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Jessica Dawson

Business and Sales Coaching

Location: Chicago, IL

Sounding board and catalyst for courageous change “The lighthouse”- enhancing your visibility and path forward Crafts galvanizing messages and guides with a disarming presence

Sounding board and catalyst for courageous change “The lighthouse”- enhances visibility, helping you see where you are going Crafts messages that galvanize and guide with a quietly disarming presence

Offerings as a WYLD Guide

  • Coaching
  • Select Workshops and Retreats
  • Keynotes and Speaking Engagements


Jessica lives in Chicago and is a former stockbroker turned learning and development consultant. Jessica has coached and advised tens of thousands of leaders all over the world. She has worked with organizations such as Twitter, Southwest Airlines, Regions Bank, Highmark Healthcare, USPS, Stanford University, and Atlanta Public Schools. Known for her powerful questions and stage presence, Jessica can craft a message that empowers and has lasting impact for an audience of any size. As a coach, her talent spotting and empathy create instant safety and trust. Regardless of where a client is starting, they consistently celebrate exponential growth in their business performance.


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  • Certified CliftonStrengths Coach, Gallup
  • PCC Coach, International Coach Federation
  • Emotions Mastery Certified Coach, 5th Element
  • Financial Mindset Certified Coach, 5th Element
  • M.B.A., Kelley School of Business, Indiana University
  • B.S. in Economics, Spelman College
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  • Founder and Head Coach, Empowered for Sales

  • 7+ years as a Senior Learning Development Consultant, Gallup
  • Business Coordinator, Neuberger Berman
  • Financial Advisor, Ameriprise Financial

Recent clients

Executive Leaders at a Fortune 500 Data Analytics Organization

HR Leaders at a
Financial Institution

Sales Leaders at a Social MediaTechnology Company


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  • A More Beautiful Question by Warren Berger
  • Breaking the Habit of Being Yourself by Dr. Joe Dizpenza
  • We Should All Be Millionaires by Rachel Rodgers
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  • “Nothing is impossible. The word itself says I’m possible.”
    – Audrey Hepburn
  • Any ancient sound healing with Solfeggio HZ Frequency Scale like this, this and this

Jessica is always engaging. I always appreciate our coaching sessions. I left with concrete steps for my goals.

Jessica's inquiry approach was outstanding. She helped me to reframe my thoughts through the lens of my strengths. And I left the call fully energized and with some great actionable ideas. Jessica is a very talented coach

Thank you Jessica for the gift of reflective time and for opening up insights for me to better know (and honor) myself and support those I supervise. I am grateful for your guiding questions, insight, and encouragement.

Jessica was amazing! She has this amazing energy that she brings to how she shows up as a coach. She put me at ease, and made me feel heard, seen, and valued in our conversation. I took so much away from our session

Wow! Jessica is a powerhouse! A wealth of knowledge and wisdom so generous and empathic!

Jessica is an AMAZING facilitator! Each time we ask a question she is very thoughtful with her responses. She makes a special effort to help the group understand.

- Coaching client
- Coaching client
- Workshop participant and coaching client
- Coaching client
- Coaching client
- Workshop participant
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