Careers inside the Beltway can last decades, even span an individual’s entire career from entry-level to retirement. But for these executives, there came a moment when they instead wanted out of the Beltway and along the Technology Corridor of 66-West. Retiring from a long career in public service to one more quiet and out of the public eye is a decision many are making.
Former Department of Homeland Security (DHS) Executive Director for the Enterprise System Development Office (ESDO) within the Office of the Chief Information Officer (OCIO) Keith Trippie, now Chief Executive Officer of The Trippie Group LLC, explains what led him to leave the government side for the private sector, addresses his new roles and offers advice for others thinking of making the switch.
WashingtonExec: Your career in government spans more than 10 years. How is your transition going? What do you know now that you did not expect after retiring from public service?
Keith Trippie: The transition has gone smoothly. I was in the private sector, as an entrepreneur before I joined the government, so I knew what I was getting myself into. And I knew what I wanted to do once I exited stage left. I knew it would take a lot of hard work and long hours to make it happen, and it is paying off. What I would tell any executive they do before leaving is to have a plan before you leave government service. No plan fully withstands the first contact with the enemy … is the old saying, and it is true. But a good, well thought out plan will prepare you for bumps along the way.
If I could wave a magic wand, I would simplify the federal contracting process to make it easier for federal entities to get the capabilities they need and reduce the administrative burden on federal contractors to comply with federal guidelines.
WashingtonExec: What prompted you to continue to support the mission in a private sector role? leave the government side for the private sector?
Keith Trippie: I really enjoyed the mission of the department. Because the missions were so diverse and expansive, going to work every day was very rewarding, yet presented complex challenges. Those challenges and being a part of a team of very talented and dedicated people is something I will always reflect fondly upon.
One of the most complex challenges for the next generation is the threat from cyber bad actors. I knew when I left DHS I wanted to collaborate with companies to meet that risk head-on. Specifically, I view the cyber threat as more of a human capital challenge than simply an IT risk. And that is where I am channeling energies today. Stay tuned.
WashingtonExec: What would your colleagues say were your top three accomplishments while at DHS? What do you consider your top three accomplishments while at DHS?
Keith Trippie: There are several areas where I think I was able to provide value as part of a larger collaborative team. First is in helping to drive cultural change at the department as it relates to IT. The legacy IT model in government and quite a few large corporations is that of an asset culture. IT professionals buy a bunch of software and hardware, cut a separate contract for hosting services, another for telecoms and then yet another for engineering services to make it all work. I can’t think of any large scale federal IT projects that came in under budget on schedule and hit original performance targets. That model does not work. Years ago that was the only option, but today with cloud, Agile and DevOps, Mobile etc. … there is no reason to stay with status quo. So I was a big proponent of a service based IT culture. Before I created the start-up office within the DHS OCIO, called the Enterprise System Development Office (ESDO), DHS had no cloud services. When I left, DHS had more than 12 private and public cloud solutions for both business and mission critical systems. DHS also had a mobile integration solution called CarWash, which brought together multiple new innovations to help reduce the time to market for new mobile applications, enhanced security and promoted reusability.
Another accomplishment I am proud of was promoting the notion that the government can run more like a business. My office was partially funded by appropriated monies, but more than 60 percent of the funding came from clients within DHS. I basically ran a start up business and grew it significantly during the nearly four years I ran that office. I had to manage monthly cash flow, client satisfaction, product development, recruit/retain human capital priorities, etc. … I wanted to prove that running like a business was a better model for the taxpayers. I think we were able to prove the model can work.
Finally, one project that I helped lead for senior management was the DHS Management Cube. This also built upon the model of how government can run more like a business. This concept was to leverage sound business principles, investment and portfolio management, coupled with data standardization and big data analytics to help the department gain further insight into its spend and budgeting. This was a very collaborative effort and was yielding results in a short amount of time. I hope other agencies would follow a similar investment/portfolio management framework to help manage their missions through reduced budget futures.
WashingtonExec: What will be your biggest challenge as CEO for The Trippie Group? How will you address it? What has had the largest learning curve or adjustment you have had to make in the private sector?
Keith Trippie: Managing my time. As a small business, you can’t be all things to all people, and I must prioritize. So I am following the plan I put together when I left DHS, with a few updates based on new opportunities that have presented themselves to me during the past six months. One of the main learning curves is on administrative tasks, where I had staff to perform those functions. Something I work on regularly and am getting better at but, more work to be done. I think every small business has a similar challenge.
WashingtonExec: What is something that you’ve learned since your transition to the private sector that you didn’t realize initially?
Keith Trippie: How the other half lives. I didn’t fully have an appreciation for how government contractors execute their business. I had been in private sector before, which was very helpful to understand how the private sector business model works. However, that model is different from companies that sell directly into the federal government. Over the years at a large government organization, I learned all the nuances from government contracting, human capital, delivering IT, etc., but I did not see how the folks on the other side of the table saw us in the government.
One area I have seen many companies expend energies since I left the government is the amount of time, resources and executive capital they expend of bidding for government contracts. I can tell you this, it is extensive. If I could wave a magic wand, I would simplify the federal contracting process to make it easier for federal entities to get the capabilities they need and reduce the administrative burden on federal contractors to comply with federal guidelines.
WashingtonExec: What are your goals for the company while in your new role?
Keith Trippie: I think the goal of any company is to build value. Whether it is innovating to solve a problem that has yet to be solved, helping companies go to market with new service or assisting in revenue generation, the priority is to help generate value. Specifically, I have objectives in providing assistance to companies going to market in the federal and commercial space, cyber gamification, building mobile apps and analytics. Longer term goals would also include helping provide value and contributing to non-profit organizations goals. I am a big believer in giving back and that is part of my longer term objective.
WashingtonExec: Do you believe a public sector executive’s top leadership qualities differ from a private sector executive’s leadership qualities? If so, how?
Keith Trippie: Great question. Whether you are in the private sector or government, there are leadership qualities that apply to either. Providing a clearly articulated vision, the ability to connect with people, driving a results culture, maturing talent and possessing sound business acumen are common traits of leaders within both government and private sector. One trait, that I think a government executive, especially an executive who has just joined the federal government needs to have, is patience and lots of it. In the private sector, results are expected on a shorter timeline, think every quarter and failure is not an option — at least not for the executive who couldn’t achieve those results. They will be gone.
The timelines to achieve results in the government are long and sometimes you don’t achieve those intended results. And that takes some getting used to. There are multiple reasons for this, including changing leadership every few years, protracted procurement cycles and to be honest, the human capital dynamics are very different between the government and private sector. To lead in the government, if you can not adjust your style to this reality, your time in government will be short.
WashingtonExec: Did you have any mentors or individuals who deeply influenced who you are or your decision to stand at the head of where you are now?
Keith Trippie: I have a couple that come to mind. Bob Jennings, my boss at my first job out of college. He taught me that family is important. I have always enjoyed working, but he taught me to balance work and family. During my government years, Richard Spires and Margie Graves, were influential. Both are very savvy business executives, who happen to lead IT organizations. They believe in hiring good people, providing guidance and allowing their staff to achieve great things. That is a successful model for any leader. Can’t be afraid of hiring talented people, that may have stronger skillsets than you may have, and fostering that talent to achieve results for the greater good. The other trait they have that resonated with me was, it was about the business and mission, first and foremost. Information technology, no matter how cool, is just a business-enabler.
WashingtonExec: What is your best piece of advice to those thinking about remaining in federal or enter the private sector?
Keith Trippie: I have had quite a few conversations with federal executives from across government during the past six months who are asking that very question. The private sector is different from civic service, with different business dynamics at play. And if you have never been in the private sector before, you may find the pace of play and the consistent drumbeat of the bottomline, challenging. At the same time, it can be very rewarding professionally and presents an endless opportunity to maximize and monetize your skillsets. I am a strong proponent of running to something vice running from something. Leave for the right reason is my main advice.
WashingtonExec: Do you see yourself “boomeranging back” to the public sector?
Keith Trippie: Well, I don’t know. I really enjoyed my time in the government and giving back. The opportunity would have to be a great fit. I wrote an article last summer where I proposed a new funding model for federal IT investments based on the venture capital model used in Silicon Valley. Should that concept ever get traction and the government needed leadership to serve on the Board of Directors, I would take that phone call.
WashingtonExec: What’s something most people don’t know about you?
Keith Trippie: I am an identical twin. We drove our poor mother crazy. Another factoid, my wife booked a trip for me and a buddy to go out to the Guadalupe Islands off the coast of Mexico a few years ago. For three days and nights, we got to go eye to eye with great white sharks. They are very curious and beautiful animals. Recommend adding that trip to your Bucket List.
1 Comment
Pingback: TWD & Associates Inc. Launches Advisory Board | WashingtonExec