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Remote Insurance Inspector Jobs in Chicago, IL (NOW HIRING)

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Remote Insurance Inspector information

What is a Remote Insurance Inspector job?

A Remote Insurance Inspector evaluates properties, businesses, or assets for insurance purposes without needing to visit in person. Using photos, videos, documents, and virtual tools, they assess risks, verify policy details, and ensure compliance with underwriting standards. This role often involves analyzing reports, communicating with policyholders, and collaborating with insurance companies. Strong attention to detail and knowledge of industry regulations are essential.

What does a typical workday look like for a Remote Insurance Inspector?

A typical day for a Remote Insurance Inspector involves scheduling and conducting inspections of properties—often by analyzing submitted photos and documentation, or occasionally performing virtual walk-throughs with clients. Inspectors review policies, evaluate risk factors, prepare detailed reports, and communicate findings to insurance companies and policyholders. Most work is performed independently, though collaboration with underwriting teams or claim adjusters may be required. Depending on the employer, you might handle a flexible workload and use online systems to organize tasks and submit your findings efficiently.

What are the key skills and qualifications needed to thrive in the Remote Insurance Inspector position, and why are they important?

To thrive as a Remote Insurance Inspector, you need a solid understanding of property and casualty insurance, attention to detail, and relevant field experience, often supported by an associate degree or industry certification. Familiarity with inspection software, digital cameras, and cloud-based reporting systems is essential for completing and submitting inspections remotely. Strong organizational skills, self-motivation, and effective communication are important soft skills that help in managing caseloads and interacting with clients. These skills ensure accurate assessments, timely reporting, and high-quality service in an independent, remote work environment.

What are the most commonly searched types of Insurance Inspector jobs in Chicago, IL? The most popular types of Insurance Inspector jobs in Chicago, IL are:
What are popular job titles related to Remote Insurance Inspector jobs in Chicago, IL? For Remote Insurance Inspector jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Insurance Inspector jobs in Chicago, IL look for? The top searched job categories for Remote Insurance Inspector jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Insurance Inspector jobs? Cities near Chicago, IL with the most Remote Insurance Inspector job openings:
Remote Insurance Inspector jobs near you
Infographic showing various Remote Insurance Inspector job openings in Chicago, IL as of July 2026, with employment types broken down into 68% Full Time, 18% Part Time, 7% Temporary, and 7% Contract. Highlights an 100% Remote job distribution.
Client Success Manager (100%Remote - Chicago Area Preferred)

Client Success Manager (100%Remote - Chicago Area Preferred)

WIN Home Inspection

Chicago, IL • Remote

Other

Medical, Dental, Vision, Retirement, PTO

Posted 5 days ago

Job description

Job Description for Client Success Manager (100% Remote - Chicago Area Preferred):

Do you take pride in creating great experiences for others?

We're hiring a Client Success Manager to help franchise owners thrive by building relationships, coordinating solutions, and collaborating across teams.

About the Role

We're looking for a Client Success Manager who enjoys variety, thrives in a collaborative environment, and takes pride in helping others succeed . In this role, you'll build trusted relationships with our franchise owners while also working closely with colleagues across marketing, training, and operations.

Some days you'll be connecting with franchise owners, understanding their needs, and coordinating support. Other days you'll be reviewing a marketing initiative for relevance, helping organize a training session, or assisting with an operational rollout. You'll never be expected to know it all, you'll always have expert teammates to lean on, but over time, you'll grow your expertise so you can guide franchisees directly with confidence.

This role is ideal for someone with excellent people skills, strong organizational instincts, and the ability to juggle multiple priorities while keeping a positive, solutions-oriented mindset.

What You'll Do:

  • Serve as a trusted point of contact for franchise owners, building strong relationships

  • Champion and coordinate requests with internal marketing, training, and operations teams

  • Provide responsive, empathetic support and follow-through on client needs

  • Contribute to projects such as training programs, marketing reviews, and process improvements

  • Deepen your knowledge of our systems and processes to provide more direct guidance over time

What We're Looking For:

  • Friendly and empathetic with strong people and communication skills

  • Natural leader with a drive to grow professionally and personally

  • Quick learner, organized, and persistent in getting things done

  • 4+ years of experience collaborating with cross-functional teams (marketing, training, or operations)

Why WIN

  • 100% remote role (Chicago-area candidates preferred)

  • Collaborative, inclusive culture built on respect and growth

  • Health, dental, vision insurance + PTO + 401(k) match

  • Career development and advancement opportunities

  • A team that values working hard, having fun, and celebrating success together 

Apply