Select Page

by G. Sax, Director of Growth Management, RESO

Welcome to “Three Questions,” an interview series that introduces you to real estate industry professionals, their businesses and how they interact with real estate standards with a goal of humanizing the tech side of the industry, fun included.

This week’s interview with Caitlin McCrory, VP of Industry Relations for Anywhere and an active RESO board member, is our “Back to School” Edition, and you’ll soon see why. Caitlin and I have heavy Midwestern roots, and we have both lived in the Wisconsin cities of Milwaukee and Madison, so we harked back to some school spirit(s) memories by the third question. Enjoy!

Q1: How does a Milwaukee South Sider become the face of industry relations for important coastal real estate brands like Redfin out west and Anywhere out east?

Caitlin: For the love of the game. I’m actually not kidding. I worked hard to land in those positions, because I genuinely love and care about this industry. You don’t do this job unless you love it. There are a lot of opinions and politics in play, so you’ve got to trust your gut and remember why you got in the game in the first place.

I like having the opportunity to make the industry easier to navigate for buyers and sellers. That’s my main draw – making transactions easier for first-time homebuyers.

Q2: We both started in real estate as communications directors for local REALTOR® associations. What can you say about your time at the Greater Milwaukee Association of REALTORS®? 

Caitlin: It was an interesting job, because I would float between two sets of responsibilities, having also split my time at Metro MLS. I found myself leaning more toward data policy than pure communications, and that’s why I ended up working for the National Association of REALTORS® next. I became interested in the lifecycle of a listing.

The people at the Greater Milwaukee Association of REALTORS® and Metro MLS were so lovely and wonderful, and I am forever thankful for my time with them. It was such an important stepping stone for me.

Q3: We have another thing in common. We are both graduates of the University of Wisconsin–Madison. Go, Badgers. What is your favorite bar in Madison and why?

Caitlin: Chasers was my favorite, but it got bulldozed. (Long, forlorn sigh.) But I loved the 3-for-1 mixers. I mean, c’mon, who doesn’t like 3-for-1s?

If I had to pick a place that is still standing, I would go with the Church Key and their $2 pitchers. Can you sense a broke college girl theme here?

RESO: Oh, wow. I haven’t been to the Church Key in literally decades. It looks like they bought out the whole building, but when I was going to school, they occupied just the second floor. There was a grocery store on the first floor that you could see down into from the balcony. Like the store would be closed at night, but the party was still rocking above the soup cans and cereal boxes.

I always thought it was nuts that people could be at a bar holding drinks in glasses and bottles over a railing above an actual grocery store. “Cleanup on aisle 5” must’ve had quite a different meaning back then.

By the way, there is now a place in town called Chasers 2.0. See you at Homecoming?

Caitlin: U-rah-rah Wisconsin!