Evolve How You Lead

Elevate what you Build

KASEY D’AMATO

High-Stakes Decision Making Expert for Family & Founder-Led Businesses

I operate at the intersection of data-driven strategy and emotional intelligence. With a background in psychology, 20 years of healthcare leadership, and three businesses built from concept to global distribution, I bring clinical pattern recognition and entrepreneurial experience to your most critical moments.

I help business leaders navigate high-stakes decisions—expansion, succession, pivots—through my Leadership Evolution Framework™. Using proprietary tools like The Polaris Point™, The Strategic Shift™, and FutureMap™, I help you gain clarity, make confident decisions, and lead with vision.

Evolve how you lead. Elevate what you build.

Is This You?

Whether you're leading a company, guiding a team, or standing at a professional crossroads — the pressure to make the right decision never stops.

I work with business leaders facing moments that matter:.

Navigating succession - buying out partners, establishing new partners, transitioning leadership, preparing the next generation

Feeling trapped by what you built - working IN the business instead of ON it, struggling to delegate, running on empty

Making high-stakes expansion or pivot decisions - with limited clarity and too much at stake to get it wrong

Leading a family business - where emotions, relationships, and legacy complicate every strategic decision

Building or rebuilding your leadership team - struggling with communication, alignment, and accountability

Ready to evolve how you lead - successful but stuck, knowing something needs to change but unsure where to start

If any of these resonate, let's talk.

ABOUT

Meet Kasey,

“I help visionary leaders make the decisions that define their next chapter.”

Why Leaders Trust Me

I bring a unique combination of clinical training, strategic thinking, and entrepreneurial experience to high-stakes leadership moments.

You don’t need more noise. You need strong emotional intelligence and communication foundation — and a path to actually execute the vision.


Background:

  • Psychology degree and 20 years as a Dermatology PA (serving as Chief of Staff to a physician founder)

  • Three businesses built from concept to global distribution

  • Certified Executive Life Coach

  • University of Miami President's Council member

  • Creator of "In Your Corner" weekly newsletter for leaders

What This Means for You:

I see patterns others miss. With clinical training in pattern recognition, real-world experience building and scaling businesses, and deep understanding of human behavior, I help you navigate complexity with both strategic clarity and emotional intelligence.

LEARN MORE ABOUT KASEY

lead boldly.

decide strategically.

EvOLVE with confidence.

Whether you're leading a company, guiding a team, or standing at a professional crossroads — the pressure to make the right decision never stops. I help high-level leaders like you cut through the noise, clarify your next move, and lead with conviction.

  • Keynote Speaking & Leadership Workshops

    Dynamic, research-backed sessions to equip leaders for high-stakes moments.

    Keynotes, leadership retreats, and workshops for conferences, corporate events, and industry associations—bringing leadership evolution frameworks to audiences ready to transform how they lead.

    Past speaking engagements: UCLA, USC, University of Miami, Family Office Events, Construction Associations, Health Insurance, Medical Conferences, and Fortune 500 Pharmaceutical.

  • Private VIP Strategic Advisory Days

    A 1:1 intensive to unlock clarity and renewed strategy
    These private 1- or 2-day experiences are built for founders, partners, or executive teams facing:

    - A Cross Road Critical Decision

    - Communication, Team Challenges, or Growth Challenges

    - Leadership Fatigue

    - Strategic Short Term Planning or Succession Planning

  • Executive Leadership Coaching & Fractional Chief of Staff

    For leaders navigating a major transition.
    This immersive coaching experience is designed to help you recalibrate and rise. In 90 day blocks, we’ll address:
    - The core challenge you’re facing (and what’s really underneath it)
    - The best aligned path forward — personally and professionally
    - An execution plan you can confidently own and implement

as seen in

Speaking

Strategic. Bold. Unforgettable.

Keynotes, podcasts, and panels for leaders navigating high-stakes decisions.

learn more about speaking

Level up your event, mastermind, or podcast

with Kasey's expertise!

Keynote topics:

Book Kasey to Speak
  • Disruptive, timely, and universal — this keynote explores why human-led leadership is the future and how to build resilience, clarity, and EQ in an AI-saturated world.

  • Kasey’s proprietary framework helps leaders break out of decision fatigue, move with confidence, and align every choice with long-term vision

  • Perfect for health insurance, finance, and healthcare sectors navigating disruption, this talk blends mindset and strategy for results-driven leadership.

  • A high-impact keynote for founders scaling fast but feeling the cracks — focused on strategy, energy optimization, and sustainable growth.

  • For anyone at a leadership crossroads, this session reignites bold thinking, clarity, and courage to grow with integrity.

podcast guest topics:

  • How emotionally intelligent leadership is your most powerful advantage in an automated world.

  • The mindset shifts that transform overworked leaders into empowered decision-makers.

  • Why most leaders plateau — and the decision frameworks that move them forward.

  • Business growth that feeds your life, not drains it — for entrepreneurs and purpose-driven pros.

  • The real story behind building a business (or career) that aligns with your vision, values, and wellbeing.

what i do

Through private intensives, executive advisory, and dynamic workshops, I help high-achieving leaders:

  • Clarify where they’re going and why

  • Make confident, high-stakes decisions

  • Restructure teams and simplify org charts

  • Align personal energy with strategic direction

  • Turn bold vision into aligned action — in 90 days or less

I use a system I’ve built from two decades of business growth, consulting, and leadership development:

  • The Polaris Point™ – Define your long-term personal and business vision

  • The FutureMap™ – Visualize your options and timelines

  • The Decision Threshold™ – Filter your choices through strategic clarity

  • The Strategic Shift™ – 90-day implementation with aligned KPIs

My services

WHAT PEOPLE ARE SAYING

THe proof is in the results

In Your Corner

In Your Corner

on the blog

Kasey gives honest insights into how she’s built and managed successful businesses, advised billion-dollar companies, and overcome major setbacks. She shares tools she has learned in business as well as from being a certified life coach. This unique combination has allowed her to build the lifestyle of her dreams, and her mission is to share the process of how to do it with you!

Read the blog

Featured blog posts

WHY REMAINING A SOLOPRENEUR WILL CRUSH YOUR DREAMS: THE CASE FOR BUILDING A TALENTED TEAM

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3 WAYS TO SET YOUR LIFE AND YOUR BUSINESS UP FOR SUCCESS!

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WHERE BUSINESS AND LIFE CONVERGE: MY JOURNEY TO DEFINE MY PERSONAL BRAND

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