Our Team of Connectors

Experts in the art of connection.

Every Connector on our team brings over a decade of experience in training, coaching, facilitating and mediating high-performing C-Suite executives and emerging leaders — and has been in those positions themselves. All have realized the power of connection transforms not only relationships with partners and coworkers inside the organization but that impact touches beyond those figurative walls.

They understand the real-world dynamics of co-leadership and what it takes to make it work.

Our connectors help leaders build trust faster, navigate relational complexity with confidence, and create cultures where connection drives performance and growth.

Jessica Holsapple, Head of Connection at Connections Matter

Jessica Holsapple

Former Co-Leader & C-Suite Advisor
Head of Connection

As a former second seat to several CEOs, and trusted C-suite advisor, Jessica brings deep expertise to every phase of the co-leadership journey.

At the heart of the journey she learned this — without true connection, nothing can rise to the level of your vision. And with help facilitating the strengthening of those connections, partners & teams rise beyond their visualized realities.

Jessica leads Connection Matters, matching the right Connectors with the right teams guiding the entire journey to ensure strong, lasting partnerships.