About Shai

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

I help growing businesses benefit from the kind of strategic thinking, commercial judgment, and executive counsel typically found inside the world's largest organizations.

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 advised founders, CEOs, and executive teams at Fortune 500 companies, including Starbucks Coffee Company, Delek US Holdings, Olin Corporation, and more on the decisions that shape organizations. My work has spanned commercial strategy, business development, high-stakes negotiations, corporate social responsibility, ethical sourcing, innovation, communications, customer experience, brand integrity, reputation, and enterprise risk.

Now I help leaders make better decisions because I've spent my career learning businesses from multiple perspectives. Rather than viewing challenges through a single function, I bring together commercial strategy, leadership, legal judgment, marketing, operations, and human experience to help organizations create lasting value.

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

Thought Partnership

I don't arrive with predetermined answers. I help leaders think through complex decisions from multiple perspectives.

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:

I help growing businesses benefit from the kind of strategic thinking, commercial judgment, and executive counsel typically found inside the world's largest organizations.