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.

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.

Jennifer comes to us with several years experience in leveling up finance operations. She's big on collaboration, teamwork, and getting stuff done the right way. When she’s not working on budgets and spreadsheets, you’ll find her hiking up a mountain, skiing down one, or just soaking up the sun (basically, living her best life).

With over 15 years of IT industry experience, Drew leads Proper Sky’s service operations across Managed Services, Professional Services, and Strategy & Alignment, ensuring clients receive exceptional support and satisfaction. Known for being “calm in chaos,” he brings contagious energy, structure, and process-driven leadership to every challenge. Outside of work, Drew enjoys competitive pinball, F1 racing, building LEGO sets and 3D puzzles, golfing, and spending time with his cats, Cheddar and Ms. Em.

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.

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.

Matt brings nearly three decades of IT industry experience and a proven track record of leading complex technology initiatives across diverse industries. As Professional Services Manager at Proper Sky, he oversees the delivery of client projects from discovery through execution, ensuring technical excellence, strong communication, and measurable business outcomes.

With a deep background in Microsoft 365, Azure, Intune, and automation, Matt is known for building efficient, scalable systems that streamline operations and enhance security. He’s passionate about process improvement, client success, and empowering teams through mentorship and innovation.

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.

Meet our 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.

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.

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.

Mary Kate (a.k.a MK) has been working in the IT field for nearly 8 years. She enjoys solving the more complex technological challenges that the help desk role has to offer, but also finds time to decompress at her job doing more run-of-the-mill work such as out-of-the-box computer builds. In her spare time, she indulges in her passion of medieval reenactment in the Society for Creative Anachronism, and dedicates her evenings to fencing practice. She has been practicing for nearly 4 years, and hopes to someday achieve the highest level of recognition this activity has to offer.

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.

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

Anthony takes great pride in delivering exceptional customer service and ensuring every client interaction exceeds expectations. His passion for IT began early—experimenting with and repairing family and friends' computers sparked a lifelong interest in technology. Today, Tony excels at developing creative solutions to complex challenges, conducting in-depth research to resolve issues, and enhancing both client workflows and cybersecurity. Outside of work, he enjoys spending time outdoors and attending live music events. Go Birds!

Jannah began her career providing customer service and administrative support for healthcare and telecommunications accounts. In 2025, she joined Proper Sky as an Executive Assistant, where she leverages her organizational skills to manage tasks, coordinate schedules, and support day-to-day operations. Outside of work, Jannah enjoys spending time at home cooking, listening to jazz and classic tunes, and occasionally practicing sport shooting for fun.