The finalists for WashingtonExec’s Chief Officer Awards were announced April 15, and we’ll be highlighting some of them until the event takes place virtually May 27.
Next is Chief Legal Counsel finalist Jim Winner, who’s executive chief legal officer and general counsel at Peraton. Here, he talks shaping the next generation of GovCon leaders, learning from failures, proud career moments and more.
What are your primary focus areas going forward, and why are those so important to the future of the nation?
Peraton’s primary focus is to continue to grow as a trusted national security mission capability provider, helping solve the nation’s most daunting challenges. My legal team must remain in lockstep with Peraton leadership and business partners to help them shape approaches and solutions that exceed customer expectations. At the same time, we must continually work to mitigate risks to the customer and the company.
How do you help shape the next generation of industry leaders?
I continually emphasize to my team to deepen the diversity of our work knowledge and to always be willing to “flex” into other functional and business areas.
For instance, a contracts manager must have the business acumen to understand the financial impacts of certain contractual modifications for an ongoing program in order to provide the most effective support and guidance to the company.
The fast-paced and ever-changing nature of our work demands that legal, compliance and contracts professionals be deep and multifaceted in their knowledge and capabilities. This depth and diversity position us to be more impactful as leaders across the company and within the national security industry.
What’s one key thing you learned from a failure you had?
I have learned to always push forward following a setback. As I tell my team (and my kids), “There is always a way forward” even when things do not seem to be going our way. There are always lessons to be learned from mistakes. But at some point, it becomes unproductive and unhelpful to dwell on mistakes for too long — backward-looking thinking must quickly give way to forward-looking action.
I have adopted one of the sayings from Peraton’s CEO Stu Shea: “Surround the problem.” When my team hits a setback, we work together to stabilize the situation, understand what occurred and then identify and mobilize the right people and resources to “surround the problem” and move us forward.
Which rules do you think you should break more as an industry leader?
If we are looking at “rules” in the sense of the law, regulations and our contracts, I view my role as chief legal officer to ensure that my business teams know the rules and are effectively advised on the operational latitude that they have, and the risks involved under those rules.
If we view “rules” in the sense of general notions and expectations of a leader and/or chief legal officer in our government contractor industry, I think those should be continually broken as, no matter what your role and position, our challenging and resource-constrained environment requires every leader to effectively stretch vertically (dive down, as needed, with sleeves rolled up to get certain important tasks done) and horizontally (flex across multiple functions in order to effectively relate to and support your other team members).
One of my most satisfying professional experiences was traveling to the U.K. to support a proposal-writing team and after a week of working together in a crowded SCIF developing a winning proposal, half of the team did not know I was “the lawyer.”
What’s the biggest professional risk you’ve ever taken?
Leaving Northrop Grumman several years ago to take on a chief legal officer role with a growing private security company was risky. This was during a time when there were several negative, highly publicized incidents involving private security companies operating overseas.
But with this perceived risky decision, I found tremendous rewards. I was honored to work with and learn from a dedicated group of professionals who constantly put their safety on the line to support their country in high-threat locations. Some of them made the ultimate sacrifice to protect our freedom.
Moreover, I was able to play a role in the implementation of PSC.1, which established industrywide professional standards and business and risk management frameworks for the conduct of private security operations.
The companies I supported, including Aegis and GardaWorld, have been leaders in ensuring effective and professional support to our country’s contingency operations. My legal counterparts at other private security companies became close and trusted colleagues, as we often collaborated in finding solutions for complex legal and operational issues overseas. Ultimately, this high-risk decision was one of the most impactful for my personal and professional development.
Looking back at your career, what are you most proud of?
I am very proud of my Peraton team. Building a diverse and capable team is one of the most rewarding things I have done. I continually challenge my team with chances for growth and development. Some have moved on to promotions with other companies, and others continue to develop and progress internally.
I always encourage my team to explore new opportunities, whether it’s an adjacent functional role, such as filling a critical role within human resources on a temporary basis, or an entirely new adventure. I am proud of the people that I get to work with every day.
What was your biggest career struggle and how did you overcome it?
One of the biggest decisions that I struggled with was leaving active duty service as an Air Force JAG and transitioning into the private sector. It was nerve wracking, as it was not clear where I would “fit” in the legal profession after practicing law in the military for several years. I pushed forward through the transition, worked hard to understand new roles and positions and kept an open mind.
Life choices are often made for you in the military, so I had to figure out these “big” decisions on my own, like where to live and what job to do. I started with a great law firm, then transitioned to working in-house as an attorney for commercial companies and then finally moved to working in-house for several federal contractors.
Working in the national security field and supporting the U.S. government again was where I found the best “fit” for my career progression and job satisfaction. So many people provided amazing mentorship and guidance to me along the way.
What’s your best career advice for those who want to follow in your footsteps?
My advice is to work hard, take care of your family and friends and treat everyone with respect — or as my dad would say, “Treat people like people.”