Ready to kickstart your career? We’ve got you covered.

Start strong. Grow fast. Your future starts here.

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Start your personal insurance career

Our Trainees are supported through their first six weeks in the branch as they work to obtain their licensing. As a Trainee, you will:

  • Participate in training virtually and on the job
  • Have your licensing costs covered by Westland
  • Be provided with a training plan to ensure you’re fully supported

New trainee programs start every month.

Insurance Trainee Program

Wondering what a career in insurance would be like? Recently graduated or want a career change? Then Westland’s Insurance Advisor Trainee program is for you (and we cover your licensing costs too)!

Make your next move and unlock new possibilities

Your journey with Westland begins with hands-on learning and real-world experience. But it doesn’t stop there. We’re committed to helping you grow into the professional you want to become.

Meet May-Leena Alderson: Sharing how she’s been supported throughout her career journey and the opportunities at Westland

Learn and grow with Westland

Diverse learning programs

Grow your career with diverse training – from brokering to IT, leadership, and beyond – wherever your path leads at Westland.

Learn your way

Choose from in-person, virtual, self-study, or e-learning courses to fit your style and schedule. 

Career development and mentorship

Our Amplify Mentorship program and leadership content help you shine with guidance from experienced pros. 

Supportive learning environment

Our team creates engaging content with resources like Westland College to keep you ahead of the game.

Tuition reimbursement

We invest in your future with tuition assistance for professional certifications like CIP, CPA, and more. 

Career paths & connections

Explore roles in personal and commercial insurance, underwriting, claims, corporate and management. Network through events, ERGs and employer partner initiatives.

Why Westland

Celebrating five years with Westland, I’m so grateful for the growth, mentorship, and opportunities I’ve had. From starting as a trainee to becoming a financial analyst with the M&A team,… Read more
Mohak, Financial Analyst Mergers & Acquisitions

September 2025

Celebrating five years with Westland, I’m so grateful for the growth, mentorship, and opportunities I’ve had. From starting as a trainee to becoming a financial analyst with the M&A team, I’ve learned so much about the industry - all while studying full-time. Westland truly invests in its people, and I’ve felt that every step of the way.

Mohak, Financial Analyst Mergers & Acquisitions September 2025 /
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As an inclusive employer, Westland is proud to partner with

Westland Insurance Ltd. encourages applications from all qualified individuals and will accommodate applicants’ disability-related needs, up to the point of undue hardship, throughout all stages of the recruitment and selection process. If you require a disability-related accommodation in order to participate in the recruitment process, please contact the recruitment team by email at [email protected]

Join our team and grow with Westland

Westland is committed to being a leader across all industries in building a diverse, equitable, and inclusive organization. We take action to grow people’s potential and create a culture where everyone belongs.

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