Director, Billing to Cash

Job Title: Director, Billing to Cash
Location: Mississauga, ON - Hybrid

**Travel to Office expectations**

For Hybrid Roles : If this role is Hybrid, there will be an expectation to reside within commutable distance to the office/location specified in the job listing. This will include, but not limited to, weekly/bi-weekly/monthly events in the office with your specific team. This is a requirement for this role.

At PointClickCare our mission is simple: to help providers deliver exceptional care. And that starts with our people. As a leading health tech company that’s founder-led and privately held, we empower our employees to push boundaries, innovate, and shape the future of healthcare.

With the largest long-term and post-acute care dataset and a Marketplace of 400+ integrated partners, our platform serves over 30,000 provider organizations, making a real difference in millions of lives. We also reinvest a significant percentage of our revenue back into research and development, ensuring our employees have the resources to innovate and make a lasting impact. Recognized by Forbes as a top private cloud company and honored as one of Canada’s Most Admired Corporate Cultures, we offer flexibility, growth opportunities, and meaningful work. 

At PointClickCare, we empower our people to be the architects of a smarter healthcare future; one that is human-first and accelerated by AI to create meaningful and lasting change. Employees harness AI as a catalyst for creativity, productivity, and thoughtful decision-making. By integrating AI tools into our daily workflows, collaboration is enhanced, outcomes are improved, and every team member has the proficiency to maximize their impact. It all starts with our hiring practices where we uncover AI expertise that complements our mission, and we continue to invest in training and development to nurture innovation throughout the employee journey.

Join us in redefining healthcare — so it doesn’t just survive, it thrives. To learn more about PointClickCare, check out and connect with us on  and  .

About the Team

The Billing to Cash team supports the full customer billing-to-cash lifecycle across PointClickCare's business units, including billing, cash application, collections, escalations, account resolution, and credit risk. The team partners closely with Accounting, Treasury, Sales and GTM leadership, Finance Customer Support, and Account Services to improve Order-to-Cash effectiveness and the customer experience.

Position Summary:

Reporting to the Senior Director, Finance Operations, the Director of Finance, Billing to Cash leads a team of high-performing managers and individual contributors to ensure the billing-to-cash process is frictionless for customers and maximizes cash collections. This highly impactful role leads a high-volume Billing to Cash department with more than $700M in annual collections. The successful candidate will bring strong customer service and business-partner skills, leadership capability, and business acumen to support Order-to-Cash effectiveness.

Key Responsibilities:

• Oversee the effectiveness and efficiency of billing, collections, escalation management, and account resolution across the Accounts Receivable portfolio for all business units.
• Ensure the effectiveness of the cash application process to support accurate customer statements.
• Identify customer payment trends and develop strategic solutions to protect revenue and support cash collection targets.
• Drive collections efficiency through payment automation, including ACH adoption, and optimized billing frequency.
• Leverage systems, enhance processes, and break down silos to create a best-in-class Billing to Cash team.
• Develop and drive Key Performance Indicator reporting for management and internal teams to support working capital targets, including DSO and inputs to Free Cash Flow, and improve operational efficiency.
• Develop and implement a customer risk management framework, policies, and procedures to maximize cash flow and minimize bad debt risk, including credit risk, bankruptcies, unclaimed property, and collateral consents.
• Serve as the Finance gatekeeper for extending credit to customers with poor payment history or elevated credit risk, while partnering with Sales and Commercial teams to structure terms responsibly and unlock revenue opportunities.
• Partner with Treasury to provide reliable cash flow forecasts.
• Partner with controllership and revenue accounting to support timely and accurate financial reporting and period-end close.
• Oversee billing validations to support invoice accuracy and timely customer delivery.
• Partner with internal stakeholders to resolve upstream issues, optimize billing operations, and minimize billing issues.
• Develop a high-performing, tech-forward team that can solve issues end to end and serve as subject matter experts in their areas.
• Perform other duties as assigned by management to support overall team objectives.

Required Skills & Qualifications:

• University education in a relevant discipline; Finance or Accounting preferred.
• 5+ years of experience leading teams of people managers.
• Ability to lead a high-volume Accounts Receivable department collecting more than $500M annually.
• Excellent verbal and written communication skills, with the ability to collaborate effectively with cross-functional teams.
• Extensive expertise in Order-to-Cash processes and best practices.
• Credit control and statutory knowledge, including Anti-Money Laundering and Escheatment.
• Strong leadership skills, including team building and motivation, transformation, and organization design.
• Demonstrated commitment to PointClickCare's core values: People, Passion, and Performance.

Preferred Experience:

• Experience in the SaaS industry and with acute and/or post-acute customers.
• Experience with major billing-to-cash systems and implementations.
• Experience working with Sales Operations, Revenue Operations, and Customer Success teams.
• M&A and integration experience.
• Experience developing reporting to measure performance.
• Experience deploying AI, RPA, or workflow automation tools within Finance or Order-to-Cash operations.

At PointClickCare, base salary is one of the many components that make up our total rewards package. The Canada base salary range for this position is $144,100 - $160,200 + bonus + benefits. Our salary ranges are determined by job and level. The range displayed on each job posting reflects the target for new hire salaries for the position across all Canada locations. Within the range, individual compensation is determined by job-related skills and knowledge, relevant experience including professional and lived experience, and/or work location. Your recruiter can share more information about our total rewards package during the hiring process.

PointClickCare Benefits & Perks

• Benefits starting from Day 1
• Retirement Plan Matching (RRSP & 401K)
• Flexible Paid Time Off
• Lifestyle/Wellness Spending Account
• Parental & Caregiver Leaves
• Fertility & Adoption Support
• Continuous Development Support Program
• Employee Assistance Program
• Learning Programs & Resources
• Employee Recognition … and more!

Equal Employment Opportunity:

It is the policy of PointClickCare to ensure equal employment opportunity without discrimination or harassment on the basis of race, religion, national origin, status, age, sex, sexual orientation, gender identity or expression, marital or domestic/civil partnership status, disability, veteran status, genetic information, or any other basis protected by law. PointClickCare welcomes and encourages applications from people with disabilities. Accommodations are available upon request for candidates taking part in all aspects of the selection process. Please contact View email address on jobs.lever.co should you require any accommodations.

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PointClickCare is committed to Information Security. By applying to this position, if hired, you commit to following our information security policies and procedures and making every effort to secure confidential and/or sensitive information.

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