Chief Executive Officer - Winnipeg Insurance Brokers Ltd.

Chief Executive Officer - Winnipeg Insurance Brokers Ltd. Province: Winnipeg, Manitoba Position: Chief Executive Officer Deadline: November 9, 2026 Posted: October 28, 2026

Job Description / Duties ROLE 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

Qualifications / Required Skills 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

Additional Information 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.

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.

Employer Profile At Winnipeg Insurance Brokers Ltd (WIB), our Why is simple but powerful: Everything we do matters because it impacts the lives of others. That belief drives us every single day. We live it out by delivering a superior client experience and by taking exceptional care of our team members and clients alike.

We work hard, move fast, and have fun doing it. We’re a high-energy, growth-focused insurance brokerage that believes creativity, teamwork, and strong relationships drive real results.

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