About The Role

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.