This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Portfolio Strategy Director based in Canada. This role serves as the strategic operating layer connecting product, engineering, and business priorities.

You will help leaders make informed portfolio decisions by creating frameworks, insights, and reporting structures that drive alignment. The position plays a critical role in translating product and engineering investments into measurable business outcomes. You will influence executive-level discussions, support roadmap prioritization, and improve how teams operate at scale.

Working across functions, you will bring clarity to complex challenges and enable stronger decision-making across the organization. This is an opportunity for a strategic operator who thrives in fast-moving environments and enjoys building scalable processes from the ground up.

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 The ideal candidate brings extensive experience in strategy, operations, product operations, or business transformation roles, with the ability to operate effectively in complex, high‑growth environments. 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.

Perks 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.

📌 Portfolio Strategy Director (Winnipeg)
🏢 Jobgether
📍 Winnipeg