Women Leading the AI Industry: “Be fearless. Unapologetically fearless.” With Keenan Skelly and Tyler Gallagher

Be fearless. Unapologetically fearless. I cannot count the number of people who told me I could never be a Bomb Technician because <insert lame comment here>. Even my recruiter told me I would fail! I can’t count the number of people who despised me for being a 26 year old female GS-14 at DHS. I […]

Be fearless. Unapologetically fearless. I cannot count the number of people who told me I could never be a Bomb Technician because <insert lame comment here>. Even my recruiter told me I would fail! I can’t count the number of people who despised me for being a 26 year old female GS-14 at DHS. I can’t count the number of people who told me “you can’t go get two more degrees in a technical field mid-career”. But the more people told me I couldn’t do it, the more I was confident that I could. And you know what, I did all of those things. You can too. Use the naysayers as fuel and know at the end of the day the only person you are competing with, is you.

I had the pleasure of interviewing Keenan Skelly. Skelly has more than 20 years of experience providing security and management solutions across a wide array of platforms to include personnel, physical, and cybersecurity. She brings over ten years in government service with a focus on National Security. Skelly served in the U.S. Army as an Explosive Ordnance Disposal Technician and went on to work for the Department of Homeland Security where she served as Chief for Comprehensive Reviews in the Office for Infrastructure Protection.

Can you share with us the ‘backstory” of how you decided to pursue this career path?

I started out in the Army as an explosive ordnance disposal technician, and I had an interesting career. I was last stationed at Andrews Air Force Base, where we focused on chemical and nuclear weapons. It wasn’t very cyber-related. While I was doing that job, I happened to be stationed at the White House on 9/11, and in that capacity I got to see the national response plan acted out. It brought me back to my past before the military, working for the Red Cross and responding to large-scale incidents. I was interested in transitioning the skills I got from the military, so I went to work for the Infrastructure Protection division of the Department of Homeland Security, where I ran vulnerability assessments across the country — nuclear, chemical, water — looking at these from a personnel and a physical security standpoint, as well as an information security standpoint. We saw then that information security was the single point of failure across all these sectors. Despite that, we weren’t really providing a lot of assets for the critical infrastructure community to mitigate these information security threats

Here we are, 15 years later, and a lot of the same issues are still being played out, but on a larger scale. That pushed me in the direction of learning more about information technology and cybersecurity. I went back to school and got a bachelor’s degree in information technology and security and came back to the field to promote some of these things at the critical infrastructure level. Since then, I’ve been working with smaller companies on ideas about how to address the cybersecurity issue.

What lessons can others learn from your story?

The biggest lesson is that if you work hard and commit to being the best that you can be (not better than anyone else), then nothing else really matters. Not opinions or judgements of other people and certainly not who you did or didn’t beat on your way. I worked tirelessly, both mentally and physically and fought to be the best version of myself; and ended up graduating the school at a time when 60% of students didn’t. That has afforded me the pride and confidence to know that I really can do anything and this has helped me immensely in the technology realm as well.

Can you tell our readers about the most interesting projects you are working on now?

In my organization, we have had the great privilege of working with several FVEY nation states in standing up truly persistent cyber training programs and exercises. Helping to stand up and shape policies that will affect the cyber domain for the next 15–20 years is very exciting. We are at a critical turning point with cybersecurity globally. Being able to insert technologies like AI/ML and gamification into cyber will enable us to not only scale cyber defenders to meet the growing need (3.5 million); but also allow us to begin augmenting and automating those defenders to be more efficient and focused on advanced threats.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
 I have been fortunate enough to have many great mentors in my life; but the first really influential person was my Team Leader at my first duty station. It was still very unusual to see a woman in an EOD unit then and many of the soldiers I was stationed with had many years with no females present in their everyday work environment. There were several, in fact who seemed very personally offended that I even graduated school, let alone that I was assigned to a specialized unit. My Team Leader, from the very beginning, reminded me that I graduated from the same school they did and had every right to be there. (Impostor syndrome is not a new thing!) He gave me the confidence to own any situation by basically throwing me in head first. When we would go out on an incident he would say “You’re in charge, tell me when you’ve made a plan”, and send me off. And as any green, young adult would I truly believed there was nothing I couldn’t do.

As you know, there is an ongoing debate between prominent scientists, (personified as a debate between Elon Musk and Mark Zuckerberg,) about whether advanced AI has the future potential to pose a danger to humanity. What is your position about this?

1. Working in cybersecurity and seeing the impact that AI and machine learning have on our daily lives, I imagine the great ways we can change humanity for the better. However, I am also worried we may hinder our best-case tech enabled future with what I call “Machine Learned Misappropriation.” As we focus on the importance of diversity in technology and in cybersecurity, especially in light of the massive shortage of skilled cyber technologists, we must also insist on diversity in AI. We have begun to use AI and machine learning to augment and automate our lives; how do we ensure we are teaching it the ‘right’ things? Are we teaching without bias? Are we training algorithms to take race, culture, sex and class into consideration? Are we building the “every-person’s AI,” or are we building something unintentionally prejudiced? As we use and rely on this technology, we have to understand that humans are creating it, training it, programming it, and by osmosis, in many ways, our conscious and subconscious biases will naturally be a part of the work we do with AI and machine learning.

2. Whenever there is great innovation or technology, there will always be those who seek to use it for nefarious means. But just like we have done in every domain before (Nuclear, Chemical, Biological…) there will be a period of normalization. A time when global norms are set and agreed to, some activities being criminalized and others being nominalized.

What can be done to prevent such concerns from materializing? And what can be done to assure the public that there is nothing to be concerned about?

1. Without a doubt, it will take time for us to come up with the best, most fair ways to train AI. The best immediate solution is, of course, diversity in hiring across the field. Build more diverse teams, and you will have a wider pool of experience and intelligence to draw from.

2. Fortunately, we are building the norms for cybersecurity right now! The policies and programs we champion now will create the kind of future we want to see in cybersecurity and AI. Global leaders must work together now to determine how to keep our future bright rather than terrifying. And the rest of us need to recognize the power we wield with tech like AI. We need to be bold in our innovation; but not fearless. After all, with great power comes great responsibility.

How have you used your success to bring goodness to the world? Can you share a story?

Being a female leader in cybersecurity I hope has inspired young girls and women to pursue careers in cyber and technology. I try to be as active as I can in groups like Cyber Patriot, Girls Who Code, and more recently Women’s Cyberjutsu. I feel that women MUST MUST MUST help other women. No matter what your level of skill or where you are in your career, there is a young woman or woman who is now where you once were. I can only try to share my experiences (good and bad) and hope they make another woman’s path a bit easier.

Currently females represent less than 12% of the global cybersecurity workforce; which is insane. Women are well suited for, and extremely talented at technical fields such as information security, security engineering, and AI engineer; however, recruiting and retaining women in these fields is not where it needs to be. We have a real messaging and branding problem. For example, I had a Cyber Patriot student, young female, who at the time of her high school graduation could code expertly in more than 16 coding languages….like it was nothing. When we talked about what she was going to study in college she was undecided, but said definitely not cyber. *GASP When I inquired as to why, she said “I’m not a dark hoodie kind of girl”. Although she had spent the last four years in every cyber club for a 50-mile radius and obviously loved it, she couldn’t picture herself in the field. That is because marketing and branding for cybersecurity has been largely focused on the guy with the hoodie; the “bad-actor”. We MUST stop this. #NoHoodie I immediately reworked my plans for the next few weeks to bring in a steady stream of Women in Cyber who were Marketers or Accountants, or Doctors or CIOs and CEOs; but who all worked in cyber and even coded. To help recruit and retain female talent we must first help them understand that cyber is everywhere, in every field and, there is a place for them there.

As you know, there are not that many women in your industry. Can you share 3 things that you would you advise to other women in the AI space to thrive?

1. Women tend to be natural nurturers and empathetic — those qualities will go a long way in progressing AI because women can use their natural characteristics to inform how we develop and use AI not just for computer programs and number analysis, but to support richer human experiences that consider emotion alongside logic and facts.

2. Don’t let your gender be a limiting factor in your ability to progress in your profession. Have confidence in your skills and abilities and show your colleagues the proof is in the pudding. #OwnIt

3. Be fearless. Unapologetically fearless. I cannot count the number of people who told me I could never be a Bomb Technician because <insert lame comment here>. Even my recruiter told me I would fail! I can’t count the number of people who despised me for being a 26 year old female GS-14 at DHS. I can’t count the number of people who told me “you can’t go get two more degrees in a technical field mid-career”. But the more people told me I couldn’t do it, the more I was confident that I could. And you know what, I did all of those things. You can too. Use the naysayers as fuel and know at the end of the day the only person you are competing with, is you.

Can you advise what is needed to engage more women into the AI industry?

Getting female students exposed to AI early in their academic journey is crucial to their development as a professional. Current women in technology need to keep mentoring young kids on the value and importance of AI and how it’ll impact their lives and the lives of the generation behind them. AI is going to become such a pervasive part of our personal and professional experiences, we need women to ensure its evolution and application is helpful to people, not hinder some.

Also see above: #NoHoodie

What is your favorite “Life Lesson Quote”? Can you share a story of how that had relevance to your own life?

“Don’t take life too seriously, you will never get out of it alive.”

This may seem a bit morbid; but it is something I saw when I was very young (15/16ish) that really impacted the course of my life. I lived in a small town in the Midwest; but craved adventure and travel and a lifetime of wonderful stories to tell my friends and family. I didn’t want to get hit by a car at 20yrs old and leave people with nothing impactful to say about it. I wanted to influence and admire others, learn from them and forget them if I had too. I wanted to experience everything I could before I died. Because if you are frantically analyzing your life with somber worry about every decision, you aren’t really living. If you want to do something or try something new, do it; and then if you don’t like it try something else. It’s all up to you. After all, none of us get out of here alive anyway.

Note: This philosophy often conflicts with my inner risk analyst; but it makes for great inner monologue.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I would like to start a platform to engage teenagers globally to promote AI development which augments or automates process to do one of these four focus groups:

1. Medical: Such as, Inexpensive AI powered nanobots for surgical procedures (See my previous article on the need for nanobots ;-D)

2. Global Economy: Such as, using AI to build economic growth in other than first world economies.

3. Food for the Future: How can we use AI to create more efficient and sustainable farming and agriculture and keep feeding the world.

4. Energy: Using AI to cut carbon emissions and create globally available, clean, cheap, reliable energy for all.

This would start with not only teaching basic AI dev and engineering; but mentoring the students to use their POWER FOR GOOD by competing worldwide and by helping them understand the global need for AI impact in Medical, Economic, Agricultural, and Energy sectors. Also instilling a desire to understand global challenges and develop solutions to solve them.


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