Proper Sky

Overview

About

Proper Sky, founded in 2006 and led by CEO Jim Smith, is a premier Managed Service Provider (MSP) headquartered in the Greater Philadelphia area. With nearly two decades of experience, the firm has built a reputation for delivering "Proper IT"—an approach that prioritizes long-term partnership over transactional service. They specialize in supporting small and mid-sized businesses (SMBs) with 20 to 300 employees, particularly those in complex, highly regulated sectors like healthcare, dermatology, and financial services. By emphasizing proactive system management and "embedded" IT support, Proper Sky helps organizations move beyond reactive break-fix cycles, turning technology into a predictable, scalable asset that drives operational efficiency. The firm’s service portfolio is designed to provide comprehensive digital peace of mind. Their core offerings include 24/7 IT helpdesk support, advanced cybersecurity and compliance management, cloud infrastructure strategy (Microsoft 365, Azure, AWS), and disaster recovery planning. Proper Sky is particularly noted for its maturity as an MSP, evidenced by its inclusion on prestigious industry rankings like the MSP 501 and the Inc. 5000. Rather than just maintaining hardware, they function as an extension of their clients' leadership teams, providing strategic vCIO consulting and "boots on the ground" support that allows companies to scale across multiple locations seamlessly. What truly distinguishes Proper Sky is its focus on transparency, communication, and human-centric service. Clients consistently highlight the firm’s "embedded" nature; their technicians don't just solve tickets—they understand the specific business challenges of the organizations they serve. Whether it’s helping a medical practice grow from a single office to 70 providers across seven states or assisting engineering firms with complex, multi-site infrastructure, Proper Sky’s methodology is built on a "learn, plan, execute" framework. This ensures that every technology solution is tailored to the client’s unique goals, risk profile, and growth trajectory. Furthermore, the company is deeply committed to technical excellence and professional development. They are a multi-award-winning partner, frequently recognized for their rapid growth and exceptional client satisfaction scores. For business leaders who are tired of "mediocre" IT support and are looking for a highly responsive, communicative, and strategically minded partner, Proper Sky offers the operational maturity and hands-on expertise necessary for lasting success. If your organization is ready to treat IT as a competitive advantage rather than a source of stress, engaging with the team at Proper Sky provides the professional roadmap needed to thrive in an increasingly digital landscape.