Senior Staff Attorney - Insurance Defense

Use your litigation experience to defend Sentry insureds against claims and represent Sentry in direct policy actions.

This position will work remotely from a home office and will require intermittent travel in California for case related matters, depositions, and court hearings.

What You’ll Do:

As a Senior Trial Attorney, you'll apply your legal skills and experience to represent the interests of Sentry insureds. In additional, 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.
• Independently manage a caseload of minimally to substantially complex matters representing Sentry and our insureds from pleadings through trial. You’ll oversee all phases of litigation—including motion practice, depositions, expert discovery, and trial prep—with minimal supervision.
• Communicate and report to policyholders and claims associates on the progress of litigation, strategy, and evolution of matters.
• Assist claims associates as requested in resolving matters through mediation, arbitration, settlement, friendly suit, or court approved resolution.

What it Takes:

• 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
• Valid license to practice law, in good standing, in the state of California
• 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

Here is what you can look forward to as part of our team:

At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.

• Continuous Learning: Unlock your potential through Sentry University and take advantage of our tuition reimbursement program
• Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.
• Work-Life Balance: Enjoy your generous Paid Time Off allowance to rest and take advantage of paid Volunteer Time Off to support your community.
• Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
• Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.
• As a Senior Trial attorney, based on experience and qualifications, the pay range for this position on an annual basis is $159,200 - $238,800.

Why Join Sentry?

At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.

Building on a Legacy

Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.

Your Career, Our Community

Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.

Ready to own your future? Join us at Sentry, opportunities await!

Joe Larsen

Talent Acquisition Specialist Senior

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.

About Us

Our associates are the most important part of our company.

We became one of the most financially strong mutual insurance companies in the U.S. by striving to provide the best possible service to our business customers. We do this by having conversations, forming relationships, and getting to know the people we work with and their businesses.

We make that same commitment to our associates. When you join Sentry, we don’t just want you to perform tasks each day. We want you to enjoy your time with us. You’re in the driver’s seat of your career path here—sharing feedback, creating goals, accessing professional development resources, and identifying how you can contribute to both your success and the success of the company.

Yes, we work hard. But we work with the purpose of helping others, and with the understanding that there’s more to life than work. We invite you to learn more about us. You’ll find we’re much more than insurance.