Executive Spotlight: Sean O’Donnell, Senior Cloud Account Executive at Oracle

Sean O’Donnell currently serves as senior cloud account executive at Oracle. He began his career in the U.S. Air Force, and his later transition into the Air Force Reserve paved a pathway for his move to the sales field. Prior to joining Oracle, he held positions at VMware, Booz Allen Hamilton and Boeing.

In a recent interview with the Potomac Officers Club, O’Donnell gave an overview of his career background, highlighted his core values and reflected on the leadership styles that have inspired him throughout his career.

Read the full interview below.

What can you tell us about your background and how you’ve been able to adapt to the ever-changing challenges of the federal landscape over the course of your career?

I’ve been in the federal space for 20 years, first on active duty in the USAF before I transitioned to the Reserves, which allowed me to pursue a career in consulting and eventually sales. At the beginning of my career, budgets were flush because of Afghanistan and Iraq, and Department of Defense customers could easily and effectively buy new technologies and services to help win the wars.

This has changed, and what has helped me adapt during this time of transition is a quote by Gen. Giulio Douhet, the airpower theorist from the Italian Air Force: ‘Flexibility is the key to airpower.’ We’d say it jokingly in the USAF when things weren’t going as planned, but I firmly believe that the only constant in life is change, and to be successful, you need to recognize it and adapt to changes. From what was once flush budgets, changing to sequestration and now continuing resolutions and government shutdowns, the entire fiscal year is continually in flux. To be successful, we need to monitor all this and ensure our books of business are managed to withstand these changes and not reliant on make-or-break efforts. 

How would you describe your management style and core values towards building a winning culture? 

I have a very open, candid personality and love being on winning teams – which don’t happen overnight and are not the result of a singular person. I am by no means an expert in everything, so I don’t try to get in the weeds and micro-manage everything. If I don’t understand something, I ask questions until I feel comfortable with the answers. I’d much rather get the experts together, provide the general direction for where we should go and allow broad leeway to get to the desired goal. If we need to course correct during the process, we can, but being a leader is about trusting your team and giving them the tools to be successful and accomplish the task at hand. 

With emerging technology influencing the federal government and industry more by the day, what are some of the challenges on the business side of innovation that aren’t always discussed as often as they should be? 

This is an interesting question and one of the big reasons I decided to pivot to a career at Oracle. In consulting, it is much less of an issue as the main product is people, so the goal is finding the right people to meet the requirements at the right price point. Tech is different, especially when it comes to large, multinational corporations that are publicly traded.

Supporting the federal government can be difficult. Recognizing the inherent sensitivity of federal data necessitates added security requirements, testing and accreditation, which, from a business standpoint, can create barriers to entry. These requirements are not always needed for commercial customers, and therefore, federal accounts are often secondary to the commercial enterprise accounts rather than being on par with them. When an organization releases new products and capabilities that are revolutionary for the enterprise, they may not be available in the federal space for 18 to 24 months because they need to go through accreditation processes. What I love about Oracle is that we take the opposite approach – we build our technology from the start to meet federal requirements. When we release a new product, we do not need to retrofit the service to meet federal requirements, which enables parity across security features. 

We’re also not putting data centers in countries that are adversarial to the U.S. I would like to see more technology companies make similar decisions by prioritizing supporting federal customers and national security over global market share. I firmly believe that to maintain our competitive edge we need more support from the tech industry to better align with our national security self-interests. 

Who are the executives that have inspired you the most over the course of your career? 

There are three leaders whose characteristics and behavior I have tried to model as my career progressed. Early in my career, I had the privilege to work with somebody who gave me a lot of leeway. When I drifted too far, she was quick to provide guardrails, but overall, she let me figure things out on my own. She also gave me great advice that a career path isn’t a straight line from A to Z. We can get so consumed on following a specific path that we forget there are side trails to follow. She took those side trails throughout her career. She was excellent and is now enjoying retirement. 

Later, I worked for an individual who taught me about flat communication. He demanded flat communication throughout his organization and made it clear that siloed communication would not be well tolerated. He wanted his team to talk and know what was happening across the board. This way, if somebody was able to answer something, they could step in if the respective subject matter expert wasn’t present. It would be tough to turn down an offer from him today if he called with an opportunity – he truly cultivated an amazing team. 

The last person is a mentor who I’m still in contact with today. He is the type of leader who you want to work for. He’ll give you stretch opportunities and challenges to push you but at the same time not set you up for failure. He wants you to be successful and gives you the tools to do so. He inspired me to take the side path away from consulting into sales and I’m beyond grateful for it.