Stripe Revenue & Payments Analyst

BoomerangFX

Location: Mississauga, Ontario - on-site, five days per week

Reports To: Finance Leadership

Mandatory Experience:

Minimum 5 years experience in managing payment operations, revenue reconciliation, subscription billing, and accounts receivable with strong attention to detail. Skilled in reconciling transactions, investigating payment discrepancies, monitoring outstanding balances, and maintaining accurate financial records. Proficient in financial reporting, Excel, and supporting efficient billing and collections processes.

About BoomerangFX

BoomerangFX is a global healthcare technology company providing SaaS, artificial intelligence and digital marketing solutions to private-pay healthcare practices worldwide.

Recognized among Deloitte’s fastest-growing technology companies, BoomerangFX helps clinics streamline operations, automate workflows, improve patient engagement and accelerate revenue growth.

We are seeking an experienced, highly detail-oriented Stripe Revenue & Payments Analyst to take hands-on ownership of our daily payment operations, revenue reconciliations, subscription billing and accounts receivable management.

The Role

This is a hands-on operational finance role, not a supervisory or management position. The successful candidate must have extensive practical experience working directly with Stripe and QuickBooks Online, with the ability to independently investigate discrepancies, reconcile transactions and execute daily financial processes.

1. Stripe Payment Operations & Reconciliation

Perform daily reconciliation of Stripe payments, payouts, refunds, processing fees and disputes.

Reconcile Stripe activity against QuickBooks Online, customer invoices, subscription records and bank deposits.

Investigate discrepancies, missing payments, duplicate transactions and incorrect billing.

Monitor multiple Stripe accounts, currencies and payment streams.

Maintain accurate transaction-level reconciliation records and supporting documentation.

2. Subscription Billing & Revenue Management

Manage and validate recurring SaaS subscription billing through Stripe.

Review customer pricing, discounts, upgrades, downgrades, cancellations and renewals.

Reconcile customer subscription records against Stripe, QuickBooks Online and CRM data.

Support accurate monthly recurring revenue (MRR), annual recurring revenue (ARR) and churn reporting.

Identify and resolve billing errors and potential revenue leakage.

3. Accounts Receivable & Collections

Monitor failed credit card transactions and outstanding customer balances daily.

Coordinate directly with Customer Success to resolve payment failures and billing issues.

Execute established collections procedures, including reminders, follow-ups, demand notices and escalations.

Maintain accurate accounts receivable aging reports.

Track payment recovery and ensure overdue balances are escalated promptly.

Document all collection activities and maintain accurate customer payment records.

4. Financial Reporting & Controls

Prepare daily and weekly reports covering successful collections, failed payments, outstanding receivables, disputes and payment recovery.

Support the preparation of weekly cash flow forecasts with accurate collection and payment data.

Assist with month-end revenue reconciliation and financial closing activities.

Identify and resolve discrepancies between Stripe, QuickBooks Online and customer billing records.

Maintain proper financial controls, documentation and audit trails.

Recommend improvements to reporting, reconciliation and collections processes.

Mandatory Qualifications

• Minimum 5 years of hands-on experience with Stripe, including payment processing, subscription billing, reconciliations, refunds, disputes and failed payments.
• Strong working knowledge of QuickBooks Online, including transaction reconciliation, accounts receivable and financial reporting.
• Advanced Microsoft Excel proficiency, including pivot tables, XLOOKUP and financial data analysis.
• Experience with SaaS subscription billing, recurring revenue and customer-level revenue reconciliation.
• Demonstrated experience managing accounts receivable, collections and payment discrepancies.
• Strong analytical, organizational and problem-solving skills with exceptional attention to detail.
• Ability to work independently, manage daily deadlines and resolve transaction-level issues without extensive supervision.

Additional Experience We Value

• CPA designation, CPA candidacy or another recognized accounting designation.
• Experience with HubSpot CRM and ChurnZero customer success software.
• Experience with Stripe Sigma, SQL, Power BI or automated financial reporting.
• Experience with international SaaS businesses, multiple currencies and multiple legal entities.
• Familiarity with SaaS financial metrics, including ARR, MRR, churn, retention and customer lifetime value.

Performance Expectations

• Accurate and timely daily reconciliation of Stripe transactions and bank payouts.
• Timely resolution of payment discrepancies and failed transactions.
• Reduction in overdue accounts receivable and unrecovered payments.
• Accurate subscription billing and customer-level revenue records.
• Reliable daily and weekly reporting to Finance leadership.
• Timely completion of month-end reconciliation activities.
• Improved efficiency, accuracy and automation of payment operations.

Compensation and Benefits

• Base Salary: $65,000 - $70,000
• Job Type: Full-time
• Work Location: This is a 5-day on-site role based in Mississauga, Ontario.
• Comprehensive health, dental, and vision coverage
• Paid vacation
• Free on-site parking

How to Apply

Submit your résumé

Accessibility Statement:

BoomerangFX is an equal opportunity employer committed to diversity and inclusion. We welcome applications from all qualified individuals for our career opportunities and are dedicated to accommodating people with disabilities. If you need accommodation at any stage of the application process, please contact us at recruitment@boomerangfx.com.