About me

What I’m doing right now (updated April 2020)

  • Executive coaching. I’ve been working as a coach for 2.5 years with my friends at Reboot and in my own independent practice, primarily working with CEOs (~80% of my clients) and CTOs (~20%). I’m not currently accepting new clients. If you’d like helping connecting with a coach, contact me or fill out Reboot’s coaching inquiry form.
  • Teaching BigCo Studio at Cornell Tech again in Spring 2020. Read more about the class in my blog post or take a look at the Spring 2019 syllabus.
  • Non-profit boards / volunteer work
    • Serve as Vice Chair of the board at St. Ann’s Warehouse, the wondrous theater in Brooklyn
    • Serve on the board at the Jalopy Theater and School of Music, the beloved home for music and music-makers in Red Hook, Brooklyn.
    • Serve on the Board of Trustees for the Brooklyn Public Library, the nation’s sixth largest public library system. I also serve on the Digital Strategy Committee, where we advise management on the digital initiatives.
    • Serve on advisory board of the Milstein Program in Technology and Humanity at Cornell University.
  • Learning piano. I started lessons in April 2019 at age 46. I wrote about progress and what I had learned at the six-month mark and again at one year.


Chad is currently a CEO coach with Reboot and is serving as a Cornell Tech Fellow, helping the Dean of the university campus on Roosevelt Island in NYC grow and scale the new institution in its early days. He is also co-leading and co-teaching a new curriculum track there that started in Spring 2019 and has continued for Spring 2020: BigCo Studio.

wordpress.345x240 - b&w

Chad was the CEO of Etsy from July 2011 to May 2017, leading the company in its mission and growing it into a global community of creative entrepreneurs and their customers. During that period, he grew the company from a chaotic startup to a global publicly-traded company, growing revenue 14x during that period. Under Chad’s leadership, Etsy was known for its company culture and commitment to social responsibility. Etsy made the Best Places to Work list every year from 2013 to 2016 and the company became a Certified B Corporation in 2012, recognizing the power of business to generate social good.

Chad was CTO at Etsy from September 2008 until July 2011, leading a team that built Etsy’s core platform in its critical early years. Before joining Etsy, Chad led Yahoo’s Brickhouse & Advanced Products incubators, and the Yahoo! Developer Network. He created the Yahoo! Hack Day initiative in 2005, the first internal innovation program of its kind in a large company.

Chad came to Yahoo! from InfoWorld Media Group (IDG) where he served as CTO for nearly five years and wrote a popular weekly column for CTOs. Prior to InfoWorld, Dickerson served as CTO of Salon.com and in various engineering positions at CNN, CNN/Sports Illustrated, The Atlanta Journal-Constitution, and The (Raleigh, NC) News & Observer.

He serves on the board of St. Ann’s Warehouse, a non-profit theater in Brooklyn, and the Jalopy Theatre and School of Music, a beloved music institution in Brooklyn. Chad holds a BA in English literature from Duke University where he focused on the works of Shakespeare, the world’s best writer on the challenges of leadership (“Uneasy lies the head that wears a crown.”)