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.

About the Role:
We’re looking for a strategic and hands-on leader to oversee finance, technology, and operations while playing a key role on the Senior Leadership Team. This role balances day-to-day financial and IT management with long-term strategic planning, including M&A, systems implementation, and organizational growth. The ideal candidate is a collaborative, forward-thinking leader who can mentor and inspire their team, drive continuous improvement across the business, and maintain an optimistic, engaging, and fun approach along the way.

Key Responsibilities:

Financial Oversight

• Manage accounting, reporting, budgeting, cash flow, and compliance.
• Streamline and automate processes to improve efficiency and scalability.
• Monitor controls, audits, and policies to safeguard the business.
• Use financial data to drive forecasting, cost control, and growth.
• Oversee collections and act as the company’s financial expert.

Technology & Cybersecurity

• Lead IT strategy, vendor partnerships, and new technology rollouts.
• Manage hardware/software needs and ensure reliable systems.
• Oversee cybersecurity training, monitoring, and staff support.
• Deliver tech projects that enable business growth and integration.

Facilities Leadership

• Coordinate branch facility needs and manage vendor relationships.
• Partner with the CEO to negotiate lease and purchase agreements.

Strategic Leadership

• Partner with the CEO and Directors on initiatives like M&A, new systems, and organizational growth.
• Lead due diligence in finance and technology, providing risk and opportunity assessments.
• Mentor and develop the accounting team, promoting collaboration and growth.
• Champion the selection and implementation of finance and IT systems.
• Serve as Privacy Officer, ensuring compliance with privacy legislation.

Qualifications:

• CPA designation (or equivalent) required.
• 3+ years of relevant experience.
• Strong understanding of financial reporting, budgeting, compliance, and cash flow management. Experience with mergers & acquisitions, due diligence, and systems integration is considered an asset.
• Knowledge of IT systems, cybersecurity practices, and vendor management.
• Ability to utilize software including Microsoft Office. An understanding of the general insurance industry and the ability to utilize the Epic Broker Management System is an asset.
• Ability to manage multiple deadlines and prioritize tasks effectively.
• Proven leadership skills with the ability to mentor and develop a team.
• Excellent communication, problem-solving, and collaboration skills.
• Ability to thrive in a fast-paced, growth-focused environment.
• Able to pass a criminal record check and bonding application

Why Join Us:

At WIB we believe in working hard, staying positive, and having fun while we do it. As part of our team, you’ll enjoy:

• A competitive salary based on skills and experience + participation in the annual performance bonus program.
• Professional development reimbursement and career growth.
• A matched Group RRSP to help you invest in your future.
• A full range of health benefits for your peace of mind.
• Generous time off — including vacation, sick time, personal days, and even volunteer days to give back to your community
• A supportive and collaborative leadership culture with opportunities to make a meaningful impact on the future of the business.
• A workplace that values teamwork, innovation, and continuous improvement including engaging team building events and leadership development training.
• A hybrid work arrangement is available. 

If you’re ready to bring your energy, passion, and drive to a team that values both hard work and fun, we want to hear from you!

Send your resume + cover letter to info@wpgins.ca. We thank all who apply, but only those selected for an interview will be contacted.