Director, Commercial FP&A

About the company

PointClickCare is a privately held, founder-led health technology company focused on enabling care providers to deliver better outcomes. Its platform supports more than 30,000 provider organizations, backed by the largest dataset in long-term and post-acute care and a marketplace of over 400 integrated partners. The company reinvests a meaningful share of revenue into research and development to fuel innovation and long-term impact. It has been recognized by Forbes as a top private cloud company and by Canada’s Most Admired Corporate Cultures for its workplace environment.

The organization emphasizes a human-first approach to healthcare, with AI used as a practical enabler for creativity, productivity, and stronger decision-making. The hiring and employee development experience is designed to identify AI capability and build it further through training and continuous learning.

Role overview

This leadership position reports to the Senior Director, Commercial Financial Planning & Analysis and is responsible for two major areas: commercial deal operational excellence and contribution margin expansion. The role works closely with GTM, Revenue Operations, Corporate Strategy, and Partnerships leaders to influence commercial choices that support ARR growth and improve margin performance. It is also expected to help modernize Commercial FP&A by using AI to improve speed, flexibility, and the team’s capacity to take on broader work.

Key responsibilities

• Lead the two main Commercial FP&A priorities: commercial deal operational excellence and contribution margin expansion.
• Act as a strategic advisor to the Senior Director on the wider Commercial FP&A agenda, especially around ARR growth and margin improvement opportunities.
• Help redesign core Commercial FP&A processes with AI so the team can respond faster, evaluate more scenarios, and increase overall throughput.
• Work with Corporate FP&A to align shared practices such as cost management and forecasting.
• Collaborate with GTM leadership to improve the operating model and governance of the DealDesk function, which is jointly supported by Finance and Revenue Operations.
• Partner with Revenue Operations to define the DealDesk strategy and governance structure.
• Set standards and frameworks that define what good deal quality looks like across the business.
• Provide guidance on promotional activity and concession structures.
• Establish the measures and accountability mechanisms used to assess deal health.
• Work with Monetization Strategy and Pricing teams to bring pricing strategy into execution.
• Support Partnerships and Corporate Strategy in negotiating terms for new strategic partnerships and marketplace partners in line with long-range financial goals.
• Assess the financial performance of existing partnerships and the marketplace, and recommend levers that can improve contribution margin.
• Own the financial partnership with GTM leadership so commercial investments are made with discipline and aligned to growth and margin goals.
• Help build the decision framework for resource allocation and investment choices.
• Define efficiency metrics and compare them with relevant benchmarks.
• Support workforce planning and headcount capacity planning tied to growth targets.
• Advise on commission design and related governance.
• Advise on investment trade-offs such as marketing channel mix.
• Ensure GTM partners maintain reliable forecasts for headcount and discretionary spend.
• Run scenario planning and stress-testing across quarterly, annual, and multi-year horizons, showing possible upside and downside impacts.
• Lead and develop a team of FP&A professionals, creating clear expectations, high standards, and a performance-driven culture.
• Build team capability through coaching, development planning, and strong performance management.
• Prepare team members for larger responsibilities while supporting succession planning and long-term organizational strength.

Requirements

• 10 to 12+ years of progressive experience in FP&A, strategic finance, or a similar field, including at least 5 years in a technology or SaaS environment.
• Strong hands-on experience with commercial subjects such as deal structure, contracting, pricing, and collaboration with GTM teams.
• Exposure to meaningful AI-led transformation in finance workflows is strongly preferred.
• Proven ability to present and influence complex financial topics for executive and C-suite stakeholders, including investor-facing situations.
• Advanced financial modelling capability, including deal structuring, scenario analysis, and contribution margin frameworks in a SaaS business.
• Track record of producing measurable commercial improvements, such as stronger deal economics, better GTM efficiency, or margin expansion in a high-growth environment.
• Strong understanding of management reporting, SaaS metrics such as ARR, NRR, CAC, LTV, and Rule of 40, as well as financial accounting practices.
• Bachelor’s degree in Business, Finance, Accounting, or a related discipline.
• An advanced degree or CPA/CFA credential is considered an advantage.

Benefits and compensation

• Benefits available from day one.
• Retirement plan matching.
• Flexible paid time off.
• Wellness support programs and resources.
• Parental and caregiver leave.
• Fertility and adoption support.
• Continuous development support program.
• Employee assistance program.
• Allyship and inclusion communities.
• Employee recognition and additional rewards.
• Base salary range in Canada: 162000 to 180000, plus bonus, equity, and benefits.
• The role is non-overtime eligible.

Location and work arrangement

This role is based in Toronto, Ontario, Canada and is designated as onsite. For roles with a hybrid expectation, candidates would need to live within a commutable distance of the office and attend in-person team events on a weekly, bi-weekly, or monthly basis as required.

Who this role suits

This position is intended for a commercially minded finance leader who has built and guided strong teams, handled complex cross-functional mandates, and is ready to help drive an AI-enabled transformation within a modern Commercial FP&A organization.