Work With Christina
I help legacy-driven leaders move through uncertainty with clear thinking, bold action, and frameworks that flex with reality. Leading through chaos takes more than grit. It takes clarity. And I can help you find it if you are the kind of leader who cares about the people you impact — in your organization and beyond.
Good. Neither am I.
You’re not here to play small.
Executive Advisor. Current CEO. Legacy-Focused Leader.
Christina Cassotis.
I flunked out of college at 20. Got my MBA at 49. Raised a family, built a career, and still believe the real flex is leaving things better than you found them. I’m bold, strategic, and wicked direct, and I care about helping people lead in ways that make sense for them and their business and the people they impact.
If you’re navigating complexity and ready to think differently, let's see if we're a fit and if I can help you be the leader who leaves a legacy.
Meet Christina
Hey, I'm Christina Cassotis.
I’m a sitting CEO, strategic advisor, and behind one of the most unexpected transformations in an unlikely industry we all need. I’ve spent the past decade turning around a critical business in an industry that wasn’t designed for disruption, and made it one of the most celebrated case studies in aviation. (Pittsburgh, anyone?)
I’ve served on boards of publicly traded companies (and still do), led culture overhauls from the inside out, and built frameworks that help other leaders do the same. No fanfare. No formulas. Just tested, tailored tools that actually work.
No plug-and-play models. No sugar-coated strategy. Just real-time support from someone who’s been there, and still is. Whether you’re seeking coaching, consulting, or a powerful keynote, I’ll help you navigate what’s next with confidence, clarity, and humanity.
It’s deep partnership for high-stakes leadership.
This isn’t surface-level support.
Executive & Leadership Coaching
Explore Coaching
For C-suite leaders and founders ready to face the big stuff with a trusted advisor. My 3- and 6-month coaching programs include in-depth in-person strategy sessions, ongoing calls, and access to my trademarked frameworks, like Legacy-First Leadership™, The Surround Strategy™, and SWOT on a Swivel™, all of which are meant for you to make your own.
Strategic Advisory & Consulting
Explore consulting
Leadership isn’t plug-and-play. Neither is strategy. I work directly with executive teams to address urgent, complex, or high-growth scenarios. This is bespoke, people-first strategic thinking co-created in real time and always in service of meaningful, measurable impact.
Speaking & Keynote
Book Christina to Speak
Whether it’s a leadership summit, executive offsite, or industry conference, I bring a clear voice and candid insight to rooms that matter. Expect bold ideas, practical takeaways, and real tools for real leaders. Favorite topics include Legacy-First Leadership™, Leading in Turbulent Times and Navigating Uncertainty.
FREE RESOURCES
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A peek inside my resource stack. The tools I trust, the voices I listen to, and the systems that help me stay grounded while leading at the highest levels.
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I’m not interested in vague advice. I write about real business challenges, what it took to solve them, and the frameworks that made the difference on my blog.
Tools, insights, and resources for leaders who give a shit.
Read the Blog
Case Studies + Process-Focused Thought Leadership
Curated Tools, Books, Podcasts + Travel Tips
Browse Recommendations
Get the Free Guide
Get my practical, no-frills framework for leading through chaos. This guide walks you through how to communicate with clarity when the stakes are high and the path isn’t clear.
Building Transparency + Trust in Uncertainty
Free Guide:
