Portfolio Strategy Director

Position Overview

This opening is for a Portfolio Strategy Director based in Canada, acting as the strategic interface linking product, engineering, and business priorities. The role is central to turning product and engineering investments into measurable business results and fostering alignment through insightful frameworks and reporting mechanisms.

Key Responsibilities

• Lead portfolio prioritization and strategic trade-off discussions by crafting analyses, frameworks, and recommendations that enable confident decision-making for roadmaps.
• Align product and engineering efforts with financial goals by overseeing capacity models, scrutinizing investment opportunities, and defining estimated returns on investment.
• Design and refine reporting tools that track product and engineering outcomes, encompassing quality, productivity, delivery, and business impact metrics.
• Convert complex operational data into clear, actionable insights to inform executive leadership and board-level dialogues.
• Collaborate with Product, Engineering, Sales, Customer Experience, and Operations teams to overcome cross-functional issues and ensure organizational coherence.
• Steer strategic projects that require coordination with senior stakeholders, supporting decisions with thorough analysis and business context.
• Develop scalable operating models, processes, and playbooks to enhance visibility and execution across portfolios.
• Serve as a trusted strategic advisor to senior leaders by identifying risks, opportunities, and improvement areas within product and engineering departments.

Candidate Profile

• Possess over 12 years of experience in product/business operations, strategy consulting, chief of staff roles, or within high-growth technology sectors.
• Demonstrate aptitude for managing ambiguous, impactful challenges and driving autonomous decision-making.
• Experienced at building operating models, strategic frameworks, executive-level presentations, and cross-functional analyses.
• Strong knowledge of SaaS operations, product development life cycles, and technology-centric business strategies.
• Capability to analyze business performance data, identify trends, and translate findings into actionable strategic guidance.
• Comfortable liaising among engineering teams, product managers, and top executives.
• Excellent communication skills tailored for technical, operational, and executive audiences.
• Track record in establishing scalable processes in previously undefined framework environments.
• Highly proactive with the capacity to independently source information and solve complex problems.
• Deep interest in insurance technology, AI, and technology commercialization.
• Bachelor's degree is preferred, although relevant experience and demonstrated impact are considered.

Compensation and Benefits

• Estimated annual remuneration between CA$140,000 and CA$155,000 including base salary and possible incentives.
• Flexible remote working arrangement available for candidates within North America.
• Comprehensive coverage including medical, dental, and vision insurance.
• Paid vacation, statutory holidays, health and wellness days, plus an additional birthday holiday.
• A collaborative work model that blends remote and in-person efforts to optimize productivity.
• Cultivation of a diverse and inclusive workplace culture valuing varied backgrounds and perspectives.
• Opportunities to contribute to strategic initiatives and engage with executive leadership.
• Support for personal and professional development in a technology-oriented organization.

Additional Information

This vacancy is listed on behalf of a partner organization responsible for application processing and recruitment progression. An AI-driven matching process is employed to evaluate applicants objectively against essential qualifications. Final hiring decisions are made by the partner's internal team.

Data privacy is respected according to applicable laws with transparent use of AI in some recruitment phases to assist human reviewers.