Portfolio Strategy Director

Accountabilities

• Facilitate portfolio prioritization and strategic tradeoff discussions by developing analysis, frameworks, and recommendations that help leaders make confident roadmap decisions.
• Connect product and engineering initiatives to financial objectives by maintaining capacity models, evaluating investment opportunities, and helping define return on investment.
• Build and enhance reporting structures that communicate product and engineering performance, including quality, productivity, delivery outcomes, and business impact.
• Translate complex data and operational insights into actionable recommendations for executive leadership and board-level discussions.
• Partner with Product, Engineering, Sales, Customer Experience, and Operations teams to resolve cross-functional challenges and drive alignment.
• Lead strategic initiatives requiring senior stakeholder coordination and ensure decisions are supported by clear analysis and business context.
• Develop repeatable operating models, processes, and playbooks that improve portfolio visibility and execution.
• Act as a trusted strategic partner to senior leaders by identifying risks, opportunities, and improvement areas across the product and engineering organization.

Requirements

• 12+ years of combined experience in product operations, business operations, strategy consulting, chief of staff roles, or high-growth technology environments.
• Proven ability to manage ambiguous, high-impact challenges and drive decisions without requiring extensive direction.
• Experience building operating models, strategic frameworks, executive presentations, and cross-functional analysis.
• Strong understanding of SaaS operations, product development processes, and technology-driven business models.
• Ability to analyze business performance, identify trends, and translate data into strategic recommendations.
• Comfortable working with engineering teams, product leaders, and executive stakeholders.
• Strong communication skills with the ability to adapt messaging for technical, operational, and executive audiences.
• Experience creating scalable processes and structures in environments where frameworks were previously undefined.
• Highly proactive, resourceful, and capable of independently gathering information and solving complex problems.
• Genuine interest in insurance technology, artificial intelligence, and technology commercialization.
• Bachelor's degree preferred, though equivalent professional experience and demonstrated impact will be considered.

Benefits

• Competitive annual compensation range of approximately CA$140,000 - CA$155,000, including base salary and potential incentive compensation.
• Remote work flexibility for candidates located in North America.
• Comprehensive medical, dental, and vision coverage.
• Paid vacation and holiday time.
• Health and wellness days.
• Additional birthday bonus day off.
• Flexible collaboration model combining remote and in-person teamwork where beneficial.
• Inclusive workplace culture that values diverse backgrounds, experiences, and perspectives.
• Opportunities to influence strategic initiatives and work closely with executive leadership.
• Professional growth opportunities within a technology-focused environment.