If you’re working with independent contractors across multiple projects, you’re not alone—and you’re not without risk. In industries like construction, tech, creative services, and logistics, the use of 1099 contractors is no longer the exception—it’s the standard.

But here’s the catch: with every additional contractor comes more administrative complexity, more legal exposure, and more insurance risk.
The good news? A few key systems can help you scale contractor management without letting things slip through the cracks.

As an insurance partner to hundreds of businesses, we’ve seen what works—and what doesn’t. Here are the top best practices to manage multiple contractors safely, efficiently, and with full compliance.

1. Centralize Your Contractor Onboarding

Whether you’re working with 3 or 30 contractors, standardization is your best friend. Every contractor should go through a unified onboarding process that includes:

Completion of a contractor agreement
Submission of a valid Certificate of Insurance (COI)
A review of their insurance coverage types and limits
Acknowledgement of project-specific expectations

Tools like Bunker’s contractor onboarding platform make this seamless—allowing you to send insurance requirements, verify compliance, and track it all in one place.

2. Define Clear Insurance Requirements by Role

Not every contractor needs the same insurance. A freelance software developer and a general contractor on a jobsite face different risks. To keep things compliant (and fair), define coverage by role:

Contractor Type	Recommended Insurance Coverage
Construction Subcontractor	General Liability, Workers’ Comp, Commercial Auto
Marketing Consultant	Professional Liability (E&O), Cyber Liability
Delivery Driver	Commercial Auto, General Liability
Software Engineer	Tech E&O, Cyber Liability

And always include “Additional Insured” language to extend certain protections to your business.

3. Don’t Rely on One-and-Done COIs

A single Certificate of Insurance doesn’t mean a contractor is insured forever. Many policies are only active for 6–12 months, and coverage can lapse at any time.

Best practice:
Use an automated COI tracking system (like Bunker) to:

Track expiration dates
Get notified of lapses in coverage
Automate renewal reminders to your contractors

Staying on top of this ensures your business is never caught off guard.

4. Assign a Compliance Owner

When multiple departments are hiring contractors across projects, insurance compliance can fall through the cracks. Avoid this by assigning a dedicated compliance coordinator or admin responsible for:

Enforcing insurance requirements
Maintaining documentation
Serving as the go-to point of contact for questions

If you’re a smaller team, tools like Bunker can act as your virtual compliance assistant—handling COI collection, validation, and tracking automatically.

5. Use Contracts That Align With Insurance Coverage

Contracts should always reflect the real-world risks of each contractor’s work. Make sure they include:

Hold harmless and indemnification clauses
Clearly stated insurance requirements
A requirement to name your business as an additional insured

Need help aligning your insurance and legal language? Bunker offers templates and consultation support to ensure your contracts and COIs work in tandem.

6. Build a Shared Project Calendar or Dashboard

From a project management perspective, it’s critical to track which contractors are working where, when, and under what scope.

Use a shared dashboard to centralize:

Project timelines
Contractor assignments
Associated COIs and agreements

This helps avoid duplicate work, expired coverage, and accidental misclassification (which can lead to fines or lawsuits).

7. Educate Your Contractors Early

Insurance shouldn’t be an obstacle—it should be part of the conversation from the start. Offer your contractors:

A guide or FAQ on required insurance
Support accessing affordable coverage (Bunker can help!)
Clear communication on the consequences of non-compliance

When contractors know what’s expected and feel supported, compliance goes up—and your legal risk goes down.

Conclusion: Structure Is the Secret to Safe Scaling

Managing multiple contractors across projects doesn’t have to be overwhelming. With the right infrastructure—standardized onboarding, automated COI tracking, and role-based requirements—you can grow your workforce without growing your risk.

At Bunker, we help businesses like yours simplify contractor management by making insurance easy for everyone involved.

Ready to streamline your contractor workflows and stay protected?
👉 Learn more at buildbunker.com