Director of Finance – Head of Finance, Player-Coach
FLiiP
full-time
Posted on:
Location Type: Hybrid
Location: Brossard • Canada
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Job Level
About the role
- 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
- 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
- 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
- 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
- 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
- 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
- Maintain cash forecasting and runway visibility (monthly cadence, clear assumptions)
- Recommend practical spend guardrails tied to performance and forecast
- 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)
Requirements
- 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)
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
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
financial analysisdashboard creationvariance analysisreconciliationscash forecastingrevenue recognitionaccounts receivablecollections managementpayments margin reportingfinancial reporting
Soft Skills
executive presenceclear communicationinfluencing stakeholdersaccountability enforcementcoachingmanagementstrategic decision supportcollaborationproblem-solvingadaptability
Certifications
CPA