Setting Up a VPN for Your Business
Setup Guide

Setting Up a VPN for Your Business

Keep your team's connections private and your business data secure — whether they're in the office or working remotely.

The Basics

What Is a VPN?

A Virtual Private Network (VPN) creates an encrypted tunnel between a device and your business network, keeping data private even on public internet connections.

Think of it this way

Imagine you're sending a letter through the mail. Normally, anyone handling the letter could read it. A VPN is like putting that letter in a locked, tamper-proof box that only you and the recipient have the key to. Even if someone intercepts the box, they can't see what's inside.

How a VPN Works

Your Device

Employee laptop or phone

Encrypted Tunnel

Data is scrambled in transit

Business Network

Office files, apps, servers

Assessment

When Does Your Business Need a VPN?

Not every business needs a VPN. Here's how to decide if it's right for yours.

You Probably Need a VPN If...

  • Employees work remotely or from home
  • Staff travel and connect to hotel/airport Wi-Fi
  • You have on-premises servers or network resources
  • You handle sensitive client data (legal, medical, financial)
  • Compliance requirements mandate encrypted connections
  • You have multiple office locations that need to share resources

You Might Not Need One If...

  • Everyone works in one office location only
  • All your business apps are cloud-based (Microsoft 365, Google Workspace) with MFA enabled
  • You have no on-premises servers to connect to remotely
  • Your business doesn't handle highly regulated data
Note: Even cloud-first businesses can benefit from a VPN for added encryption when employees use public Wi-Fi.
VPN Types

Types of Business VPNs

Remote Access VPN

Connects individual employees to the business network from a remote location. Each user runs a VPN client on their device.

Best for: Businesses with remote workers who need to access office resources like file servers, printers, or internal apps.

Site-to-Site VPN

Connects two or more office networks together so resources can be shared as if they were on the same local network.

Best for: Businesses with multiple physical locations that need to share servers, databases, or phone systems.
Solutions

Comparing VPN Solutions

Click each solution to see details, pricing, and who it's best for.

Type

Mesh VPN (WireGuard)

Peer-to-peer connections, no central server needed

Pricing

Free for up to 3 users

Starter plan $5/user/mo for larger teams

Setup Difficulty

Very Easy

Install the app, sign in, done. No firewall config.

Key Features: Zero-config mesh networking, works behind firewalls/NAT, uses WireGuard protocol for speed, integrates with SSO providers, access control lists (ACLs), MagicDNS for easy device naming.

Type

Cloud-managed VPN

Centralized dashboard for managing all connections

Pricing

$8/user/mo

Lite plan, billed annually. Higher tiers available.

Setup Difficulty

Easy

Admin dashboard + apps for all platforms

Key Features: Dedicated servers & IPs, threat protection, device posture checks, SSO integration (Azure AD, Okta, Google), split tunneling, centralized management console.

Type

Open-source VPN protocol

Lightweight, fast, modern cryptography

Pricing

Free (open source)

Only cost is your server hosting (~$5-10/mo on cloud)

Setup Difficulty

Advanced

Requires Linux server admin skills

Key Features: Fastest VPN protocol available, minimal code base (4,000 lines vs 100,000+ for OpenVPN), runs on Linux/Windows/macOS/iOS/Android, full control over configuration and logs.

Type

Enterprise VPN

Requires Cisco firewall or cloud gateway

Pricing

Varies (enterprise pricing)

Typically bundled with Cisco security appliances

Setup Difficulty

Complex

Requires network engineering expertise

Key Features: Enterprise-grade security, integrates with Cisco security ecosystem, endpoint compliance checks, split tunneling, supports thousands of concurrent connections, trusted by Fortune 500 companies.

Feature Tailscale NordLayer WireGuard Cisco
Starting PriceFree / $5/user$8/user/moFreeEnterprise
Setup EaseVery EasyEasyAdvancedComplex
Best Team Size1-5010-5001-2050+
Managed ServiceYesYesNo (self-host)Yes
Our RecommendationMost SMBsGrowing teamsDIY techiesEnterprise
Getting Started

Setting Up Your VPN — Step by Step

We recommend Tailscale for most small businesses. Here's how to get started in under 15 minutes.

1

Create Your Account

Sign up at tailscale.com using your business identity provider (Google Workspace, Microsoft 365, or GitHub). This creates your private network — called a "tailnet."

Tip: Use your company's SSO provider (Microsoft or Google) so employees can log in with their existing work credentials.
2

Install on Your Devices

Download and install the Tailscale app on each device that needs VPN access. Available for Windows, macOS, Linux, iOS, and Android.

Also install on: Any servers, NAS devices, or office machines that remote employees need to reach.
3

Sign In and Connect

Each employee signs in with their work account. Once authenticated, their device is automatically added to your private network and can reach other devices on the tailnet.

4

Configure Access Controls (Optional)

By default, all devices on your tailnet can reach each other. Use ACLs (Access Control Lists) to restrict which employees can access which resources.

Example: Allow the sales team to access the CRM server but not the finance server. Allow IT admins to access everything.
5

Test the Connection

From a remote device, try accessing an office resource (file share, printer, internal app). If it works — you're done! If not, check the Tailscale admin console for status and troubleshooting.

Remote Security

VPN + Remote Work Security Tips

A VPN is just one layer of protection. Combine it with these practices for maximum security.

Always Use MFA

Enable multi-factor authentication on the VPN itself and all cloud services. A VPN protects the connection, but MFA protects the account.

Company Devices Only

Whenever possible, restrict VPN access to company-managed devices. Personal devices may lack security updates and endpoint protection.

Avoid Public Wi-Fi Without VPN

Train employees to always activate the VPN before connecting to coffee shop, hotel, or airport Wi-Fi. These networks are prime targets for eavesdropping.

Revoke Access Promptly

When an employee leaves the company, remove their VPN access immediately. This is often overlooked but is a critical security step.

Keep VPN Software Updated

VPN software itself can have vulnerabilities. Enable automatic updates and check the admin console regularly for outdated clients.

Use Split Tunneling Wisely

Split tunneling lets personal traffic bypass the VPN for faster browsing. Only enable it if your VPN solution supports it safely — otherwise, all traffic should go through the tunnel.

Action Items

VPN Setup Checklist

Track your progress — click each item as you complete it.

Progress 0 / 10
Assess whether your business needs a VPN (remote workers, on-prem servers, compliance)
Choose a VPN solution that fits your team size and technical skill level
Create an admin account and set up your VPN network
Install VPN software on all office servers and machines that need remote access
Install VPN client on all employee devices (laptops, phones)
Configure access controls so employees only reach what they need
Enable multi-factor authentication (MFA) for VPN access
Test the VPN connection from a remote location
Create a policy: "Always activate VPN on public Wi-Fi"
Document your off-boarding process to revoke VPN access for departing employees

Need Help Setting Up a VPN?

Simplissit can recommend, configure, and manage the right VPN solution for your business — so your team stays connected and secure.

Get Expert Help

© 2025 Simplissit. All rights reserved.