Jenn Drummond

I help founders, executives, and sales leaders access courage in high-stakes environments.

I am a world record-holding mountaineer, exited entrepreneur, global keynote speaker, and mother of seven who reinvented her life after a near-fatal car accident forced a hard question:

What would I do if time were no longer guaranteed?

Before that moment, I had never slept in a tent.
I had never climbed a mountain.

Since then, I became the first woman to climb the second-highest peak on every continent, built and exited a financial services firm, and now work with leaders operating where decisions carry real consequence and the margin for error is thin.

I don’t teach motivation.
I teach courageous clarity.

Because the real breakdown for high performers, founders, executives, and sales leaders is rarely a lack of discipline.
It’s hesitation.

Knowing what matters.
But not acting on it.

On the mountain, hesitation gets you killed.
In leadership and sales, it quietly costs you trust, momentum, health, and conviction.

My work helps leaders:
• Make courageous decisions when the stakes are high
• Stay steady and regulated under pressure and uncertainty
• Act in alignment with values, even when it’s uncomfortable
• Build resilience without burnout
• Show up powerfully in high-stakes leadership and sales conversations
• Lead without outsourcing courage to circumstances

I draw from extreme environments, neuroscience, leadership psychology, and lived experience where fear is data, ego is expensive, and courage must be practiced in real time.

Today, I work with:
• Founders and executives navigating inflection points and decisive moments
• Sales leaders and teams operating in high-pressure, quota-driven environments
• Investors and operators carrying invisible responsibility
• Organizations that need leaders who can act, not stall

I speak globally on leadership, courage, decision-making, and human performance in high-stakes environments.
I host private advisory circles and high-trust leadership intensives.
I design curated leadership and mountain experiences where courage is embodied, not discussed.

If you are building something meaningful and feel the weight of the decisions in front of you, you are my people.

Areas of engagement:
• Keynotes and leadership intensives
• Executive advisory and private leadership work
• Curated mountain and experiential leadership experiences
• Media and speaking engagements

The summit requires courage.

Motivational Speaker + Mountaineer

A dynamic & inspirational leader who lives by the credo of “take the hill or die trying, failure is not an option!” Diversity of experience defines my career. Along the way, I've had the opportunity to oversee the sales, marketing, operations, distribution, collections, and accounting functions of companies; both public and private, and have successfully put that knowledge to use in my own companies, for employers, and clients. 

Awards/Recognition/Honors:

* Keynote Speaker, Recommerce Expo, India 
* Keynote Speaker, European Brokers Meeting, Dublin Ireland 
* Keynote Speaker, International Trade Conference, Malta
* Keynote Speaker, Gadget Repair Expo 
* Keynote Speaker, Mobile Disrupt
* Keynote Speaker, ITAD Summit 
* Keynote Speaker, All Wireless & Prepaid Expo 
* Keynote Speaker, CPR Repair Franchise Conference 
* Panel Moderator, Competitive Carriers Association
* Advisory Board Chairman, All Wireless & Prepaid Expo
*  Board of Directors, Junior Achievement of   Butler County. (Western Pennsylvania Chapter)
*  Advisory Board, Young Lives, Three Rivers
*  Advisory Board, Atlas Dreams Languages
*  Advisory Board, Entrepreneurial Thursday's 
*  Pittsburgh Top 100, 2003-2006, Pittsburgh Business Times
*  Nominated as a Top "50 Under 50 Executive"
*  Board of Directors, CEO Forum of Pittsburgh
*  Board of Directors, Tuscarawas County Chamber 
*  Board of Trustees, ACAC
*  Board of Elders, ACAC 
*  Empire "Who's-Who"
*  Manager of the Quarter, US Cellular 
*  President's Club, Bell Atlantic Mobile Systems. (2 times)

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The Battle

Jenn Drummond

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