Rob Williams

Rob Williams

Leadership Coach & Senior Advisor

Rob brings over 25 years of leadership experience as a senior executive to his coaching. From 1996 to 2008 he held a succession of senior leadership positions at Clear Channel Radio (now iHeart Media). At Clear Channel Rob led the largest region by revenue and profit, managing $540 million in annual revenue including the largest US media market, New York. Rob was recognized as Executive of Year by Clear Channel’s CEO; and, as one of the best managers in radio numerous times by industry trades. Later, Rob pursued entrepreneurial interests in digital media and launched a boutique digital services and consulting firm. Rob then went on to serve as Senior Vice President at Townsquare Media and excelled at recruiting and developing a talented sales team and transforming the company’s revenue model.

Now an Executive Leadership Coach, Rob believes that helping leaders to understand their unique strengths allows them to become more intentional in their actions, better identify their mission, and articulate a compelling vision to their teams. He stresses that at its core, great leadership comes from those people who present as fully authentic, deeply compassionate, transparent, and committed to their team’s success.

Rob is known to guide leaders on a path of self-discovery and inquiry to assist them in raising their performance and overall effectiveness. Rob has coached leaders who have gone on to hold senior and C-suite positions at some of the largest media companies in the world including iHeart Media, Spotify, Pandora, Google, and Facebook. He has also coached leaders in other industries including manufacturing and fintech.

Rob has long been a dedicated endurance athlete who has completed numerous marathons, triathlons, and other events including the 2022 Race Across America (RAAM). RAAM is a nonstop, 3080-mile bicycle race from Oceanside, CA, to Annapolis, MD. Along the way, what Rob treasures most are the relationships and team leadership lessons learned as well as the confidence that comes from overcoming self-doubt to achieve a goal for a cause bigger than self.

In 2023, Rob will run his third NYC Marathon, raising funds for Guardian Revival, an organization committed to preventing suicide among veterans and first responders. Rob is a member of Guardian Revival’s Athlete Hall of Fame. An avid golfer, Rob currently serves as president at one of the premier clubs in the U.S.

Rob lives in Wilton, Connecticut where he and his wife Katy raised their four grown children.

Education & Credentials

  • Certified Practitioner of The Leadership Circle Profile 360 Assessment
  • International Coaching Federation (ICF) seeking Associate Certified Coach accreditation
  • The Neethling Brain Instrument (NBI) Certification
  • Columbia University of New York: Columbia Credentialed Professional Executive Coach
  • Tulane University, B.A. with Honors
  • Hogan Assessment Certification


Embrace the opportunity to grow your brand and reputation as a company that truly invests in helping employees grow their capabilities – even and especially during an employee off boarding experience. When viewed through the development lens, this is a valuable opportunity for employers to learn and improve organizational and people development practices, build brand ambassadors, and enable departing employees to reflect on gains in skills and capabilities.


Facilitate strategic conversations with senior leaders to explore and define ways conscious people development can be integrated into the culture and daily workflow to power your business, your people, and your employer brand. 


Incorporate learning and development objectives into retention activities to prepare employees for new roles and opportunities. This can be done through engagement and feedback surveys, recognition and rewards programs, promotion, succession planning, and more.

Social Contribution

“Build it so they will want to come, flourish, and stay, knowing that someday they may leave.

Thus, it is imperative to define what you want them to say about their growth experience with your organization and what you want the outside world to say about how you invest in and contribute capable people to society.”

-Ed Offterdinger & Catherine Allen
Conscious, Capable, and Ready to Contribute. (p. 173)

Integrated Capability Development and Performance Management

Integrate learning, growth, and capability development goals and activities into your performance management rather than relying on day-to-day responsibilities alone to create a more engaging, productive, and helpful process.


Adapt onboarding to set new hires up for success in a continuous learning environment through orientation activities that introduce the principles and practices that support everyday learning and development for each employee.


Integrate practices, principles, and tools to better evaluate a candidate’s orientation to continuous learning and development as a factor in their overall fit for a position. This provides:

  • Improved candidate interviewing, assessment and selection practices
  • Better candidate selections with learning and growth mindset
  • An early introduction to your company’s development culture focus


Embed messages about commitment to people development to attract your ideal candidates.