Underwriting Assistant Jobs in Massachusetts
Underwriting Assistant jobs in Massachusetts are open across Boston, Worcester, and Middlesex County and other Massachusetts metros, with employers like The Hanover Insurance, Arch Insurance Group, and Corebridge Financial hiring at every experience level. Find a role that fits below and apply directly.
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INTRODUCTION
At Stewart, we know that success begins with great people. As a Stewart employee, you’ll be joining a company that was named a 2024-2025 Best Company to Work For by U.S. News & World Report, and a 2025 Top Workplace by USA Today. We are committed to helping you own, develop, and nurture your career. We invest in your career journey because we understand that as you grow, so does our company. And our priority is smart growth – by attaining the best people, investing in tools and resources that enable success, and creating a better home for all.
You will be part of an inclusive work environment that reflects the customers we serve. You’ll be empowered to use your unique experiences, passion and skills to help our company and the communities we serve constantly evolve and improve. Together, we can achieve our vision of becoming the premier title and real estate services company.
Stewart is a global real estate services company, providing title insurance, settlement, underwriting, and lender services through our family of companies. To learn more about Stewart, visit stewart.com/about.
More information can be found on stewart.com. Get title industry information and insights at stewart.com/insights. Follow Stewart on Facebook @StewartTitleCo, on Instagram @StewartTitleCo and on LinkedIn @StewartTitle.
JOB SUMMARY
Provide underwriting expertise and support to agents, customers, and company personnel, related to the issuance title insurance commitments and policies. Utilize underwriting standards and guidelines within delegated authority limits and make appropriate risk analysis to underwrite the issuance of title insurance in a wide array of real estate transactions. The ideal candidate brings strong technical underwriting judgment, clear communication skills, and a collaborative mindset. This is an on-site position in Waltham, Massachusetts.
JOB RESPONSIBILITIES
- Review, analyze, and evaluate title searches, surveys, and insurance risk factors relative to the issuance of title insurance for real estate transactions.
- Responsible for evaluating risk and exposures to determine acceptability of business.
- Provide high-level support to agents and approved attorneys ensuring accurate and appropriate commitments, pro forma policies, and final title policies are issued.
- Clearly explain underwriting requirements, exceptions, and risk considerations to internal and external customers in a straightforward manner.
- Serve as a subject-matter expert on title insurance and related law in Massachusetts.
- Determines premiums, terms and conditions based established rules, rates, and guidelines.
- Individual contributor working with direct oversight.
- Perform all other duties as assigned by management.
Education
- Juris Doctor (JD) is required.
Experience
- Typically requires 2+ years of related work experience.
- Admission to Massachusetts Bar.
PAY RANGE & BENEFITS
- $130,588.32 - $217,647.19 Annually. The base salary range provided is consistent with similar roles at the Company. The base salary range is not an absolute, but a guide, and actual offers will be based on the individual candidate’s knowledge, skills, education, experience, location, market conditions, and other compensation components. Depending upon all of the preceding considerations, the base salary may be lower or higher than the stated range.
Stewart offers eligible employees a competitive benefits package that includes, but is not limited to a variety of health and wellness insurance options and programs, paid time off, 401(k) with company match, employee stock purchase program, and employee discounts.
Equal Employment Opportunity Employer
Stewart is committed to ensuring that its online application process provides an equal employment opportunity to all job seekers, including individuals with disabilities. If you have a disability and need assistance or an accommodation in the application process, please contact us by email at careers@stewart.com.
See All 7 Underwriting Assistant Jobs in Massachusetts
Find roles in Massachusetts that match your experience and apply in just a few clicks.
Find Underwriting Assistant JobsUnderwriting Assistant Jobs by City in Massachusetts
Where Massachusetts roles are concentrated, by current openings.
Underwriting Assistant Job Market in Massachusetts
A snapshot from current Massachusetts openings, updated as new roles post.
Who's Hiring
- The Hanover Insurance2

- Arch Insurance Group1

- Corebridge Financial1

- First American1

- Starr Insurance Holdings1

Top Industries Hiring
- Insurance6
- Banking & Financial Services1
- Construction & Real Estate1
- Investment & Asset Management1
What Massachusetts Employers Look For
The qualifications that appear most often in underwriting assistant jobs across Massachusetts.
- Associate's or bachelor's degree in business, finance, or a related field
- Proficiency in underwriting management systems such as Applied Epic or ImageRight
- Experience reviewing insurance applications, policies, or endorsements for accuracy
- Strong data entry skills with attention to detail in high-volume processing environments
- Familiarity with property and casualty or life and health insurance products and terminology
- Progress toward or completion of an AINS, CPCU, or similar insurance designation
Underwriting Assistant Jobs in Massachusetts: Frequently Asked Questions
How many underwriting assistant jobs are there in Massachusetts?
There are 7+ underwriting assistant openings in Massachusetts on Migrate Mate as of June 2026, with the most roles in Boston, Worcester, and Middlesex County. New positions post regularly as employers across Massachusetts hire.
Which Massachusetts cities have the most underwriting assistant jobs?
Boston, Worcester, and Middlesex County have the most underwriting assistant openings in Massachusetts right now, with additional roles spread across smaller metros statewide.
Which companies hire underwriting assistants in Massachusetts?
Employers hiring underwriting assistants in Massachusetts include The Hanover Insurance, Arch Insurance Group, and Corebridge Financial, based on current listings on Migrate Mate as of June 2026.
Are there remote underwriting assistant jobs in Massachusetts?
Yes. About 57% of underwriting assistant openings tied to Massachusetts are remote or hybrid as of June 2026. The rest are on-site roles based in Massachusetts metros.
How do I apply for underwriting assistant jobs in Massachusetts?
You can apply to underwriting assistant jobs in Massachusetts directly on Migrate Mate. Search the listings above, find roles that match your experience and preferred Massachusetts location, then apply to each one that fits.
See All 7 Underwriting Assistant Jobs in Massachusetts
Find roles in Massachusetts that match your experience and apply in just a few clicks.
Find Underwriting Assistant Jobs