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Insurance Field Inspector

Derbyshire Field Services, Inc.
Woodbury, CT Contractor
POSTED ON 8/28/2026
AVAILABLE BEFORE 9/26/2026

IMMEDIATE FLEXIBLE FIELD WORK – Northern Fairfield, Litchfield, and Parts of Hartford County Regions

 

Primary coverage area is a 39 mile radius of Woodbury Connecticut.


If you enjoy working independently, planning your own day, and producing consistent results, this opportunity is built for you.

 

Derbyshire Field Services is seeking disciplined Independent Contractors to complete exterior residential and commercial field inspections for national insurance carriers. Our inspectors are the eyes of the insurance companies we represent.

 

This role is focused on the Northern part of Fairfield County Connecticut Region, parts of Hartford County and Litchfield County.

 

We are looking for a driven individual who values being on time, organized, and consistent. High performers who plan their routes well routinely complete 25 to 35 cases per day and build strong, steady income.

 

Who thrives here
You are a self starter who plans your day
You enjoy working alone and managing your own schedule
You take pride in finishing work correctly and on time
You are hungry to provide and grow
Veterans strongly encouraged to apply

 

About us
Derbyshire Field Services was founded with purpose. Our company exists in part to honor and support the survivors and the widow of a fallen officer who saved lives during a violent attack on our community in 2018. Discipline, service, and doing things the right way matter here.

 

What the work looks like
Exterior only property inspections
Residential and light commercial
Most cases do not require phone calls
Insureds are notified in advance by their insurance company
Route based work designed for efficiency

 

Training and support
Paid test cases during onboarding
One on one guided training to qualify for full field work
Live field support available when questions arise
Opportunities to expand territory and earnings based on performance

 

Requirements
Brief initial phone call before applying
Pass background check and drug test paid for by us
Reliable vehicle and practiced driving skills
Up to date smartphone
Willingness to use a selfie pole and measuring wheel which we guide you to obtain
Ability to work any hours with flexibility from Monday through Saturday between 8 am and 8 pm
Ability to submit work on time. Most cases are due within 14 days and some within 7 days

 

Compensation
Contract position
Typical earnings range $35 to $65 per hour based on productivity and cases completed per hour

 

Work location
On the road within a 39 mile radius of Woodbury, Connecticut.


With experience, opportunities to work in other areas of Connecticut, Massachusetts and New York

 

If you want flexible work with real volume, clear expectations, and the ability to grow based on performance, schedule a short 15 minute introductory call so we can see if this is a good mutual fit.

Company Description

We are the eyes of the major national insurance companies helping them assess policy risk by our quality photos from our field visits!

Salary : $35 - $65

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