Small Business Insurance Resources

Free actionable resources for small business owners shopping for commercial insurance — checklists, decision guides, and comparison matrices. Every resource is reviewed by Jason Wootton, our California-licensed P&C insurance agent (CA License #0I94454).

Available Resources · 10 items

Checklist · 12 steps

New Business Insurance Checklist

Step-by-step checklist for the commercial insurance decisions every new business owner faces. Reviewed by CA-licensed P&C agent Jason Wootton.

Open resource →Checklist · 11 steps

Food Truck Launch Insurance Checklist

Step-by-step insurance checklist for food truck operators — build-out to first event. Reviewed by CA-licensed P&C agent Jason Wootton.

Open resource →Playbook · 6 steps

Certificate of Insurance (COI) Request Playbook

How to request a COI from your agent, what's on it, and what to do when a client demands additional-insured status. Reviewed by Jason Wootton.

Open resource →Playbook · 6 steps

First 72 Hours After a Claim Playbook

What to do in the first 72 hours after an incident: document, notify your agent, preserve evidence, control communication. Reviewed by Jason Wootton.

Open resource →Checklist · 7 steps

Annual Insurance Renewal Review Checklist

What to check before insurance renews: limit adequacy, gaps, mid-year changes, premium drivers, questions for your agent. Reviewed by Jason Wootton.

Open resource →Checklist · 9 steps

Hiring Your First Employee: Insurance Checklist

What happens to your insurance when you hire employee #1: workers comp becomes mandatory, EPLI exposure begins, payroll-driven premium math kicks in.

Open resource →Playbook · 7 steps

Year-End Workers Comp Audit Prep Playbook

Year-end WC audit prep playbook: avoid 1.5-3x audit-bill shock. Records, NCCI codes, payroll definitions per state. What to gather before audit day.

Open resource →Playbook · 8 steps

First 72 Hours After a Cyber Incident: Response Playbook

First 72 hours after a cyber incident: forensic isolation, evidence preservation, ransom decision, breach-notification deadlines by state, regulators.

Open resource →Playbook · 7 steps

Subcontractor COI Collection Playbook (Prime Contractors)

Step-by-step COI collection playbook for prime contractors managing subcontractor compliance. NCCI proxies, lien-protection checklist, audit-trail template.

Open resource →Checklist · 8 steps

Buying a Business: Insurance Due-Diligence Checklist

Insurance due-diligence for small-business acquisitions: predecessor liability, claims-made tail coverage, COI assignment, loss runs, mod-factor migration.

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📘 Editorial standards. Resources are general educational tools — not insurance advice, not individual recommendations, not a solicitation in any state. Insurance regulations vary by state. For coverage decisions specific to your business, consult a licensed insurance agent in your state. See our editorial team.