About Proper Sky Don't settle for mediocrity.

2,500 +
Users Supported
99 %
Customer Satisfaction Score
18 +
Years in Business

A Better Way to Manage IT- The Proper Way

At Proper Sky, we offer a better way to manage IT—The Proper Way. It’s not just IT support; it’s a philosophy that transforms technology into a strategic asset for your business. With real-world expertise, impactful conversations, and relentless execution, we deliver IT solutions that free you to focus on what truly matters.

The result? More time, more revenue, and more confidence to achieve your mission—whatever that may be.

No shortcuts, no nonsense. Just IT the Proper Way, only from Proper Sky.

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Exceptional People. Exceptional IT.

We pride ourselves as expert problem-solvers. We look at challenges as opportunities and we’re eager to work with you to address your IT needs quickly and efficiently so you can get back to doing what you do best.

When you speak with a Proper Sky team member, you are collaborating with people who are committed to keeping solutions practical while delivering expert support that’s backed by kindness, honesty and authenticity.

We know tech support is a hard job. This is why your IT is our priority.

Our Values What Drives Us? Our Core Values.

HARDWORKING

We associate ourselves with doers, pragmatists and executors. We believe effort ignites ability and turns it into accomplishment. We understand that our clients value effort, dedication and determination. We know they expect the same commitment and energy that they put into solving problems to be matched by a partner that sees work the same way they do.

APPROACHABLE

Transparency, an openmind, and willingnessto listen make usdifferent. From ourstanding morningmeetings to thesolutions we sell ourcustomers, we areopen, accessible andeasy to connect with.We create acomfortable,lighthearted space forcollaboration,communication, andinteraction foreveryone we workwith.

CURIOUS

Our customers and ouremployees seeobstacles asopportunities, labs totest hypotheses, andultimately viewembracing risk as partof what it takes to builda better mousetrap.We value pushingboundaries, exploringnewness and seekingto solve things better,faster, and smarter.

KIND

Tech support is a hard job. Because it’s hard, it’s important for us to associate ourselves with people and organizations whose attitude is one of kindness. The IT industry is rife with stereotypes of the bitter technician, and we work hard everyday to erase that. We give the benefit of the doubt, allow space for failure and success and do so with an attitude of kindness.

DRIVEN

We set, reach and exceed goals. We deliver value, outcomes and results because exceeding expectations for ourselves, our team and our customers is in our DNA. We hire and train experts: folks who love tech, folks who are builders, makers, and problem solvers, who help us build and nurture a culture of technical excellence.

Think you have what it takes?

Check our our open positions!

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Our History

  • March 1st, 2006

    Jim Smith Founds Company

    After returning from the US Peace Corp and in a fit of entrepreneurial fervor, Jim Smith decides to found an IT company dedicated to helping Small Business and Non-Profits with their technology.
  • April 6th, 2006

    Settled on Name

    Jim Smith writes algorithm to generate company names and petitions friends and family to weigh in on new name: Proper Sky is the winner. Trademark is registered and FEIN is submitted.
  • June 6th, 2006

    Hitting the Ground Running

    Proper Sky lands it’s first consulting contract. Builds Philadelphia Data Center for acquisitions and integrations. First physician group gets acquired, 4 providers, 24 staff in 4 locations, Proper Sky starts managing infrastructure and scaling for growth.
  • July 14th, 2006

    Official Google for Business Partner

    Proper Sky becomes an official Google for Business partner.
  • January 1st, 2008

    First Full-time Employee

    Proper Sky hires its first full-time employee.
  • February 1st, 2011

    First Office Opens

    Proper Sky opens it’s first office in Glenside, PA where it will remain for the next 9 years.
  • December 19th, 2014

    Proper Sky Joins HTG Peer Groups

    Proper Sky joins HTG peer groups (eventually IT Nation Evolve) and begins transition towards Managed IT Services.
  • January 15th, 2015

    Transition to Fully Managed Services Clients Only

    Physician group breaks up, with Proper Sky helping to grow the organization to 70 providers with 60 offices in 7 states with over 700 employees. Begins transition to fully managed services clients only.
  • October 15th, 2015

    Open First Managed Private Cloud Facility

    Proper Sky opens up its first managed private cloud facility in conjunction with Cogent and 365 Main at 37th and Market Street in Philadelphia.
  • February 17th, 2016

    Awarded First Microsoft Award

    Proper Sky is awarded it’s first Microsoft Silver Small and Midmarket Cloud Solutions competency
  • January 1st, 2017

    Website Launch & +1M in Revenue

    Proper Sky hit’s it’s first year of over 1M in revenue, launches propersky.com

  • August 20th, 2018

    #66 on the Philly 100 For the First Time

    Proper Sky lands number 66 on the 2018 Philly 100 List for the first time.

  • October 5th, 2019

    Amazon Partner and Certifications and Move to the Cloud

    Proper Sky becomes a certified Amazon Web Services partner with two Certified Cloud Practitioner Exams and 2 Cloud Solutions Architect certifications. Commits to “Killing the Server”, closes private data center at 3701 Market Street and transitions all our data center customers to public cloud.
  • December 4th, 2020

    "Hack the Ham" Sponsorship

    Proper Sky begins sponsoring the Cheltenham High School’s Computer Science Honor Society “Hack the Ham”,

  • November 11th, 2021

    New Office to Facilitate Growth. +2M in Revenue

    Proper Sky moves to 1916 Old York Rd, Abington PA to accommodate additional growth and expansion, hits 2M in revenue

  • November 6th 2023

    Wins ConnectWise IT Nation Evolves Soaring Star Partner Award

    Proper Sky wins ConnectWise IT Nation Evolves Soaring Star Partner award, awarded to fastest growing Revenue and EBITDA partner in the Evolve Peer group community.

  • March, 2024

    20th Employee, 16th Anniversary

    Proper Sky hire’s it’s 20th employee. Celebrates 16th anniversary of its first employee, creating the William Cariola award.

  • November 25th, 2024

    More Growth, More Awards

    Proper Sky wins Philly 100 for a second time, makes the CRN 150 (#101) as well as the IT Nation Evolve Longest Putt.

  • December 31st, 2024

    60% Growth Rate YoY, hits 4M in Revenue

    60% Growth Rate, year over year, hits 4M, Proper Sky, completes it’s newest rebrand and launches new website.

FAQs

Where did the Proper Sky name come from?

The first script Jim wrote upon his return to the country generated the new company’s name: Proper Sky. The second script Jim wrote scanned Craigslist for computer gigs and pinged his phone with promising leads. (If you’re thinking of launching your own IT company, you can still try out this code yourself.)

That script uncovered an opportunity to help a dermatology practice that wanted to jump start their business model with a new data center—that needed to be built from scratch. We helped that organization grow from just three providers to over 70, spread across seven states, running their company with secure databases and communications systems we built or managed along the way.

Over the past eleven years, Proper Sky has grown from a single expert to a team of ten with decades of experience between them. As a managed service provider, we’ve learned a lot about compliance, policy, and information security. We’ve also learned what success looks like by growing alongside our clients and helping them achieve their own goals.

How did Proper Sky come into existence?

After working full-time while attending school part-time for nearly 7 years, founder Jim Smith decided to join the Peace Corps. Spending much of 2003 stationed in a tiny, amazing country in the South Pacific called Tonga, Jim learned a thing or two about information technology.  

“I was assigned to run the nation’s largest technical college in the country, which at the time had about 400 students,” Jim recalls. “We had a 128 kbps modem equal in bandwidth capacity to the national bank and a budget that was equally hard to find on the map. It was in Tonga that I bumped into dozens of amazing organizations that all had one thing in common: terrible IT.”

Jim vowed that when he returned to the U.S, he would start an IT company where competency ruled, where solutions were practical, where we could work with honest companies that cared about their mission, and where customers looked at technology as a real differentiator instead of as a line item.

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From Philadelphia with love
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