This post is based on an interview with Bobbie Stempfley. It is part of our series of interviews of OODA Network members. Our objective with these interviews is to provide actionable information of interest to the community, including insights that can help with your own career progression. We also really like highlighting some of the great people that make our continued research and reporting possible.

 Career Progression: Bobbies’ plan to escape her hometown of Sierra Vista, AZ sounded like a sure thing! She would study a hardcore Engineering Discipline at the University of Arizona and then sort through all the job offers to find her destiny.   The U. S. Economy had other ideas.  Just before graduation, a recession hit, and jobs became suddenly scarce.  Despite her top-notch degree in Engineering Mathematics (that’s what computing was called in the ’90s), she quickly accumulated a depressing stack of Rejection letters. With nowhere to turn, she found herself back home.

She picked up a job at the nearby Army base, Fort Huachuca as an “Intern Engineer”.  Almost immediately she realized that her destiny had found her anyways – she loved being a Public Servant.  The Army struggled with how to deploy its “in garrison” capability down to the tactical level. They were building mostly Government Off-the-shelf Technology (GOTS).  She worked on teams that devised ways to make equipment (everything from radios to personnel management systems) ruggedized for the battlefield.  She personally created a system that could “predict” when supply parts would be needed (this is long before just-in-time Inventory systems existed). Empowering the deployed Soldiers with this type of capability was very rewarding; a huge force multiplier! She loved the work.

When she became pregnant with her first child, she expected that she would somehow handle the additional responsibility somehow.  This was before the Family and Medical Leave Act of 1993.  She only received three weeks off.  That’s the amount of time determined to “medically recover from childbirth”.  While she was out, she had been “laterally moved” into the job of Deployment Engineer; a job that required about 46 weeks a year away from home, which meant she needed a new plan.

Bobbie had noticed a disconnect at work between the Engineers in Fort Huachuca and the Program Managers in Fort Belvoir.  She drafted a plan to present to the Commanding General recommending some of the staff move east. Because she was too young to know any better, she pushed it up the Chain of Command.  To everyone’s surprise, the General supported the plan and Bobbie was the first one to move.  Two problems solved: different working conditions and she escaped her home town.

Many hours of hard work later, Bobbie progressed from Army Intern to Journeyman Engineer. Her great passion was leveraging technology to better the lives of the Soldiers.  She wanted to expand her reach across DoD, so she took a GS-12 Position at Defense Information Systems Agency (DISA).  While at DISA, Bobbie played out the same types of struggles that she had seen in the Army: how to mobilize technology to the tactical level, and how to balance GOTS and COTS to get the best value for the Government and the best capability for the Warfighter.

Coaxed over to the Department of Homeland Security by Admiral Brown, he asked her to help him build credibility in DHS to expand their roles as the Cyber Coordinator.  This was a turbulent time; they were struggling to define their authorities and responsibilities.  She quickly rose to the position of Deputy, and then Acting, Assistant Secretary of Cybersecurity and Communications.

While talking to Bobbie, one thing stood out.  She loved every job she had.  “This was the BEST job in the world!” she said, for each of her positions!  “My motivation is twofold,” she says.  “I want to help people be the best version of themselves, and through them and technology, I want to make a better world!”  Bobbie had an “ah-ha!! moment a few years ago.  “I realized your job is not who you are.  Your job is part of your platform!  Figure out what motivates you, and then you can identify the opportunities that help build the platform you need to get it done.”

A Serial Over-Achiever, Bobbie was running the DISA DoD CERT (computer emergency response team) when she had her third child, which she had strategically timed for a Christmas Break delivery.  She was also going to night school to get her Masters degree and was devastated when she got a “C” on her coursework.  Today, in addition to running the Carnegie Mellon University CERT Division at the Software Engineering Institute (300 employees helping Corporations, Organizations and Nations establish their own CERT capability) she is enrolled through Georgetown University in a non-traditional Doctoral program.  She’s teasing out the “Impact of Disintermediating Technology on Mature Governments”.  Bobbie says “The world is changing; now because of technology, Governments interact with their constituents in very different ways.  What happens when you remove the Intermediaries?  What will it do to our conception of “governing”?  Who is responsible for what?”

Surprises:  Bobbie is surprised by how often organizations crystallize their dysfunctions into the technologies they create.  “The organizations write the contracts and the specifications for the technologies.  The dysfunction gets baked into software and hardware in ways they didn’t intend! It’s easier to blame the technology than to fix the organizational dysfunction.” she says.

Advice for Decision Makers:  “Political leaders should be more grounded in the art of the technologically possible as they write their policies.” Bobbie says.  “They are writing laws that will be on the books for a long time.  If they don’t do it right, they will limit our Countries ability to sustain our technical edge; this could change the world!”    Additionally, Bobbie recommends “Companies should train their senior leadership and their Boards so they understand the threat. They can’t accurately represent the risk to the company, and make informed decisions about the risk if they don’t understand it.”

Security Improvements:  Bobbie credits good cyber hygiene and more methodical controls for significant security improvements in recent years.  “Simple things like auto-updates, secure defaults… they make a big difference!”

Risks in The Near Future: “We are a data-fueled world.” Bobbie says.  “We need to better understand data providence, data security, data management, etc.  We tend to think about data from a perspective of LOSS.  But it’s more than that.  Has the data been corrupted? Changed? Shared?  We need to grasp the full impact of our data dependencies.”

Technology of Interest:  “There are so many new technologies that are transformative and coming together at the same time:  Quantum communications and computing, transformation to a 5G network backbone, machine learning, etc.  Everything is becoming DATA and SOFTWARE, even biology, and printing!  It’s fascinating!”

Views on Thought Leaders:  Bobbie follows Matt Devost for his keen insights.  Steve Bellovin is still carrying the heavy load of balancing security and privacy. She also likes to get inputs from people early, mid, and late in their careers, to get different perspectives.

Quick Hits:

• Book Recommendations: Moral Tribes: Emotion, Reason and the Gap Between Us and Them by Joshua Greene. The Righteous Mind, by Jonathan Haidt
• Favorite piece of content on OODAloop: Articles about how AI is being incorporated into business.
• LinkedIn: https://www.linkedin.com/in/bobbiestempfley/