Corporate Education Sales Trainer

Chubb in; Chicago (IL); Hybrid; USD 70,000 - 95,000; Full time

Benefits offered by this job

Health insurance

401(k) matching

Tuition reimbursement

Disability insurance

Life insurance

Employee referral bonuses

Job summary

Chubb Benefits is seeking a Corporate Education Sales Trainer fluent in English and Spanish to join our Chicago team. You will deliver high-impact, in-person and virtual training to independent agents, brokers, and leadership across sales systems and skills.

The ideal candidate has 3–5 years of facilitation experience, strong communication, and proficiency with Office; familiarity with WebEx, LMS, and learning tech is a plus. Hybrid in Chicago location.

Qualifications

• 3–5 years of facilitation experience in face-to-face and live virtual settings.
• Ability to train diverse audiences, from agents to leadership.
• Experience across sales systems, selling skills, soft skills, and leadership.
• Bilingual fluency in English and Spanish to facilitate programs.
• Strong written and verbal communication; organized and self-directed.
• Proficiency with Microsoft Office Suite (Word, PowerPoint, Excel, Outlook).

Responsibilities

• Deliver high-impact training for independent agents, brokers, and staff, in person and virtual.
• Cover sales systems, selling skills, soft skills, and leadership development.
• Partner with Instructional Designers as SME to validate training content.
• Collaborate with sales and functional teams to reflect current practices.
• Identify skill gaps and administer assessments; track progress.

Skills

Bilingual English/Spanish

Facilitation

Verbal & written communication

Microsoft Office

Education

Bachelor's degree in Business/Communications/Education

Learning & development certifications a plus (ATD, CPTD)

Tools

WebEx

Adobe Connect

LMS

Job description

Corporate Education Sales Trainer (Finance)

JOB DESCRIPTION

Chubb Benefits is seeking a Corporate Sales Trainer (fluent English/Spanish) to join our fast-paced, high energy, growing company. We are proud of our tradition of success in the insurance industry of over 100 years. Come join our team of hard-working, talented professionals!

About the Role

Chubb Benefits a Chubb company has spent nearly a century helping people protect what matters most. We're growing - and we're looking for a skilled Bilingual Corporate Trainer who can bring that same commitment to the people who represent us every day.

If you're energized by the classroom, curious about new ways to teach, and motivated by watching others grow, this role is built for you.

What You'll Do

You’ll deliver high-impact training across a broad audience - new and experienced independent agents, brokers, sales leadership, and functional staff and leadership. Your sessions will span sales systems, selling skills, soft skills, and leadership development - in person and virtually. Your goal is consistent: build capability, close skill gaps, and keep people performing.

• Facilitate face-to-face and live virtual training for independent agents, brokers, sales leadership, and internal staff and leadership.
• Deliver training across multiple skill domains: sales systems, selling skills, soft skills, and leadership development.
• Partner with Instructional Designers as a subject matter expert to inform and validate training content - you are not responsible for design.
• Collaborate with sales and functional teams to ensure training reflects current field practices and business priorities.
• Proactively identify skill and knowledge gaps across your training audiences.
• Administer assessments and track participant progress against training objectives.
• Maintain training records, attendance, and calendars.
• Communicate observations, trends, and recommendations to leadership regularly.

Required Qualifications

• 3-5 years of facilitation experience in both face-to-face and live virtual settings.
• Demonstrated ability to train diverse audiences - from field agents to senior leadership.
• Experience facilitating across multiple skill domains (sales, systems, soft skills, and/or leadership).
• Bilingual fluency in English and Spanish to facilitate training programs
• Strong verbal and written communication skills.
• Ability to engage and flex delivery style across audience levels and experience.
• Proficiency in Microsoft Office Suite (Word, PowerPoint, Excel, Outlook).
• Organized, detail-oriented, and self-directed.

Preferred Qualifications

• Experience training independent agents and/or brokers in a group insurance or benefits environment.
• B2B insurance sales background.
• Familiarity with WebEx, Adobe Connect, or similar virtual training platforms.
• Experience with LMS or other learning technology.
• Multi-channel training delivery experience.

Education

• Bachelor's degree in Business, Communications, Education, or a related field preferred.
• Learning & development certifications a plus (ATD, CPTD, etc.).

Office Location:

8750 W. Bryn Mawr Ave, Chicago, Illinois 60631 near Rosemont, IL.

In-Office Expectation:

4x per week, 1 day remote

Why Chubb Benefits

You’ll join a team that takes training seriously - with the backing of a global organization and the agility of a company that’s still growing. Your work directly shapes how agents, brokers, corporate staff and leaders show up for customers every day. That matters here.

ABOUT US

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

Combined Insurance Company of America (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.

ABOUT CHUBB

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.

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