Business Details
20 Years
experience
Emergency
services
Your Trusted Partner for IT Solutions
At Proper Sky, we revolutionize IT management through our unwavering commitment to practical solutions and client-centric philosophy. Founded in 2006, our company has grown from a single expert to a team of 20 professionals with decades of combined experience. We specialize in transforming technology into strategic assets through fully managed IT services, cybersecurity, and cloud solutions tailored to each client's unique needs. Our approach combines real-world expertise with continuous improvement, ensuring businesses achieve operational excellence and long-term growth. With 18+ years in business, 99% customer satisfaction, and recognition as ConnectWise IT Nation Evolve's Soaring Star Partner, we deliver 24/7 expert support that safeguards data, minimizes downtime, and maximizes productivity.Our team of certified professionals maintains transparency through strategic business reviews and personalized communication, aligning technology roadmaps with organizational goals. Backed by partnerships with Microsoft, AWS, and Google, we provide scalable solutions that adapt to evolving business landscapes while maintaining strict compliance and security standards.
Services
Fully Managed IT
Co-Managed IT
Managed Cybersecurity
Digital Transformation
Incident Response
Cloud Services
IT Strategy Alignment
Data Backup & Recovery
VOIP Solutions
Vendor Management
Details
- Year established: 2006
Highlights and features
- 18+ years delivering managed IT solutions
- 99% customer satisfaction score
- 24/7 expert support available
- Strategic IT planning with Virtual CIO access
- Cost optimization through predictable pricing
Associations and certifications
- Microsoft Silver Certified
- Amazon Web Services (AWS) Partner
What people say
Embedded staff
Perfect solution
Amazing support
24/7 availability
Cost savings
Services
Fully Managed IT
Comprehensive IT management covering infrastructure, security, and support. Our team handles strategy, monitoring, and maintenance while your employees focus on core business activities. Services include network management, Microsoft 365 administration, and vendor coordination with 24/7 helpdesk access. Proactive monitoring reduces downtime by addressing issues before they impact operations.
Managed Cybersecurity
24/7 threat monitoring and response protecting against ransomware, phishing, and data breaches. Solutions include endpoint detection, multi-factor authentication, and compliance management for HIPAA, SOC2, and CMMC standards. Our security operations center provides real-time alerts and incident response to minimize breach impact while maintaining regulatory compliance through regular audits and staff training.
Digital Transformation
Modernization services transitioning businesses to cloud platforms like Microsoft 365 and AWS. We implement secure collaboration tools, automate workflows, and optimize cloud costs while maintaining data integrity. Our cloud-first approach eliminates legacy server dependencies, enabling remote access and scalable infrastructure that grows with business needs while maintaining strict security protocols.
Co-Managed IT
Collaborative IT support augmenting internal teams with specialized expertise. Services include strategic planning, technical escalation support, and implementation of best practices for organizations maintaining in-house IT departments. We provide access to advanced tools and certified engineers without requiring full IT outsourcing, allowing internal teams to focus on strategic initiatives.
IT Strategy Alignment
Custom roadmap development aligning technology investments with business objectives. Our Virtual CIO service creates 3-year technology plans, conducts risk assessments, and optimizes IT budgets through lifecycle management. Strategic business reviews ensure continuous alignment between technology infrastructure and organizational growth goals while implementing standardized operating procedures for operational maturity.
People
Jim Smith
Founder & CEO
Founded Proper Sky in 2006 after Peace Corps service in Tonga. Drexel University MIS graduate with expertise in enterprise security and compliance. Recognized leader in strategic IT implementation for nonprofits and small businesses through 18+ years of industry innovation.
Rob
COO
18+ years operations leadership experience driving organizational efficiency improvements. Focuses on optimizing internal processes and client experience through cross-departmental synergy initiatives. Implements operational maturity frameworks that enhance service delivery consistency across all client engagements.
Jennifer Kennedy
Director of Finance
Finance operations expert specializing in budget optimization and strategic resource allocation. Brings extensive experience in financial planning for technology companies. Manages accounting functions while ensuring fiscal responsibility aligns with growth objectives through data-driven decision making.
Juan
Technology Alignment Architect
Certified A+, Security+, and Network+ technician with healthcare IT systems expertise. Specializes in electronic health records integration and SQL database management. Provides technical guidance aligning technology solutions with specific industry requirements while maintaining strict compliance standards.
Taylor
Security & Automation Engineer
Five-year IT security specialist developing automated threat response systems. Combines creative problem-solving with technical expertise to implement innovative security solutions. Conducts vulnerability research while maintaining practical security implementations that balance protection with operational efficiency.
Questions
What differentiates Proper Sky from other IT providers?
Our client-centric approach combines strategic planning with hands-on execution. Unlike traditional MSPs, we act as technology partners through Virtual CIO services, customized roadmaps, and transparent communication while maintaining 24/7 operational support.
How does billing work for managed services?
We use predictable monthly flat-fee pricing based on managed endpoints, typically $120-$200 per user. Additional services receive clear statements of work with defined deliverables to ensure complete cost transparency.
Do you support remote offices nationwide?
Yes, 90% of work is handled remotely with nationwide partner network support for onsite requirements. We maintain consistent service quality across all locations through centralized monitoring and standardized operating procedures.
How do you handle after-hours emergencies?
Our 24/7 monitoring team proactively detects and resolves issues before they escalate. Critical alerts receive immediate attention through dedicated incident response protocols, with direct helpdesk access available at 215.305.8899 for urgent matters.
Can you work with existing technology investments?
We maximize ROI by integrating with current infrastructure where possible. However, we may require upgrades for end-of-life systems or security vulnerabilities to maintain service quality and compliance standards.
What compliance frameworks do you support?
Our cybersecurity programs address HIPAA, SOC2 Type II, CMMC, and GDPR requirements. We conduct risk gap analyses, implement necessary controls, and provide documentation to ensure audit readiness for regulated industries.
