Better perspective leads to better decisions.

For over 15 years, I've helped founders, CEOs, and executive teams navigate complex, cross-functional decisions spanning strategy, commercial negotiations, legal risk, brand reputation, people, and transformation.

Today, I help leaders make better decisions and write about ideas, and the signs of life, that shape meaningful businesses, careers, and lives.

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Shai Littlejohn seated at her desk in The Bungaloom which is a room with a vibrant floral wallpaper and rustic ceramic pottery.

Writer · Speaker · Strategic Advisor

ALIVENESS IS STRATEGY
Brian Jackson & Shai Littlejohn on Owl Have You Know Podcast
Audio Reflection
A cozy area with a round wooden table set with two cups of coffee, a black leather planner, an open notebook with a pen, and a laptop. Two upholstered chairs with decorative pillows surround the table, and a green sideboard with books, a potted plant, and decorative items is in the background near a window with cream curtains.
Minimalist logo with the letters S and L, accompanied by a small branch with leaves and subtle decorative elements on a light background.

I’m Look for Signs of Life.

In businesses. In leaders. In careers.

I advise founders, CEOs, and executive teams on commercial strategy, business development, partnerships and high-stakes negotiations, helping them see opportunities, navigate complexity, and make better decisions.

What makes my perspective different is that I've advised executive teams through cross-functional challenges involving strategy, legal, marketing, corporate responsibility, reputation, operations, and transformation for nearly two decades. Seeing business through multiple lenses helps me uncover possibilities that others overlook.

Better perspective leads to better decisions.

  • I advise founders and executive teams on growth, meaningful brand identity, commercial strategy, and high-stakes business decisions.

  • Develop stronger leadership and teams where people and performance thrive together.

  • Create more meaningful customer and employee experiences that strengthen trust, loyalty, and long-term value.

  • Provide one-on-one thought partnership for founders and senior leaders navigating growth, difficult decisions, leadership challenges, and organizational change.

  • Keynotes, fireside chats, executive retreats, panels & moderation.

How I Help Founders & Executive Teams:

How I Help Professionals:

  • I help professionals navigate career transitions with confidence and perspective.

  • Redefine success without sacrificing ambition.

  • Build a more meaningful life and career.

  • Discover practical ideas for living well through essays and video.

The Journal

The Conversation That Changed My Life
Featured Shai Littlejohn Featured Shai Littlejohn

The Conversation That Changed My Life

After my mom was diagnosed with brain cancer, I flew to visit her at least monthly. I was General Counsel of the DC Sports and Entertainment Commission during that time, so having a flexible leave policy and the ability to work remotely from Houston was the only way I made it through.

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How to Make Sure Your Cup Is Full
Featured Shai Littlejohn Featured Shai Littlejohn

How to Make Sure Your Cup Is Full

The farmer who wants to produce a high quality harvest to sell to the market at premium prices must execute a strategy that fuels her intention to produce a quality bean. She must exercise patience, and craft, to allow the tree to time produce. It can take 3 to 4 years of cultivating a coffee tree before it ever produces fruit. There are routine steps that all farmers must take, but if she can tend to the trees under just the right conditions, the cherries will ripen right on time.

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Stylized logo with the letters 'S' and 'L' inside a circular border, featuring a small branch with leaves on the left side, and surrounded by a gradient cluttered background.