Kasey D’Amato

Leadership Strategist. Speaker. Trusted Advisor for High-Stakes Decisions.

With 20 years as Chief of Staff to a physician founder and three businesses built from scratch, I bring a rare combination: the emotional intelligence of clinical practice and the leadership acumen of scaling companies.

Now, I work with CEOs of family-owned and founder-led businesses as a Fractional Chief of Staff and Executive Coach—helping you navigate high-stakes decisions, develop your leadership team, and build sustainable systems without sacrificing what matters most.



Schedule a Call with Kasey's Team

HOW IT ALL STARTED

My story

I’m the strategic partner in your corner when the stakes are highest.

After 20 years as Chief of Staff to a physician founder and building three businesses from scratch, I've learned this: The hardest decisions you face aren't purely strategic OR purely emotional—they're both.

Should you fire the executive who's been with you since day one but can't scale with you? That's strategy AND relationships.

How do you build succession plans without damaging family dynamics? That's vision AND emotion.

Can you scale to the next level without sacrificing your health, marriage, or peace? That's growth AND well-being.

Most advisors force you to choose: get strategic guidance OR emotional support.

I give you both.

I bring the emotional intelligence and pattern recognition of 20 years in clinical healthcare, combined with the leadership acumen of building businesses.

This means no conversation is out of scope. No situation is too complex. No decision is too tangled.

I'm the CEO's secret weapon—the trusted advisor and right hand for leaders of family-owned, founder-led, and scaling businesses who need someone who can hold both the strategic reality and the human truth at the same time.

WHAT I DO

I partner with CEOs and leadership teams as a Fractional Chief of Staff, Executive Coach, and Strategic Leadership Advisor. Through embedded partnerships, private intensives, executive coaching, and leadership workshops, I help visionary leaders:

  • Navigate high-stakes decisions with clarity and confidence (expansion, succession, pivots, exits)

  • Develop leadership teams that can handle aggressive growth without breaking

  • Build communication systems and accountability structures that scale

  • Align long-term vision with sustainable execution

  • Lead from intention instead of reactivity

  • Integrate business strategy with personal fulfillment

I work with 2 Fractional Chief of Staff clients at a time, embedding as your right hand to develop you as the leader, your team's capability, and the operational systems that support both.

Let’s talk if you’re:

  • Leading a family-owned, founder-led, or scaling business ($5M-$50M+)

  • Navigation succession, expansion, or major strategic decisions

  • Feeling trapped by what you built (working IN vs. ON the business)

  • Ready to develop your leadership team but need someone embedded, not consulting from the sidelines

  • Looking for a strategic partner who can handle any conversation—leadership, business, personal, or all three

  • Wanting a trusted advisor who understands BOTH strategic clarity and human complexity

If this resonates, let’s talk.


Schedule a Call with Kasey's team

my frameworks:

I use proprietary tools I've built from two decades of leadership, business growth, and executive coaching:

  • The Polaris Point™ – Define your long-term vision (business + life integrated)

  • The FutureMap™ – Visualize your options and timelines with clarity

  • The Decision Threshold™ – Filter choices through head, heart, and gut alignment

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

  • Leadership Evolution Report Card™ – Track measurable progress across 7 core categories of leadership development

These aren't academic frameworks—they're field-tested with CEOs navigating real complexity, real growth, and real human dynamics

background and credentials:

  • Psychology degree – Foundation in human behavior and emotional intelligence

  • 20 years as Dermatology Physician Assistant – Served as Chief of Staff to physician founder, grew one of the top aesthetic divisions in the country

  • Three businesses built from concept – Including global skincare brand featured in Men's Health, Life & Style, New Beauty, MSN, InStyle, Marie Claire and more

  • Certified Executive Coach – Formal training in leadership development

  • Business strategist and advisor – Worked with entrepreneurs, medical professionals, growth-stage teams, and Fortune 500 companies

  • National speaker – USC Marshall School of Business, University of Miami, Opal Financial Group, Medical and business Associations

  • University of Miami President's Council – Active in leadership development and entrepreneurship

  • Author of "In Your Corner" newsletter – Weekly strategic clarity for leaders making high-stakes decisions

MY APPROACH

Clarity isn't a luxury—it's a leadership requirement.

I help you slow down, zoom out, and see what you can't see when you're in the thick of it. Then we build the plan that feels right AND the systems to execute it.

You don't need more information. You need a strategic partner who understands the numbers AND the human reality. Someone who can hold space for the emotional weight of your decisions while helping you make the call that serves your vision.

You don't need someone to fix your business. You need someone to develop you as the leader—and build the team and systems that can handle what's ahead.

That's what I do. And I only work with leaders who are ready to evolve how they lead so they can elevate what they build.

Ways to connect
with KASEY

Whether it is at an event, working together 1:1, or sharing my stories in blogs and vlogs, I look forward to connecting with you!

  • Keynote Speaking & Leadership Workshops

    Dynamic, research-backed sessions to equip leaders for high-stakes moments.
    From national conferences to intimate executive retreats, I speak on the topics that matter most:

    - Decision-making under pressure

    - Leadership in uncertain times

    - Emotional intelligence and executive presence

    - Vision-setting and navigating transitions

    Learn More

  • Private VIP Strategy Days

    A 1:1 intensive to unlock clarity, strategy, and renewed confidence.
    These private 1- or 2-day experiences are built for founders, executives, or small leadership teams facing:

    - Cash flow challenges

    - Team restructuring or org chart changes

    - Leadership fatigue and overwhelm

    - Strategic planning for growth or exit

    Learn More

  • 90 Day Navigation Program

    For leaders navigating a major decision or transition.
    This immersive coaching experience is designed to help you recalibrate and rise. In 90 days, 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

    Learn More

What people are saying

  • “The financial success I have achieved from investing in Kasey’s services was well worth it! I almost doubled my income!”

    - -Kelly J. (Entrepreneur)

  • "“I had an incredible call with Kasey D’Amato who is a concierge coach who constantly blows my mind! She has been helping me big time figure out my shiz!”"

    - Jera F (Social Media Expert & Speaker)

  • “Kasey spared me from anguish, tears, and the potential loss of time…aka a gift I can’t express enough gratitude for. If you find yourself in need of business guidance, I wholeheartedly endorse connecting with Kasey. Her patience, empathy, and exceptional competence make her a standout in her field. To Kasey, a heartfelt THANK YOU!”

    - Amy N (Real Estate Broker)

  • “Kasey is a great coach! She saved me so much time and brought clarity so I can take action much faster! She also helped me scale my business at an incredibly fast rate!”

    - Wilson L (Financial Coach)

  • "Kasey has been integral in helping us develop business practices that we need desperately to manage our team, monitor our KPIs and ensure that we continue to see the growth that we've seen so far. Kasey has helped us work together in our business so that our business doesn't run us and she has helped us enjoy our success together! After every call we feel reassured, energized and so guided! We cannot be more thankful for working with Kasey!"

    - Carly & Hunter (Medical Practice Owners)

  • "In addition to her impressive professional skills, Kasey D'Amato truly captures the essence of what it means to be an outstanding speaker. Her passion, articulateness, and natural ability to motivate attendees are unparalleled! Her talk profoundly resonated with our audience, playing a crucial role in the triumph of our 2024 Summit. I wholeheartedly endorse Kasey for any organization seeking a speaker who can deliver a powerful, engaging, and memorable presentation!"

    - Shawn Q. (Serial Entrepreneur & CEO)

  • "Over a year ago, I was burned out, overwhelmed, and honestly ready to throw in the towel. As a business leader, I felt broken. But Kasey? She saw the mess, rolled up her sleeves, brushed off the dirt, straightened my crown and said "Let's Rebuild!" And we did! Together. Today, I am stronger, smarter and clearer. A better leader, a more present wife, a more intentional mom, a more confident business owner. My agency is now thriving, my leadership team is laser focused, and leading with intention. Our partnerships are booming. And I feel more aligned than ever."

    - Tyler F. (Business Owner)