Mid Level Underwriting Assistant Jobs
Mid level underwriting assistant jobs go to professionals ready to own the underwriting workflow end to end, guide junior staff, and deliver accurate risk assessments with minimal supervision. Openings run across Insurance, Banking & Financial Services, and Investment & Asset Management, with Corebridge Financial, GEICO, and AIG and other established carriers and financial services firms hiring at this level now.
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The preferred candidate for this position will reside in the Jackson, MS - Mobile, AL - Birmingham, AL triangle with travel required in and around that territory.
What You'll Do
The Territory Underwriter Specialist will be responsible for agent and broker relationships. In addition, you’ll:
Solicit accounts through select agents and brokers
Evaluate, underwrite, and price prospective accounts to select independent agents
Serve as the primary contact with assigned agents and brokers
Provide comprehensive sales expertise to increase production through agency channels
Work with assigned agents and brokers on the coordinating of resolutions
What it Takes
Bachelor’s degree or equivalent work experience
Minimum of 5 years related work experience, with multi-line middle market underwriting experience handling accounts in construction, manufacturing, wholesale, real estate, and service industries preferred
Knowledge of the Mississippi and Alabama marketplace, and existing or past relationships with larger independent agents preferred
Previous technical insurance experience, preferably with sales
Experience with underwriting large complex accounts
Exceptional communication and relationship building skills
Strong business and pipeline development skills
Ability to meet travel requirements as you’ll be prospecting new business opportunities in an agent office; meeting with insureds during safety inspections, and participating in mid-year claims review meetings
Ability to travel and have a valid driver’s license with the ability to maintain an acceptable motor vehicle record
What You'll Receive
At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.
Company car with gas card.
401(K) plan with a dollar-for-dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.
Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program
Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off
Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle.
Well-being and Employee Assistance programs
Sentry Foundation gift matching program to encourage charitable giving.
About Sentry
We take great pride in making Forbes’ list of America’s Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.
Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority.
Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.
Get ready to own your future at Sentry. Opportunities await!
Joe Larsen
Senior Talent Acquisition Specialist
Joe.Larsen@Sentry.com
Equal Employment Opportunity
Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.
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Find JobsMid Level Underwriting Assistant Job Market
Who's Hiring
- Corebridge Financial32

- GEICO7

- AIG6

- Origence3

- Arch Insurance Group3

Top Industries Hiring
- Insurance69
- Banking & Financial Services17
- Investment & Asset Management13
- Technology & Software5
- Consulting & Professional Services2
Mid Level Underwriting Assistant Jobs: Frequently Asked Questions
How do I get a mid level underwriting assistant job?
Position your experience around ownership and outcomes, not just task completion. Highlight specific files you managed independently, complex risks you assessed, and any process improvements you drove. Tailor your resume to show depth in a line of business, whether commercial lines, personal lines, or specialty coverage, and emphasize your comfort working directly with underwriters and brokers with limited oversight.
Which companies hire mid level underwriting assistants?
Companies hiring mid level underwriting assistants right now include Corebridge Financial, GEICO, and AIG, based on current listings on Migrate Mate as of July 2026. National carriers, regional insurers, and specialty markets are the primary employers at this level, often seeking candidates who can step in with minimal ramp-up time.
Are there remote mid level underwriting assistant jobs?
Yes, remote and hybrid options exist at this level, though many roles still prefer some on-site presence for team collaboration and file review. About 69% of mid level underwriting assistant openings are remote or hybrid as of July 2026, so flexibility is available if you target the right employers and lines of business.
How do I move up to a mid level underwriting assistant role?
The path to mid level is built through consistent demonstration of deeper technical skill and growing independence. Focus on mastering policy documentation, exposure to multiple coverage lines, and taking full ownership of submission workflows rather than just supporting others. Earning relevant designations and showing measurable impact, such as reduced error rates or faster turnaround times, signals readiness for the next level.
Which industries hire the most mid level underwriting assistants?
Mid Level underwriting assistant roles concentrate in Insurance, Banking & Financial Services, and Investment & Asset Management, based on current listings on Migrate Mate as of July 2026. These sectors drive hiring because they maintain large, complex books of business that require experienced support staff who can handle volume and nuance without constant supervision.