CFO Associate

Mastery CFO; Winnipeg; Hybrid; CAD 120,000 - 180,000; Full time

Job summary

Mastery is seeking a driven Fractional CFO Associate in Winnipeg, blending financial analysis, problem-solving, and advisory thinking. You will support CFOs, analyze performance, build forecasts and cash flow models, and help clients scale through smart financial leadership.

This is a CFO-in-training role designed to develop strategic advisory skills and deepen understanding of how owners use financial data to grow a business. Hybrid work with on-site Winnipeg collaboration.

Qualifications

• Strong accounting/finance background with controllership or advisory experience.
• Experience with budgets, forecasts, cash flow, or management reporting.
• Ability to build financial models and KPIs for client leadership.

Responsibilities

• Analyze business performance and drivers of financial results.
• Create budgets, forecasts, cash flow models, and scenario analyses.
• Identify margin, pricing, and operational performance issues.
• Prepare for growth, financing, and major business decisions.
• Develop stronger reporting and financial systems for clients.
• Translate data into actionable recommendations for CFO-level discussions.
• Grow into advisory work with increasing client exposure.
• Collaborate with Mastery CFO team to guide client decisions.

Skills

Financial analysis

Budgeting

Forecasting

Cash flow modeling

Excel proficiency

Education

CPA/CFA/CBV

Bachelor/MBA in finance

Tools

QuickBooks Online

Spreadsheet software

Job description

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 strong 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 Mastery

We're looking for someone who wants to develop over several years and grow with the firm.

Who This Role Is Not For

This role is not a fit if you:

Want a purely technical accounting role

Prefer repetitive or highly predictable work

Are uncomfortable working through ambiguous business problems

Do not enjoy analysis, problem-solving, or advisory thinking

Prefer to avoid client-facing work long term

Are looking for a short-term stepping-stone role

This role is for someone who wants to grow into a broader, more strategic finance professional.

Compensation

Compensation includes a strong base salary with opportunities for performance-based incentives as responsibility and client involvement increase.

As Mastery continues to grow, this role has the opportunity to grow with the firm through greater responsibility, client exposure, advisory work, and earnings.

Our goal is to develop long-term financial advisors who can eventually operate as trusted strategic partners to business owners.