Managed IT & Support
Cybersecurity
Cloud, Backup & Network
A security risk assessment shows where your Chicago business could be hurt, how likely it is and what to fix first. You get a ranked, written plan in plain English, not a pile of scan output.
Get a Free IT AssessmentA security risk assessment answers three questions. What do you have that is worth protecting? What could go wrong? What should you fix first? It looks at your people, your devices, your accounts, your vendors and your habits, not just your firewall. The result is a short list of real risks, each with a rating and a recommended fix.
Many Chicago owners come to this after something unsettles them. A client sends a security questionnaire. A cyber insurance renewal asks questions nobody can answer. An employee clicks a bad link, or a laptop goes missing on the Blue Line. An assessment turns that vague worry into facts. You learn what is already solid, what is exposed and what would be expensive to ignore.
This is different from a vulnerability scan or a penetration test. Those tools find technical weaknesses. A risk assessment puts them in context. A flaw on a printer that holds no data matters less than a shared mailbox with no multi-factor sign-in that holds client contracts. You get a ranking that matches how your business actually runs, so your budget goes where it reduces the most risk.
Chicago has a dense mix of law firms, medical offices, accounting practices, agencies and distribution companies. Many hold client records, payment data or health information. Attackers do not care that you are small. They look for easy targets, such as reused passwords, unpatched laptops and email accounts with no second step. Most small business incidents start with something ordinary and fixable.
Pressure also comes from outside. Larger clients, lenders and insurers now ask how you protect data, and they want real answers. A written assessment gives you those answers and a dated record of what you reviewed and fixed. It also helps you plan. Instead of buying tools in a panic, you spend on the few items that matter most and schedule the rest over the next year.
Everything below is part of one monthly plan. Pick a topic to see what is handled for you and how it works in a Chicago office.
We start by listing what matters. That means client files, financial records, email, line-of-business software, laptops, phones and cloud accounts. We ask where sensitive data lives, who can reach it and how it moves in and out of your office.
Most owners find data in places they forgot about. Old shared drives, personal cloud storage and exported spreadsheets show up often. Mapping them first keeps the rest of the assessment honest, because you cannot rate a risk to something you do not know you have.
Next we check how your defenses hold up against the attacks that actually hit small businesses. Phishing, stolen passwords, ransomware, lost devices and misconfigured cloud settings come first. We look at email protection, multi-factor sign-in, patching, endpoint security and backup health.
We also review how your team behaves. Do people share passwords? Do departing staff keep access? Is anyone approving payment changes by email alone? These human gaps often cause more damage than missing software, and they are cheap to close once you see them.
Every finding gets two ratings: how likely it is to happen and how badly it would hurt. A weak password rule on a payroll system scores higher than an old monitor policy. The scores sort a long list into a short one you can act on.
We explain each rating in plain words. You will see why an item is high, what it could cost you in downtime or lost trust and what the fix involves. If you disagree with a rating because you know something we do not, we adjust it together.
The report ends with a sequenced plan. Quick wins come first, such as turning on multi-factor sign-in or removing unused accounts. Larger items, such as replacing aging equipment, are laid out over the coming months with typical cost ranges.
You decide what to do and who does it. Your current IT provider, an in-house person or our team can carry out the work. The plan is written so any capable technician can follow it, and it gives you a clear way to track progress.
A good assessment also tests your readiness. Who do you call first? Who can shut off an account at night? Where are the backups and when was the last restore test? Many businesses learn they have no written answer to these questions.
We help you capture the basics: contact lists, decision owners and first steps. That short page can save hours during a real incident. It also shows insurers and clients that you have thought about the worst day before it arrives.
Plenty of companies can fix a laptop. These are the three reasons clients mention most when they explain why they picked Ping Chicago.
Your technicians know how Loop high-rises handle building access, why basement server closets flood in summer storms and how long it really takes to reach Oak Brook at 4 p.m. That local knowledge turns into faster, calmer fixes.
Your network, devices and backups are watched around the clock. Most issues are caught and fixed before anyone in your office notices, and the rest are explained to you in plain English.
You get a written per-user quote after a free assessment, with every included service listed. No hourly surprises, no emergency rates and no fine print about what counts as extra.
Risks look different in a Loop high-rise than in a West Loop agency or a warehouse near O’Hare. We adjust the assessment to your building, your staff and the data you handle.
Most Loop offices share a building’s internet riser, wiring closets and security desk. Managed IT here means working with property management on access and cabling, keeping remote access stable for commuters and scheduling after-hours work around building rules.
Creative agencies need fast Wi-Fi for large files and constant video calls, while medical offices near Northwestern Memorial need HIPAA-ready systems. Both get the same help desk, with security matched to the data they store.
Teams here grow fast, so new hires need laptops, accounts and access on their first day. Managed IT keeps onboarding repeatable and the network ready for the next floor or the next office.
Point-of-sale systems, guest Wi-Fi and a handful of laptops can still take a shop offline. Managed IT separates guest and business networks and keeps payment systems updated and monitored.
Event, hospitality and professional offices near McCormick Place deal with seasonal rushes. Managed IT scales support around busy weeks and keeps shared and public spaces secure.
Practices and offices in Evanston and Skokie get the same remote help desk as downtown clients, with on-site visits scheduled for hardware, cabling and network work.
Logistics and distribution businesses near O’Hare run warehouses, scanners and shipping systems around the clock. Managed IT monitors those networks 24/7 and plans updates outside shift changes.
Many companies in Oak Brook, Naperville and Schaumburg run a suburban headquarters with a city branch. Managed IT connects both sites securely and supports staff at either location.
These three are often confused. Each answers a different question, and many businesses start with the risk assessment because it sets priorities for everything else.
| Topic | Ping Chicago | Automated Vulnerability Scan | Penetration Test |
|---|---|---|---|
| Main question answered | What are my biggest business risks? | Which systems have known flaws? | Can an attacker actually break in? |
| Covers people & policies | Yes, including habits & access | No, software only | Rarely, mostly technical |
| Typical output | Ranked risks & written action plan | Long list of technical findings | Technical report of exploited weaknesses |
| Plain-English results | Yes, written for owners | Often raw tool output | Technical, needs interpretation |
| Typical cost | Fixed price, scoped to your size | Low, often a few hundred dollars | Higher, typically thousands per test |
| Best starting point | Yes, sets priorities | Useful as one input | Best after basics are fixed |
| Helps with insurers & clients | Yes, dated written record | Limited on its own | Helpful but narrow in scope |
You finish with clear facts, a ranked plan and a budget you can approve with confidence.
You see every system, account and data store that carries real risk.
Each risk is rated so you fix the most dangerous items first.
A plain-English document you can share with partners, clients or insurers.
Each fix comes with a typical cost range so you can plan the year.
Different industries carry different data and different pressure, so the assessment focuses on what you must protect.
Client files, email security and access control matter most, with checks planned around court calendars.
Healthcare PracticesPatient data, shared workstations and imaging systems get close attention without disrupting appointments.
Accounting FirmsTax season raises the stakes, so we review file sharing, remote access and client data handling.
Financial ServicesAccount access, vendor risk and written records help you answer client and examiner questions.
Our old provider took a day to answer. Now a typical ticket is closed in about 12 minutes, and password resets happen while I’m still on the phone. Our staff stopped complaining about IT within the first month, which never happened before.
We were nervous about changing providers with deadlines ahead. The whole move took three weeks, email and files kept working throughout, and every login and device was documented. Not one person missed a day of work because of it.
We used to get surprise invoices every time something broke. Now it’s one predictable monthly bill, and problems get flagged before we notice them. Planning our IT budget takes five minutes instead of an argument with the owner.
After a free assessment you get a written, fixed-price quote. It lists what we will review, what you receive and when, with no surprise add-ons.
It is a structured review of what you need to protect, what threatens it and how well your defenses hold up. You receive a ranked list of risks, a written report and a practical plan for fixing the most important items first.
Most small business assessments are priced as a fixed project, typically from a few thousand dollars up, depending on staff count, locations and systems. Larger or regulated environments cost more. You get a written quote before any work begins.
Most small and mid-size businesses finish in two to four weeks. Interviews and data gathering take a few days, then analysis and the written report follow. Larger offices, multiple sites or regulated data can extend the timeline.
Very little. Most work happens in the background through reviews, interviews and read-only checks. We ask for short meetings with key people and schedule anything intrusive after hours or around your busy periods.
A risk assessment looks at your whole business and ranks what could hurt you most. A penetration test tries to break into specific systems. Most businesses benefit from the assessment first, then a test once the basics are fixed.
Many insurers ask detailed security questions at application and renewal. A written assessment helps you answer honestly and shows what you have done. It also points out gaps that could affect your coverage or premium.
Once a year is a sound habit for most businesses. Repeat sooner after a move, a merger, a major software change or a security incident. Smaller check-ins during the year keep your action plan on track.
We need limited, read-only access in some areas, such as your email settings and device lists. We agree on exactly what we will see in advance, and we do not change anything without your written approval.
Yes, if you want us to. You can also hand the plan to your current IT provider or in-house person. The report is written so any capable technician can follow it, and there is no obligation to hire us for the fixes.
Yes. Attackers use automated tools that hit thousands of businesses at once and look for easy openings. Small Chicago firms with client data, payment details or weak email protection are common victims, so a plan matters at any size.
Need something slightly different? These services cover the same ground from another angle.
A free assessment shows your biggest risks, what they could cost and what it takes to fix them.