Billing Operations Lead

Accountabilities:: Own billing operations: Oversee billing portfolios across strategic retail partners and multiple revenue streams, ensuring accurate day-to-day invoicing, appropriate revenue recognition inputs, and timely month-end close. Maintain billing policies and standards: Develop and maintain billing policies, standard operating procedures, and quality controls while ensuring discrepancies and escalations are resolved efficiently with Finance Systems, Business Development, and Revenue stakeholders. Drive reporting and visibility: Build and maintain dashboards, reporting, and key performance indicators that provide clear visibility into billing health and enable proactive identification and resolution of issues. Lead billing system initiatives: Partner with Product and Engineering to scope and deliver billing system enhancements, integrations, and automation opportunities that reduce manual effort and improve scalability. Lead cross-functional quote-to-cash projects: Take ownership of billing and quote-to-cash initiatives from requirements definition through user acceptance testing and launch, coordinating stakeholders and ensuring successful implementation. Strengthen controls and compliance: Ensure billing activities align with internal controls, audit requirements, contractual billing terms, and applicable financial and revenue recognition considerations. Improve operational efficiency: Identify opportunities to streamline workflows, automate repetitive processes, improve data quality, and strengthen the overall billing operating model. Mentor and support the team: Provide guidance and mentorship to junior team members while helping scale billing operations to support continued business growth. Requirements: Education: Bachelor’s degree in Accounting, Finance, Information Systems, or a related field, or equivalent practical experience. Billing operations experience: At least 5 years of experience in Billing Operations, Order-to-Cash, or Accounts Receivable, ideally within technology, ecommerce, marketplace, subscription, or SaaS environments. Cross-functional project leadership: At least 2 years of experience leading billing or quote-to-cash projects as an individual contributor, taking initiatives from requirements gathering through UAT and production launch. Billing technology expertise: Hands-on experience with Salesforce CPQ , at least one billing platform such as Zuora, Chargebee, or Stripe Billing, and at least one ERP system such as NetSuite, SAP, or Oracle. Data analysis skills: Strong Excel capabilities, including pivot tables and lookups, along with basic SQL skills for reconciliations, reporting, and billing data analysis. Financial controls knowledge: Working knowledge of billing controls, SOX requirements, and revenue recognition principles such as ASC 606 as they relate to invoicing, credits, adjustments, and related processes. Automation mindset: Experience using data modeling or automation tools such as Alteryx to improve billing workflows is an advantage. AI and process improvement: Demonstrated ability or strong aptitude for using AI-based solutions to improve billing processes, efficiency, and operational decision-making. Operational excellence: Strong analytical thinking, attention to detail, problem-solving ability, and a continuous-improvement mindset, combined with the ability to collaborate effectively across technical and business teams. Benefits: Competitive Canadian compensation: Base salary of CA$95,000–CA$100,000 , depending on factors such as experience, skills, and work location. Equity opportunity: Eligibility for a new-hire equity grant as well as potential annual refresh grants. Remote work: Fully remote position for candidates permanently located in Ontario, Alberta, British Columbia, or Nova Scotia . Flexible work approach: Flexibility to choose where you work while remaining connected through regular opportunities for collaboration and community building. Competitive benefits: Access to market-competitive compensation and benefits applicable to the employee’s location. Growth and development: Opportunity to take ownership of strategic billing operations, cross-functional systems initiatives, automation, and scalable process improvements. Team collaboration: Work closely with Finance, Business Development, Financial Systems, Legal, Product, Engineering, and Revenue teams in a highly cross-functional environment. Scalable impact: Opportunity to help build billing processes, systems, reporting, and controls that support continued organizational growth.