Portfolio Strategy Director

Applied Systems Canada•,

14h•CA$140,000 - CA$155,000•Remote

About The Position

We're seeking a Portfolio Strategy Director. This is the portfolio strategy and operating layer for Product and Engineering. You build the operating cadence, frameworks, and reporting that help product and engineering leaders make and defend their decisions, and that translate portfolio performance for the E-Team and the Board. This is a role with real strategic weight. You are the person in the room who connects what we’re building to why it matters, who pressure-tests the business cases behind the roadmap, and who operates at the portfolio level to make sure our product and engineering outcomes achieve our long-term goals. You will have direct visibility into E-Team decisions and influence across every function at Applied, with a true end-to-end perspective on how we build, launch, and realize value from our software.

Requirements

12+ years combined across product operations, business operations, chief of staff roles, strategy/operations consulting, or high-growth SaaS operations
High agency. You take ambiguous, high-stakes problems and drive them to a decision without waiting to be told how
You can build an operating model, structure a complex cross-functional analysis, and pull together a board-ready deck in the same week
Comfortable being the operational and analytical backbone in a room full of engineers, product managers, and commercial leaders
Scrappy enough to pull your own data when the perfect report doesn’t exist yet
Communicates naturally across audiences: Teammates, engineering teams, product leaders, C-suite
You've built the playbook in places where one didn't exist, then made it repeatable
Genuine curiosity about insurance technology and AI commercialization

Responsibilities

Facilitate portfolio prioritization and tradeoff conversations. Bring the analysis and frameworks that make roadmap tradeoff conversations productive between product, engineering, and ultimately business leaders. Help product and engineering leaders make allocation decisions they can confidently defend to the E-Team and the Board, including tradeoffs and risks to manage.
Connect product and engineering work to the financial plan. Articulate how the roadmap connects to meeting our long-term financial goals. Maintain our product and engineering capacity model and use it to define ROI. This is the bridge between what Product defines, Engineering builds, and what the E-Team/Board see.
Define the reporting architecture for product and engineering outcomes. Work with engineering and product on what gets measured (quality, productivity, delivery), how it is framed, and when it surfaces, from regular operating rhythms to E-Team reviews to Board-level narratives. Build the structures that translate product and engineering data into action, not just updates, by combining the data with the real-world context and cross-team relationships that produce game-changing insight.
Partner across functions on major cross-functional programs. You’ll have a dotted line to the COO and direct access to E-Team conversations. When a cross-functional tradeoff between Product, Engineering, Sales, or CX needs senior alignment, you bring the framing that makes the decision actionable and ensure the right leaders are in the room to resolve. From time to time, you will be asked to lead critical initiatives across these teams.