I believe “strong back, open heart” leadership is the key to building great companies. The strong back is represented by fiscal discipline, strong process, and accountability. The soft, open-hearted front are values, purpose, connectedness, and compassion. Organizations and people are at their best when they manifest both in equal balance.
I have been working as an executive coach since November 2017, working with CEOs, CTOs, and other C-level execs and their teams to help them grow themselves and their businesses. My job as a coach is to help leaders be the best leaders they can be, facing the challenges of leadership with conviction, grit, integrity, and compassion.
Over the course of a 25 year career, I’ve been a CTO and CEO through three boom-and-bust business cycles in Silicon Valley and New York City. During that time, I’ve hired, re-organized, fired, and acquired. I’ve raised venture money on the private markets, raised money on the public markets in an IPO, and built out a public company board of directors. During my career, I’ve been merged, acquired, and fired myself (once -- not fun but a truly meaningful learning experience).
As a CEO for six years, I was directly responsible for hiring the top executives for every key function in a hyper growth company and served as chair of a public company board. I’ve sat in the leadership chair just like my clients have, so I come to my coaching work with a deep sense of empathy and commitment to help. I made my share of mistakes as a leader and I think my reflections on those mistakes have helped make me a more effective coach.
My most profound leadership experience took place over my nine years at Etsy, where I came in as CTO of a 50-person startup and built/rebuilt the engineering team, who then rebuilt the platform. Then I stepped into the CEO role and led the company for six years, leading through hyper growth as the company matured from a chaotic startup through IPO and then its first two years as a public company. During my tenure as CEO, we grew revenue nearly 14x, operating profit almost 15x, and gross merchandise sales (GMS) 9x while leading the kind of intense organizational growth and change you can only experience in building a billion-dollar success story that touches lives around the world.
We did all of this while maintaining intense commitment to values-led culture and social responsibility. When Etsy went public in April 2015, we did it as a B Corp, a special kind of company that makes a formal commitment to both people and profit. We made the Best Places to Work list every year from 2013 to 2016 and did pioneering work in areas like family leave and diversity and inclusion. I’m deeply familiar with all of the issues leaders have to consider when trying to build and run a “good” company (and it’s not easy!)
Before Etsy, I held leadership roles in technology and product management at companies of many sizes, stages, and cultures: Yahoo, IDG/InfoWorld, Salon, CNN, The Atlanta Journal-Constitution and The (Raleigh, NC) News & Observer. I’m not a “big company” or “startup” person. I’m comfortable in both. The common thread in my career is that I gravitate towards mission-driven companies that inspire passion and create meaning for their communities.
But that’s just my professional bio. An effective coaching engagement is much more than helping a client succeed in their work. It’s also about helping a client lead the fullest and most coherent life possible, with work as a key component but not one’s entire identity. The word “integrity” is used so often that we almost forget what it means: “the quality or state of being complete or undivided.” Leading with integrity means integrating one’s life completely, in its entire wholeness -- and messiness.
I’ve tried to model integrity by building a very full life outside of work. I’m an adoptive father of an 8-year-old boy, a musician (piano and guitar - ask me about my Soundcloud), and a writer. I co-teach a graduate-level class at Cornell Tech called BigCo Studio about building products in larger companies. I’m on the board of three non-profits in Brooklyn that mean a lot to me: St. Ann’s Warehouse, The Jalopy Theater and School of Music, and the Brooklyn Public Library. Each of these activities contributes to my coaching approach in powerful ways.
Fundamentally, leadership is multi-disciplinary by nature and I draw from all disciplines in my practice, including the liberal arts. In fact, I was an English major with a focus on Shakespeare in my undergraduate studies at Duke. In the fall of 2015, I saw a production of Shakespeare's Henry IV at St. Ann's Warehouse in Brooklyn. As I sat there in the darkness as Act III, Scene 1 opened, I was moved as King Henry IV appeared in his night clothes, cursing his inability to sleep under the weighty responsibilities of his leadership, ending with the famous line: "Uneasy lies the head that wears a crown." As the CEO of a public company at the time, I felt truly seen by those centuries-old words.
Sometimes a Harvard Business Review article is what you need, or a passage from Peter Drucker, or maybe Andy Grove's classic High Output Management. But no one expressed the burdens of leadership more powerfully than Shakespeare so I've been known to bring a pair of Henry IV tickets to a coaching session if a production is in town. It helps to know that others -- kings even -- have shared the burdens you feel. That spirit of empathy and understanding is what I try to bring to my coaching practice.