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Field Inspector 1099 Contractor

June 2, 2026

Company Story:

Seek Now is a customer experience-technology company leveraging a network of professional experts to provide data-driven inspections.

We deliver ground truth to property & casualty, real estate, and finance customers that enable them to solve their business problems in a matter of hours…minutes…seconds.

Seek Now is well-positioned to disrupt the inspection world through a combination of our hard-working 3rd party contractors, talented employees, vast network, and cutting-edge technology. For us, it is all about solving business problems for our customers. Our proven methods, commitment to excellence, and diverse team of professionals are what set Seek Now apart.

The claim volume and opportunity has never been greater than it is now. So, if you have been thinking about making a change, this may be a great fit for you and your business!

Position Summary:
Seek Now is searching for reliable, skilled, and experienced 1099 independent contractors to provide accurate, impartial, and complete home and commercial property inspections. Our 1099 Field Inspectors are experienced claim handlers with the capability and desire to access and inspect steep, high roofs and assist Outside and Inside Insurance Adjusters with amazing customer service.

Ideal candidates include 1099 independent contractors with:

Insurance Adjuster experience
Roofing sales or building experience
Strong team-first customer service attitude
Humility
Ability to access every roof
A reliable truck, van, or SUV
An operational laptop and smartphone
Ability to travel frequently, especially during catastrophic events such as hurricanes and tornadoes
Desire to increase income
HAAG Certification

Field Inspector 1099 independent contractor positions are available in all major US markets.

Whom You Are:

Climber – you can access every roof
Guardian – you make customers feel safe with you as you enter their homes and inspect around their most valuable possessions
Traveler – you support our clients immediately after a hurricane, tornado, or other weather catastrophe by traveling to those locations hit by the catastrophe
Dependable – you understand how critical your role is to the success of our business and yours, so you show up to appointments on time and on schedule consistently; you don't want to let your team or our customers down
Empathetic – you truly connect with customers and want to make every client a Seek Now brand advocate
Accountable – you create high-quality, accurate inspection reports on time every time
Tech Savvy – you know the basics of using a laptop and a smartphone – typing, navigating to different screens, working in Microsoft Outlook, Word, Excel, using different phone applications, etc.
Humble – you understand that you are a member of a team, and the team is only as strong as its weakest link
Customer Advocate – you deliver excellent customer service to every homeowner, adjuster, and client you encounter

Whom You are Not:

9 – 5 Office Worker – one that likes to work inside with the same schedule day after day
Acrophobic – one that is afraid of heights
Reactive – one that gets easily agitated by others
Current Roofing Contractor – one that wants to or will continue to work for/own roofing replacement or roofing repair company, as that would be a conflict of interest
Immobile – one that is unable to travel within a 100-mile radius daily and unable to be on assignment out of state for two (2) to six (6) weeks at a time multiple times a year

Essential Functions and Duties:

Climb two-story+ and steep roofs
Carry, set up, and safely climb a 32-foot extension ladder multiple times a day, several days a week
Lift, carry, and set up ladders and other equipment up to 100 pounds multiple times a day, several days a week
Sketch and measure roof and/or room components
Calculate the area of different sized and shaped roofs, rooms, and other inspection areas
Perform accurate, impartial, and complete roof inspections, which includes but is not limited to identification of roof age, leaks, deterioration, hail damage, wind damage, and previous repairs
Perform accurate and high-quality home and commercial property inspections
Enter required photos, measurements, and documentation via proprietary software application via smart phone and laptop within required reporting guidelines
Travel daily within a 100-mile radius to perform scheduled inspections, which includes an average of two (2) to five (5) hours of driving a day
Travel more than a 100-miles radius to perform inspections in areas hit by weather catastrophes when needed, which includes assignments averaging two (2) to six (6) weeks at a time
Maintain professional and safety standards required by insurance carriers
Partner with internal Seek Now team to complete daily tasks
Escalate customer and/or client issues when appropriate
Perform other duties as assigned

Supervisory Responsibilities:

This position has no supervisory responsibilities.

Knowledge, Skills, and Abilities:

Ability to climb and walk on any type of roof
Skilled in both verbal and written communication
Ability to use a laptop and a smartphone, which includes navigating between applications, entering data, and using Microsoft Office products
Ability to earn HAAG Certification within first year
Ability to submit complete, quality reports on time
Skilled in customer service
Skilled in organization and prioritization
Ability to be a self-starter and a quick learner
Ability to take assignments on short notice
Ability to travel daily within a 100-mile radius to perform scheduled inspections, which includes an average of two (2) to five (5) hours of driving a day
Ability to travel more than a 100-miles radius to perform inspections in areas hit by weather catastrophes when needed, which includes assignments averaging two (2) to six (6) weeks at a time

Education and Experience Requirements:

High school diploma or equivalent experience required
Minimum of two (2) years of experience in construction, service, or sales preferred
Previous experience as a roofer ideal
Experience with Microsoft Outlook, Word, and Excel required
HAAG Certification a plus
Experience with property and liability insurance coverage and standards a plus

Other Requirements:

HAAG Certification within first year, if not already obtained
Clean, reliable truck, van, or SUV
32-foot ladder
Operational laptop and smartphone
Professional appearance
Roofing boots
Valid driver's license
State Issued Workers Compensation
Certificate of General Liability Insurance
LLC Articles or Certificate of Organization

Work Environment:

Mostly outdoor for external inspections of property
Occasional indoor inspections of property
Fully remote

Physical Demands:

Must be able to stand and/or walk for long periods of time
Must be able to drive up to five (5) hours a day
Must be able to kneel, squat, or bend
Must be able to work outdoors in hot and cold weather conditions
Must be able to climb, crawl, stoop, reach, and work overhead
Must be able to lift, carry, push, and pull, up to 100 pounds
Must have continual use of manual dexterity in both hands
Must be able to lift files, open filing cabinets, and bend or stand on a stool as necessary
Must be able to routinely use standard office equipment such as computers, phones, and photocopiers

Position Type and Hours:

1099 independent contractor
You provide your availability

Travel:

100% of travel expected

Benefits and Perks:

Great earning potential – six figures plus, as we are Inc Top 200 fastest growing companies in America!
Paid weekly
Team-first environment
State-of-the-art, technology-based tool for inspections
Strong support team for our 1099 independent contractor field inspectors
Hotel fees paid/reimbursed on CAT jobs

Other Duties Disclaimer:

This job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee. Activities, duties, and responsibilities may change, or new ones may be assigned at any time with or without notice.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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