International Women's Day Featuring Jessica B. Fairchild

International Women’s Day is more than a moment — it’s a movement. A celebration of resilience, ambition, creativity, and the countless ways women show up for their communities and themselves every single day. At ALLY, we believe that when women are supported in their careers, in their lives and even in the shoes they wear — they move through the world with greater confidence and power. Today, we honor and feature a visionary lawyer who is building, leading, and redefining what’s possible. Meet Jessica Fairchild.

ALLY Shoes: What motivated you to pursue a career in law?

Jessica: I majored in accounting, but as I neared graduation, I realized it wasn’t the right path for me. My business law class sparked a pivot - I applied to law school instead. Law offered diverse career options and the chance to hone my strategic and analytical thinking skills. Since my parents weren’t lawyers, the field felt new and exciting. It wasn’t until law school that I discovered my true passion: transactional work rather than litigation.

ALLY Shoes: What led you to co-found Croke Fairchild Duarte & Beres? Was there a gap in the legal industry that you felt passionate about addressing?

Jessica: Sometimes life brings opportunities, and you have to be ready to seize them. Before co-founding Croke Fairchild, I had practiced in several settings – Big Law, in-house as General Counsel for Chicago’s 2016 Olympic bid, and as a solo practitioner. I felt ready to build something different, something with my own mark on it. When I met with my current co-founders, everything clicked. They were looking to do something new, the timing was right, and I was immediately filled with excitement about the possibilities.

We saw an opportunity to create something special in our hometown of Chicago: a law firm where we could broadly serve clients, hire the best entrepreneurial talent, and give them a platform to grow. When my partner Lisa joined, we made a strategic decision to become majority women-owned and obtain Women’s Business Enterprise (WBE) certification. This was mainly something we did for our culture – wanting to demonstrate that women can found and run a highly successful law firm. We’ve exceeded our initial expectations, growing from 10 to 110 lawyers in just six years. I think we made the right decision to launch the new firm!

ALLY Shoes: In the early days, what was the biggest challenge you faced in starting your own firm, and how did you overcome it?

Jessica: Like most new businesses, we faced many initial challenges: launching only months before the pandemic shutdown, not having enough lawyers early on for incoming work, and lacking the operational infrastructure to support growth. As a founder, I was willing to do whatever the firm needed - not just practicing law, but also recruiting, building brand awareness, and filling operational gaps.

I believe three things have been key to our success: our willingness to go the extra mile for clients, building trust and forging strong relationships; allowing flexibility for our team members during and after the pandemic; and leveraging the different, yet complementary, skills of our co-founders, which has allowed us to tackle any business challenge.