Portfolio Strategy Director

Role Description

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.

What You’ll Do

• 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.
• 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.
• Build the structures that translate product and engineering data into action, not just updates.
• Partner across functions on major cross-functional programs.
• Bring the framing that makes the decision actionable and ensure the right leaders are in the room to resolve.
• Lead critical initiatives across teams when asked.

Qualifications

• 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.

Requirements

• Ability to work from an Applied Systems office or 100% remotely.
• Candidate will need to reside in North America, working arrangement will be remote.

Benefits

• A culture that values who you are and recognizes that you aren’t just an employee; you are a teammate, and you matter.
• We flex our time together, collaborating remotely and in-person.
• A comprehensive benefits and compensation package that centers our teammates:
• Medical, Dental, and Vision Coverage
• Holiday and Vacation Time
• Health & Wellness Days
• A Bonus Day for Your Birthday