Demo

Corporate Trainer, Sr

Chubb Benefits
Chicago, IL Full Time
POSTED ON 4/4/2026
AVAILABLE BEFORE 5/7/2026

Chubb Benefits is seeking a Corporate Trainer to join our fast-paced, high energy, and growing company. For nearly 100 years in the insurance industry, our company has been passionate about serving our customers and providing them peace of mind and protection when they need it the most. Come build your career here, along with other positive, hard-working, talented professionals—just like you!

The Corporate Trainer is responsible for preparing and facilitating training sessions for Combined Insurance’s Operations and Claims staff in both classroom and live virtual settings. Facilitation includes technical demonstrations, product line explanations, and business process training. Audience includes both new employees to the company as well as existing staff.

A successful trainer continuously maximizes their student’s effectiveness by utilizing a variety of best practices, techniques, and educational concepts. Maintaining a high energy level and positive morale is essential. A successful trainer also exhibits a healthy “curiosity” when it comes to both the subject matter being delivered and experimenting with new training delivery approaches involving the latest technology.

Major duties:

  • Prepares and facilitates both face-to-face and live virtual training for corporate staff to suit an adult learner.
  • Ensures training program delivery builds skills in both Combined/Chubb systems and the product lines for proper preparation of employees to service clients.
  • Collaborates with functional areas across the organization in the onboarding of new employees who support Group clients.
  • Partners with sales and sales training colleagues to learn about and prepare for new blocks of group business lines.
  • Plays role in creation of Group training content: is comfortable with identifying initial training needs for new product or systems implementation.
  • Identifies gaps in new hire training content and delivery.
  • Continuously seeks ongoing feedback and keeps lines of communication open to classroom participants, peers and management team.
  • Issues assessment tools to monitor participant progress.
  • Consistently monitors and assesses a participant’s performance, trends, and identifies specific skill/gaps to ensure training objectives are satisfied.
  • Communicates with leadership on an ongoing basis.
  • Provides input and makes recommendations regarding the procedures and practices of training.
  • Performs basic administrative functions to maintain organization and classroom management; tasks could include managing attendance, training calendars, and records.
  • Performs other related duties and activities as required.

SKILLS/EXPERIENCE:

  • 3-5 years of facilitation experience
  • Demonstrated proficiency in both face-to-face and virtual live training
  • Broker / Group Insurance relationship or training experience preferred
  • Experience and knowledge working with Disability claims and policies
  • Proficiency with WebEx and Adobe Connect training platforms preferred
  • B2B Sales experience (Insurance industry), preferred
  • Experience delivering through multiple channels
  • Experience with learning technology
  • Excellent oral and writing skills
  • Bilingual English/Spanish, preferred but not required
  • Proficient in using MS Suite (MS word, PowerPoint, Excel, and Outlook)
  • Organized and detail oriented
  • Ability to communicate with a variety of levels within the organization

EDUCATION:

  • Undergraduate degree in a learning related field or business preferred
  • Learning certifications, a plus


The pay range for the role is $62,200 to $105,800. 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.


OUR BENEFITS

As a Chubb corporate employee, you have access to one of the most comprehensive benefit plans in the business, designed to meet your needs and help you reach your financial goals. More details can be found here. Chubb is committed to supporting its employees with a comprehensive compensation package that is appropriate in the market where they work. Below are several of the many benefits we offer our employees:

  • Health insurance
  • Dental insurance
  • Tuition reimbursement
  • A company-match 401(k) plan
  • Disability insurance
  • Life insurance
  • Employee referral bonuses


About Chubb Benefits

Chubb Benefits is a leading provider of supplemental accident, health, disability, and life insurance products in the U.S.** and Canada. Headquartered in Chicago with a tradition of more than 100 years of success, we are committed to making the world of supplemental insurance easy to understand. The company has an A rating by the Better Business Bureau and an A (Superior) financial strength rating by AM Best. ** In New York, products are underwritten by Combined Life Insurance Company of New York (Latham, N.Y.).

ABOUT CHUBB

Chubb is the world's largest publicly traded property and casualty insurance company. With operations in 54 countries and territories, 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. As an underwriting company, we assess, assume and manage risk with insight and discipline. We service and pay our claims fairly and promptly. The company is also defined by its extensive product and service offerings, broad distribution capabilities, exceptional financial strength and local operations globally. Parent company Chubb Limited is listed on the New York Stock Exchange (NYSE: CB) and is a component of the S&P 500 index. Chubb maintains executive offices in Zurich, New York, London, Paris and other locations, and employs approximately 31,000 people worldwide.

Salary : $62,200 - $105,800

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