Jonathan Dalrymple’s career has tracked the operational backbone of the national security enterprise, from military service to senior leadership roles across major aerospace and defense contractors.
In this Q&A, the CEO of Chugach Alaska Corp. talks about what it takes to lead a purpose-driven enterprise at scale, how mission, stewardship and growth intersect in practice and how he is preparing Chugach to compete and deliver in an increasingly demanding federal market.
Can you provide a brief overview of your professional background and career progression?
My career spans more than 25 years across aerospace, defense, and intelligence contracting, with a consistent focus on growth, operations, and mission delivery. Throughout that time, I have been drawn to purpose-driven work and to organizations where success is rooted in a shared sense of responsibility and community. That perspective was shaped early in my military service and has carried through every chapter of my career. I have held senior leadership roles at organizations such as Raytheon, L3, Textron, and VSE Corporation, working across strategy, business development, and execution.
What ultimately brought me to Chugach Alaska Corporation was the opportunity to lead an enterprise where that same sense of purpose and community is foundational. Chugach aligns growth with stewardship and long-term responsibility, ensuring that business success directly supports shareholders and communities. The chance to steward a portfolio of businesses with an ambitious growth goal, while creating lasting, generational impact made this role a natural fit.
Why was this the path you chose, and how influential was it to your career?
I have always been drawn to work that serves a clear purpose and requires long-term thinking. Early in my career, including my time in the U.S. Navy, I learned the importance of shared responsibility, discipline, and accountability. Those lessons shaped how I approach leadership and decision-making.
This path has been influential because it reinforced that sustainable growth comes from doing the fundamentals well, investing in people, and staying focused on the mission. Over time, that approach has guided the choices I have made and the organizations I have been proud to serve.
Do you have a personal connection to the current mission you support? If so, please explain.
I have had the privilege in my professional career of supporting national security either through military service, or in leadership roles in aerospace and defense firms directly supporting warfighters.
At Chugach Alaska Corporation, the mission is deeply rooted in community and long-term responsibility. The work we do supports national priorities while also creating lasting opportunity for Alaska Native shareholders and communities. That connection makes the mission personal and reinforces the importance of leading with care and integrity.
What are your current top priorities and responsibilities? How do these relate to your company’s overall mission/growth strategy?
My primary responsibilities are to provide clear strategic direction, strengthen leadership across the enterprise, and ensure disciplined execution across our portfolio of companies. I work closely with the Board and leadership team to align growth with long-term value creation.
Our strategy is built around responsible growth. We focus on building resilient businesses that perform well today while remaining strong and adaptable for the future. That balance is central to Chugach’s mission and how we operate.
Where do you and your team see growth opportunities in your current field or portfolio you support, or what do you anticipate to be your customers’ top pain points?
Our customers are facing increasing complexity, tighter resources, and greater expectations around performance and accountability. They need partners who are dependable, adaptable, and able to deliver consistently in demanding environments.
Organizations that can simplify complexity and deliver reliable outcomes will continue to earn long-term partnerships.
How are you and your team planning to address/prepare for these opportunities?
At Chugach Alaska Corporation, our strength lies in combining operational excellence and technical capability with trusted, consistent execution. We are focused on reinforcing that foundation while remaining agile and responsive to evolving customer and mission needs. This includes continued investment in our people, strengthening integration across our businesses, and enhancing the systems and processes that support disciplined execution and informed decision-making.
At the same time, we are committed to continuous improvement and intentional growth. By applying lessons learned, aligning our enterprise, and planning proactively, we are ensuring our teams are prepared to meet customer needs today while positioning Chugach to scale and lead as new opportunities emerge.
How important is mentorship & networking in GovCon? Were they influential to your career?
Mentorship and networking are important in any industry, and especially in GovCon, where experience and trust matter. Throughout my career, I have benefited from leaders who have shared their perspectives and helped me grow. Every interaction is an opportunity to develop a relationship.
I believe mentorship is part of responsible leadership. Developing people and preparing the next generation strengthens organizations and ensures continuity over time.
What is something most people don’t know about you personally?
I place a high value on gaining perspective from diverse viewpoints and experiences, and travel has played an important role in how I see the world and approach leadership. Spending time in different countries and cultures, including living and studying abroad, reinforced the importance of listening, humility, and understanding context before making decisions.
That global exposure shaped how I think about people, teams, and communities. It reminded me that while challenges may look different across regions, the fundamentals of trust, respect, and shared purpose are universal. Those lessons continue to influence how I lead and how I think about building organizations that operate responsibly and thoughtfully over the long term.