Senior Director of Finance & Operations

BoomerangFX

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

Reports to: Chief Executive Officer

Mandatory Experience

A Canadian CPA designation and hands-on experience leading finance and operations for a PE-backed SaaS company scaling ARR from $5 million to $50 million are mandatory. Only applicants meeting these requirements will be considered for the role.

Why Join BoomerangFX?

BoomerangFX is a global healthcare technology company bringing SaaS, artificial intelligence and digital marketing together to help private-pay healthcare practices operate and grow. Recognized through Deloitte’s Technology Fast 500 program, we are building technology that simplifies practice management, strengthens patient engagement and helps healthcare businesses reach more people.

With operations in the United States, Canada, the United Kingdom, Australia and India, we are scaling internationally and working at the forefront of AI in healthcare. Our teams collaborate across countries and disciplines to turn new ideas into products and services that make a practical difference for customers.

Joining BoomerangFX is an opportunity to build your career alongside a growing global business. You will have meaningful responsibility, exposure to international markets and the opportunity to contribute ideas, develop your skills and see the impact of your work. We welcome people who take ownership, move quickly and want to help build what comes next.

The Role

Reporting to the CEO, you will lead financial management and general operations with strong financial acumen, commercial judgment and a practical approach to execution.

You will oversee the Controller and Accountant while taking responsibility for talent acquisition, human resources, vendor negotiations and corporate infrastructure. You must be comfortable reviewing the detail, challenging assumptions and resolving issues personally while building an accountable team.

Financial Leadership and Accounting Oversight

• Directly oversee the Controller and Accountant, setting clear expectations for accuracy, reporting deadlines, financial controls and accountability. Review their work and provide hands-on guidance on complex issues.
• Own the quality and timeliness of monthly, quarterly and annual financial reporting. Review financial statements, balance-sheet reconciliations, management reports and material accounting judgments.
• Oversee billing, subscription revenue recognition, deferred revenue, collections, accounts payable, payroll and intercompany reporting. Maintain clear controls over approvals, payments and financial records.
• Coordinate external accountants, auditors and tax advisers, and strengthen accounting policies and controls as the company scales.

Financial Performance and Cash Management

• Lead annual budgeting, rolling forecasts, financial modelling and variance analysis. Challenge assumptions and translate financial results into clear recommendations for the CEO and department leaders.
• Own a rolling 13-week cash-flow forecast and longer-term liquidity projections. Improve collections, working capital, spending discipline and visibility into financial commitments.
• Analyze profitability by product, service and market. Use SaaS metrics, including ARR, retention, churn, gross margin, customer acquisition cost and payback, to evaluate performance and investment decisions.
• Assess hiring plans, pricing, operating costs and major expenditures against expected returns. Drive measurable improvements in margins, productivity and progress toward sustainable profitability.

Talent Acquisition and Human Resources

• Oversee talent acquisition and human resources, including internal staff and external providers. Align recruitment priorities and headcount plans with approved budgets and business needs.
• Oversee recruitment execution, agency relationships, hiring timelines, onboarding and workforce planning. Hold hiring managers accountable for clear requirements, timely decisions and hiring outcomes.
• Oversee HR administration, employee records, compensation and benefits coordination, performance-review processes, employee relations and offboarding, working with qualified advisers where required.

Vendor Negotiations and Corporate Infrastructure

• Lead vendor negotiations and oversee procurement, contracts and renewals. Secure commercially sound pricing, payment terms and service commitments, and hold providers accountable for delivery.
• Oversee corporate infrastructure, including offices, facilities, equipment, business systems and outsourced services. Ensure these resources support reliable daily operations and future growth.
• Work with technology leaders on corporate IT providers, software licences, infrastructure spending and business continuity arrangements. Improve utilization and eliminate unnecessary or duplicate costs.

Operating Performance and Team Leadership

• Establish operating KPIs, management dashboards and regular performance reviews across finance and the functions under your oversight.
• Improve workflows, approval processes and reporting through practical automation and stronger data quality. Ensure corrective actions have accountable owners and deadlines.
• Lead and develop the finance team and collaborate with Sales, Marketing, Customer Success, Product and Technology leaders to improve execution and resource allocation.

Mandatory Qualifications

• CPA designation in good standing in Canada.
• At least 10 years of progressive finance experience, including hands-on leadership across financial reporting, controllership, budgeting, forecasting, cash management and operating performance.
• At least three years of hands-on experience in a fast-paced SaaS business, including leadership of finance and operations for a PE-backed SaaS company scaling ARR from $5 million to $50 million.
• Strong financial acumen and commercial judgment: the ability to interrogate financial results, build credible forecasts, evaluate SaaS unit economics and make sound decisions on costs, headcount and investment.
• Proven experience directly supervising a Controller and accounting staff, reviewing their work and maintaining high standards for financial accuracy, control and delivery.
• Direct experience overseeing talent acquisition, human resources, vendor negotiations and corporate infrastructure, with accountability for operational results.
• Advanced financial modelling and Excel or Google Sheets skills, proficiency with accounting and reporting systems, and the ability to explain financial issues clearly to business leaders.
• A record of personal ownership and effective execution in an environment with rapidly changing priorities, tight deadlines and limited resources. You must be willing to work on-site in Mississauga five days per week.

Additional Experience We Value

• Measurable success improving profitability, cash generation or progress toward break-even.
• Experience managing multiple entities, currencies or international operations.
• Experience in healthcare technology or a business combining SaaS subscriptions and services.
• Experience implementing finance systems, automating reporting or supporting transaction readiness.

Compensation and Benefits

• Base salary: CAD $135,000–$150,000 annually.
• Annual target performance bonus: 50% of base salary, based on achievement of agreed performance objectives.
• Total target compensation: CAD $202,500–$225,000 annually.
• Performance objectives will reflect measurable outcomes in profitability, cash management, financial reporting and operational execution.
• Comprehensive health, dental and vision coverage.
• Paid vacation and free on-site parking.
• An opportunity to work closely with the CEO and senior leadership and make a measurable contribution to a growing global healthcare technology business.

How to Apply

Submit your résumé with a brief summary of your experience in high-growth software or technology-enabled companies, including two or three measurable financial or operational results you personally delivered.

Shortlisted candidates should be prepared to discuss their experience with financial oversight, operational leadership, strategic planning, and board reporting. CPA credentials, employment experience, and professional references will be verified.

Accessibility Statement

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