Learn About CIO Landing: Chicago's Trusted IT Partner
Since 2012, we’ve been helping Chicago businesses leverage enterprise level-IT capabilities to drive growth and success.
Supporting Today’s Operations and Tomorrow’s Ambitions
CIO Landing was founded in 2012 with a clear vision: helping small and midsized Chicago businesses access the same level of IT capabilities previously only available to Fortune 500 companies.
We strive to be the most client-driven technology partner that, through our extensive business experience and quality of IT services, gives peace of mind to our clients so they can focus their time, energy, and resources on the unique demands of their company.
Our Mission?
Preparing your business for tomorrow by understanding your business today.
People First
We prioritize meaningful relationships with clients and team members, recognizing that technology serves people (not the other way around).
Focus on Needs
We not only focus on fulfilling a request but on the real need to be addressed.
Integrity
We communicate honestly, fulfill our commitments, and make recommendations based on what's genuinely best for your business.
Initiative
Rather than letting problems surface, we proactively identify and resolve potential issues before they impact operations.
Take Ownership
We shoulder responsibility for your technology success, treating your business with the same pride and care we show our own.
EOS-Driven Excellence
We operate using the Entrepreneurial Operating System (EOS) – a comprehensive business methodology that ensures every team member is aligned, accountable, and focused on delivering exceptional client outcomes.
For you, that means:
Consistent Service Delivery
Our systematic approach eliminates the variability that plagues many IT providers in Chicago.
Clear Accountability
Every member of our team knows their role and responsibilities in your success.
Proactive Problem-Solving
We’re skilled at identifying and addressing potential issues before they become your problems.
Continuous Improvement
Regular reviews and refinements ensure we’re always getting better at serving you.
Our Proven Process
Our comprehensive process takes you from identifying your IT needs to continually improving your technology landscape. We become a strategic ally, gaining deep insights into your business with our dedicated account managers and seamlessly integrating into your team.
Our approach transcends traditional IT support, offering stability, proactive solutions, and strategic guidance to equip your business for future success while addressing your current needs.
"Total peace of mind!"
“We have peace of mind knowing that CIO Landing handles our IT problems and is on point at any hour of the day or night. They have done so – hassle-free –for more than five years.”
Debbie
Law Services
Meet Our Innovators
At CIO Landing, innovation is in our DNA. Our team of dedicated IT professionals are passionate about revolutionizing the way businesses manage their technology infrastructure – none more so than our leadership team.
Juan Carlos Bosacoma
Founder and President
Find out more here!
Juan Carlos brings 30 years of IT industry experience and deep technical expertise to ensure CIO Landing clients receive the highest quality technology solutions.
Born in Bolivia and educated at the University of Buffalo (B.A. Computer Science) and University of Chicago (MBA), JC previously founded USHost.com, one of Chicago’s first Internet Service Providers, before establishing CIO Landing in 2002 to bring Fortune 500-level technology capabilities to small and medium-sized businesses.
JC is also a member of the Chicago CEO Roundtable, Illinois Hispanic Chamber of Commerce and University of Chicago Investment Club, and is an ex-oficio for the Honorary Vice-Council of Bolivia.
Hernan Silva
COO
Find out more here!
Hernan combines technical excellence with entrepreneurial experience, holding certifications including MCSE, HIPAA, VMware, and CompTIA Security+, plus a Cybersecurity certification from MIT.
Born in Argentina, he founded White Paper Computacion in Buenos Aires before moving to the US and establishing USA IT Help, which successfully merged with CIO Landing.
Hernan is known for solving complex technical problems while ensuring clients become raving fans of the company.
Santiago Susbielles
Finance Manager
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Santiago has been integral to CIO Landing’s financial operations since 2013, bringing extensive banking and financial expertise from his previous roles at Patagonia Bank and BICE in Argentina.
He holds a degree in Economics from the National University of the South and advanced Intuit QuickBooks certifications.
Beyond finance, Santiago is an accomplished author of “Build Your Financial Freedom” and brings a unique perspective shaped by his professional basketball background and passion for personal development.
Mauro Cretari
Director of Operations
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As Director of Operations at CIO Landing, Mauro Cretari brings over nine years of experience in the MSP industry, combining deep technical knowledge with strategic leadership to drive operational excellence.
Born and raised in Buenos Aires, Argentina, Mauro developed a strong sense of adaptability and out-of-the-box thinking—traits that have shaped his approach to solving complex challenges and leading high-performing teams.
At CIO Landing, he leads the alignment of operations with the EOS framework, oversees automation initiatives, and champions a company-wide culture of continuous improvement. Mauro also drives the company’s AI innovation strategy, identifying real-world applications that enhance service delivery, internal efficiency, and decision-making.
His leadership is grounded in a customer-centric philosophy and a strong security-first mindset—ensuring that every process, system, and solution is designed to protect clients while delivering measurable value. Now based in the U.S., Mauro brings a global perspective and results-driven focus to building systems and teams that consistently perform at their best.
Want to join the team?
Explore our open positions.
Frequently Asked Questions
Answers to the questions we hear the most often as one of the Midwest’s top cloud service solutions providers.
Think we’ve missed something?
Customer Service
Do I talk to a live person when I call?
Yes. During business hours (M-F 7AM – 7PM CST), our support team answers calls live. After hours, your call will be answered by our live answering service, and urgent issues will be escalated to our on-call technician. After-hours charges may apply.
How fast will you respond to my problem and is it guaranteed?
We guarantee to have a technician working on a problem within 60 minutes or less of your call. This is written into every service agreement we give to our clients because it’s standard procedure. So, yes it is guaranteed.
Will your technicians answer my questions in terms that I can understand and not speak geek-speak?
We believe we have perfected our hiring process and hire technicians are who are good communicators, can answer technical questions in plain English and will take time to answer your questions and explain everything in simple terms.
Do you offer new ways to improve my network’s performance?
We believe every small business should have a CIO or Chief Information Officer to oversee their technology needs. We conduct quarterly review meetings with our clients to look for new ways to help improve their operations, lower costs, increase efficiencies and resolve any problems that may be arising.
Our goal is to make sure our clients have the technology they need to be more profitable, efficient and competitive.
Do you provide detailed invoices that clearly explain what I am paying for?
We provide detailed invoices that show what work was done, why it was done and when it was done so you never have to guess what you’re paying for.
Do you have adequate errors and omissions insurance as well as workers compensation insurance to protect us?
In this litigious society we live in, we have chosen to be adequately insured with both errors and omissions insurance and workers compensation – and don’t be shy about asking to see our latest insurance policies!
Do you guarantee to complete projects on time and on budget?
Projects are fixed priced and guaranteed to be completed on time, in writing. This is important because many computer guys will only quote “time and materials,” which gives them free reign to nickel and dime you as well as take as much time as needed on completing a project.
Maintenance Of Your Network
Why do you insist on remote monitoring?
Our remote network monitoring system proactively monitors your network constantly looking for developing problems, security issues and other problems so we can address them before they turn into bigger problems.
Do you provide any reports that show what you did as far as all the updates, security patches, and status of every machine on our network so we know for sure our systems have been secured and updated?
Our clients get a detailed report that shows an overall health score of their network and the updates we provided to their antivirus, security settings, patches and other important network checks (like hard drive space, backups, etc.).
Do you provide any reports that show what you did as far as all the updates, security patches, and status of every machine on our network so we know for sure our systems have been secured and updated?
Our clients get a detailed report that shows an overall health score of their network and the updates we provided to their antivirus, security settings, patches and other important network checks (like hard drive space, backups, etc.).
Is it standard procedure for you to provide us with written, network documentation detailing what software licenses we own, critical passwords, user information, hardware inventory, etc.?
All clients receive this in written and electronic form at no additional cost. Quarterly updates are performed on this material to make sure certain key people from your organization have this information and know how to use it. We believe it is critical for you to have complete control over your network at all times.
It is our belief that you should never allow an IT person to have that much control over you and your company. If you get the sneaking suspicion that your current IT person is keeping this under their control as a means of job security, get rid of them (and we can help to make sure you don’t suffer any ill effects). This is downright unethical and dangerous to your organization, so don’t tolerate it!
Do you have other technicians on staff who are familiar with our network in case your regular technician goes on vacation or gets sick?
Yes. We keep detailed network documentation (basically a blueprint of your computer network) and updates on every client’s account so any of our technicians can pick up where another one has left off.
When you offer an “all-inclusive” support plan, is it truly all-inclusive, or are their “gotchas” hidden in the fine print?
Our “all-inclusive” support plan is just that – all inclusive. One of the more popular service plans offered by consulting firms today is an “all-inclusive” or “all-you-can-eat” managed services plan. These are actually a good thing because they’ll save you a lot of money in the long run – however, make sure you really understand what is and isn’t included. Some things to consider are:
- Is phone/e-mail help desk included, or extra?
- What about network upgrades, moves, or adding/removing users?
- Is hardware and/or software included?
- What are the costs/consequences of early cancellation?
- What if you aren’t happy with their services? Do they offer a money-back guarantee?
- If the hardware and software is included, what happens if you cancel the contract?
- Is offsite backups included? To what degree?
- If you have a major disaster, is restoring your network included or extra?
- What about onsite support calls? Or support to remote offices?
- Are home PCs used to access the company’s network after hours included or extra?
Backups & Disaster Recovery
Do you insist on monitoring an offsite as well as an onsite backup?
We do not encourage our clients to use tape backups because they are incredibly unreliable and leave you unprotected in many circumstances including fires, vandalism, floods, etc. We recommend our clients have an online backup service that meets the needs of their business.
Do you perform periodical test restores of your backups to make sure the data is not corrupt and could be restored in the event of a disaster?
We perform a monthly “fire drill” and perform a test restore from backup for our clients to make sure their data can be recovered in the event of an emergency. After all, the worst time to “test” a backup is when you desperately need it.
Do you backup up our network before forming any type of project or upgrade?
We do; and that’s simply as a precaution in case a hardware failure or software glitch causes a major problem.
Technical Expertise and Support
Do your technicians maintain current vendor certifications and participate in on-going training – or are they learning on our dime?
Our technicians are required to keep the most up-to-date vendor certifications in all the software we support. Plus, our hiring process is rigorous and most candidates do not make the grade.
Are you familiar with (and can they support) our unique line of business applications?
We own the problems with all line of business applications for our clients. That doesn’t mean we can fix faulty software – but we will be the liaison between you and your vendor to resolve problems you are having and make sure these applications work smoothly for you.
Do your technicians arrive on time and dress professionally?
Our technicians are professionals that you would be proud to have in your office. They dress professionally, show up on time and if they cannot (for some odd, unforeseen reason) we always notify the client immediately. We believe these are minimum requirements for delivering a professional service.
Trusted by Industry Leaders, Recognized for Excellence
Our excellence in managed IT services has been recognized by top industry lists, including the MSP Titans Award for Legal Services, MSP 501, CRN MSP 500, and the Inc. 5000.
Ready to Stop Worrying About IT?
Book a discovery call today.
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