Job Description

We are seeking a dynamic Sales Training Facilitator to create, customize and deliver bespoke sales training programs. There will be an initial focus on the North America business units with the potential to expand globally. This role is responsible for hands-on collaboration with business leaders and subject matter experts to customize and deliver sales content that reflects real-world challenges and opportunities unique to each respective business unit. The ideal candidate will have a strong background in underwriting and proven experience working with agents and brokers.

This position offers the flexibility to work fully remote; however facilitation of training programs will require 25–50% travel within the United States.

Facilitation & Collaboration

• Customize and facilitate in-person and virtual sales training programs globally, ensuring sessions are engaging, interactive, and tailored to the audience.
• Collaborate with subject matter experts to co-create learning solutions and incorporate their expertise into training design.
• May be called on to teach other classes as needed and as capacity allows

Needs Assessment

• Collaborate with internal stakeholders to identify training needs
• Identify critical sales competencies and learning objectives through multiple methods including, but not limited to interviews, surveys, and focus groups.

Sales Program Management

• Lead and manage all aspects of the sales training program, ensuring strategic alignment, effective execution, and post-training support to meet evolving business needs.
• Continuously evolve and improve the sales curriculum based on feedback, business needs, and industry best practices.
• Build strong relationships with agents, brokers, and underwriters to ensure training relevance and effectiveness
• Ensure all training materials are relevant, practical, and directly informed by underwriting expertise.
• Learn and incorporate Chubb’s full suite of products into training over time

Measurement & Continuous Improvement

• Track, measure and report on training effectiveness based on key learning metrics.
• Continuously enhance and refine sales training programs by actively soliciting, analyzing, and incorporating feedback from participants, business leaders, and stakeholders.
• Regular communication with stakeholders regarding progress, challenges, and opportunities.

• Professional and engaging presentation skills.
• 5-7+ years of Underwriting experience
• Demonstrated expertise in Chubb’s sales processes, strategies, and culture is preferred.
• Travel 25–50% of the time, as required to deliver training and support business needs
• Strong analytical skills to evaluate, analyze, and interpret technical information.
• Excellent verbal and written communication skills.
• Ability to collaborate with business leaders and subject matter experts.
• Proven ability to work independently and as part of a collaborative team.
• Ability to flex hours to teach audience in a variety of times zones. This could require you to work earlier or later throughout the year.
• Ability to operate autonomously and with accountability for the success of the sales training program.

The pay range for the role is $99,000-$143,000. The specific offer will depend on an applicant’s skills and other factors This role may also be eligible to participate in a discretionary annual incentive program. Chubb offers a comprehensive benefits package, more details on which can be found on our careers website The disclosed pay range estimate may be adjusted for the applicable geographic differential for the location in which the position is filled.

Chubb is a world leader in insurance. With operations in 54 countries, Chubb provides commercial and personal property and casualty insurance, personal accident and supplemental health insurance, reinsurance, and life insurance to a diverse group of clients. The company is distinguished by its extensive product and service offerings, broad distribution capabilities, exceptional financial strength, underwriting excellence, superior claims handling expertise and local operations globally.

At Chubb, we are committed to equal employment opportunity and compliance with all laws and regulations pertaining to it. Our policy is to provide employment, training, compensation, promotion, and other conditions or opportunities of employment, without regard to race, color, religious creed, sex, gender, gender identity, gender expression, sexual orientation, marital status, national origin, ancestry, mental and physical disability, medical condition, genetic information, military and veteran status, age, and pregnancy or any other characteristic protected by law. Performance and qualifications are the only basis upon which we hire, assign, promote, compensate, develop and retain employees. Chubb prohibits all unlawful discrimination, harassment and retaliation against any individual who reports discrimination or harassment.