Sarah C. Jaffe is Senior Broker at Cross Street, a residential and commercial real estate company that helps individuals rent apartments, professionals buy investment properties. Cross Street also works with developers who want to lease up their multifamily properties quickly.
Jaffe has thrived at Cross Street, drumming up plenty of business from the company’s Chicago office. She is also sales leader at the firm, a nice accomplishment considering that she only joined Cross Street in 2024.
Here is a look at Jaffe’s career so far and her future goals in residential and commercial real estate.
Tell us about your background. Where did you grow up? Where did you go to school?
I’m originally from Cleveland, Ohio, from a family of five (I’m the youngest of three girls). I went to Indiana University – Bloomington to study nonprofit management and stayed for a master’s degree in public affairs (similar to public policy) with concentrations in nonprofit management and international development. When I graduated in 2018, I moved to Chicago and started a job as an Events and Travel Coordinator at a foreign policy think tank called the Chicago Council on Global Affairs.
How did you get your start in the industry?
When the pandemic hit in 2020, I was still working at the Chicago Council on Global Affairs as an Events and Travel Coordinator. Given the nature of my role there, I knew the pandemic rendered my role obsolete and that it was only a matter of time before I was out of a job. Coincidentally, I was already feeling a bit pigeon-holed in the industry and was looking to pivot into something new and exciting; so, I took a few months to have in-depth conversations with my close friends and family to explore different paths that I may thrive in and enjoy, and I landed on residential real estate.
Did you have a mentor who helped you get on your feet, or is there someone you turn to now for support?
Yes, absolutely, but not until I was fully in the industry. Going into it, I had zero background in real estate. I didn’t own any property (I was 25). I didn’t come from or know any investors, and no one in my family was in the industry or even from Chicago. I definitely took a leap of faith and relied on my people skills to get my start. But once I was in the industry, I turned to many colleagues – Mike Greco, Matt Thomas, and Kate O’Neill, to name a few – to grow into a sophisticated broker as quickly as I could.
What does an average day at work look like?
It’s changed a lot over the years. Earlier this year, when I joined Cross Street, I took on a role as a Sales Leader for the company (in addition to full-time brokering), which requires that I’m in-office quite a bit (which I love). Every day looks different, but most of the time, it’s a mix of touring homes, networking with industry professionals, advising other brokers in the office, transaction management, and administrative work. Going into 2025, a colleague and I will be hiring a full-time operations manager which will allow me to take myself out of the weeds of my own business and focus on scaling.
What do you like most about your job?
I like that no two days or deals are the same. I’m constantly learning something, facing a new challenge, pushing my business to new heights. Being a real estate broker is about 10% showing homes, 90% growing a business. I’m OK trading the 9-5 and the work-life balance that can come with it for the gratification of building something from the ground up, calling the shots, and being my own boss.
Looking to the future, what do you hope to achieve/work on that you haven’t already?
From a business perspective, I’m hoping that hiring a full-time operations manager will propel my business to $25M+ in annual volume production (2024 was $18M). I’m also hoping that it will allow me to dedicate more focus toward building out the sales division at Cross Street alongside several other colleagues. From a personal perspective, I’m looking forward to getting married to my long-term partner in May!
How do you spend your time away from the office?
I enjoy interior design (specifically sourcing second-hand furniture), hosting friends, sharpening my photography skills, traveling with my fiancé, Sam, going on long walks around the West Town neighborhood, exploring vintage markets, trying new restaurants, and going to concerts.
