About me

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

  • Executive coaching. After working as a coach for 2.5 years with my friends at Reboot, I transitioned to my own independent practice called Strong Back Open Heart (blog post), primarily working with CEOs (~80% of my clients) and CTOs (~20%). My client list is more or less full at the moment, but if you’d like to talk about coaching, contact me.
  • Non-profit boards / volunteer work
  • Taught 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.
  • 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. I’m still at it and loving it.


Chad runs his own executive coaching practice (Strong Back Open Heart) and is serving as a Cornell Tech Fellow, co-leading and co-teaching a curriculum track there that started in Spring 2019 and continued through Spring 2020: BigCo Studio.

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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.”)