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Director of Finance (Head of Finance, Player-Coach)

📍 Montreal, Canada

Finance and Insurance FLiiP

Job Description

Location:

Quartier dix-30 - Brossard, QC (Hybrid) Reporting to : CEO

About FLiiP FLiiP is a vertical B2B SaaS platform that powers health club management — from membership and scheduling to billing and payments. We serve a growing base of fitness businesses across North America, helping them run smarter and scale faster.

We are

VC-backed by two funds

(Montreal and US-based), we’ve grown at a

high pace , and we are

preparing for a Series A . We are a team of 40 building for scale, with a finance function that needs to move fast, stay accurate, and support growth decisions.

Why this role exists We need a hands‑on finance leader who owns the fundamentals with rigor: monthly close, cash visibility, revenue recognition, payments economics and reconciliation, AR and collections, and board‑level reporting. Payments is a meaningful revenue stream for us. Your job is to make our numbers accurate, fast, and decision‑ready, so leadership can scale confidently.

This is a hands‑on role You will personally own the monthly close, revenue recognition, reporting cadence, and the finance operating rhythm. You will build processes and structure while coaching a Financial Analyst and managing external partners. If you want a role where you only review other people’s work, this is not it.

Growth path We are looking for someone who can grow into a VP Finance / CFO over time. The right person will earn that path through operational excellence first, then expand into strategic finance and fundraising support as the company progresses toward a future Series A.

What you will own Strategic decision support

Support leadership strategic decisions by providing the right data, clear analysis, and a strong point of view

Build decision‑ready dashboards and ad hoc analyses to inform trade‑offs (pricing, investments, hiring, cash allocation)

Partner with the CEO and exec team to challenge assumptions and improve forecast accuracy over time

Close, Accounting, and Controls

Own monthly close in Xero and deliver accurate management financials by day 10 after month‑end

Own balance sheet integrity: reconciliations, accruals, deferred revenue, and clean audit trail

Implement lightweight controls that scale as we grow

Revenue Recognition (SaaS + annual contracts + payments)

Own and maintain revenue recognition policies and execution across subscriptions, annual contracts, and payments‑related revenue

Ensure alignment between billing (ChargeOver), accounting (Xero), and operational reality

Partner with external accountants as needed — but you own the result

Reporting cadence and board packages

Own weekly KPI reporting with clear definitions and consistency

Produce a monthly tactical board package (KPIs and operating commentary) and support quarterly deep‑dive reporting

Provide variance analysis that drives decisions, not just reporting

AR, Collections, and Billing operations

Own AR and collections for annual contracts, and maintain a predictable collections rhythm

Maintain and improve dunning processes, follow‑ups, and internal accountability

Report AR aging and collection performance trends

Payments economics and reconciliation (Revenue driver)

Own payments margin reporting: take rate revenue, processing costs, refunds, chargebacks, disputes

Ensure clean reconciliation between payments activity, ChargeOver billing, and Xero accounting

Manage payment partner relationship from an execution and economics standpoint (commercial terms, reporting, controls)

Build dashboards that show payments profitability and operational risk clearly

Cash management and forecasting

Maintain cash forecasting and runway visibility (monthly cadence, clear assumptions)

Recommend practical spend guardrails tied to performance and forecast

Team and admin support

Coach and manage a Financial Analyst and external bookkeeper

Manage external bookkeeping and accounting partners as needed

Support basic HR‑admin workflows (onboarding/offboarding documentation, payroll coordination) on an interim basis, until a dedicated People function is in place

Support legal and admin workflows related to finance (vendor paperwork, contracts coordination, compliance support)

Your tools

Accounting: Xero

Billing: ChargeOver

Expenses & Payables: Float

Payroll: EmployeurD

What we’re looking for

Executive presence : confident, clear communicator with the ability to influence senior stakeholders and represent Finance in board‑level and investor conversations

5 to 10 years

in finance/accounting in a startup, scale‑up, or operator environment

Proven ownership of monthly close, reporting, AR/collections, and cash forecasting

Comfortable in the weeds: reconciliations, process building, and system hygiene

Strong communication and backbone: can enforce timelines and accountability

CPA is a strong asset (or equivalent depth in accounting rigor)

We’re building the operating system for health clubs, and we need a finance leader who wants to build with us. If you want ownership, speed, and a seat at the table from day one — send your resume to jobs@myfliip.com.

Benefits

Health insurance

Health and wellness credit: $500 annually

Cell phone and internet credit: $75 per month to cover work‑related phone and internet usage

Unlimited sick days (short‑term illness, with reasonable use and manager support)

Home office setup support

Professional development support

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Job Details

Posted Date: February 21, 2026
Job Type: Finance and Insurance
Location: Montreal, Canada
Company: FLiiP

Ready to Apply?

Don't miss this opportunity! Apply now and join our team.