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Small Business Financial Strategist

We are hiring for this role now but the timeframe is flexible – from immediate start to Labour Day start. It is more important that we find the right fit.

About us

Podium Prosperity Group is a unique wealth advisory firm with offices in Barrie and Edmonton. Along with our sister company, Tradewinds Group, Podium had developed a unique and comprehensive approach to help small business owners turn revenue to profit, and profit to wealth. Our small business programs incorporate leadership coaching, management training and extensive, complex business and financial planning and solution advice.

On AI: We are not luddites. We believe AI is a powerful tool but we also believe that it is people that are the true resource, that earn the place of trusted advisor by deeply understanding the client and their goals first and tailoring all advice to the unique needs of that client, their business, and their family.

Our values are: Real Advice; Growing Businesses; Strong Families; Compassionate Communities.

Job Summary:

Most small business owners never get the financial guidance they actually need.

The banks are built to sell products. The big accounting firms are built around compliance and the clients large enough to move their numbers. The owner running a smaller firm doesn’t have the team who can advise them to the level they need.

We work in that gap — the white space where smart business planning meets genuine wealth planning — because that’s where the most valuable work for an owner actually lives. It’s the difference between filing the past and shaping the future.

We’re looking for someone to grow into that work alongside our team: someone who’s good with both the numbers and the people, who’s hungry to learn, and who’s quietly frustrated that small business owners are so often underserved.

You might recognize yourself here if…

  • You’re in a corporate FP&A or finance seat with real modeling and analysis chops, but you’re done with month-end variance packs and want work with actual client contact and meaning.
  • You’re in business banking or commercial lending and tired of being measured on products sold rather than problems solved.
  • You’re at an accounting or advisory firm where partner isn’t realistic, or your firm was recently acquired or consolidated and you’ve watched smaller clients quietly slide down the priority list.
  • You’re a controller or finance lead doing the heavy lifting in a growing company and ready for work with more variety.
  • You’re equally comfortable in a financial model and in a conversation with an owner who doesn’t speak finance.
  • Your longer-term aspirations are in business leadership and growth.

You don’t think of yourself as a “financial planner” yet.
You are looking to deepen your business and finance experience. You have the curiosity to learn the planning side, and the humility to master a proven system within a team that puts the business owner needs first and treats them with the respect they need.

What you’ll do

This role blends two things most firms keep in separate silos: business planning and wealth planning. On any given client you’ll move between both — and the real value is in connecting them.

On the business side, you’ll:

  • Build and maintain financial models, forecasts, and scenario/sensitivity analyses for owner-managed businesses — not corporate divisions.
  • Controller-adjacent work that translates often-imperfect financial and operational data into clear, plain-language insights owners can act on.
  • Analyze results to surface trends, variances, and the drivers behind them.

On the wealth side, you’ll:

  • Build client financial plans in Podium’s propriety ICL™ framework
  • Support the preparation of client portfolio and insurance reviews, and income tax reviews — presentation-ready.
  • Attend client and prospect meetings, both alongside the team and, over time, independently.
  • Make sure every required material and task is handled before, during, and after client meetings.

And you’ll connect the two — helping owners see how their business performance feeds their personal long-term wealth and goals. That integration is precisely what their banker and their accountant rarely do for them.

  • Prepare recurring and ad hoc reports, dashboards, and summaries that give owners real visibility into their performance. This duty ties into proprietary tools, automations, and AI supported frameworks.

As part of the team, you’ll:

  • Work within our service framework to deliver a seamless, consistent client experience.
  • Liaise with the service team for form preparation, statement requests, and other administrative needs.
  • Liaise with clients’ other professional advisors — lawyers, accountants, and bankers.
  • Help standardize and improve our planning, forecasting, and reporting processes and the tools behind them, documenting assumptions and methods as you go.
  • Support client communication, tailoring how you explain things to each owner’s level of financial fluency.
  • Manage multiple client deliverables and bring each to a finished outcome, on time.
  • Document your assumptions and methods so the work stays transparent and consistent.

What you bring

  • Roughly 3–6 years working closely with business or client finances — corporate FP&A or finance, business banking or commercial lending, accounting/advisory, or a controller/finance seat in a growing company.
  • Strong Excel. You’re comfortable with multi-variable dynamic models, complex formulas, and running scenario analysis to make causal links between inputs and outcomes.
  • CPA, or strong personal and small-business tax knowledge. You don’t have to be a tax specialist, but you’re comfortable with the fundamentals of individual and corporate tax.
  • Fluency in the language of business finance — budgets, P&Ls, financial statements, and the nomenclature that goes with them.
  • A genuine passion for small business and a desire to learn finance and tax planning for small corporations.
  • Coachability. You’re energized by mastering proven frameworks and tools before reinventing them — mastery first, innovation second. This role suits someone who wants to get great at a craft within a team, not a lone operator who already has all the answers.
  • Strong communication, written and verbal, and the instinct to meet clients at their level of understanding.
  • An intrapreneurial, resourceful streak — you finish what you start, sweat the details, and still hold the big picture.
  • CRM literacy and general comfort with financial systems and reporting tools.
  • A real interest in current events, business news, the economy, and investing.
  • You’re a team player who’s connected to your community.

Nice to have

  • A credential — CPA, CFP / QAFP, TEP, MBA, BComm — or you’re a bit less traditional in your learning path but can show the aptitude to back it up.
  • Familiarity with one or more financial planning platforms (Navigator, FPS, Razor, Planworth, Snap, or similar). A real plus — but we’ll train you on ours.
  • Experience supporting budgeting, forecasting, or performance management.
  • Familiarity with financial modeling, scenario analysis, or variance analysis techniques.

Why this Role

This isn’t a seat where you’ll be left to sink or swim. We’ll invest in you: training, courses, and direct mentorship as you grow into the planning side of the work. You’ll learn an existing set of powerful tools and frameworks — and once you’ve mastered them, you’ll help make them better.

It’s mission-driven work with real variety, real client impact, and a clear path to grow into financial planning. If you’ve been waiting for a place that takes the small business owner seriously, this is it.

How to Apply

Email: cher.cunningham@podiumprosperity.com with the subject line “Application: Business & Wealth Planning Associate”
(No employment firms please.)

NOTE: We read every application. Templated, generic submissions won’t advance — tell us something specific and real.

Please submit your resume along with short answers to both questions below:

  1. Which background above is closest to yours, and what specifically made you ready to leave it?
  2. The scenario below.

Scenario. Meet a fictional client, Maple Ridge Landscaping Inc. — owner-managed, one shareholder. Last year:

  • Revenue: $1,200,000
  • Direct costs (materials + subcontractors): $540,000
  • Wages, including the owner’s $90,000 salary: $410,000
  • Operating expenses: $180,000
  • Net income before tax: $70,000
  • Owner also took $60,000 in dividends

In four or five sentences: what would you want to ask the owner first, and what’s the first thing you’d model?