Program Manager, Broker Development

Winnipeg, MB, 829 Henderson Highway, Winnipeg, Manitoba, Canada •

Quebec City Area, QC, Canada •

Waterloo, ON, Canada

Posted Thursday, February 19, 2026 at 8:00 AM

Are you searching for new possibilities? Westland Insurance Group has an exciting opportunity for a
Program Manager, Broker Development
.This is a
hybrid
role that can be based anywhere nationally close to a Westland office.

We’re looking for a strategic, forward-thinking learning leader to join our team as Broker Development Program Manager. In this role, you’ll design, implement, and manage programs that enhance broker capabilities across Westland. You’ll ensure our Personal and Commercial Lines brokers have the skills, knowledge, and tools they need to deliver exceptional client experiences and achieve business objectives.

Expected Compensation:The expected hiring range for this role is $84,800 to $106,000based on a 35-hour work week.

Your rate of pay will be determined based on your individual qualifications and experience, while considering internal equity.

Westland also offers a competitive annual short-term incentive program that enables employees to share in the rewards of the business and emphasizes the measures that are key to our success.

Reason for Vacancy:This is a new opportunity within our team
Westland is committed to continuous learning where employees can grow their potential and write the stories of their careers. Financial assistance is available for approved work-related training and development programs, including courses, seminars, and conferences that support your professional growth.

Discover what’s possible, with Westland.

The Westland story is all about growth - and that means plenty of possibility for everyone on our team. Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment. As we continue to open new doors, we’re inviting amazing people like you to join us.

Do you thrive on building impactful learning programs that drive real business results? Are you passionate about developing talent, strengthening performance, and creating scalable capability solutions? If so, you’ll feel right at home on our collaborative Learning & Development team, where growth and continuous improvement are at the core of what we do.

Why you'll love Westland:

• An open, flexible and welcoming workplace
• Plenty of opportunities to grow and learn
• Autonomy to drive your own success
• Be part of our inclusive culture, alongside an extraordinarily talented community of people with a wide variety of backgrounds
• A total rewards program that takes care of your financial, physical, and mental health
• Flexible paid Values Days to celebrate days important to you
• Paid Volunteer Days for employees as part of Amplifying Communities, a program to support causes that matter most to our employees and clients

Why we’ll love You:

• Minimum 5 years of experience in program management development within insurance or financial services
• Proven expertise in instructional design and adult learning theory, with experience facilitating engaging virtual workshops
• Experience building and managing coaching or mentorship programs that drive measurable performance outcomes
• Demonstrated ability to design robust assessment frameworks that connect learning initiatives to business impact
• Strong project management skills with the ability to lead complex, cross-functional initiatives and manage multiple priorities
• Proficiency with rapid development tools (e.g., Vyond, Articulate), LMS platforms (e.g., Docebo or eLoomi), and advanced Microsoft Office applications (Word, PowerPoint, Excel, Co-Pilot, Teams)
• Experience translating AI trends and evolving business needs into scalable, experiential learning solutions, supported by strong communication and stakeholder management skills

Once here, you'll:

• Develop and execute a comprehensive broker capability strategy aligned with organizational goals
• Design and deliver impactful programs focused on skills development, product knowledge, tools, processes, and operational excellence
• Create a bridge program to transition high-potential talent from non-insurance…