The Power in the Pit: A Fireside Chat with Jessica Agnew
With Subject Matter Experts
Jessica Agnew, Executive Coach, Program Designer, Facilitator, Sixth Wing
Matt Sitter, CEO, AFN and Partner, Sixth Wing
What if your most difficult leadership moments—burnout, failure, disruption—weren’t setbacks, but turning points?
In this conversation, Sixth Wing Executive Coach and Program Designer Jessica Agnew joins Matt Sitter to explore The Power in the Pit, a powerful course that helps leaders transform breakdowns into breakthroughs. Drawing on behavioral science, emotional regulation, and values-based leadership, Jessica will walk through the key concepts behind the program and why it resonates so deeply with executives navigating high-stakes moments.
This isn’t a motivational talk—it’s a grounded conversation about how real disruption can become a source of clarity, alignment, and better decision-making.
You’ll leave with a taste of the framework and a sense of how this offering could support your team or leadership development goals.
Jessica Agnew
Executive Coach, Program Designer, Facilitator, Sixth Wing
Jess Agnew is an executive coach and skilled facilitator dedicated to optimizing team effectiveness and helping individuals achieve their peak performance. With a background in leadership program design and facilitation, she is passionate about creating exceptional development experiences for leaders and their teams.
Jess brings a broad array of coaching expertise to Sixth Wing, having led the design, development, implementation and execution of multiple global leadership and team effectiveness programs. Her experience facilitating hundreds of leadership and group coaching experiences, and serving as a trusted consultant and talent manager to senior executives makes her coaching and facilitation style uniquely impactful.
As an executive and team coach, Jessica believes people are naturally creative and resourceful. She is passionate about coaching leaders and teams to harness the power of their authentic leadership styles. Certified Professional Co-Active Coach as well and holds her ACC with the International Coaching Federation. Jess leverages design thinking methodologies and their application to life design as a foundation to her practice.
Prior to serving as the Global Head of Team Effectiveness for a Fortune 100 tech company, Jessica served as a Surface Warfare Officer after graduating from the United States Naval Academy. In the Navy, Jessica had the honor of leading teams of engineers ranging in size from 10 to over 180 direct reports, and serving as officer of the deck and engineering training officer over multiple deployments in support of humanitarian missions and Operation Enduring Freedom. After completing the Maritime Staff Operators Course she served as a Pacific Fleet Ballistic Missile Defence Watch Officer and lead briefer before being hand-selected by the Pacific Fleet Commander to serve on his executive staff.
Jessica currently lives in the San Francisco Bay Area with her husband and two daughters, and has found a true passion in helping others realize their full potential through the power of executive coaching.
Matt Sitter
CEO, AFN and Partner, Sixth Wing
Matt Sitter is the CEO of Advantage Foundry Network (AFN), a global network of CEOs and senior executives committed to leveraging collective intelligence to find opportunity in change. Through AFN, he supports leaders across industries—from private equity and healthcare to tech and defense—navigating inflection points, rapid growth, and transformational shifts.
Matt is also a partner at Sixth Wing, where he brings a powerful mix of executive coaching, operational insight, and communication strategy to the firm’s work in burnout resilience, networked leadership, and human-centered performance. His dual roles allow him to blend big-picture systems thinking with on-the-ground leadership support.
Previously, Matt held senior roles at The McChrystal Group and CrossLead and served as an executive in the healthcare diagnostics and health tech sectors. Whether advising a founder, coaching a CEO, or aligning a leadership team, his work is grounded in a core belief:
“Leadership is the privilege of working through others.”
Matt champions the idea that networks—not org charts—create real movement, and that the right conversation at the right moment can unlock breakthrough performance.
He holds an AB in Public Policy from Brown University and an MBA from Dartmouth’s Tuck School of Business. He lives in the San Francisco Bay Area with his wife and two sons.
