Senior Director, Product (Employer of Record)

Canada
Remote
Posted Oct 7, 2026
1 position

Opens an external site

Employment type: Full-time
Experience level: Lead · 10+ years
Posting language: English
Working hours: 40 hours per week

Job summary

The Senior Director will own the product vision, strategy, and roadmap for the Employer of Record offering while leading cross-functional teams to deliver measurable business outcomes. They will transform complex employment regulations into automated workflows and implement AI-first approaches to product discovery and delivery.

Job details

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Director, Product (Employer of Record) based in Canada. This is a senior product leadership role with ownership of a complex Employer of Record (EOR) product spanning the full global employment lifecycle. You will define the product vision, strategy, and roadmap across multiple product development teams and connect execution directly to business and customer outcomes. The role sits at the intersection of technology, operations, legal, finance, compliance, and customer experience. You will transform highly localized employment requirements into scalable, automated workflows while balancing regulatory needs, technical debt, operational improvements, and new capabilities. As a member of the senior leadership team, you will influence broader business strategy and make decisions that shape a critical area of the organization. You will also develop product leadership talent, strengthen cross-functional collaboration, and introduce AI-first approaches to product discovery, experimentation, and delivery. This is an ideal opportunity for an experienced product leader who thrives in distributed environments, organizational change, and high-impact, operationally complex products. \n Accountabilities Own the overall product vision, strategy, and roadmap for the EOR offering, ensuring team-level priorities are connected to measurable company and customer outcomes. Take accountability for the end-to-end performance of the platform, including operational processes and downstream impacts beyond the product features themselves. Translate complex and highly localized employment regulations into scalable, automated product workflows that reduce reliance on manual operational processes. Prioritize investments across new product capabilities, regulatory requirements, technical debt, and operational improvements across multiple teams. Lead and develop a team of Product Managers and Group Product Managers, helping them transition from feature delivery toward problem ownership and measurable outcomes. Partner closely with Engineering and Design leadership to make effective trade-offs, challenge assumptions, and maintain strong alignment on product direction and execution. Collaborate with Operations, Legal, and Finance to shape product strategy while balancing customer value, operational efficiency, business margins, and risk. Establish an AI-first approach to product development, using AI to improve discovery, prototyping, experimentation, decision-making, and learning. Set direction at the business-unit level and build meaningful stakeholder alignment, particularly when priorities or strategic objectives change. Lead through organizational and structural change while maintaining momentum, clarity, accountability, and high performance. Requirements 10+ years of product management experience, including approximately 5–7 years leading and developing Product Managers, with a demonstrated record of delivering measurable customer and business outcomes. Experience in operationally or legally complex B2B or fintech environments; experience in HR technology, Employer of Record, payroll, employment, or compliance is highly desirable. Strong systems-thinking and first-principles problem-solving skills, with the ability to diagnose complex challenges before defining solutions. Hands-on experience using AI to meaningfully transform team workflows, product discovery, experimentation, or decision-making—not simply incorporating AI into shipped products. Demonstrated ability to establish product vision and strategy at business-unit level and generate strong organizational buy-in as priorities evolve. Proven people leadership skills, including coaching product managers into stronger leaders, maintaining high performance standards, and addressing difficult issues directly and constructively. Experience leading through significant organizational or structural change, with the ability to navigate ambiguity and turn uncertainty into opportunity. Strong executive communication and stakeholder-management skills, with the ability to turn strategic alignment into coordinated execution. Comfortable collaborating across Product, Engineering, Design, Operations, Legal, Finance, and other senior functions. Fluent English communication skills, both written and verbal. Reliable home internet access suitable for a fully remote working environment. Ability to work effectively within a distributed, asynchronous, and globally diverse organization. Benefits Fully remote work with the flexibility to work from anywhere, subject to local employment authorization and team requirements. Approximately 40 days of paid time off per year, including holidays and vacation, or more where required by local regulations. Mental health support through a dedicated wellbeing service. Monthly wellbeing allowance that can be used across a broad range of eligible options. Flexible parental leave, including at least three months of paid leave for new parents, with job protection for up to 12 months or as required locally. Work-from-home stipend to support laptop and home-office equipment. Inclusive, globally distributed working environment with asynchronous collaboration. Opportunities to influence a high-impact global product and work at the intersection of technology, employment, compliance, operations, and AI. Supportive environment focused on professional growth, trust, collaboration, and continuous improvement. Reasonable accommodations available throughout the recruitment process for qualified candidates with disabilities. \n How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Why Apply Through Jobgether? Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time. #LI-CL1

What you’ll do

Requirements

Candidates must have 10+ years of product management experience, including 5-7 years in leadership roles within complex B2B or fintech environments. Strong systems-thinking skills and a proven ability to lead through organizational change are essential for this role.