Contractors and Seasonal Staff: Close the Security Gap Owners Miss

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Every fall, small businesses add people fast. The National Retail Federation expects retailers to hire between 325,000 and 375,000 seasonal workers this holiday season, and plenty of smaller shops, restaurants and service firms bring on extra hands that never show up in that number. Add freelancers, bookkeepers and part-time contractors, and your real team is bigger than your payroll list.

The people who join in a hurry are often the ones who get the least security setup. This is a practical guide to closing that gap without turning the owner into a full-time IT department.

Why Outside and Temporary People Matter

Verizon's 2026 Data Breach Investigations Report found that breaches with third-party involvement are up 60% from last year and account for 48% of total breaches. For small and medium-sized businesses, third-party involvement was 55%. The same report lists the top ways in for smaller businesses as exploiting vulnerabilities (26%), credential abuse (13%) and phishing (9%).

A caution on that number: Verizon's "third party" mostly means vendors, suppliers and service providers, not individual freelancers. The lesson still carries over. Anyone outside your core, well-managed staff, whether a company or a person, is part of your exposure, and a stolen login or a phished contractor is how many attacks begin.

The group is large, too. The Bureau of Labor Statistics counted 11.9 million independent contractors in July 2023, about 7.4% of employment. Broader surveys that count anyone who works independently put the figure far higher. If you pay people who are not on your regular payroll, you are working with this group.

The Shortcuts That Go Wrong

• Sharing one login. It is quick on day one and a mess on day thirty. You cannot tell who did what, and you cannot remove one person without changing the password for everybody.
• "Use whatever VPN you like." You will not know who is protected, and some free apps create problems of their own. See the risks of free VPNs.
• Nothing at all. A seasonal worker on shop Wi-Fi, a freelancer in a coffee shop and a contractor on hotel internet all use networks you do not control.
• Forgetting the exit. The access that was convenient in November is still alive in March. Our guide to the offboarding security gap covers what lingers.

A Simple Approach That Scales Up and Down

1. Give each person their own account

With CyberFence Teams, each person gets their own account. You invite people from the web dashboard, and they accept the invitation, set up their account and install CyberFence on their supported devices. A member can use their account across supported devices without buying a separate seat for each device.

2. Check that setup actually happened

The dashboard shows setup, device and connection information, so you can see who has connected, who has an account but has never connected, and whose invitation is still pending. CyberFence's own page is careful about this: use that information to guide follow-up, not as proof of continuous protection. A short message to anyone who has not connected yet usually solves it. For more, see how to know if employees are using the VPN.

3. Keep it respectful

Contractors and temps are more likely to cooperate when they know what you can and cannot see. The dashboard provides setup, device and connection information. It does not show their browsing history, DNS queries or destination IP addresses. Say that up front in your onboarding note.

4. Add seats when you hire, and reuse them when people leave

Seats can be added from the dashboard, with charges prorated to the current billing cycle. When someone leaves, you can revoke their access and make that seat available for another member. That matters for seasonal work: the person who finishes in January frees a seat for the freelancer you hire in February. Pricing starts at $24 a month for two people, billed annually, which is $12 per person/month. You can also choose monthly billing at checkout, which may suit a short seasonal team better, so look at both options before you buy.

5. Check the breach side too

Each seat includes Breach Monitor for the member's email address. It helps identify known exposure; it does not prevent a breach, and it cannot promise to find every exposure. If a contractor's email appears in a known breach, you can ask them to change that password before it causes trouble. See credential stuffing attacks to understand why reused passwords matter.

What It Looks Like in Practice

Picture a three-person gift shop heading into December. The owner brings on four seasonal helpers and a freelance bookkeeper who works from home two days a week. Instead of passing around the shop's logins, the owner invites each of the five new people from the team dashboard, asks them to install the app and connect on day one, and checks the dashboard that afternoon. Two helpers have not connected yet, so a quick text sorts it out. In January, three helpers finish. The owner revokes their access in one place, then reuses those seats for the spring part-timers. Nothing about it needs an IT department, only about ten minutes at the start and ten at the end.

What This Does Not Do

It is worth being straight about the limits, because a security tool is only part of the picture.

• It protects internet connections, not your company systems. CyberFence Teams helps protect each person's internet connection and blocks harmful websites with Web Shield, which uses lists of known bad sites. For private company systems or dedicated IP addresses, the Teams page tells you to contact the team to confirm requirements before purchasing.
• It does not replace access control. Give contractors only the accounts and folders they need, use multi-factor authentication, and remove access in your email, cloud storage and software tools when the contract ends.
• It is not a compliance shortcut. Team reporting can support your internal reviews, but no single product makes a business compliant.

A One-Page Checklist

Before day one

1. Decide which accounts and files the person needs, and nothing more.
2. Create their own logins. No shared passwords.
3. Turn on multi-factor authentication for every account they use.
4. Invite them to your team dashboard and ask them to install and connect on their devices.

In the first week

1. Check the dashboard to see that they have connected.
2. Remind them to use only company-approved tools and to report odd emails right away.

The day they finish

1. Revoke their access in the dashboard so the seat can be reused.
2. Remove their email, cloud and tool access.
3. Change any passwords they ever knew.

For permanent hires, our new-hire checklist goes deeper, and a simple remote work security policy gives you something to hand to everyone. If you are comparing options, read team VPN versus individual subscriptions.

The Bottom Line

The extra people who keep your business running through a busy season are not a security problem, but the way they are onboarded can become one. Give each person their own account, check that setup happened, respect their privacy, and take access back the day they finish.

Want to go deeper? Read the CyberFence competitor comparison hub , our free privacy and security tools , or CyberFence plans and pricing .