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Sentry Insurance Jobs (NOW HIRING)

Sentry Insurance

Trial Attorney - In-House Counsel

CA · Remote

$159K - $238K/yr

Represent the interest of the insured and Sentry in defending claims, ensuring that there is no conflict of interest between the policyholder and Sentry. * Handle a full caseload of minimally to ...

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$31K

$65.8K

$83K

How much do sentry insurance jobs pay per year?

As of Jun 15, 2026, the average yearly pay for sentry insurance in the United States is $65,848.00, according to ZipRecruiter salary data. Most workers in this role earn between $60,000.00 and $75,000.00 per year, depending on experience, location, and employer.

Is Sentry Insurance a good company?

Sentry Insurance is a well-established insurance provider known for its stability and employee benefits. The company generally receives positive reviews for its work environment and job stability, making it a reputable employer in the insurance industry.

What are the key skills and qualifications needed to thrive as an Insurance Agent at Sentry Insurance, and why are they important?

To thrive as an Insurance Agent at Sentry Insurance, you need strong sales abilities, knowledge of insurance products, relevant state licensure, and often a bachelor’s degree or equivalent experience. Familiarity with customer relationship management (CRM) software and quoting systems is typically required. Outstanding interpersonal skills, active listening, and problem-solving abilities help agents build trust and address client needs effectively. These skills are vital for meeting sales targets, ensuring customer satisfaction, and maintaining compliance in a competitive insurance market.

What is the difference between Sentry Insurance vs Claims Adjuster?

AspectSentry InsuranceClaims Adjuster
CredentialsLicenses, insurance certificationsLicenses, insurance certifications
Work EnvironmentOffice, remote, fieldOffice, remote, field
Industry UsageInsurance provider, underwritingInsurance, claims processing
Primary RoleInsurance provider, risk assessmentEvaluate and settle insurance claims

While Sentry Insurance is a provider offering various insurance products, a Claims Adjuster is a professional who evaluates insurance claims on behalf of insurers like Sentry. Claims Adjusters work directly with policyholders to assess damages and determine payouts, whereas Sentry Insurance manages the overall insurance policies and underwriting processes.

What opportunities for professional development and advancement are typically available to employees at Sentry Insurance?

At Sentry Insurance, employees often benefit from a range of professional development opportunities, including ongoing training, mentorship programs, and support for industry certifications. The company encourages internal mobility, allowing employees to explore different roles or departments based on their interests and performance. Advancement is typically based on a combination of demonstrated skills, leadership potential, and contributions to team goals. Employees are also supported through structured performance reviews and clear career pathways, helping them to grow within the organization.

Is Sentry a good company to work for?

Sentry Insurance is generally regarded as a stable employer with a focus on employee benefits and professional development. The company offers a collaborative work environment and values skills in insurance, risk management, and customer service. Employee reviews often highlight positive workplace culture and opportunities for growth.

What is the highest paid job in insurance?

In the insurance industry, executive roles such as Chief Executive Officer (CEO) or Chief Underwriting Officer tend to be the highest paid, often earning six-figure salaries plus bonuses. These positions require extensive experience, leadership skills, and industry knowledge, and may involve overseeing company strategy, risk management, and operations.

What is the highest paying insurance agent job?

The highest paying insurance agent roles are typically senior or specialized positions such as captive agents working for large insurance companies or those with extensive experience and a strong client base. These roles often offer higher commissions, bonuses, and incentives, especially for agents selling high-value or complex policies like commercial or specialty insurance. Earning potential increases with certifications, expertise, and sales performance.

What is Sentry Insurance?

Sentry Insurance is a mutual insurance company that provides a variety of insurance products, including business insurance, personal auto insurance, and life insurance. Founded in 1904 and headquartered in Stevens Point, Wisconsin, Sentry serves policyholders across the United States. The company is known for its strong financial stability and focus on customer service, offering solutions for businesses of all sizes as well as individuals seeking personal coverage.
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Sentry Insurance jobs near you
Insurance Senior Trial Attorney - Work From Home

Insurance Senior Trial Attorney - Work From Home

Sentry Insurance

Houston, TX • Remote

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 9 days ago

Sentry Insurance rating

8.6

Company rating: 8.6 out of 10

Based on 42 frontline employees who took The Breakroom Quiz

74th of 261 rated insurance

Job description

As an experienced litigator, you’ll apply your experience to represent the interests of Sentry insureds by defending claims made under our insurance policies.

The ideal candidate for this position would reside in or around Houston, TX. This is a remote position with limited travel.

What You’ll Do:

As a Senior Trial Attorney, you will...

  • Represent the interest of the insured and Sentry in defending claims, ensuring that there is no conflict of interest between the policyholder and Sentry.

  • Communicate and report to policyholders and claims associates on the progress of litigation, strategy, and evolution of matters.

  • Handle a full caseload from minimal to highly complex matters through trial.

  • Handle pleadings, motion practice, depositions, written discovery, expert witness retention and discovery, dispositive motions, and trial preparation and presentation with minimal oversight.

  • Conduct examinations under oath, sworn statements, and similar non-litigated matters as may be necessary.

What it Takes:

  • Bachelor’s degree and Juris Doctor Degree

  • 7+ years of related work experience with experience as a licensed attorney in at least one state with some insurance defense litigation, and including experience taking/defending depositions, court appearances, handling dispositive motions, retaining expert witnesses, and trial experience as first chair or solo trial counsel

  • Vald license to practice law, in good standing the state of TX

  • Proven ability to deal with people where conflict and controversy exist

  • Ability to self-manage and operate as an attorney with a full caseload and minimal daily oversight

  • Bilingual preferred

What You'll Receive:

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.

  • In addition to the laptop, Sentry will provide equipment for your home office. 

  • 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!

Jessica Welsh

HR Specialist

Jessica.Welsh@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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