Chief Executive Officer, Winnipeg Insurance Brokers

OVERVIEW

Guided by Winnipeg Insurance Brokers Ltd. mission and values, the Chief Executive Officer (CEO, WIB) leads and directs a multi-branch insurance brokerage. This position maintains overall accountability and responsibility for the strategic direction and all general operations of the brokerage including, financial management, service, sales and business development, vendor relations, human resources, marketing, information technology, project management, administration, compliance and facilities management. In addition, the CEO, WIB actively works to identify and secure quality merger and acquisition opportunities.

KEY ACCOUNTABILITIES

• Leads the development of the brokerage’s long term strategic and annual operating plans, the development of goals and oversees the execution of initiatives supporting plans
• Overall operation and performance of all brokerage branches
• Developing, implementing and monitoring service delivery standards for the brokerage
• Establishing, implementing and maintaining business development, sales and marketing strategies and management routines that support the achievement of sales objectives and the overall plan
• Developing, implementing and managing the brokerage budget including all capital, operating and personnel expenses
• Preparing financial and statistical reports detailing overall brokerage performance and growth
• Ensuring all compliance and internal control standards are developed, communicated, and followed
• Recruiting, developing and leading a team of qualified, professional and capable insurance brokerage employees
• Developing, communicating, and adhering to human resource policies, compensation guidelines, and performance review procedures
• Developing and consistently promoting the brokerage brand through all marketing efforts
• Ensuring the consistent performance of the brokerage’s information technology resources including hardware, software, security and delivery systems
• Ensuring back office and other administrative services support the efficient delivery of superior service
• Managing all brokerage facilities and the negotiation of related contracts
• Developing and managing the relationships and contracts with third-party insurance companies including MPI
• Maintaining current and relevant knowledge of insurance industry trends, competitor products and strategies
• Developing and maintaining an external network to establish, build and promote positive relations with dealerships, other brokerages, insurance companies and vendors
• Integrating the commitment to corporate social responsibility into brokerage business culture
• Identifying and securing merger and acquisition opportunities
• Representing the brokerage and credit union on insurance industry boards, committees, or working groups

Education and experience

The competencies for the position would typically be acquired through a Bachelor’s degree or diploma requiring three to four years of full time study, plus a Level 3 Nominee licence. Life, Accident & Sickness licencing is an asset. Ten or more years of job related experience, with a minimum five years leading a team of professional staff, or an equivalent combination of education and experience is required.

KNOWLEDGE, SKILL & ABILITY (KSA) PROFILE

This role requires demonstrated success in key core competency areas including:

• Leading Self
• Client Service
• Delivering Results
• Communication
• Change
• Team Leadership
• Problem Solving & Decision Making
• Organizational Acumen

In addition, the Chief Executive Officer, Winnipeg Insurance Brokers:

• Maintains an unwavering focus on the market and client, evolving client needs and exceeding client expectations
• Is enthusiastic about and keeps ahead of trends in the insurance industry and understands the implications for Winnipeg Insurance Brokers
• Has an eye for talent, is passionate about leadership and seeing people on the team grow and succeed
• Demonstrates contemporary sales and service leadership; clearly articulates responsibility, measures and coaches for progress and results
• Builds and nurtures valuable networks inside and outside the organization
• Can simultaneously and effectively operate strategically, operationally and tactically
• Understands the importance of efficiency to the success of the operation; simplifies complex processes to get the most out of limited resources
• Has established financial management, risk management, vendor relations, human resources, marketing, information technology, administration, compliance and facilities management skills
• Understands insurance brokerage operations and is knowledgeable in current insurance products, services and the regulatory environment

If doing things differently and doing more is part of who you are, join us on a rewarding journey where your personal aspirations and career goals can align.

If you are interested in applying for this position, please submit your application by Monday, November 9, 2026, at 4:00 pm.
We thank everyone who applies, but only candidates selected for an interview will be contacted.

We are committed to workforce diversity and actively recruit people with diverse backgrounds, experiences, and perspectives reflecting the community in which we live and work. Applicants may request reasonable accommodation related to the materials and activities used throughout the selection process.

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