to handle.
What does a day in the life of Kristen Alessi look like?
There really is no beginning or end to my day as the property manager of Eleven Thirty (1130 S. Michigan Avenue). I’m responsible for 656 units, over 1,000 residents and four commercial retail spaces; anything can happen at any time. A few weeks ago I had to run down 36 flights of stairs in a ball gown due to a fire alarm—right as I was heading to the ceremony where I received the ARM of the Year award for the IREM Chicago Chapter. I spend my day in the office overseeing a 120-unit renovation project, other major capital projects and a staff of 26 team members, as well as spending time coordinating with the leasing team. I strive to be an active manager so I love taking tours, working on leasing files and whatever else I can be a part of for my entire staff.
What do you like most about your job?
The people. Some of the residents of Eleven Thirty have been with us since 1967 and it’s an amazing opportunity to sit with them and chat about what the South Loop neighborhood used to be like and how they’ve seen the area and the property evolve over those 50+ years. I believe the residents appreciate that I take the time to put a face to the name on their file—they are more than just a lease here.
Looking to the future, what do you hope to achieve/work on that you haven’t already?
My future goal is to always love what I do and never dread going in to work. With that said, my next career aspiration is to manage a brand-new build or a property in a lease up. It’s a completely different experience taking on a property that has zero residents than one that is established. Outside of my current position, I also look for ways to help develop the next generation of property managers. In 2017 I co-developed a program for Draper and Kramer that takes high-performing employees and helps develop and mentor them personally and professionally, positioning them to be the future leaders of our industry.
How do you spend your time away from the office?
Outside of work I spend time with my fiancé and our two dogs. We are also big family people so we spend a lot of time with our siblings and exploring the city with our friends.
What is your favorite place that you have traveled to? Where do you hope to go next?
My fiancé and I have been to some amazing places for weddings over the years and a few of my favorites are Panama and Guatemala! Next up is our honeymoon, so anything goes!
Who would you like to see answer these questions?
Lucille Ball—she’s the exemplary example of a woman becoming vastly successful in an otherwise male-dominated industry.