Corporate Education Sales Trainer

Chubb Benefits is seeking a Corporate Sales Trainer (fluent English/Spanish) to join our fast-paced, high-energy, growing company. With over 100 years of success in the insurance industry, we’re proud of our tradition and invite you to 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 looking for a skilled Bilingual Corporate Trainer who shares our commitment to developing 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.

Responsibilities

• 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.

Requirements

• 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.

Qualifications

• Bachelor’s degree in Business, Communications, Education, or a related field preferred.
• Learning & development certifications a plus (ATD, CPTD, etc.).
• Experience training independent agents and/or brokers in a group insurance or benefits environment (preferred).
• B2B insurance sales background (preferred).
• Familiarity with WebEx, Adobe Connect, or similar virtual training platforms (preferred).
• Experience with LMS or other learning technology (preferred).
• Multi-channel training delivery experience (preferred).

Schedule

• In-office 4 days per week, 1 day remote.

Location

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

Benefits

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

Chubb offers one of the most comprehensive benefit plans in the business, designed to meet your needs and help you reach your financial goals.