Amazing people. Exceptional results. Our Team

A Philly native, Jim studied Managed Information Systems at Drexel University. He served in the Peace Corps in Tonga, where — after facing the challenge of managing IT at a college of 400 students with no budget — he found his true calling of providing cost-effective IT solutions to small businesses and nonprofits. Jim is a leader in the enterprise security space, including policy, compliance, best practices, and lately, as a small business owner, on using metrics to consistently drive organizational improvements.

Finance has been in Shana’s blood from an early age. Prior to joining Proper Sky full-time in 2015, Shana privately consulted for regional companies in the areas of accounting, budgeting, and forecasting, with Proper Sky as one of her first clients in 2011. Leveraging this broad market experience, Shana joined Proper Sky full-time to help oversee the financial department, manage client relations, and execute on projects with team members.

Rob comes to Proper Sky with over 18 years of experience in leading and managing various aspects of business operations, including service, account management, and client experience across different industries. As the COO, Rob’s focus is on improving the operational maturity and efficiency of the company to better serve our clients and creating better synergies between teams and departments to align the culture with the vision and values of the organization.

Rob started at Proper Sky in October 2023 but has been in IT for 17 years. He enjoys working IT because there is always more to learn and things changing - it doesn't get dull. Outside of work he enjoys watching any and all Philadelphia sports teams.

Prior to joining Proper Sky, Michael has worked various Client Strategy roles in the managed services industry -- helping small business clients achieve their goals through technology. He enjoys giving clients a supportive positive experience, and loves bringing value to client's businesses through IT. He is passionate about seeking measurable change, via metrics and reporting. Outside of IT, he enjoys a good book, trying new foods, gaming and creating art.

Kalin’s interest in computers and information technology began at an early age; his mother taught programming and informatics at the local school, and she would take him with her to classes. Later, he attended Drexel University, where he became a “double dragon,” earning both a BS and an MS in information systems. Since October 2015, Kalin has been part of the Proper Sky team and is currently overseeing mission-critical systems such as remote monitoring and management and cloud- based services.

Taylor has been diving deep into the world of IT for a solid five years now, rocking a role that's all about security and automation. But what really lights up his day at Proper Sky? It's when he gets to blend his creative mojo with his tech savvy to whip up some seriously cool solutions for our customers. When he's not crunching code, you'll probably find Taylor knee-deep in vulnerability and security research. But hey, the guy's not all about bits and bytes – he's also a big fan of nature. Give him a forest to wander through, and he'll happily get lost for hours. And if you catch him on the right night, you might even hear him sharing a few words with the moon.

Incredibly good looking & modest, Juan came to Proper Sky at the end of 2019. Juan is an A+, Security +, and the Network+ certified technician. Juan also has experience working with electronic health records and SQL databases. He really enjoys helping customers as well as his peers.

Prior to Proper Sky, Mack built his career in customer/project management. He enjoys IT because of how fast it moves. He gets satisfaction seeing the measurable difference in his efforts and likes that the environment is ever-changing. Outside of work, Mack enjoys playing the guitar, spending time with his family, and fighting the war against gravity in the gym.

Meet our vibrant Director of Marketing, Andrea, who thrives on data and user experience. With a knack for crafting and implementing comprehensive marketing strategies, she comes to us with a 15-year track record in the MSP space, driving new business though innovative digital marketing campaigns. You name it – from strategic planning to lead generation to rolling out new products and expanding market reach, Andrea has a hand in it. If there's one thing you can count on, it's her unwavering dedication to the team and success of the business. An avid traveler and frequent concert goer, Andrea loves living life to the fullest.

Daine started at Proper Sky in May of 2022. Before Proper Sky, he worked as a call center agent in healthcare, ISPs, and TV tech support, as well as one of the larger B2B fitness software providers in the world. Outside of work, Daine enjoys trying new foods and listening to new music.

Philip has been at Proper Sky for a year and has been in IT equally as long. He is a collector of vinyl and is musically inclined. He enjoys difficult puzzles which largely contributes to his love for his IT. He is new to the field but is working towards being a penetration tester.

David is a Level 1 Technician at Proper Sky. He's worked in IT for 8 years. While he did go to school to be a Computer Programmer, he found IT was more fulfilling after college. He's a scratch golfer, loves tabletop games, and is probably better than you at World of Warcraft (amongst other games).

Miles is a Field Technician at Proper Sky, where he thrives on engaging with customers in person to troubleshoot their IT issues. Raised in a homeschooling environment, Miles developed a passion for technology from a young age, which ultimately drove him to pursue an IT degree at Penn State University. He is currently dedicated to obtaining various certifications to further enhance his expertise. Beyond his professional pursuits, Miles enjoys hobbies such as writing and producing hip hop music, as well as video editing.

Mike, one of our Field Engineers at Proper Sky, finds joy in delving into our clients' businesses and understanding their unique technological needs. His passion lies in assisting others, finding fulfillment in witnessing his daily efforts contribute to lasting client success. Beyond work, Mike immerses himself in reading, watching movies, exploring the city on day trips, or simply enjoying the company of friends. Additionally, he indulges in his love for music by playing the piano.

John, a recent college graduate in 2023, embarked on his first IT job with Proper Sky and is doing so with zeal and enthusiasm. He finds fulfillment in IT work due to the constant problem-solving opportunities and the ever-evolving challenges it presents, all while having the chance to make a meaningful impact by assisting others. Outside of the IT world, John treasures moments spent with family and friends, whether it's engaging in snowboarding adventures or passionately cheering on Philadelphia sports teams.

With 20+ years in the restaurant industry and four in IT, PJ knows how to connect with people and solve business challenges. His background in sales and leadership makes him a perfect fit for helping clients find the right tech solutions. He thrives on teamwork, collaboration, and Proper Sky’s supportive environment. PJ loves making a real impact by helping businesses run more efficiently.

Charlie is a dedicated Helpdesk Technician and the first point of contact for many of our clients, handling incoming calls and resolving issues quickly and efficiently. With over a decade of experience in IT support, he brings deep technical knowledge and a commitment to excellent customer service. Always ready to troubleshoot and assist, Charlie ensures smooth and swift resolutions to keep businesses running. Outside of work, he’s a proud father of four and an avid sports enthusiast