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Insurance Leadership Jobs in Calgary, AB (NOW HIRING)

Wawanesa Insurance

Lead Executive Claims Analyst

Calgary, AB · Hybrid

CA$90K - CA$115K/yr

  • Retirement

  • PTO

Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of ...

Wawanesa Insurance

Product Innovation Strategist

Calgary, AB · Hybrid

CA$90K - CA$110K/yr

  • Retirement

  • PTO

Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of ...

Wawanesa Insurance

Senior Architect - Salesforce

Calgary, AB · Hybrid

CA$120K - CA$160K/yr

  • Retirement

  • PTO

Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of ...

Wawanesa Insurance

Salesforce Lead Developer

Calgary, AB · Hybrid

CA$100K - CA$130K/yr

  • Retirement

  • PTO

Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of ...

Wawanesa Insurance

Senior Architect - Data & AI

Calgary, AB · Hybrid

CA$115K - CA$160K/yr

  • Retirement

  • PTO

Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of ...

Wawanesa Insurance

Catastrophe Risk Specialist

Calgary, AB · Hybrid

CA$85K - CA$115K/yr

  • Retirement

  • PTO

Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of ...

Wawanesa Insurance

Senior Financial Analyst

Calgary, AB · Hybrid

  • Retirement

  • PTO

Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of ...

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Insurance Leadership information

What is the difference between Insurance Leadership vs Insurance Underwriter?

AspectInsurance LeadershipInsurance Underwriter
Required CredentialsTypically requires leadership experience, industry certifications, and sometimes advanced degreesRequires industry certifications like CPCU or AIC, and a relevant bachelor’s degree
Work EnvironmentStrategic, managerial, and cross-departmental focus in corporate settingsAnalytical, detail-oriented work primarily in underwriting departments
Employer & Industry UsageUsed in insurance companies, agencies, and brokerages for leadership rolesCommonly employed in insurance companies, focusing on risk assessment and policy pricing

Insurance Leadership roles focus on strategic decision-making, team management, and overall company direction, often requiring extensive industry experience. Insurance Underwriters concentrate on evaluating risks, setting premiums, and approving policies, with a strong emphasis on analytical skills. While both roles are vital in the insurance industry, they serve different functions and require distinct skill sets.

What are some common challenges faced by professionals in insurance leadership roles, and how can they be addressed?

Insurance leaders often encounter challenges such as adapting to evolving regulations, managing a diverse workforce, and driving digital transformation within their organizations. Successfully addressing these challenges requires strong change management skills, continuous professional development, and fostering open communication across teams. Leaders who prioritize innovation, invest in staff training, and maintain a customer-centric approach are better equipped to navigate industry shifts and guide their organizations toward sustained growth.

What is insurance leadership?

Insurance leadership refers to the roles and responsibilities of individuals who guide and manage insurance organizations or teams. Leaders in this field set strategic direction, oversee operations, ensure compliance with regulations, and drive growth and innovation within the company. They often focus on developing talent, improving customer experience, and adapting to industry changes such as new technologies and evolving risk landscapes. Effective insurance leaders require strong communication, analytical, and decision-making skills to succeed in a dynamic and highly regulated industry.

What are the key skills and qualifications needed to thrive in insurance leadership?

To thrive in Insurance Leadership, you need deep knowledge of insurance products, market trends, and regulatory requirements, typically supported by a degree in business, finance, or a related field and significant industry experience. Familiarity with insurance management platforms, data analytics tools, and relevant certifications such as CPCU or CLU is often expected. Strong strategic thinking, communication, and team management skills distinguish top performers in this role. These capabilities are essential for driving organizational growth, ensuring compliance, and effectively leading teams in a competitive and regulated industry.

What are popular job titles related to Insurance Leadership jobs in Calgary, AB?

For Insurance Leadership jobs in Calgary, AB, the most frequently searched job titles are:

What job categories do people searching Insurance Leadership jobs in Calgary, AB look for?

The top searched job categories for Insurance Leadership jobs in Calgary, AB are:

What cities near Calgary, AB are hiring for Insurance Leadership jobs?

Cities near Calgary, AB with the most Insurance Leadership job openings:

Insurance Leadership jobs near you
Infographic showing various Insurance Leadership job openings in Calgary, AB as of August 2026, with employment types broken down into 71% Full Time, and 29% Contract. Highlights an 86% In-person, and 14% Remote job distribution.

Actuarial Consultant - Financial Planning & Analysis

Wawanesa Insurance

Calgary, AB • Hybrid

Full-time, Part-time

Retirement, PTO

Posted 9 days ago

Job description

Job ID: 10253 


Employment Type: Existing Role

Work Environment: We offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations: Winnipeg, MB; Wawanesa, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Lethbridge, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Quebec City, QC, Moncton, NB; Dartmouth; NS. 

Working Business Language: Financial Planning & Analysis  

Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan, leave of absence top-up programs and provided with generous vacation time, personal days, premium free benefits and pension plan. 
 

The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role. The salary offered is estimated to be within the following range. Candidates with salary expectations outside of the range are still encouraged to apply.

  • Senior Actuarial Analyst $90,000 - $110,000
  • Actuarial Consultant $105,000 - $130,000
  • Senior Actuarial Consultant $120,000 - $145,000

About The Wawanesa Mutual Insurance Company
Founded in 1896, The Wawanesa Mutual Insurance Company is one of Canada's largest mutual insurers, 100% owned by its members, with more than $4.1 billion in annual revenue and $12.5 billion in assets. Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of personal and business insurance. In March of 2026, Wawanesa entered into an agreement to acquire Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy.


Wawanesa proudly serves more than 1.8 million members and we are home to more than 3,000 employees across Canada. The company actively gives back to organizations that strengthen communities, donating more than $4 million annually to charitable organizations, including more than $2 million each year in support of people on the front lines of climate change. Learn more at wawanesa.com.

We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.

Job Overview

Working with a high degree of autonomy, the Actuarial Consultant, Financial Planning & Analysis contributes to the organization by enhancing the tools, models, and reporting that support Wawanesa's budgeting, forecasting, and financial planning processes. Leveraging actuarial expertise, programming skills, and business knowledge, they transform complex data into meaningful insights that enable informed decision-making across the enterprise.

The Actuarial Consultant develops and maintains scalable solutions using modern analytical and visualization tools, including R, Python, SQL, and Power BI. They collaborate with stakeholders across Finance, Actuarial, and other business areas to identify opportunities for process improvement, strengthen data-driven decision-making, and ensure planning capabilities continue to evolve in support of organizational objectives.

We are open to these levels: Senior Actuarial Analyst, Actuarial Consultant, or Senior Actuarial Consultant level.

Job Responsibilities
  • Researches, extracts, and manipulates complex data from relevant sources, and assesses data quality.
  • Supports the business and overall team by performing analyses/reviews and completing ad-hoc requests/special projects in a timely manner with minimal support from peers and leaders.
  • Evaluates procedures and processes, and recommend alternatives or improvements .
  • Evaluates existing processes to find areas for increased efficiency.
  • Identifies opportunities for automation of routine tasks and implementation of advanced techniques while ensuring ethical and responsible application of solutions.
  • Develops new approaches to problem solving and assess impacts of solution options with minimal support from leaders.
  • Identifies emerging industry trends and analyzes the impact they will have on Wawanesa.
  • Encouraged to represent Wawanesa at external events that may include universities, actuarial clubs, industry organizations, and charitable causes.
  • Commits to professional development and continuous experiential learning to build cross-functional knowledge, technical skills, and mastery in competencies.
  • Focuses learning activities on bringing new knowledge and skills to team in order to address any existing gaps.
  • Provides regular project updates to stakeholders. Anticipates obstacles and raises them in advance.
  • Leads projects from beginning to end. Includes implementation of final product. May include training and documentation of the project.
  • Actively contributes to the mentorship, training and development of actuarial analysts.
  • Provides feedback, instruction, and development guidance to help others excel in their current or future job responsibilities.
  • Builds trust and credibility with peers.
  • Develops strong working relationships across teams.
Qualifications
  • Bachelor's degree in Actuarial Science, Mathematics, Statistics, or other related discipline.
  • More than 4 years of actuarial experience an asset.
  • 7 CAS exams or ACAS designation an asset.
  • Advanced oral and written communication skills, demonstrating the ability to convey business terminology and insights that are meaningful and well received.
  • Ability to clearly document major projects and key processes.
  • Effective at comfortably communicating analysis and results to senior leaders in written and/or oral form, and influencing direct leader to accept recommendations.
  • Discusses ideas in terms familiar to colleagues in different functional areas and teaches the necessary actuarial concepts when needed.
  • Proficient with Power BI, R, Excel, SQL, R, Python and/or other related software/programming languages/actuarial software.
  • Ability to easily adapt to new enterprise system environments.
  • Ability to identify areas for improved efficiency and suggest solutions.
  • Advanced knowledge of actuarial science, mathematics, probability, statistics, principles of finance and business, and strong ability to apply this knowledge to problems in insurance.
  • Ability to develop efficient and viable solutions to problems and assess impacts of these solution options.
  • Strong attention to detail when performing analysis with minimal technical errors.
  • Ability to identify errors and areas of concern that may significantly impact analysis.
  • Ability to balance materiality/efficiency and accuracy/detail.
  • Ability to prioritize and complete multiple concurrent assignments, both individually and as a leader of a group, in a timely manner while proactively keeping leader informed of progress.
  • Develops timelines for project plans.
  • Ability to work efficiently and co-operatively in a team environment.
  • Keeps abreast of current industry and professional standards and applies them directly to requirements and decisions.

#LI-AF1 #LI-Hybrid


Diversity Equity, Inclusion& Belonging
At Wawanesa, we are committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believe that our strength lies in the diversity of our people - this is supported by having a representative workforce.

We welcome applications from all qualified candidates, including racialized persons, women, Indigenous Peoples, persons with disabilities, members of the 2SLGBTQIA+ community, gender-diverse and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas. 
 

We aim to ensure our recruitment process is accessible to all candidates. If you require accommodations during any stage of the recruitment process, please reach out in confidence to jobs@wawanesa.com.
 

All Wawanesa job applicants are subject to Wawanesa's Privacy Policy.

Please note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants. All final decisions are taken or reviewed by human recruiters and human hiring leaders in compliance with all applicable legislation.  
 

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