Careers

We’re a team of go-getters who bring energy, heart, and a sense of fun to helping clients make sense of insurance.

Why Work Here?

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’re a motivated team of hardworking people who love insurance (yes, really!) and are passionate about helping clients navigate it with confidence. We move together in the same direction, playing off each other’s strengths, and celebrating the wins along the way.

Here, it’s positive vibes only. Excuses? Not our style. We know you get out what you put in — so we put in our best, every time. That means building clear, consistent processes that keep things running smoothly, so our clients always get the best service and our team can focus on what matters most: people.

We embrace our differences and love that we can serve clients in many languages. Inclusivity is in our DNA — everyone is welcome, everyone is heard, and everyone matters. Around here, people feel recognized and supported, which gives us the courage to try new things, share big ideas, and even fail sometimes (because that’s how you learn and grow!).

We also care deeply — about our clients, about each other, and about our planet. We’re approachable, compassionate, and not afraid to ask for help when we need it. We keep our doors (and minds) open, solve problems together, and hold ourselves accountable to getting things done.

And while we take our work seriously, we don’t always take ourselves seriously. You’ll hear laughter in our halls, see curiosity in action, and feel the energy of a team that’s thriving in a safe, respectful, and fun environment.

At WIB, we work with integrity and enthusiasm, and push ourselves to keep growing. Because when everything you do matters, you make sure it counts — and you have some fun along the way!

Current Opportunities

Chief Executive Officer

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 through the link below 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.