About Shai

Shai Littlejohn headshot in dark shirt with earings and beaded jewelry for Shai Littlejohn Studio.

I’m an executive leader, strategist, and advisor whose career has been shaped by curiosity about business, people, creativity, and what makes ideas work.

My career spans executive leadership, business strategy, corporate law, communications, and brand. I hold a J.D. and a B.A. in Journalism and Advertising from Howard University, an Executive MBA and Leadership Coaching Certification from Rice University Jones Graduate School of Business, and I also studied at Berklee College of Music. Together, these experiences have shaped the way I think: across disciplines rather than within them.

Before my career in executive leadership and corporate law, I studied music because I was fascinated by creativity, expression, and the human experience. I never imagined those experiences would become central to my work. Today, they shape the way I listen, solve problems, lead conversations, and help organizations think differently.

Throughout my career, I've worked alongside founders, CEOs, and executive teams at companies including Starbucks, Delek US Holdings, and Olin Corporation to solve complex problems and move important ideas forward. My work has taken me across enterprise strategy, innovation, customer and employee experience, corporate communications, sustainability, brand reputation, business transformation, and commercial growth.

Highlights include:

  • Starbucks Coffee Company, Director & Counsel

  • Olin Corporation, Vice President & General Counsel North America

  • Delek US Holdings, Associate General Counsel

  • Federal Trade Commission (FTC)

  • Executive MBA, Rice University Jones Graduate School of Business

  • Juris Doctor, Howard University School of Law

  • Bachelors of Arts in Journalism and Advertising, Howard University

  • Leadership Coaching Certification, Rice University

Multidisciplinary Perspective

Having worked across business strategy, executive leadership, legal, communications, marketing, procurement, sustainability, and innovation, I help leaders see opportunities, risks, and connections that others often miss.

Commercial Judgment

Having advised executive leadership teams inside Fortune 500 companies, I understand how experienced leaders weigh opportunity alongside risk. I help founders and business leaders apply that same level of commercial judgment to negotiations, strategic decisions, partnerships, disputes, and growth opportunities.

Thoughtful Communication

Complex decisions deserve thoughtful conversations. I ask questions, listen carefully, challenge assumptions respectfully, and communicate with clarity so leaders can move forward with confidence.

What Clients Can Expect:

Make better decisions. Build a stronger business.