Join a High-Caliber Fractional CFO Firm, Specialized in Construction & Trades This is a Full-time, On Staff position - Not Contract or Freelance Location: Hybrid - 3 days per week at our Winnipeg office, 2 days remote. You must be located in or near Winnipeg, Manitoba.

The Mission Behind Mastery

We bring top-tier financial leadership to $3M+ Canadian construction & trades companies — helping them build stronger systems, make smarter decisions, and scale with confidence.

Why This Role Matters As a Fractional CFO Associate, you will work directly with the Mastery CFO team to help solve real financial and business problems for our clients.

This isn’t bookkeeping or a traditional accounting role where the work ends when the financial statements are prepared.

You’ll help analyze business performance, build forecasts and cash flow models, identify financial and operational issues, and develop recommendations that business owners actually use.

This is a CFO-in-training role — giving you exposure to the business judgment, financial leadership, and strategic advisory work required to become a high-value financial advisor.

The Kind of Work We Do At Mastery, you will help our CFOs and clients: Understand financial performance and identify what is driving the numbers

Build budgets, forecasts, cash flow models, and scenario analyses

Identify margin, pricing, and operational performance issues

Prepare for growth, financing, and major business decisions

Navigate liquidity challenges and cash flow pressure

Develop stronger reporting, financial systems, and KPIs

Turn accounting data into practical business insight

Prepare for and support CFO-level client meetings

This role blends financial analysis,



problem-solving, communication, and advisory thinking.

Over time, you will take on increasing responsibility for analysis, recommendations, client discussions, and eventually direct advisory work.

Who We’re Looking For This role is for someone with a strong financial and business foundation who wants to grow into broader, more strategic financial leadership.

There is no single required path, but we are looking for someone who already brings meaningful experience and credibility to the table.

A CPA, CFA, or CBV with meaningful accounting, finance, or business experience

An experienced Controller or senior finance professional, particularly within construction, trades, project-based businesses, or owner-managed companies

Someone with a BComm, MBA, or similar business education, combined with strong practical finance and business experience

Someone who has developed strong financial judgment through a combination of education, industry experience, and increasing responsibility

What matters is that you understand financial statements, can think analytically, have strong business sense, and are ready to move beyond reporting the numbers to helping business owners make better decisions.

You are looking for something more entrepreneurial, strategic, and business-facing.





You want to deepen your understanding of how companies operate, how owners make decisions, and how financial leadership can improve the performance of a business.

You also want to continue developing the judgment, confidence, communication skills, and advisory ability required to become a high-value financial leader.

Experience and Qualifications Strong candidates will bring a combination of:

Meaningful accounting, finance, controllership, or business experience

Strong financial statement and financial analysis fundamentals

Experience with budgets, forecasts, cash flow, or management reporting

Strong Excel or spreadsheet skills

The ability to analyze financial information and identify meaningful business issues

Strong business judgment and problem-solving ability

A genuine interest in advisory work, business strategy, and client-facing financial leadership

Experience with construction, trades, project-based businesses, owner-managed companies, or QuickBooks Online is a solid asset.

The most important qualities are intelligence, judgment, curiosity, work ethic, business sense, and the desire to grow into a broader financial leadership role.

Core Strengths We Value The right person will be:

Analytical, but practical

Detail-oriented, but able to see the bigger picture

Curious about how businesses make money

Comfortable working through ambiguous problems

Technically strong and eager to keep learning

Confident enough to contribute and humble enough to be coached

Strong work ethic, highly accountable, reliable, and client-focused

Interested in building a long-term future with M

📌 CFO Associate (Winnipeg)
🏢 Business Consulting
📍 Winnipeg