Chief Executive Officer - Winnipeg Insurance Brokers Ltd.

Chief Executive Officer - Winnipeg Insurance Brokers Ltd.; Winnipeg; On-site; CAD 180,000 - 280,000; Full time

Job summary

Winnipeg Insurance Brokers Ltd. (WIB) seeks a Chief Executive Officer to lead a multi-branch insurance brokerage, driving strategic direction, financial management, sales and business development, HR, marketing, IT, and governance.

The CEO will actively pursue merger and acquisition opportunities and ensure compliance and operational excellence across all branches. The role requires extensive leadership experience in insurance brokerage, strong strategic vision, and the ability to build external

Qualifications

• Bachelor’s degree or diploma requiring 3–4 years of full-time study and a Level 3 Nominee licence.
• Life, Accident & Sickness licensing is an asset.
• Ten or more years of related experience, with a minimum of five years leading a team of professional staff.

Responsibilities

• Lead the development of long-term strategic and annual operating plans and oversee execution.
• Ensure the overall operation and performance of all brokerage branches.
• Develop and monitor service delivery standards and sales/marketing strategies.
• Prepare financial and statistical reports detailing performance and growth.
• Recruit, develop and lead a high-performing insurance brokerage team.
• Develop and manage HR policies, compensation guidelines, and performance reviews.
• Oversee budget management and vendor/partner relationships.
• Represent the brokerage on industry boards and with external networks.

Skills

Leadership

Client service

Communication

Decision making

Problem solving

Change management

Team leadership

Organizational acumen

Education

Bachelor's degree or diploma (3–4 years)

Level 3 Nominee licence

Life, Accident & Sickness licensing (asset)

Job description

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.