Remote and hybrid work has permanently changed the cybersecurity landscape for small businesses. These 10 practical tips will help Chicago-area teams stay secure no matter where they're working from.
The shift to remote and hybrid work didn't just change how Chicago businesses operate — it fundamentally expanded the attack surface that cybercriminals can target. When your employees were all in one office, your IT team could build a security perimeter around a single location. Now, every home office, coffee shop, and hotel lobby is a potential entry point into your business.
The good news: a focused set of security practices can dramatically reduce your risk, even with a fully distributed team. Here are 10 actionable steps every Chicago-area business should implement in 2025.
1. Require a Business VPN for All Remote Connections
A Virtual Private Network (VPN) encrypts the connection between a remote employee's device and your company network. Without it, data traveling over home or public WiFi is potentially readable by anyone on the same network.
Business-grade VPN solutions like Cisco AnyConnect, Palo Alto GlobalProtect, or WatchGuard's VPN client are very different from consumer VPN apps. They integrate with your identity system, log connection events, and enforce policy. Every employee working remotely should be required to connect via VPN before accessing any company resource.
2. Enable Full-Disk Encryption on All Devices
If a laptop is lost or stolen, full-disk encryption renders the data on it unreadable without the correct credentials.
- Windows: Enable BitLocker through your device management platform
- macOS: Enable FileVault in System Settings
- Mobile devices: Both iOS and Android encrypt by default when a passcode is set
Verify encryption is actually enabled — don't assume. A centralized device management tool makes this easy to confirm across your entire fleet.
3. Separate Work and Personal Devices
Allowing employees to use personal devices for work (BYOD) creates serious security gaps:
- Personal devices are less likely to have business-grade security software
- You can't enforce policies or remotely wipe a personal device the same way
- Personal and work data intermingle, increasing breach risk
Where possible, issue company-owned devices with managed security settings. If BYOD is unavoidable, implement a Mobile Device Management (MDM) solution that creates a secure work container on personal devices.
4. Keep Everything Patched and Updated
Outdated software is the number one vector for ransomware and malware infections. Every unpatched vulnerability is an open door.
Remote workers often miss patches because their laptops aren't on the corporate network when updates run. A managed patching solution pushes critical updates to devices regardless of where they're located.
Patch priority order:
- Operating system security updates
- Browsers (Chrome, Edge, Firefox)
- Office productivity software
- VPN and security clients
- Any software with internet-facing functions
5. Enforce Multi-Factor Authentication Everywhere
Multi-factor authentication (MFA) requires users to verify their identity with something they have (a phone app or hardware token) in addition to their password. Even if a password is stolen through phishing, MFA blocks the attacker from logging in.
MFA should be mandatory for:
- Email (Microsoft 365, Google Workspace)
- VPN access
- Any cloud application
- Remote desktop connections
- Financial and HR systems
Use an authenticator app (Microsoft Authenticator, Google Authenticator) rather than SMS codes — SMS is vulnerable to SIM-swapping attacks.
6. Secure Home WiFi Networks
Home routers are often years old, running outdated firmware, and using default credentials. Advise employees to:
- Change the default router admin password
- Use WPA3 encryption (or WPA2 if the router doesn't support WPA3)
- Keep router firmware updated
- Create a separate guest network for IoT devices (smart TVs, thermostats, etc.)
- Never conduct work on a public WiFi network without a VPN active
A simple one-page "Home Office Network Security Guide" distributed to all remote employees goes a long way.
7. Train Employees to Recognize Phishing
Phishing remains the most common entry point for business data breaches. Remote workers are particularly vulnerable because they're outside the social environment of the office where someone might say "did you really send that email?"
Run regular simulated phishing tests using tools like KnowBe4 or Proofpoint Security Awareness Training. Employees who click simulated phishing links receive immediate, in-context training. Track click rates over time — they should drop as training matures.
Key red flags to teach:
- Unexpected urgency ("Act now or your account will be suspended")
- Sender address that doesn't match the display name
- Links that hover to a different URL than displayed
- Requests for credentials or financial action
8. Deploy Endpoint Detection and Response (EDR)
Basic antivirus is not enough in 2025. Endpoint Detection and Response (EDR) tools like CrowdStrike Falcon, SentinelOne, or Microsoft Defender for Endpoint use behavioral analysis to detect threats that signature-based antivirus misses.
EDR provides:
- Real-time threat detection and automated response
- Visibility into what's happening on every device
- Forensic data when an incident occurs
For a small business, a managed EDR service through a provider like TechniWorx gives you enterprise-grade protection without needing an in-house security analyst.
9. Back Up Everything to the Cloud
Remote workers create and modify files on local drives, in cloud storage, and in SaaS applications — often in ways that your on-premise backup doesn't capture. A comprehensive cloud backup strategy should include:
- Microsoft 365 / Google Workspace data: Email, Teams chats, SharePoint/Drive files — these are NOT automatically backed up by Microsoft or Google
- Local device backups: Cloud-based endpoint backup (Acronis, Veeam) for files stored locally
- SaaS application data: CRM, accounting software, project management tools
Test restores quarterly. A backup you've never tested is not a backup.
10. Implement Mobile Device Management (MDM)
MDM platforms like Microsoft Intune, Jamf, or Hexnode give IT administrators control over every device accessing company resources, whether company-owned or personal. MDM enables:
- Remote wipe if a device is lost or stolen
- Enforcing screen lock, encryption, and minimum OS version policies
- Blocking access from non-compliant devices
- Pushing security configurations and certificates remotely
When an employee leaves your company, MDM lets you immediately revoke all access and wipe company data from their device — even if it's a personal phone.
Putting It All Together
You don't have to implement all 10 of these measures at once. A phased approach — starting with MFA, VPN, and patching — delivers the biggest risk reduction fastest. From there, layer in endpoint protection, MDM, and backup to build a comprehensive remote security posture.
The goal isn't perfect security — it's making your organization a harder target than the next one, and having the visibility to detect and recover when something does go wrong.
Need Help? TechniWorx helps Chicago-area businesses build and manage remote workforce security programs. From MDM rollout to phishing training to full security assessments, we make enterprise-grade security accessible for growing companies. Claim your free security consultation at techniworx.com.