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Entry Level Chicago Title Insurance Jobs (NOW HIRING)

Chicago Title

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Title Insurance Underwriter

Winston Salem, NC · On-site

$35K - $55K/yr

Occasional travel may be required for client meetings or training Company Description Chicago Title Insurance Company dates back more than 150 years through the succession of several firms and ...

Robinson Engineering, LTD

Land Surveyor

South Holland, IL · On-site

$83K - $104K/yr

Consulting with vendors regarding research and documentation resources (i.e., Property Insight, Chicago Title Insurance, Wheatland Title Insurance, Sidwell Company, HubTack). * Providing results of ...

USLI

Insurance Associate - Entry Level

Wayne, PA · On-site

$33K - $45K/yr

Benefits Canada Benefits Insurance Associate - Entry Level Location: Wayne, PA Team: Policy ... Policy Services & Underwriting Support FT/PT Status: Full Time Job Title: Insurance Associate ...

Monument Title Insurance Company

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Receptionist/Order Entry Specialist

Indianapolis, IN · On-site

$20/hr

Provides entry level administrative support including but not limited to typing, filing, printing ... CERTIFICATIONS, LICENSES, INSURANCE Title Producer's License (required) and will be completed ...

Monument Title Insurance Company

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Receptionist/Order Entry Specialist

Indianapolis, IN · On-site

$20/hr

Provides entry level administrative support including but not limited to typing, filing, printing ... CERTIFICATIONS, LICENSES, INSURANCE Title Producer's License (required) and will be completed ...

Crown Title Corporation

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Real Estate Law Processor/Paralegal

Catonsville, MD · On-site

$55K - $75K/yr

We are a busy title insurance company and real estate law practice seeking an entry-level or experienced real estate law paralegal or processor for our Catonsville office. Hybrid remote work ...

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Infographic showing various Entry Level Chicago Title Insurance job openings in the United States as of July 2026, with employment types broken down into 2% As Needed, 85% Full Time, 11% Part Time, and 2% Contract. Highlights an 90% Physical, 5% Hybrid, and 5% Remote job distribution.

Title Insurance Underwriter

Chicago Title

Winston Salem, NC • On-site

$35K - $55K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 18 days ago

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Job description

Job Title: Title Insurance Underwriter

Location: In Office – Winston-Salem

Job Summary

The Title Insurance Underwriter is responsible for reviewing, analyzing, and underwriting real estate transactions to determine insurability and issue title commitments and policies. This role involves assessing risk, resolving title defects, advising internal teams and clients, and ensuring compliance with underwriting guidelines, state regulations, and company standards.

Essential Duties and Responsibilities

  • Underwrite title insurance commitments, endorsements, and policies in accordance with company and regulatory guidelines
  • Review and analyze title searches, surveys, recorded documents, zoning matters, easements, restrictions, and other real property issues
  • Identify title defects, risks, and exceptions, and develop solutions to clear or insure over complex title matters
  • Draft and approve policy exceptions, requirements, endorsements, and special underwriting provisions
  • Provide underwriting guidance and technical support to escrow, closing, sales, and legal teams
  • Communicate effectively with clients, attorneys, lenders, and developers regarding underwriting decisions and risk mitigation
  • Interpret contracts, leases, loan documents, and other transaction‐related materials for underwriting purposes
  • Stay current on industry trends, underwriting practices, and applicable state and federal laws
  • Assist with training and mentoring staff, as needed
  • Maintain accurate documentation and ensure timely issuance of commitments and policies

Qualifications

  • High School Diploma or Bachelor’s degree strongly preferred
  • Minimum of 2+ years of experience in title insurance underwriting, real estate law, or related field
  • Strong understanding of real estate transactions, including acquisitions, refinances, and development projects
  • Excellent analytical, problem‐solving, and decision‐making skills
  • Ability to manage multiple files and deadlines in a fast‐paced environment
  • Strong written and verbal communication skills
  • Proficiency with title production systems and underwriting tools

Preferred Skills and Experience

  • Familiarity with complex endorsements and insured lender requirements
  • Background working with attorneys, lenders, and developers
  • Ability to balance risk management with client‐focused solutions

Work Environment & Physical Requirements

  • Primarily office‐based
  • Prolonged periods of sitting and computer use
  • Occasional travel may be required for client meetings or training

Company Description

Chicago Title Insurance Company dates back more than 150 years through the succession of several firms and corporations. We have a dynamic group and enormous opportunities for growth.