Director, Product Operations

This is a fully remote position, open to applicants in Canada.

📋 Description

• Act as a trusted advisor and strategic partner to the CPO regarding organizational priorities, portfolio trade-offs, and long-term planning.

• Prepare the CPO and CTO for executive meetings, business reviews, and strategic planning sessions.

• Conduct research, synthesize insights, and create executive-ready materials and recommendations.

• Provide standardized planning frameworks for Product VPs and PMs.

• Facilitate the quarterly and annual product planning processes.

• Maintain portfolio views, identify trade-offs, and recommend sequencing for projects.

• Organize roadmap reviews, delivery check-ins, risk/decision forums, and retrospectives.

• Establish status and change-control mechanisms.

• Promote the adoption of AI-native methodologies across Product and Design teams.

• Develop AI enablement resources and lead the automation of manual product tasks.

• Oversee and optimize the product tooling ecosystem.

• Set standards and guidelines for responsible AI usage.

• Manage and nurture the Product PMO/product launch team.

• Lead capacity planning for the PMO.

• Establish operational readiness frameworks for significant releases.

• Coordinate launch strategies with Product Marketing and Go-To-Market (GTM) teams.

• Facilitate post-launch evaluations and ongoing improvements.

• Enhance the structure, processes, governance, and operational norms of the Product organization.

• Collaborate with Finance on revenue targets, Product P&Ls, plan-versus-actual performance, and headcount planning.

⛳️ Requirements

• Over 15 years of experience in Product Operations, Program Management, strategy/business operations, or a Chief of Staff-type position.

• Significant exposure to SaaS or technology sectors.

• Proven experience supporting senior executives and facilitating executive-level planning and reporting.

• Strong business acumen linking product strategy to company goals and customer outcomes.

• Capability to lead intricate, cross-functional initiatives from conception to execution.

• Experience in managing and developing a team.

• Excellent analytical and synthesis abilities.

• Proficiency in product tools like Jira and analytics/experimentation platforms.

• Data-driven approach to decision-making.

• Practical knowledge of AI tools such as Claude, ChatGPT, prompt engineering, and AI-assisted workflows.

• Proven history of promoting AI adoption within a business function.

• Exceptional facilitation and stakeholder management skills.

• High level of discretion, judgment, and professionalism when handling sensitive information.

• Bachelor’s degree is required.

🏝️ Benefits

• Open PTO policy.

• Quarterly Days of Disconnect.

• Parental & Pawternity Leave.

• Quarterly Best Life fitness reimbursement.

• Medical/Dental/Vision coverage.

• Employee Assistance Program (EAP).

• Calm App subscription for employees and up to 4 dependents over age 16.

• Bonuses, commissions, equity, or other incentive programs may be offered where applicable.

• Values-focused culture.

• Opportunities for professional development.

• Access to mentorship.

• Inclusive workplace.