Program Manager, Broker Development
Top Benefits
About the role
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 $106,000 based 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 industries into successful broker careers
- Curate and integrate best-in-class content from learning partners to elevate program offerings
- Build and lead a strong coaching and mentorship network across the organization
- Evaluate and recommend cross-functional rotational opportunities to broaden broker experience
- Partner with Learning & Development, Sales, and Operations to embed capability programs into existing frameworks
- Monitor program effectiveness using KPIs, assessments, and feedback to drive continuous improvement
- Lead communication and engagement strategies while building strong relationships with internal and external stakeholders to ensure program adoption and long-term success
As part of our commitment to transparency, we want to let you know that while our recruitment system includes AI capabilities, these are never used to screen, evaluate, or select candidates. The only AI functionality that Westland uses is for transcribing notes during candidate calls, and this occurs with your consent. These tools aren't used to make any hiring decisions throughout our recruitment process.
#LI-LH1
#LI-Hybrid
Want to get to know each other better? Send your resume our way.
You belong here
We strive to be much more than a great place to work. Here, you join a collective of incredibly vibrant, purpose driven, and open-minded people. Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment. You will be supported and respected for who you are and for the voice you add to the conversation.
At Westland, you will feel the power of community. Westland Insurance Ltd. is an inclusive organization that values diversity in its workforce. We listen, champion equity and diversity, and create safe welcoming spaces where everyone has a voice and is free to be themselves. 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 careers@westlandinsurance.ca
Not the right fit? Search for Program Manager, Broker Development jobs in Winnipeg, MB
About Westland Insurance Group
Westland Insurance Group is one of the largest and fastest-growing independent property and casualty insurance brokers in Canada. With a national network of 300 locations and over 3,000 employees, the company continues to expand coast to coast. Westland's brokers provide expert advice to home, business, farm, life, and auto insurance clients. Since its founding in 1980, Westland has remained a family-owned company that is committed to supporting its local communities. For more information, please visit westlandinsurance.ca
Westland Amplifying Communities initiative:
Over the course of 40 years, Westland Insurance has established itself as the largest independent, Canadian-owned brokerage in the country. While the company has become national in scope, it has never forgotten its roots or the neighbourhoods and communities in which it serves. Through the establishment of the Westland Amplifying Communities initiative, $1 million is being made available to support projects or programs that contribute to the fabric of communities.
For more information and to submit an application, visit westlandinsurance.ca/communities or email
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Program Manager, Broker Development
Top Benefits
About the role
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 $106,000 based 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 industries into successful broker careers
- Curate and integrate best-in-class content from learning partners to elevate program offerings
- Build and lead a strong coaching and mentorship network across the organization
- Evaluate and recommend cross-functional rotational opportunities to broaden broker experience
- Partner with Learning & Development, Sales, and Operations to embed capability programs into existing frameworks
- Monitor program effectiveness using KPIs, assessments, and feedback to drive continuous improvement
- Lead communication and engagement strategies while building strong relationships with internal and external stakeholders to ensure program adoption and long-term success
As part of our commitment to transparency, we want to let you know that while our recruitment system includes AI capabilities, these are never used to screen, evaluate, or select candidates. The only AI functionality that Westland uses is for transcribing notes during candidate calls, and this occurs with your consent. These tools aren't used to make any hiring decisions throughout our recruitment process.
#LI-LH1
#LI-Hybrid
Want to get to know each other better? Send your resume our way.
You belong here
We strive to be much more than a great place to work. Here, you join a collective of incredibly vibrant, purpose driven, and open-minded people. Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment. You will be supported and respected for who you are and for the voice you add to the conversation.
At Westland, you will feel the power of community. Westland Insurance Ltd. is an inclusive organization that values diversity in its workforce. We listen, champion equity and diversity, and create safe welcoming spaces where everyone has a voice and is free to be themselves. 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 careers@westlandinsurance.ca
Not the right fit? Search for Program Manager, Broker Development jobs in Winnipeg, MB
About Westland Insurance Group
Westland Insurance Group is one of the largest and fastest-growing independent property and casualty insurance brokers in Canada. With a national network of 300 locations and over 3,000 employees, the company continues to expand coast to coast. Westland's brokers provide expert advice to home, business, farm, life, and auto insurance clients. Since its founding in 1980, Westland has remained a family-owned company that is committed to supporting its local communities. For more information, please visit westlandinsurance.ca
Westland Amplifying Communities initiative:
Over the course of 40 years, Westland Insurance has established itself as the largest independent, Canadian-owned brokerage in the country. While the company has become national in scope, it has never forgotten its roots or the neighbourhoods and communities in which it serves. Through the establishment of the Westland Amplifying Communities initiative, $1 million is being made available to support projects or programs that contribute to the fabric of communities.
For more information and to submit an application, visit westlandinsurance.ca/communities or email