Jessica Holsapple

Jessica Holsapple

I AM

A decade in middle management evolved into a ten-year career learning alongside visionary founders and leadership teams through growth, pressure, reinvention, and scale.

Watching businesses grow from the inside taught me that leadership is rarely a systems problem alone — it is often a clarity, alignment, communication, and trust problem first.

It shaped me into a strategic second-in-command who helps leaders recognize the patterns beneath the pressure, align people around what matters most, and create momentum through clearer decisions and stronger relationships.

I BELIEVE

Five years as a fractional operations leader and trusted second-in-command led to advising founders and executive teams through SCG Consulting Group across more than 50 companies.

That experience reinforced what I believe deeply: sustainable growth happens when leaders are aligned internally first — with themselves, each other, and the story guiding the business forward.

I believe strategy works better when communication is honest, meetings create movement, systems support people, and leaders stop carrying unnecessary friction alone.

Books & Philosophy

Free books, downloads, and philosophies around leadership, systems, alignment, and growth.

I DO

Today, I help leaders make aligned decisions, resolve what’s getting in the way, tell their story better, and build revenue growth engines that scale.

Strategic Meetings
We Run Meetings™

Strategic meeting design and facilitation that transforms complex conversations into clarity, aligned decisions, and action.

werunmeetings.com →
Executive Mediation
Connection Matters™

Mediation and alignment work for founders, partners, and leadership teams navigating pressure, tension, and growth.

connectionmatters.net →
Story & Media
The Redd Legend Agency™

Helping businesses tell their story better through narrative strategy, StoryLab™, and strategic media experiences.

thereddlegendagency.com →
Revenue Growth
In-House Agency Builder™

Building strategic partnerships and scalable revenue growth engines for established businesses ready for expansion.

inhouseagencybuilder.com →

WORDS FROM PARTNERS

“Jessica sees clearly the right work that needs done with tactical execution that delivers results.”
Devin A. • Founder
“Jessica is truly exceptional at balancing organizational insight and humanity.”
Justin H. • Founder
“Jessica’s rare ability to align people and process for clarity and impact is impressive.”
Bill M. • Founder