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 Role

We 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 Responsibilities

• Own month-end close across multiple Canadian and U.S. entities
• Prepare monthly financial statements and management reporting
• Maintain accurate general ledgers, journal entries, accruals and supporting schedules
• Complete bank, credit card and balance sheet reconciliations
• Manage intercompany accounting and reconciliations
• Reconcile high-volume transaction data across banks, payment processors, internal systems and the GL
• Support monthly invoicing and billing reconciliation
• Investigate and resolve variances and unmatched transactions
• Manage multi-currency accounting, including CAD/USD, FX gains and losses and month-end remeasurement
• Work directly with Canadian and U.S. CPAs on tax filings, year-end reporting, audits and other requirements
• Ensure financial records are accurate, well documented and audit-ready
• Develop scalable accounting, reconciliation and reporting processes
• Use technology and AI to automate repetitive workflows, improve controls and increase reporting efficiency
• Partner with Operations and Technology teams to resolve financial-data and systems issues

What We’re Looking For

• 7+ years of progressive accounting or financial operations experience
• Strong experience with month-end close and financial statement preparation
• Multi-entity and multi-currency accounting experience
• Strong reconciliation and analytical skills
• Experience working with large volumes of transactional data
• Advanced Excel skills; Power Query or similar data tools preferred
• Experience working directly with CPAs, auditors and tax advisors
• Strong understanding of accrual accounting, intercompany accounting and FX
• Highly organized, detail-oriented and comfortable working independently
• Strong problem-solving skills and a willingness to investigate issues through resolution
• Comfortable working in a fast-paced, remote environment

Strongly Preferred

• Canadian CPA designation
• Experience supporting both Canadian and U.S. entities
• Payments, fintech, banking, financial services or SaaS experience
• High-volume payment or transaction reconciliation experience
• Experience implementing accounting automation
• Hands-on use of AI to improve financial or accounting workflows
• Familiarity with SQL, APIs, Python or BI tools is an asset

The Right Person

You 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.