Portfolio Strategy Director

Overview

This strategic leadership position connects product, engineering, and business priorities to enable informed portfolio decisions through frameworks, insights, and reporting tools. The Portfolio Strategy Director plays a crucial role in converting product and engineering investments into tangible business results by influencing executive discussions, supporting roadmap prioritization, and enhancing team operations at scale. The role requires collaboration across functions to clarify complex challenges and empower stronger organizational decision-making in a fast-moving environment.

Key Responsibilities

• Lead portfolio-level strategy, decision frameworks, and operating models that maximize the impact of product and engineering efforts.
• Guide strategic tradeoff and prioritization conversations by preparing analyses, frameworks, and clear recommendations to support confident roadmap choices.
• Align product and engineering initiatives with financial goals by maintaining capacity models, assessing investments, and defining return on investment metrics.
• Create and refine reporting systems to communicate performance indicators such as quality, productivity, delivery results, and business impact.
• Transform complex data and operational insights into actionable guidance for executive leadership and board meetings.
• Collaborate with Product, Engineering, Sales, Customer Experience, and Operations teams to resolve cross-departmental challenges and ensure harmony.
• Oversee senior stakeholder-aligned strategic initiatives, ensuring decisions are backed by thorough analysis and business context.
• Develop repeatable processes, playbooks, and operating models to improve portfolio transparency and execution.
• Serve as a trusted advisor to senior leaders by identifying risks, opportunities, and ongoing improvement areas within product and engineering functions.

Candidate Requirements

• Minimum of 12 years' experience across product operations, business operations, strategy consulting, chief of staff roles, or growth-oriented tech settings.
• Proven track record managing ambiguous, impactful challenges and driving decisions independently.
• Expertise in constructing operating models, strategic frameworks, executive communications, and cross-functional analyses.
• Strong grasp of SaaS operations, product development methodologies, and technology-enabled business models.
• Ability to analyze business performance data, discern trends, and provide strategic recommendations.
• Comfort collaborating with engineering teams, product leadership, and executive stakeholders.
• Excellent communication skills adaptable to technical, operational, and leadership audiences.
• Experience building scalable processes and infrastructure where frameworks were initially absent.
• Highly proactive and resourceful with strong problem-solving abilities and self-directed information gathering.
• Genuine enthusiasm for insurance technology, artificial intelligence, and technology commercialization.
• Bachelor's degree preferred; significant professional experience and impact considered equivalent.

Employment Benefits

• Competitive total annual compensation ranging approximately between CA$140,000 and CA$155,000, including base salary and potential incentives.
• Remote work option available for candidates based in North America.
• Comprehensive medical, dental, and vision insurance coverage.
• Paid vacation and holiday entitlement.
• Health and wellness leave days included.
• Additional paid day off for birthday.
• Flexible hybrid collaboration model balancing remote and in-person work as appropriate.
• Supportive and inclusive workplace culture valuing diverse perspectives and backgrounds.
• Direct involvement in influential strategic initiatives alongside executive leadership.
• Opportunities for ongoing professional advancement within a technology-driven environment.

Additional Information

This job is offered on behalf of a partner company that handles all applications and subsequent recruitment steps. Applications are evaluated through an AI-assisted matching process to ensure fairness and relevance. Final hiring decisions and assessments are made internally by the partner organization. Candidates are advised to consider data privacy and the use of AI tools integrated into the recruitment process, with human oversight ensuring all employment determinations.