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Matt: Automattic’s First New Board Member: General Ann Dunwoody

Matt: Automattic’s First New Board Member: General Ann Dunwoody

As Automattic keeps growing we’ve been bringing in a lot of talented people behind the scenes to help expand on our vision as we go from hundreds to thousands of colleagues, and hundreds of millions to billions in revenue. Recently, former New York Times digital executive Kinsey Wilson joined our team as president of WordPress.com, the Chief Digital Officer of Axios Alexis Lloyd has joined as head of Design Innovation, and today I’m excited to announce a change to my bosses, the board of directors.

Gen. Ann Dunwoody served for 37 years in the U.S. Army, and she is the first woman in U.S. Military history to achieve a four-star officer rank. She’s also the author of A Higher Standard: Leadership Strategies from America’s First Female Four-Star General, a book I really loved and highly recommend. Automattic’s board has had no new members since its founding in 2005, so this is our first addition in 13 years. I became familiar with General Dunwoody’s work while researching distributed organizations outside of technology, which led me to the military, which led me to geek out on logistics, which led me to her book and eventually flying out to Florida to meet in person.

Below is a brief interview with Gen. Dunwoody — we chatted with her about global leadership, finding your passion, and building a business.

We’re excited to have you onboard, General Dunwoody. It’s interesting — at Automattic we like to point out that we’re all over the globe (over 740 employees in more than 60 countries) but you oversaw 69,000 military and civilians across 140 countries! Were there any big leadership lessons from managing operations across such a wide range of distances, timezones, and cultures?

That’s a great question. When I started out as a young officer in the Army, the leadership philosophy that was espoused back then was “Leadership by walking around.” When you’re in charge of a platoon, a company or even a battalion or Brigade that is not globally dispersed this philosophy is very sound. When you’re running a global organization with 69,000 folks in 140 countries, you have to leverage technology to keep real-time communications flowing and keep leaders updated. I would host (with the leadership) a global video teleconference every Wednesday connecting every organization from Afghanistan, Kuwait, Iraq, Europe, etc. and sites — hundreds across the United States. Our headquarters  would provide an operational update and then we go around the globe to get update from from everyone — what’s going well, where they need help or additional resources. In the old days I think people believed information was power and often withheld information to use for personal advantage, but I believe shared information is power. By leveraging the power of the entire industrial base we could solve problems in real time. I still travelled around a lot to see our people, but it is not possible to keep everyone informed and in the loop with current operations without leveraging technology.

I love your answer about “shared information is power.” Did you ever find it difficult to break down the silos and embrace that concept?

Oh my, yes. They weren’t just silos, they were silos with concertina wire around them!   Parochialism was rampant and everyone wanted their own system and own their own information. We had over 200 stand alone systems that didn’t talk to each other. So to field and design an enterprise IT system that leveraged systems with the needed information to support “foxhole to factory” was challenging and exciting.

And how did you decide what technological means to communicate an idea or a directive, versus, say, meeting in-person?

I would say it depended on the idea. If it was personal, probably a phone call (one on one); if trying to generate support for an idea or transformational concept, meet in-person with my initiatives group to socialize the idea and get their input modifications and buy-in. Then Commanders conference to socialize idea with them, as they will have to implement it. Once socialized with leadership, we worldwide videoconference with the entire organization to define and describe the purpose, intent, how, and why — so everyone knew what we were trying to do and what their role was in execution. I found you cannot over-communicate when trying to make changes.

It’s an incredible accomplishment to become the first woman in U.S. Military history to achieve the four-star officer rank. Can you tell me about how things changed (or maybe still need to change further) in terms of your experience during your 37 years of service, and how you addressed diversity and inclusion in the military?

First, I certainly didn’t accomplish this by myself — I had a lot of help along the way! I joined the Army as part of the Women’s Army Corps (WAC) back in 1975. A few years later they disestablished the WAC and began the integration of women into the regular Army. This was the first time women had the opportunity to have the same career opportunities as their male counterparts in the branches now open to women. The challenge for the women who came into the Army back then was to force the integration — fight being put into traditional jobs like being a secretary, admin, clerk, or cook — and fight to be platoon leaders, etc., to support and move the integration of women into the regular Army.

What I witnessed during my time in the Army was that the doors continued to open. Yes, there were roadblocks — but there were also many leaders along the way who were willing to help. I never worked for a woman. I worked for men who either believed in me or didn’t. My experience in my almost four decades was that the doors continued to open for women. I thought jumping out of airplanes was really neat — now my niece in the USAF is an A-10 fighter pilot, and we have women graduating from Ranger school!  

On diversity, I realized that being the only female in many forums, my voice was hard to be heard. And I also realized that most folks promoted and surrounded themselves with people in their own image. What my philosophy was — and I still think it is an issue today — is that diversity is not about numbers, it’s about getting the best and brightest from all walks of life, to help leaders solve the very complex issues that face us today. Don’t surround yourself with only people that think or act or look like you.

Who are the leaders that inspire you today?

I think we are products of our past — Mom and Dad, even though not here on earth, gave me the values that still guide me. Many of my military mentors, Gen. Hugh Shelton, Gen. Pete Schoomaker, Gen. Gordon Sullivan, Gen. Dick Cody, are still coaches and mentors to me today.  

Folks I admire: Warren Buffett, only met him once but I like his concern for the betterment of our country; Oprah Winfrey, although I have never met her I admire her for what she does for our country how she presents herself and how she handles herself — awesome; Gen. Mattis — wow, I admire him for taking on this extremely tough assignment for the good of our country and our defense. Secretary Gates served two administrations, Republican and Democrat.

People that inspire me are people I believe are true leaders — valuing honesty and having the best interests of the country at heart. No hubris!


As Automattic keeps growing we’ve been bringing in a lot of talented people behind the scenes to help expand on our vision as we go from hundreds to thousands of colleagues, and hundreds of millions to billions in revenue. Recently, former New York Times digital executive Kinsey Wilson joined our team as president of WordPress.com, the Chief Digital Officer of Axios Alexis Lloyd has joined as head of Design Innovation, and today I’m excited to announce a change to my bosses, the board of directors. Gen. Ann Dunwoody served for 37 years in the U.S. Army, and she is the…

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