Insurance Team Lead - Learning & Development

HUB International; Windsor; Hybrid; CAD 68,000 - 75,000; Full time

Benefits offered by this job

Group Health and Dental Benefits

RRSP Company Matching Program

Paid vacation, sick and personal days

Employee discounts on personal, home,‑

Job summary

HUB International is seeking a Team Leader, L&D/Nesting to guide broker trainees and a team of Training Coaches. Based in Windsor, ON, this role supports the Learning & Development function, evaluates training effectiveness, and ensures on-the-job performance reflects learning initiatives.

You will drive coaching plans, manage performance reviews, collaborate with HR, and contribute to cross-divisional process improvements while maintaining a positive, growth‑focused work environment.

Qualifications

• 3+ years experience as a Broker within a brokerage environment.
• Experience in contact centre training or facilitation is an asset.
• Experience in training, learning and development is an asset.
• Management experience is an asset.
• Post-secondary education preferred.
• Availability to work various shifts to support staff.
• Ability to handle fluctuating volumes in a fast-paced, customer-focused environment.
• Ability to work independently and in a team.
• Ability to communicate clearly and concisely.

Responsibilities

• Lead Broker Trainees and Training Coaches; develop performance plans as needed.
• Assess how training translates to on-the-job performance and gather feedback.
• Update training content and delivery to meet staff and business needs.
• Support Broker Trainees during their transition to the HUB environment with ongoing guidance.
• Conduct regular performance reviews, coaching sessions, and create individualized coaching plans.
• Collaborate with Department Managers and HR on performance and behaviour issues including progressive discipline.
• Maintain knowledge of data systems, portals, CRM, and policy management; provide training and guidance.
• Assist with staff scheduling and time management to meet contact center targets.
• Participate in interview and selection process and communicate results to HR with notes.

Skills

Broker experience

Contact centre training

L&D experience

Management experience

Communication

Education

Post-secondary education

Job description

The Role: We are seeking a Team Leader, L&D/Nesting to join our Learning & Development team.

Location: Windsor, ON - We offer in-office, hybrid, and fully remote work flexibility.

Who we are: HUB Customer Central (HCC) is a leading insurance contact center in Canada. Our technology-driven and digital expertise is unique, making us an industry trailblazer.

Why we are different: In 2021, HUB won the prestigious Stevie Award for Employer of the Year - Insurance. This award recognizes the world’s best companies to work for and their ongoing commitment to the growth, development, and wellness of employees. We’re about communities too. HUB/HCC is committed to a formal program – HUB Gives – that encourages employees to donate their time, creativity, and passion to community causes. We believe in contributing to where we live, work and play.

Position Overview:

The Team Leader, Nesting is responsible for developing and supporting new Broker Trainees as well as a team of Training Coaches, ensuring that all department goals are met within company standards. The Team Leader will assist in overseeing the multi-faceted operations of the Learning and Development team including training program evaluation and enhancement, ensuring that learning is effectively transferred to on-the-job performance. The Team Leader will also participate in cross divisional process alignment discussions to maximize efficiency while maintaining a positive work environment and an effortless customer experience.

Duties and Responsibilities:

• Assess how effectively training is translated into on-the-job performance through regularly gathering feedback and reviewing training programs and materials.
• Recommend updates and participate in the development of training content and delivery to ensure that learning solutions are relevant and meet the needs of both the staff and the business.
• Assess Broker Trainees’ progress throughout their learning journey, identifying and implementing development plans as needed to provide support and stimulate growth.
• Support new Broker Trainees in their transition to the HCC environment, providing ongoing guidance and support throughout each phase of training.
• Support Broker Trainees and Training Coaches by identifying developmental needs through active monitoring of work activities and assist employees in reaching their full potential by completing regular performance reviews, coaching sessions, and creating individualized coaching plans when necessary.
• Recognize and encourage areas of strength and initiate corrective steps to address areas of concern through coaching opportunities and documenting important details.
• Collaborate with Department Managers and HR on employee performance and behaviour issues including progressive discipline, up to and including terminations.
• Act as a technical and workflow resource for the team by maintaining a good working knowledge of all applicable data systems, portals, customer relationship management and policy management systems, providing procedural training, guidance, and feedback to the team.
• Handle and document the outcome of escalations and use the situations as developmental and coaching opportunities to avoid future occurrences.
• Actively participate in management meetings focused on evaluation of results and planning for anticipated volumes.
• With management, participate in cross divisional process alignment discussions and effectively communicate required information to staff.
• Assist with staff schedule coordination and oversee the time management system to ensure contact centre performance expectations are met.
• Participate in the interview and selection process of potential candidates and communicate results to HR with detailed interview notes and examples.
• Participate in extracurricular team building activities which may occur outside of office hours.
• Perform other duties as assigned.

Required Skills & Qualifications:

• 3+ years experience as a Broker, within a brokerage environment.
• Contact centre training or facilitation experience is an asset.
• Training, learning and development experience is an asset.
• Management experience is an asset.
• Post-secondary education preferred.
• Availability to work various shifts and days of the week as required in order to support the staff.
• Ability to handle fluctuating work volumes in a fast paced, customer focused environment.
• Ability to work independently and in a team environment.
• Ability to communicate clearly and concisely.

Salary Expectations:

The expected salary range for this position is $68,000 to $75,000 and will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope, and level. HUB International is proud to offer comprehensive benefit and total compensation packages which include health benefits, RRSP matching, paid-time-off benefits, and eligible bonuses, and commissions for some positions.

AI and Automation Notice:

HUB International uses limited AI and automation tools within our recruitment systems to enhance efficiency in the hiring process and in the candidate experience. These tools do not independently make hiring decisions or screen out candidates — all decisions are made through human review.

The Perks:

• Group Health and Dental Benefits.
• RRSP Company Matching Program.
• Paid vacation, sick and personal days.
• Employee discounts on personal, home and auto insurance policies.
• Corporate discounts on gym memberships and other services/products.
• Company-paid Employee and Family Assistance Program.
• Health and wellness initiatives.
• Ongoing recognition programs and opportunities for advancement.

Our Commitment:

• An environment that fosters continuous learning and improvement.
• A leadership team dedicated to your growth and success.
• To listen. Our employees have great ideas. We implement them.
• Appreciation of your efforts. Every day.

Take the first step toward creating a future that combines a diverse and challenging work environment in a rapidly growing company that offers significant opportunity for advancement and growth.

If you require assistance or accommodation during our recruitment process, please notify Human Resources so that we can review and consider how we may be able to assist you based on your individual needs.