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Director Loss Sensitive Billing (CSS)
- Travelers Insurance Company (Hartford, CT)
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Who Are We?
Taking care of our customers, our communities and each other. That’s the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 160 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it.
Job Category
Operations
Compensation Overview
The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.
Salary Range
$101,300.00 - $167,000.00
Target Openings
1
What Is the Opportunity?
Job Description Summary
The Director of Loss Sensitive Billing will play a pivotal role in leading strategic and operational initiatives that directly support the CSS business segment—one of the most complex areas within the LSRM portfolio. This leader will bring deep CSS expertise to the role, serving as a trusted partner to CSS leadership, operational teams, and key customers to develop innovative, customer-focused billing solutions tailored to the needs of large, sophisticated clients.
Reporting to the AVP of Loss Sensitive Billing, the Director will lead a high-performing team focused on optimizing operational effectiveness, resolving complex business challenges, and shaping future-state billing processes. This role serves as a critical liaison between the Loss Sensitive Billing team, CSS business partners, and external stakeholders—including customers, brokers, and carriers—to ensure alignment and the delivery of an exceptional billing experience.
This position is well-suited for a strategic thinker with a strong CSS background and a passion for collaborative problem solving, operational excellence, and customer-focused innovation.
What You Will Do:
+ Participate in the development and execution of short- and long-term operational strategies that enhance efficiency, ensure contractual compliance, and align with CSS goals.
+ Analyze operational performance metrics (e.g., productivity, quality, timeliness, Voice of the Customer) and financial results, using insights to implement improvements and optimize outcomes.
+ Serve as a strategic advisor and liaison between Loss Sensitive Billing, CSS business partners, customers, brokers, and carriers to resolve issues, support change, and ensure alignment.
+ Champion process, system, and policy enhancements across teams, ensuring effective deployment, training, and long-term adoption of best practices and technology solutions.
+ Collaborate with stakeholders to identify performance gaps, recommend improvements, and ensure consistency with industry standards and competitor trends.
+ Manage and develop a high-performing team, fostering a culture of accountability, collaboration, and continuous improvement in support of business performance and customer experience goals.
+ Perform other duties as assigned
What Will Our Ideal Candidate Have?
+ Bachelor’s degree preferred, along with proven experience leading operational initiatives and managing cross-functional projects from planning through execution.
+ Deep subject matter expertise in TPA billing, with the ability to navigate its complexities and develop tailored solutions that meet the needs of CSS partners and clients.
+ Strong background in Loss Sensitive and/or CSS-related billing operations, with the ability to translate business needs into effective, scalable processes and solutions.
+ Demonstrated leadership capabilities, including managing staff performance, fostering development, and building high-performing, collaborative teams.
+ Excellent communication skills, both verbal and written, with the ability to influence stakeholders, build alliances, and maintain trust across all levels of the organization.
+ Strategic thinker with a customer-first mindset and the ability to anticipate business challenges, identify innovative solutions, and align initiatives to enterprise goals.
+ Strong decision-making, prioritization, and problem-solving skills, with a sense of urgency and a commitment to continuous improvement and operational excellence.
What is a Must Have?
+ Five years work experience in Finance, Operations or Collections required.
What Is in It for You?
+ **Health Insurance** : Employees and their eligible family members – including spouses, domestic partners, and children – are eligible for coverage from the first day of employment.
+ **Retirement:** Travelers matches your 401(k) contributions dollar-for-dollar up to your first 5% of eligible pay, subject to an annual maximum. If you have student loan debt, you can enroll in the Paying it Forward Savings Program. When you make a payment toward your student loan, Travelers will make an annual contribution into your 401(k) account. You are also eligible for a Pension Plan that is 100% funded by Travelers.
+ **Paid Time Off:** Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
+ **Wellness Program:** The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs. In addition, our mental health program provides access to free professional counseling services, health coaching and other resources to support your daily life needs.
+ **Volunteer Encouragement:** We have a deep commitment to the communities we serve and encourage our employees to get involved. Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.
Employment Practices
Travelers is an equal opportunity employer. We value the unique abilities and talents each individual brings to our organization and recognize that we benefit in numerous ways from our differences.
In accordance with local law, candidates seeking employment in Colorado are not required to disclose dates of attendance at or graduation from educational institutions.
If you are a candidate and have specific questions regarding the physical requirements of this role, please send us an email ([email protected]) so we may assist you.
Travelers reserves the right to fill this position at a level above or below the level included in this posting.
To learn more about our comprehensive benefit programs please visit http://careers.travelers.com/life-at-travelers/benefits/ .
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Director Loss Sensitive Billing (CSS)
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