Portfolio Strategy Director

Canada External Job Ad

Position Overview  

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.

• 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.

We’re looking for someone who:

• Has the ability to work from an Applied Systems office or 100% remotely
• Your experience should include some or all of the following:
  • 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
  • We know that talent comes from all backgrounds and experience levels. We encourage military members and their spouses as well as candidates without a degree or a background in tech to apply!  

Location

Candidate will need to reside in North America, working arrangement will be remote.

When You Join Team Applied, You Can Expect:  

A culture that values who you are and recognizes that you aren’t just an employee; you are a teammate, and you matter. We thrive on the benefits of our different experiences and celebrate the uniqueness our teammates bring to work with them every day.  

We flex our time together, collaborating remotely and in-person to empower our teams to work in the ways that work best for them.  

A comprehensive benefits and compensation package that centers our teammates and helps them to bring their best to work every day:  

Medical, Dental, and Vision Coverage  

Holiday and Vacation Time  

Health & Wellness Days  

A Bonus Day for Your Birthday  

  Learn more about the people behind our products at https://www1.appliedsystems.com/en-us/about-us/jobs/  

Your Security Matters:   Our candidates’ personal information and online safety are top of mind for us. At Applied, we proactively protect your personal information and only communicate with candidates via a secure @appliedsystems.com email or through our official careers portal. Recruiters will never request payments, ask for financial account information or sensitive information like social security numbers.   

EEO Statement    

Applied Systems is proud to be an Equal Employment Opportunity Employer. Diversity and Inclusion is a business imperative and is a part of building our brand and reputation. At Applied, we don’t discriminate, and we are committed to recruit, develop, retain, and promote regardless of race, religion, color, national origin, sexual orientation, gender identity, disability, age, veteran status, and other protected status as required by applicable law.   

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