Current Industry

Date Joined

Referred By

Erin Underwood

It's a pleasure to introduce myself to the Chief of Staff Network. Here's a brief overview of my background and interests: My professional journey began in the Air Force, where I proudly served for 12 years before medically retiring. During my time in the Air Force, I had the incredible opportunity to fly F-15Es and also worked in the intelligence field. These experiences taught me the value of discipline, teamwork, and strategic thinking. Following my military service, I transitioned into the private sector as a government contractor. Here, I led product development and software delivery teams, leveraging my expertise to stand up specialized units within the USINDOPACOM. This experience sharpened my skills in project management and team leadership outside of the military. Currently, I serve as the Chief of Staff at a generative AI company, which has been at the forefront of utilizing AI to respond to both government and commercial RFPs. In this role, I am passionate about creating high-functioning and healthy organizations, while also fostering the development of brave leaders. Most recently, I made the bittersweet move back to the East Coast after spending the past four years living in Hawaii. While I miss the island life, I embrace the fresh opportunities that the East Coast offers. I have never met one that I didn't like and I cannot help myself from saying hello with a friendly head scratch! My professional journey has been diverse, encompassing military service, government contracting, and now the exciting realm of AI. I am passionate about building strong organizations, nurturing courageous leaders, and positively impacting both the government and commercial sectors. I look forward to connecting and collaborating with fellow members to discuss experiences, insights, and ideas!

Top Areas of Focus

Business Transformation / Org Change
Exec Team Organization & Mgmt
Government Relations
Internal Comms
Organizational Structure
People & Culture
Performance Development
Product Development
Project Management
Strategy & Planning
Team Offsites & External Events
Tech & Business Tools (Procurement)
Strategic Partnerships / BD
Change Management

CoS Start Date

Aug 21, 2023

Current Industry

Company Size




Previous Experience

Pro Tip

Sometimes it is better to sit back and take in a scenario than jump right in. Organizations want to move at the speed of light, and while it is important, it's also important to pace your decision-making and help your leaders pace theirs. By not jumping into the fray of a decision immediately, but listening to all sides and reflecting on the impact of both the big and small pictures, you'll provide better advisement to your leaders.


With over 15 years of experience in leading and building organizations of various sizes from inception, my expertise ranges from the precise demands of military structures to the dynamic processes of the civilian sector. In both military and civilian roles, change presents a significant challenge. I have experienced the highs and lows of implementing change within different organizations, yielding substantial insights into effective strategies and procedures. Recognizing the importance of easing employees through such changes, I focus on clear communication, empathetic leadership, and proactive strategies to mitigate resistance and enhance organizational acceptance. I am no stranger to personality conflicts within leadership teams. Successfully resolving these disputes requires understanding both interpersonal relationships and the broader impact on the organization. My approach involves fostering relationships and nurturing a proactive dialogue to prevent potential negative influences that can derail a team’s focus and productivity. I am very good at seeing both the tactical and strategic levels at the same time, which is a blessing and a curse! This dual perspective, although complex, allows me to visualize the intricate interplay of day-to-day operations with long-term objectives. However, I've learned that you often have to guide people up to the level at which you are talking or take them back down the stairs to see the day-to-day. Learning how to take people through each perspective without getting lost has been a huge learning curve for me, and is a competency in and of itself. This ability to shift between micro and macro-level management has been an invaluable skill in my journey.


I am really looking forward to the potential the Chief of Staff Network offers an excellent avenue for open conversations and collaborative problem-solving, invaluable in enhancing our skills within this role. I am hoping to sharpen my skills in informed decision-making, strategic planning, and organizational leadership. Leveraging shared challenges as a springboard for innovative solutions is something I look forward to in this network. I am keen on participating in workshops, conferences, and other group activities aimed at keeping up with industry trends. I also anticipate contributing my share of insights and experiences when they might be of value to fellow members. I'm excited about the journey of professional development and beneficial connections this network can offer.