Our Team

AMAZING PEOPLE, EXCEPTIONAL RESULTS.

Jim Smith

Jim Smith

Founder & CEO

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.

Shana

Shana

CFO

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.

Kalin

Kalin

Centralized Services Manager

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.

Juan

Juan

Help Desk Manager

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.

Anthony

Anthony

Sales/Leadership

Always operating on the basis of "Do the right thing", Anthony joined Proper Sky's sales team as he saw that there was a similar sentiment shared here. He played college football, beat lymphatic cancer, has worked in the managed IT space for 15 years, is an avid fishermen, and does what he knows best - makes connections and lifts those around him

Daine

Daine

Dispatcher

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

Philip

Help Desk Technician

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.

Jodie

Jodie

Executive Administrator

Jodie recently joined Proper Sky and has since dove headfirst into the world of IT. Despite being new to the tech realm, she's fascinated by how IT influences our daily lives. Jodie's attention to detail and knack for administrative tasks make her a valuable asset in her role and to our team. Outside of work, Jodie loves unwinding at the beach, playing the guitar and collecting pink Himalayan sea salt.

Robert

Robert

Project Engineer

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.

Taylor

Taylor

Security & Automation Engineer

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.

 

 

Dan

Dan

Sr. Project Manager

Dan is Sr. Project Engineer at Proper Sky and has, objectively speaking, the best hair in the office. He's been in IT for 12 years and continues to learn something new every day. In his spare time you might catch him at the park with his dogs, out for drinks, or traveling the world.

 

GO BIRDS! 

David

David

Help Desk Technician

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).

Mack

Mack

Account Manager

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.

 

Lester

Lester

Help Desk Technician

Lester, based in our Philippines office, brings 15 years of diverse International BPO experience to Proper Sky, spanning roles in technical support, service desk, and customer success. Outside of work, he finds joy in playing basketball, a passion cultivated since his competitive days in high school and college. Lester cherishes his time with family and his eight furry companions – four dogs and four cats – at home.

Miles

Miles

Field Technician

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.

Andrea

Andrea

Director of Marketing

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.

 

 

 

 

Mike Z.

Mike Z.

Field Technician

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.

Michael G.

Michael G.

Strategic Alignment Manager

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.

John

John

Help Desk Technician

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.