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 leads every aspect of Proper Sky, from the talented leadership team that drives our day-to-day excellence to the long-term strategy that shapes how we serve clients for years to come. Working closely with Proper Sky's Founder and CEO, Rob translates vision into action, ensuring the entire organization is aligned, focused, and moving in the same direction. With over 20 years of experience running businesses across multiple industries, Rob brings a rare blend of operational depth and genuine passion for the client experience.

A mentor at heart, Rob is as invested in developing the leaders around him as he is in serving clients. He believes that when you build great leaders, you build a great company, and that belief shows up in how Proper Sky's team shows up for you every day.

His approach is simple: technology should work for your business, not the other way around. Rob is relentless about building scalable, proactive ways to manage your technology so your team can focus on what they do best, and you never have to wonder if your IT partner has your back.

Beyond keeping things running, Rob is deeply committed to thought leadership, helping business owners and leaders understand how the right technology strategy can drive real business outcomes, create competitive advantages, and support growth. He shows up not just as a vendor, but as a strategic partner who cares about where your business is headed.

That's not a tagline. That's IT the Proper Way.

Senior sales leader with 20+ years of experience in managed services, enterprise growth, and relationship-driven selling. I lead and coach high-performing sales teams, building strong pipelines, sharpening deal strategy, and creating a culture of accountability and execution. My focus is on demand generation, long-term client partnerships, and outcome-based solutions that deliver real business impact. I stay hands-on with teams and offerings to ensure we win in competitive, evolving markets.

When he's not carving up the mountain on his snowboard or cruising down the open road on his motorcycle, you'll likely find him in the backyard with tongs in hand, grilling for the people he loves most. Family is at the center of everything he does, whether that's spending quality time with his wife or simply soaking up time with those closest to him. A true enthusiast at heart, his passions span performance vehicles, two wheels, and the great outdoors, and he brings that same energy to the tech industry, where he's found his calling in leading and inspiring people who believe great teams are built on trust, passion, and a willingness to push beyond the familiar.

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).

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.

Brandon brings well over a decade of award-winning experience to Proper Sky, leading diverse teams, business development, and sales prospecting—spanning commercial and SLED (State, Local, and Education) contracting—for US-based IT organizations.

Brandon grew up in the fast-paced, culturally diverse suburbs of Washington, DC. He is an avid traveler who likes visiting destinations across the US and worldwide. Closer to home, he enjoys exploring Virginia's Blue Ridge Mountains and Shenandoah Valley. Outside of work, Brandon loves grilling on his deck for family and friends, and relaxing with his cat.

Taylor joined Proper Sky in February 2026 as an Account Manager on the Sales team. With a background in recruiting, customer service, sales support, and operations, she brings a well-rounded perspective to the business side of IT. At the core of everything she does is a genuine love for people — finding the right solution, building lasting relationships, and making sure every interaction leaves someone feeling supported.

Beyond her role at Proper Sky, Taylor's love for music, from live shows to working within the industry, reflects that same passion for people and meaningful experiences. 

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.

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.

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

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.

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!

Arthur was highly sought after and hired by Proper Sky in March of 2026 as a Sr. Help Desk Technician because he brings a multitude of highly refined skills in the IT field, a significant sized list of several completed certifications, as well as many years of experience that inspire his passionate drive in the IT field to his team and many of his clients. Between studying for his next certification or training, he is able to exceed expectations of his team, and customers. Additionally, he has a fun side too, he is an artist with skills in baking, cooking, and gaming. While heavily enjoying art- such as photography, drawing, painting, etc., He also loves to fish and play billiards. How can he be of service to you today?

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.

 

 

Luis joined Proper Sky in April 2026 as a Support Desk Technician. Like a lot of folks who end up in tech, his origin story starts with video games — watching the hardware leap forward from one console generation to the next was enough to keep him curious for life. He earned both his bachelor's in web design and his master's in cybersecurity from Chestnut Hill College, eventually pivoting to cyber after deciding he'd rather match wits with creative threat actors than watch AI quietly absorb the web design industry. Off the clock, Luis is on a mission to try every cuisine he can find, dreams about his next trip somewhere warm, and will go on record that pastelón is a perfect food.