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

Millennial Specialty Insurance

Lead 80+ colleagues in Operations, Agency, Contact Center, and Quality teams in a rapidly growing insurance tracking and compliance AI InsurTech  and insurance MGA business.
Design and launch operational excellence, efficiency and quality strategy enabling organic growth and transforming operations from early stage to enterprise.  Quality improvement by 50% in 90 days. 
Build and expand offshore support call center with 50+ colleagues spread across Asia, Latin America & Europe.  Transition call support to offshore. 
Lead large scale automation efforts with AI tools delivering major efficiency and improved customer experience.
Using Lean Six Sigma and Agile tools, delivered 23% reduction in Contact Center emails and 18% reduction in call volume in 12 months. 
Upskill existing colleagues, hire and build team to support exponential growth and increasing client expectations

Managing Director, Head of Operations, Multifamily LeaseTrack

S&P Global Ratings

Lead and transform global operations and editorial teams for Ratings Division - a $3B+ division of SPGI.
Leading 240 colleagues in 22 countries during record breaking 32% volume increase while maintaining historic low errors and delays.  Delivered $4.5M savings through automation, lean process improvement, upskilling and offshoring. Provided all operational support for new product launches such as Green and ESG evaluations.  Built out and executed transformation strategy for content editing leading to 98% increase in website visitors and 52% increase in article views.

Global Head of Ratings Operations and Editorial | Strategy | Business Transformation

Oversaw the credit risk of a portfolio of over 8,000 existing securitized transactions with a total issuance over $91B, and 21 analysts. Developed deep cross sector expertise in Structured Finance and U. S. Public Finance including derivatives, asset backed commercial paper, credit card backed transactions, letter of credit backed transactions, and tender option bonds

Senior Director and Analytical Manager

Citigroup

Managed cash operations for 14 Eastern European Financial Institutions. Analyzed and evaluated short-term investment alternatives for clients.  Investigated and resolved over 5,000 client operational problems per year. Awarded Service Excellent Award by Chairman as a top 5% performer in Financial Institutions.

Cash Management Officer

Combining Operations, Leadership & Credit risk in Financial Services and Insurance | Operational Excellence | COO roles | Business & Digital Transformation | Scaling businesses through lean and agile tools | CHIEF

I build and scale best-in-class teams of operators, agents, analysts and creatives to drive profitable growth for companies by deploying lean and agile tools, low code automation, and building future capabilities.  With deep expertise in operations, & leadership, I create value for financial services and insurance companies.

From Wall Street Journal interviews to Board presentations and meetings with large clients & investors, I am an expert in complex financial instruments and insurance. 

My passion is uncovering value in operations ‘engine room’ teams by transforming support teams to high impact business partners who improve margin and enable growth. I lead a large global operations team of a fast growing insurance brokerage & tracking business and previously managed a global team of 240 operations specialists and editors in 22 countries, who drove the release of 1,000,000+ ratings and 50,000+ reports per year.  I specialize in leading global teams with a focus on millennials and Gen-Z. 

Top 25 Global Operational Excellence Leaders to follow in 2024
Winner of Rising Star Award by the Women's Bond Club.   
Winner of OPEX Awards- Best Digital Transformation Project under 90 days
Speaker and Judge at OPEX World Summit 
Advisory Board for PEX (Process Excellence) Network 

Specialties: fixed income | capital markets | global head | leading millennials and Gen -Z | global operations leader | strategy | balancing BAU with innovation | automation through RPA | process improvement | | lean six sigma | agile | digital transformation | fixed income analysis | complex financial instruments | securitization | derivatives | emerging markets |Middle Office Operations | Project Management | Risk Management | Insurance

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Jenn Drummond

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