Meet Andrew (Drew), one of the newest members of the Proper Sky team and our Director of Service Operations. Drew brings more than 15 years of experience in the managed services industry, where he’s built and refined operational frameworks for service excellence.
Drew leads Proper Sky's service operations across Managed Services, Professional Services, and Strategy & Alignment, ensuring our clients receive the highest level of satisfaction and support. His responsibilities include driving utilization and efficiency, developing team talent, and aligning service delivery with company strategy and vision.
When asked what he enjoys most about Proper Sky, Drew says it’s the people, the vision, and the clients—all of which make the work both meaningful and rewarding.
What truly sets Drew apart is his balanced blend of energy, structure, and leadership. He brings a contagious enthusiasm to the team while maintaining a deep commitment to process-driven operations and continuous improvement. His focus on clear documentation and consistent execution helps keep the team aligned and efficient. Known for being “calm in chaos,” Drew has an exceptional ability to steady the ship when challenges arise—making him a true anchor in the fast-paced world of IT services.
When he’s not leading the team, Drew enjoys playing competitive pinball (he once traveled nine hours just to play!), watching F1 racing, and building intricate LEGO sets and 3D puzzles. He’s also an avid golfer and has 2 cats, Cheddar and Ms. Em.
