Jessica Fairchild | How Flexibility and an Entrepreneurial Mindset Can Lead To Explosive Growth

Jessica FairchildJessica Fairchild is a Partner at Croke Fairchild Duarte & Beres, a certified women’s business enterprise counseling clients ranging from startups to Fortune 500 companies. As a lawyer, law firm leader, women’s advocate, and entrepreneur, she serves as Co-chair of the firm’s Management Committee.

Over her 23-year legal career, Jessica has served as a mergers and acquisitions attorney, counseling founders, private equity sponsors, family enterprises, and corporations on both the buyer and seller sides. She also has experience with general counsel law and corporate governance, securities, joint ventures, and negotiating sponsorship transactions and key commercial agreements.

Before founding Croke Fairchild, Jessica founded and managed several additional law firms and served as General Counsel for Chicago 2016, the non-profit and civic organization that led Chicago’s bid for the 2016 Olympic and Paralympic games. Her flexible and entrepreneurial approach to acting as a legal and business advisor has allowed her to facilitate explosive growth for diverse organizations.

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Here’s a glimpse of what you’ll learn: 

  • Jessica Fairchild’s journey from BigLaw to the managing partner of a midsize law firm 
  • Jessica shares her experience counseling Chicago’s bid for the 2016 Olympics
  • How Jessica honed her entrepreneurial drive
  • Standard mistakes lawyers make when scaling their firms 
  • Building a diverse team through a flexible culture 
  • Strategies for including non-lawyer professionals in a firm’s culture
  • What is Jessica’s recommendation for launching and growing a firm?

In this episode…

Many lawyers don’t have an entrepreneurial background and may struggle to grow their firms effectively. These professionals either don’t know how to execute a strategy or lose top talent when trying to maintain culture at scale. How can you build a durable and impactful law firm?

After serving as general counsel for Chicago’s 2016 Olympic bid, the city lost the competition, prompting business-minded attorney Jessica Fairchild to explore additional opportunities. Her passion for entrepreneurship and desire for flexibility allowed her to launch and scale a firm that values professional growth. One of the most vital aspects of firm success is building an attractive and valuable culture. This involves providing attorneys with the flexibility to pursue their passions and allowing each team member to share ideas and voice their concerns directly to management, creating a unified environment.

On this episode of The Lawyer’s Edge Podcast, Jessica Fairchild, a Partner at Croke Fairchild Duarte & Beres, joins Elise Holtzman to talk about growing a law firm through flexibility and entrepreneurship. Jessica shares her transition from BigLaw to founding a midsize law firm, the common mistakes of scaling a firm, and how to include your entire team in your culture. 

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 Sponsor for this episode…

Today’s episode is brought to you by the Ignite Women’s Business Development Accelerator.

Ignite is an 8-month business development program created by women lawyers for women lawyers.

Ignite is not just a one-off seminar or a series of seminars. It’s a carefully designed business development program containing content coaching and a community of like-minded women who are committed to becoming rainmakers and supporting the retention and advancement of other women in the profession.

To learn more about Ignite, visit

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