About me

What I’m doing right now (updated February 2024)

• Executive coaching. I run my own coaching practice under the name Strong Back Open Heart (blog post), primarily working with CEOs (~80% of my clients), CTOs (~10%), and other senior executives (~10%). 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
  • Serve as Vice Chair of the board at St. Ann’s Warehouse, the wondrous theater in Brooklyn
  • Serve on the board and as Treasurer 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 co-chair the Digital Strategy Committee (advising management on digital initiatives), and serve on the Diversity Equity and Inclusion and Marketing/Development Committees.
  • Member of the 1834 Project, a group of men who pool expertise, money, and resources to help non-profits and their leaders throughout Brooklyn create a better community for all.
• Music. I started piano lessons in April 2019 at age 46 after half-assedly fooling around on guitar for 20+ years. I wrote about progress and what I had learned in my piano lessons at the six-month mark and again at one year. I’m still at it and loving it. In summer 2020, I started taking college-level music classes at Berklee Online and completed an 8-course Advanced Professional General Music Studies certificate in Fall 2022. On the heels of that, I started a band (Humbled by the Void, named from a lyrics in this David Berman /Purple Mountains song) and we played our first show in summer 2023 for friends at a party. We’re working on new stuff and hope to play out in spring 2024!

More formal bio

Chad runs his own executive coaching practice (Strong Back Open Heart) where he works with CEOs, other C-level execs, and teams to help them grow themselves and their businesses. He has done coaching work in 40+ companies to date and is generally working with ~15 clients at any given time.

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 2017 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.

Chad also served as a Cornell Tech Fellow for three academic years (2019-2021) designing and co-teaching a class called BigCo Studio about building digital products in large companies. 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.”)