We’re Hiring: Fractional CFO Associate  

 

Join a High-Caliber Fractional CFO Firm, Specialized in Construction & Trades

 

This is a Full-time, On Staff position - Not Contract or Freelance

 

💡 How to Apply: details below.

📍 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.

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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.

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

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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.

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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.

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The Kind of Work We Do

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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

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This role blends financial analysis, problem-solving, communication, and advisory thinking.

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

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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.

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

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You may be:

• 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.

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

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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.

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

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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

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

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

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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.

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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.

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Compensation 

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

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

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

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How to Apply 

 

Send an email to info@masterycfo.com with the subject line: Fractional CFO Associate — Application

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In the body of your email, include a short note covering:

• Why this role interests you at this stage of your career

• Why Mastery Fractional CFO Services, in particular, appeals to you

• Your compensation expectations

• What kind of finance career you are looking to build

 

Include your resume.
We may request additional information from shortlisted candidates.​​​

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We hire carefully and deliberately. We are looking for someone with the technical foundation and potential to develop into an exceptional financial advisor and grow with Mastery over the long term.

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Shortlisted candidates will be contacted to move to the next step of the process.

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