Senior Product Manager, Accounting

Accountabilities:: Define and execute the product vision and roadmap for accounting capabilities, balancing regulatory and compliance requirements, business intelligence needs, customer value, and opportunities for AI-powered bookkeeping. Establish a clear product perspective on where AI can accelerate, automate, and improve accounting workflows while identifying areas where human judgment and oversight should remain essential. Partner with Design, Engineering, and Data teams to ensure product initiatives have clear success criteria, appropriate metrics, feedback loops, and measurable outcomes. Develop strong relationships with firm administrators, bookkeepers, accountants, managing partners, and other financial stakeholders to understand how financial decisions are made within legal practices. Champion both compliance and business insight, helping customers maintain accurate financial processes while gaining a clearer understanding of their firm's financial performance. Translate complex accounting concepts, bookkeeping workflows, and regulatory requirements into clear product requirements and intuitive customer experiences. Collaborate across Billing, Payments, Reporting, and Platform teams to ensure accounting capabilities integrate effectively with the broader product ecosystem. Partner with go-to-market, Customer Success, and Compliance stakeholders to increase adoption, reduce customer friction, and support successful expansion of accounting capabilities. Communicate product strategy, priorities, roadmap decisions, and trade-offs clearly to diverse audiences, from technical teams to senior executives. Apply design thinking and business process analysis to simplify complex workflows and create experiences that are intuitive without compromising accounting accuracy or compliance. Maintain a strong customer focus by regularly engaging with users, incorporating their feedback into product decisions, and using customer experience alongside data to guide priorities. Take ownership of outcomes across organizational boundaries, proactively addressing challenges and aligning multiple teams around measurable customer and business impact. Requirements: 6+ years of product management experience, including meaningful experience in B2B SaaS, with a background in FinTech, accounting software, business operations tools, or a related domain strongly preferred. Strong working knowledge of bookkeeping and accounting fundamentals, including double-entry bookkeeping, reconciliation, trust accounting, and financial reporting. Ability to engage credibly with accounting and finance practitioners without necessarily holding a CPA or equivalent certification. Genuine interest in helping businesses understand and act on their financial performance rather than simply tracking financial information. A thoughtful perspective on the role of AI in accounting and bookkeeping, with sound judgment around practical opportunities, limitations, accuracy, and responsible implementation. Experience applying design thinking, product strategy, and business process analysis to simplify complex workflows and deliver intuitive user experiences. Exceptional communication skills, with the ability to present strategy and recommendations to executives while also translating requirements into actionable direction for technical teams. Demonstrated ability to collaborate across multiple functions, align stakeholders, and drive initiatives toward measurable outcomes. Entrepreneurial mindset with a strong sense of ownership and willingness to work beyond traditional role boundaries when needed to deliver results. Strong outcomes orientation, with a demonstrated ability to connect product decisions and initiatives to meaningful customer and business metrics. Customer-focused approach, including regular customer engagement and the ability to balance quantitative data with qualitative customer insights. Experience in legal technology or another regulated industry such as financial services, healthcare, or professional services is a plus. Familiarity with trust accounting regulations or legal-specific compliance requirements is beneficial. Experience with accounting integrations such as QuickBooks or Xero, or with FinTech data pipelines, is advantageous. Experience launching AI-first features in high-trust or compliance-sensitive environments is a plus. Benefits: Salary: Expected range of $137,500–$186,100 CAD , with initial placement based on geographic region, experience, skillset, and other relevant factors. Health coverage: Competitive health, dental, and vision insurance. Work arrangement: Hybrid flexibility, with employees near designated hubs generally expected to work from the office at least twice per week. Time off: Flexible time-off policy, with approximately 20 days encouraged annually. Wellness support: $2,000 annual counseling benefit. Retirement and family savings: RRSP matching and RESP contributions. Recognition: Long-term service recognition through a dedicated anniversary program. Professional environment: Opportunity to shape a new product role and influence accounting technology, AI-enabled workflows, and financial operations for professional services. Cross-functional exposure: Collaboration with Product, Engineering, Design, Data, Compliance, Customer Success, Billing, Payments, and Reporting teams.