Portfolio Strategy Director
New
J
JobgetherInsurance technology, AI
Remote work flexibility for candidates located in North America.Full-TimeDirector
SalaryCompetitive annual compensation range of approximately CA$140,000 – CA$155,000, including base salary and potential incentive compensation.
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Job Details
- Experience
- 12+ years of combined experience in product operations, business operations, strategy consulting, chief of staff roles, or high-growth technology environments.
- Required Skills
- Data AnalysisProduct OperationsBusiness OperationsSaaS
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.
Responsibilities
- 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.
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