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At Modern Counsel, we spotlight the legal minds driving strategy, innovation, and integrity across today’s complex and rapidly changing business landscape.
This month, we’re bringing you a list of six impressive litigation executives to watch. These women work in companies that span tech, food, retail, auto and transportation, and real estate. What do they have in common? They’re shaping the future of corporate litigation with strategic insight, sharp instincts, and a strong command of risk.
Know a leader who should be part of the Modern Counsel network? Introduce us.
Ayana Free
Deputy General Counsel, Regulatory Compliance and Litigation
Via
Ayana Free leads global litigation and regulatory compliance with a rare blend of legal acumen, emotional intelligence, and intentionality. Drawing on her background in private practice, government, and in-house roles, she brings a human-centered approach to litigation—managing complex, high-stakes matters while fostering a culture of empathy, learning, and institutional knowledge across her lean, high-performing team.
Connect with Ayana Free on LinkedIn.
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Jessie Castellucci
VP and Associate General Counsel, Employment, Litigation & Compliance
Datadog
Jessie Castellucci has built her entire legal career in-house, bringing a uniquely pragmatic and collaborative approach to employment, compliance, and litigation. At Datadog, she has elevated the legal team’s role from reactive to strategic—ensuring litigation and risk are proactively managed across a global footprint.
Connect with Jessie Castelluccion LinkedIn.
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Kofi Semenya
Senior Counsel, Litigation & Employment
Chipotle
Kofi Semenya serves as a key legal partner to the company’s HR team, handling complex employment issues, ADA claims, and nationwide agency responses. With a background rooted in civil rights and a passion for practical problem-solving, he’s become a trusted advisor navigating a dynamic legal landscape for a workforce of over 120,000.
Connect with Kofi Semenya on LinkedIn.
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Mindy Harper
VP, Legal
Crown Castle
Mindy Harper spearheads the company’s litigation strategy across employment, real estate, zoning, and regulatory matters—guiding a nationwide team through high-stakes disputes while steering risk management during activist-shareholder pressures and major corporate transactions.
Connect with Mindy Harperon LinkedIn.
Are you a legal expert in your industry? Introduce yourself! We’d love to meet you.
Madeline Tzall
Senior Legal Counsel, Litigation
Harley-Davidson
Madeline Tzall manages all US litigation for Harley-Davidson’s iconic brand—covering product liability, commercial disputes, and tort claims. With a lean in-house team and trusted outside counsel, she navigates high-volume, high-stakes matters with precision, speed, and a deep respect for the company’s legacy of freedom and performance.
Connect with Madeline Tzall on LinkedIn.
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Rayan Naouchi
Associate General Counsel, Labor & Employment
VF Corporation
Rayan Naouchi has played a pivotal role in building VF Corporation’s employment law function from scratch. With a sharp instinct for litigation strategy, she leads a lean team in managing complex employment disputes across corporate, retail, and distribution operations—bringing both agility and creative problem-solving to a dynamic global workforce.
Connect with Rayan Naouchi on LinkedIn.
This article was produced with the assistance of AI.
