Claims Manager

ExecutiveID & Search; Connecticut; On-site; USD 110,000 - 160,000; Full time

Job summary

USA Waste & Recycling is seeking a seasoned Claims Manager to lead the insurance function across a diverse set of operations, including heavy trucking, facilities, and entertainment venues. This role partners with the executive team to minimize risk and optimize claims handling.

The successful candidate will bring 5–7 years of P&C experience, strong analytical and communication skills, and a willingness to travel to our multiple sites. A bachelor’s degree in a related field is required.

Qualifications

• Bachelor’s degree in Insurance, Finance, Business, Risk Management, or related field.
• 5–7 years of progressive P&C insurance experience with multi-entity exposure.
• Experience with commercial auto and fleet risk, auto liability, GL, and workers’ compensation.
• Comfort in blue-collar field environments as well as hospitality/agriculture operations.
• Strong analytical skills with data-driven recommendations.
• Excellent communication and relationship-building across diverse teams.
• Ability to lead small teams and influence others.
• Valid driver’s license and willingness to travel regularly.

Responsibilities

• Oversee and manage claims across auto, general liability, workers’ compensation, and property.
• Monitor metrics and lead cost-of-risk reduction initiatives.
• Partner with Legal, Operations, HR, Safety to investigate incidents and perform root-cause analyses.
• Monitor litigated claims with insurer counsel to evaluate strategy and expenses.
• Review claim files and provide technical oversight for consistency.
• Identify recurring loss drivers and drive corrective actions with cross-functional teams.
• Assist with administration of insurance programs and risk management practices.
• Support due diligence and integration of newly acquired businesses.

Skills

Analytical skills

Communication

Leadership

Travel readiness

Education

Bachelor's degree in Insurance, Finance, Business, Risk Management, or related field

Job description

USA Waste & Recycling and its affiliated family of companies are growing, investing, and innovating – and we’re looking for a Claims Manager who wants to grow with us. This is an opportunity to take on a role where your technical claims expertise is valued immediately, while having the opportunity to expand into broader risk management responsibility. We’re a multi‑generational, family‑led organization with a roll‑up‑your‑sleeves, first‑name‑basis culture where people know each other and wins are celebrated together.

In this role, you’ll partner with the Executive team to lead the insurance function across a unique mix of businesses: heavy trucking and waste/recycling operations, a private golf club (Greathorse), a family entertainment center (Sonny’s Place), and Lindy Farms’ horse racing and breeding operations. If you like variety, enjoy building relationships, and appreciate both structure and informality, this is a place where you can see the full picture and help shape the future.

Key Responsibilities

Claims, Loss Control & Operations

• Oversee and manage claims across auto, general liability, workers’ compensation, and property, including TPA performance, litigation strategy, reserves, and settlements.
• Monitor key metrics (frequency, severity, lag time, incurred vs. paid, closure rates) and lead initiatives to reduce total cost of risk.
• Partner with Legal, Operations, HR, and Safety to investigate serious incidents, perform root‑cause analyses, and implement corrective actions in trucking, facilities, entertainment venues, and equine operations.
• Monitor litigated claims and work closely with insurer-provided counsel to evaluate litigation strategy, legal expense, settlement opportunities, and overall exposure.
• Review claim files and provide technical oversight to ensure claims are being handled appropriately and consistently.
• Identify recurring loss drivers and work with Operations, Safety, HR, and Legal to conduct root‑cause analysis and implement corrective actions.

Insurance & Risk Management

• Assist with the administration and management of the company’s commercial insurance programs, including auto liability, general liability, workers’ compensation, property, excess/umbrella, environmental, and other specialty coverages.
• Develop a practical understanding of the company’s retentions, deductibles, limits, self‑insured exposures, and risk‑financing structure.
• Work with the CFO, brokers, carriers, TPAs, and other insurance partners on renewals, claims issues, coverage questions, loss information, and program administration.
• Develop and maintain basic risk management reporting, including claims trends, loss data, key exposures, and areas requiring management attention.
• Help identify opportunities to strengthen risk transfer through contracts, leases, vendor agreements, waivers, certificates of insurance, and other documentation.
• Support the company’s captive insurance and/or self‑insured programs and develop greater responsibility in these areas over time.
• Assist with insurance and risk‑related due diligence and integration of newly acquired businesses.

Fleet, Safety & Loss Control

• Partner with Operations and Safety to identify and address risk across an 800+ truck fleet, facilities, and other operating environments.
• Leverage telematics, in‑cab cameras, driver safety technology, and claims data to identify trends and improve fleet performance.
• Participate in investigations of serious accidents and losses and help translate findings into practical corrective actions.
• Work comfortably in field‑based environments, including visiting yards, shops, facilities, golf operations, entertainment venues, and equine/agricultural operations.
• Help build and maintain a practical risk management framework appropriate for a privately held, multi‑entity organization.
• Maintain awareness of key organizational risks and help develop reporting around significant exposures and loss trends.
• Partner with leadership to identify emerging risks and recommend practical mitigation strategies.
• Contribute to the development and standardization of risk and claims policies, procedures, and processes while recognizing that different businesses may have different operational needs.
• As the role develops, take on increasing responsibility for broader risk management, insurance.

The Successful Candidate Will Bring:

• Bachelor’s degree in Insurance, Finance, Business, Risk Management, or related field (advanced degree a plus).
• 5-7 years of progressive P&C insurance experience. Risk management experience, including multi‑entity or multi‑location responsibility is a plus.
• Meaningful experience with: Commercial auto and fleet risk, ideally heavy trucks or transportation/logistics & Claims oversight and litigation management in auto liability, general liability, and workers’ compensation.
• Comfort working in blue‑collar, field‑based environments as well as hospitality and agricultural operations; you enjoy walking the yard, shop, farm, and course, not just sitting behind a desk.
• Strong analytical skills and the ability to turn data into clear, practical recommendations.
• Exceptional communication and relationship‑building skills across diverse teams and industries.
• Ability to lead small teams, and also, lead through influence.
• Valid driver’s license, reliable transportation, and ability to travel regularly for site visits.

Why You’ll Love Working Here

• A large, growing, entrepreneurial organization with a long‑term family ownership mindset.
• A casual, approachable culture with a direct line to decision‑makers and clear visibility to the impact of your work.
• The chance to work across a genuinely unique mix of operations—trucking, waste and recycling, golf, entertainment, and equine.