Courtney UnderwoodCEO | Senior Strategist

Underwood Bio Pic 2021
areas of expertise
  • Strategic Planning 
  • Management Consulting
  • Engagement and Culture
  • Leadership Development 
  • Executive Coaching
  • Performance Management
  • BA, Organizational Communication, Depaul University
  • SHRM-SCP Certified
  • Gallup Certified Strengths Coach
  • ISO 9001 Certified Auditor

Courtney Underwood is the Senior Strategist and CEO of Kassar Consulting. 

With over 21 years of experience in Human Resources and Leadership Development, Courtney Underwood understands the unique challenges that leaders face when building and managing their teams. She is an award-winning thought leader, noted public speaker, published author, SHRM Senior Certified Professional and a Gallup Certified Strengths Coach. As the CEO of Kassar Consulting, she teaches her clients how to navigate the business of people, increasing both their profitability and peace of mind.

Kassar Consulting focuses on delivering practical tools and resources that solopreneurs and small businesses can actually implement. We are invested in the success of our clients, and that is what sets us apart from the competition.

A proud Chicago native, Courtney graduated from Whitney Young High School. She then attended DePaul University, where she graduated with honors, majoring in both Relational and Organizational Communications and African and Black Diaspora Studies. She went on to pursue several certifications throughout her career in Project Management, Leadership Development, Conflict Resolution and Executive Coaching.

She has served companies of all sizes across several industries, and is dedicated to sharing her expertise to leaders that understand the power of the right person, in the right position at the right time. Utilizing her signature systems, framework, and tools Courtney helps executives build a healthy team, learn how to effectively manage them in order to scale their business, providing improved service, and increasing their revenue.

When she is not working, Courtney spends quality time with her family, volunteers with organizations throughout the Chicagoland area, and travels extensively.


Contact Us Today

Whether you’re just starting out or need a completely outsourced HR partner, we have the solutions you need.

Courtney Underwood is the real deal! I was fortunate enough to meet Courtney when we both spoke on a panel at Success Junkie Summit. Since then, I’ve gotten to experience her phenomenal work with Kassar Consulting. From seeing this great work, I asked her to come to speak to my students at Chicago Urban League’s NextDEAL Entrepreneurship program. She lead an amazing presentation on best HR and business practices, and she was one of the classes favorite presenters. I highly recommend Courtney if you need a dynamic speaker, presenter, or HR needs for your business.

Kevin Davenport
Founder & President, The Ideal Candidate

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