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Director Insurance Jobs in Calgary, AB (NOW HIRING)

Td

TD Insurance, Counsel I

Calgary, AB · Hybrid

CA$110K - CA$150K/yr

Our Life and Health business is the number one provider of critical illness insurance and direct life and health insurance in Canada. At TD Insurance, we are committed to fostering an inclusive ...

Vision Group

District Director

Calgary, AB · On-site

As a District Director, you will play a key role in translating regional priorities into ... You are eligible for the group insurance plan, which includes telemedicine and an Employee ...

Vision Group

District Director

Calgary, AB · On-site

As a District Director, you will play a key role in translating regional priorities into ... You are eligible for the group insurance plan, which includes telemedicine and an Employee ...

FCT

Director, National Underwriting

Calgary, AB · On-site

FCT provides industry-leading title insurance, default solutions and other real estate related ... The Director, National Underwriting is responsible for safeguarding the Company's risk profile by ...

National Bank

Director Commercial Banking

Calgary, AB · On-site

A career as a Director, Commercial Banking at National Bank means being responsible for growing the ... Flexible group insurance * Generous pension plan * Employee Share Ownership Plan * Employee and ...

Fluor

HSSE Director

Calgary, AB · On-site

... direct-report managers and supervisors. Provide guidance for the implementation of HSSE ... insurance carriers and regulatory agencies in order to provide assistance and resolution in regard ...

HUB

Director Business Development

Calgary, AB · On-site

Specializing in life insurance, investments, and wealth management, we provide independent ... About The Role The Director, Business Development role delivers sales support to an assigned block ...

RONA

Site Director - Distribution Center

Calgary, AB · On-site

About the Role Reporting to the Distribution Director (Ontario and Western Canada), you will lead ... Benefits: insurance (certain conditions apply), annual salary review, etc. * Opportunities for ...

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Director Insurance information

See Calgary, AB salary details

$21K

$105.3K

$219K

How much do director insurance jobs pay per year?

As of Aug 22, 2026, the average yearly pay for director insurance in Calgary, AB is $105,331.00, according to ZipRecruiter salary data. Most workers in this role earn between $61,000.00 and $138,000.00 per year, depending on experience, location, and employer.

What does a director insurance do?

A Director of Insurance is responsible for overseeing an organization's insurance programs and risk management strategies. They ensure that the company has adequate coverage for various risks, negotiate with insurers, and develop policies to minimize potential losses. Additionally, they may manage a team, stay updated on industry regulations, and analyze data to make informed decisions about coverage and claims. Their goal is to protect the organization’s assets while optimizing insurance costs.

What are the key skills and qualifications needed to thrive as a director insurance, and why are they important?

To thrive as a Director of Insurance, you need in-depth knowledge of insurance products, risk management, regulatory compliance, and leadership experience, often backed by a bachelor’s or master’s degree in finance, business, or a related field. Familiarity with industry-standard insurance management software, data analytics platforms, and relevant certifications such as CPCU or ARM is essential. Strong strategic thinking, negotiation, and team leadership skills set exceptional candidates apart. These skills and qualifications are vital for driving organizational growth, ensuring regulatory adherence, and leading high-performing teams in a complex and evolving industry.

What are some common challenges faced by a director insurance when leading cross-functional teams?

A Director of Insurance often leads teams that include underwriting, claims, compliance, and sales professionals, requiring strong coordination and communication skills. Common challenges include balancing differing departmental priorities, aligning on regulatory requirements, and ensuring seamless customer experiences. Successfully managing these dynamics involves fostering collaboration, setting clear objectives, and staying updated on industry trends. Directors also need to adapt quickly to regulatory changes and technological advancements that impact workflow and client needs.

What is the difference between Director Insurance vs Insurance Manager?

AspectDirector InsuranceInsurance Manager
CredentialsTypically requires a bachelor’s degree in insurance, business, or related field; professional certifications like CPCU or ARM are commonUsually holds similar degrees and certifications, such as CPCU or ARM, but may have less seniority
Work EnvironmentOversees multiple teams or departments, strategic planning, and high-level decision-making within insurance companiesManages daily operations of insurance teams, handles policy administration, and ensures compliance
Employer & Industry UsageFound in large insurance firms, corporations, and brokerage firms, focusing on strategic leadershipCommon in insurance companies, agencies, and departments, focusing on operational management

The main difference between a Director Insurance and an Insurance Manager lies in their scope and level of responsibility. Directors typically focus on strategic planning and leadership at a higher level, while Managers handle day-to-day operations and team management. Both roles require relevant credentials and industry experience, but Directors usually have broader oversight and influence within the organization.

What are the most commonly searched types of Insurance jobs in Calgary, AB?

The most popular types of Insurance jobs in Calgary, AB are:

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

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

Director Insurance jobs near you
Infographic showing various Director Insurance job openings in Calgary, AB as of August 2026, with employment types broken down into 50% Full Time, and 50% Part Time. Highlights an 100% In-person job distribution, with an average salary of $105,331 per year, or $50.6 per hour.

Director, Underwriting Operations, Commercial Mid-Market - West

Wawanesa Insurance

Calgary, AB • Hybrid

CA$180K - CA$200K/yr

Full-time, Part-time

Retirement, PTO

Posted 17 days ago

Job description

Job ID: 10247 


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; Vancouver, BC; Calgary, AB; Edmonton. 

Working Business Language: English 
 

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: $180,000 - $200,000. Candidates with salary expectations outside of the range are still encouraged to apply.

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

The Director, Underwriting Operations, Commercial Mid-Market is responsible for leading Wawanesa's Middle Market Property & Casualty, Agriculture and Fleet teams across Western Canada - driving profitable growth, portfolio diversification, and operational excellence within a nationalized underwriting structure. Focused on larger commercial business, this role provides technical leadership in underwriting, pricing, risk selection, portfolio management, and broker engagement to deliver competitive solutions for mid-sized businesses across Western Canada.

Working closely with the VP, Mid-Market, this leader will help shape the future of Commercial Middle Market at Wawanesa, while leading and coaching underwriting leaders and teams, maintaining a strong market presence with brokers, and advancing strategic priorities. The role holds the highest underwriting authority for the segment, providing expertise and guidance on complex commercial risks and large account opportunities.

Responsibilities

  • Oversee underwriting processes, workflows, and governance to ensure accuracy, speed and ease of doing business.
  • Standardize practices, procedures, and tools across regional underwriting teams to drive national alignment while maintaining regional expertise and broker service models.
  • Monitor underwriting performance metrics and operational KPIs, implementing corrective action where needed. Provide oversight of catastrophe-exposed and large complex accounts to ensure strong risk management, underwriting discipline, and portfolio profitability.
  • Collaborate and provide input into the design and implementation of the transformation roadmap for Commercial Small Business.
  • Move at pace by applying a test-and-learn approach, failing fast and pivoting quickly in response to learnings.
  • Use effective collaboration and communication with key stakeholders to navigate roadblocks and governance processes.
  • Empower, mentor, and develop a high-performing underwriting operations team in Commercial Small Business, fostering a culture of accountability, collaboration, and innovation. Provide leadership and coaching to underwriting leaders and teams across BC, AB, MB, and SK.
  • Attract and retain top talent, focussing on capabilities that will accelerate the transformation and thrive in the future state.
  • Serve as a key liaison between underwriting, distribution, actuarial, claims, finance, and compliance functions.
  • Build strong relationships with brokers and partners to ensure service expectations are met and exceeded. Maintain a visible market presence and strengthen strategic broker relationships to support profitable growth.
Qualifications
  • Minimum 10 years of experience in commercial insurance, with deep expertise in mid-market underwriting in the specific segment.
  • At least 5 years in a leadership role, preferably within a national insurer, with experience leading regional underwriting teams, broker relationships, and complex commercial portfolios.
  • Bachelor's degree in business, insurance, risk management, or related field. MBA, CRM, CIP, or FCIP are considered assets.
  • Product development and portfolio management experience considered an asset.
  • Strong understanding of the mid-market business environment, commercial lines regulatory frameworks, and broker distribution models.
  • Proven ability to grow income, with a focus on long-term portfolio health, proactively managing risk and building member value.
  • Excellent relationship management, communication, and stakeholder engagement skills.
  • Bilingualism in English and French is considered an asset.
  • Ability and willingness to travel nationally to engage with regional teams and brokers.


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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