Sentry Insurance
InsuranceDirect Workday career site

Senior Staff Attorney - Insurance Defense

Pay
$159,200 – $238,800 per year
Location
Remote, CA (Remote)
Job type
Full-time
Level
Director
Experience
7+ years
Listed
31 days ago

Skills & highlights for this role

  • Attorney license (California)
  • insurance defense litigation
  • deposition practice
  • trial advocacy

Stated benefits & perks

  • Group medical
  • Dental
  • Vision
  • 401k match
  • Tuition

About the role

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.

Pay and benefits

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!

Read the original posting

From Sentry Insurance's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

Rolev.ai is a job search and application tool for US job seekers. For this Senior Staff Attorney - Insurance Defense role at Sentry Insurance, it shows how your resume fits, tailors your resume to the posting, and prepares the application for you to review.

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Common questions

What is the salary for the Senior Staff Attorney - Insurance Defense role at Sentry Insurance?

The Senior Staff Attorney - Insurance Defense posting at Sentry Insurance states compensation of $159,200 – $238,800 per year. It is listed as a full-time position. Final pay may depend on location, experience, and interview evaluation on Sentry Insurance's official career site.

Where is the Senior Staff Attorney - Insurance Defense job at Sentry Insurance located?

Yes, this Senior Staff Attorney - Insurance Defense opening at Sentry Insurance is listed as Remote, CA (Remote). Always check Sentry Insurance's application page for specific state eligibility or relocation policies.

What qualifications are required for Senior Staff Attorney - Insurance Defense at Sentry Insurance?

For the Senior Staff Attorney - Insurance Defense role, Sentry Insurance highlights 7+ years of relevant experience; experience with insurance defense litigation, deposition practice, trial advocacy. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Senior Staff Attorney - Insurance Defense position at Sentry Insurance?

This listing links directly to Sentry Insurance's Workday application page. You can apply directly on Sentry Insurance's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Workday application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.