We’re Hiring: Fractional CFO Associate

A CFO-in-Training Role with Mastery Fractional CFO Services

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.

💡 How to apply: Details below.

The Mission Behind Mastery

Most growing companies don't fail because of bad products or services.

They struggle because they never build the financial leadership, systems, and insight needed to scale with confidence.

Mastery Fractional CFO Services solves that problem.

We provide high-level financial leadership to growing businesses, with a current focus on construction and project-based companies. We help business owners understand their numbers, make better decisions, improve cash flow, strengthen margins, and build companies that are more scalable, more valuable, and better managed.

Why This Role Matters

We're looking for a Fractional CFO Associate / Financial Analyst to work directly with the Mastery CFO team.

This is not a traditional accounting role.

It's not bookkeeping.

It's not a narrow corporate finance position where you prepare reports that disappear into a folder.

This is a hands-on advisory role where you will help solve real business problems for real clients.

You will be working closely with Ryan Chenier and the Mastery CFO team to prepare financial analysis, build forecasts, review business performance, identify key issues, develop advisory recommendations, and support client-facing CFO work.

In many ways, this is a CFO-in-training role.

You will be developed, coached, and exposed to the kind of business judgment, financial leadership, and strategic advisory work that many finance professionals do not get to experience until much later in their careers.

The Kind of Work We Do

At Mastery, we help clients:

Understand their financial position more clearly
Improve reporting and decision-making
Build budgets, forecasts, and cash flow models
Identify margin issues and operational inefficiencies
Prepare for growth, financing, or major business decisions
Navigate liquidity challenges and cash flow pressure
Build stronger financial systems and processes
Turn accounting data into practical business insight

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

You will help turn financial information into clear, useful recommendations that business owners can act on.

What You'll Be Doing

As a Fractional CFO Associate / Financial Analyst, you'll support CFO-level client work by:

Preparing financial analysis, reports, forecasts, and dashboards
Reviewing client financial statements and identifying key trends or issues
Building cash flow models, budgets, and scenario analyses
Helping assess profitability, margins, pricing, and operational performance
Supporting client meetings through preparation, analysis, and follow-up
Helping develop advisory recommendations alongside Ryan and the Mastery team
Turning raw financial data into clear business insight
Supporting the development of financial systems, reporting processes, and KPIs
Learning how to think, communicate, and operate like a trusted financial advisor

Over time, the goal is for you to grow into more direct client advisory work and take on increasing responsibility within the firm.

Who We’re Looking For

This role is ideal for someone who has recently earned their CPA designation or is close to doing so, and who wants a different kind of finance career.

You may have spent the last few years building your technical foundation in accounting, audit, tax, controllership, financial reporting, or industry finance.

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

You want to understand how companies actually work.

You want to learn how business owners think.

You want to develop the judgment, confidence, and advisory skills required to become a high-value financial leader.

Required Experience and Qualifications

CPA designation, or strong progress toward completion
Strong accounting and financial analysis fundamentals
Experience working with financial statements, budgets, forecasts, or management reporting
Strong Excel or spreadsheet skills
Ability to analyze financial information and identify meaningful business insights
Interest in advisory work, business strategy, and client problem-solving
Experience with QuickBooks Online, construction, project-based businesses, or owner-managed companies is an asset

The most important qualities are intelligence, judgment, curiosity, work ethic, and the desire to grow.

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
Strong enough technically to be credible
Humble enough to learn
Confident enough to contribute
Professional, reliable, and client-focused
Interested in building a long-term future with Mastery

We are looking for someone who wants to be developed over several years, not someone looking for a short stop on the way to the next job.

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
Are looking for a short-term stepping-stone role
Prefer to avoid client-facing work long term

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

Compensation

We offer a competitive compensation model based on experience, capability, and long-term fit.

As Mastery continues to grow, this role has the opportunity to grow with the firm through increased responsibility, client exposure, performance-based incentives, and long-term career development.

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

How to Apply

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

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.

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