Senior Accounting & Financial Operations Manager

Company Description SimplePin is a financial operations automation platform purpose-built for insurance agencies, MGAs, and carriers. The company streamlines the full financial operations lifecycle, from billing and binding through direct bill reconciliation and general ledger posting. By automating commission tracking, statement capture, and reconciliation, SimplePin reduces costly manual work and errors while integrating seamlessly with leading agency management systems.About the RoleWe are looking for a hands-on Senior Manager, Accounting & Financial Operations to own the accounting function across multiple U.S. and Canadian entities.This is a senior, highly autonomous role responsible for everything from transaction-level reconciliation and multi-currency accounting through month-end close, financial statements and coordination with external CPAs.We are also looking for someone who is technology-forward and actively looks for opportunities to improve and automate accounting processes using AI and other modern tools.Key ResponsibilitiesOwn month-end close across multiple Canadian and U.S. entitiesPrepare monthly financial statements and management reportingMaintain accurate general ledgers, journal entries, accruals and supporting schedulesComplete bank, credit card and balance sheet reconciliationsManage intercompany accounting and reconciliationsReconcile high-volume transaction data across banks, payment processors, internal systems and the GLSupport monthly invoicing and billing reconciliationInvestigate and resolve variances and unmatched transactionsManage multi-currency accounting, including CAD/USD, FX gains and losses and month-end remeasurementWork directly with Canadian and U.S. CPAs on tax filings, year-end reporting, audits and other requirementsEnsure financial records are accurate, well documented and audit-readyDevelop scalable accounting, reconciliation and reporting processesUse technology and AI to automate repetitive workflows, improve controls and increase reporting efficiencyPartner with Operations and Technology teams to resolve financial-data and systems issuesWhat We’re Looking For7+ years of progressive accounting or financial operations experienceStrong experience with month-end close and financial statement preparationMulti-entity and multi-currency accounting experienceStrong reconciliation and analytical skillsExperience working with large volumes of transactional dataAdvanced Excel skills; Power Query or similar data tools preferredExperience working directly with CPAs, auditors and tax advisorsStrong understanding of accrual accounting, intercompany accounting and FXHighly organized, detail-oriented and comfortable working independentlyStrong problem-solving skills and a willingness to investigate issues through resolutionComfortable working in a fast-paced, remote environmentStrongly PreferredCanadian CPA designationExperience supporting both Canadian and U.S. entitiesPayments, fintech, banking, financial services or SaaS experienceHigh-volume payment or transaction reconciliation experienceExperience implementing accounting automationHands-on use of AI to improve financial or accounting workflowsFamiliarity with SQL, APIs, Python or BI tools is an assetThe Right PersonYou want to own the numbers, not simply process them.If something does not reconcile, you figure out why. If a process takes hours every month, you look for a better way to automate it.You are equally comfortable investigating a transaction-level discrepancy, preparing financial statements and explaining financial results to senior leadership.Most importantly, you take ownership and produce financial information the business can trust.Compensation & Location$140,000–$165,000 base salary plus performance bonus, depending on experience.This is a fully remote role based in the United States, working with leadership and teams across Canada, the U.S. and internationally.