What You’ll Do:

As the Director of Casualty Claims - Commercial Lines, you’ll serve as a leader of leaders, providing strategic and operational direction to a large team of leaders and claim associates within our casualty claim environment. In this critical role, you will drive comprehensive claim strategies for complex exposures—including Commercial Auto, Transportation Trucking, General Liability (premises and product liability), and other commercial liability scenarios—with a sharp focus on bodily injury evaluation, effective negotiation and settlement, and robust litigation strategies to serve and defend our policyholders. In addition, you will…

• Lead and Develop Leaders: Provide strategic oversight and mentorship to your management team, fostering a high-performing culture centered on continuous learning, accountability, and the ongoing upskilling of technical proficiency across diverse claim scenarios.

• Guide Financial and Technical Outcomes: Navigate complex authority reserving requests and provide expert settlement and negotiation guidance, ensuring equitable, timely, and compliant resolution of claims while managing expenses to support profit and growth objectives.

• Drive Strategic and Regulatory Compliance: Spearhead strategic initiatives related to claim operations, regulatory compliance, and internal best practices, establishing robust management controls, audit standards, and protocols to achieve departmental objectives.

• Optimize Workflows with Technology: Continually evaluate and identify opportunities to streamline claim workflows and processes utilizing technology-enabled solutions to drive operational efficiency and modernization.

• Shape Policy and Systems: Collaborate on objective setting, the development of claims policies, and the implementation of necessary systems to support seamless claim handling and adherence to departmental standards.

• Oversee Audits and Governance: Oversee department and corporate audits by managing communications, supplying requested data, providing supporting documentation, and addressing audit findings to ensure successful completion.

• Represent Sentry Externally: Act as a brand ambassador, representing the company in industry associations, committees, boards, and bureaus.

What it Takes:

• Bachelor’s degree or equivalent work experience, Juris Doctor preferred

• 8+ years of related work experience, with successful and increasingly responsible management and leadership experience, including broad background in claims, including exposure to multiple lines of coverage and policies, preferably in commercial auto, transportation, and general liability

• Strong analytical, communication, and human relations skills

• Knowledge of Sentry's philosophies, products, and systems

• Technical expertise in assigned area of claim policies and practices as well as insurance products

• Knowledge of applicable laws affecting claims; preferably technical expertise

• Strong working knowledge of contracts, service level agreements, and application of terms and conditions

• Strong negotiation skills

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.

• Hybrid Flexibility: Enjoy the best of both worlds. With optional work from home on Mondays and Fridays and join your team in the office Tuesday through Thursday to collaborate and learn. We provide the technology and tools you need for both your office and home workspace from day one.

• Dining on Us: Depending on your location, we may provide a stipend that can be used at our on-site cafeteria or a meal allowance to keep you fueled.

• 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.

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

Senior Talent Acquisition Specialist

[email protected]

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.