Senior Manager, Product Strategy & Operations

Caseware•Toronto, ON

1d•CA$115,000 - CA$130,000•Hybrid

About The Position

As Senior Manager, Product Strategy & Operations, you will own how drive the product strategy work that decides where we play and how we win. Our strategy agenda is bigger than ever: an AI-native product transformation, major portfolio decisions, pricing and packaging, and market strategies across the globe. This is a Full-time permanent position and a new position. The role offers board-level narrative ownership, direct C-suite proximity, on a team that works AI-natively, with Claude in the workflow every day.

Requirements

3–5 years of experience spanning top-tier management consulting and/or in-house corporate strategy of comparable rigor.
Demonstrated leadership of strategic workstreams: analyses and storylines you drove and defended to senior executives yourself.
Structured problem-solving fluency: hypothesis-driven storylines, top-down communication, synthesis of ambiguous inputs.
Excellent written communication: decision documents and executive materials that stand on their own.
Executive presence: comfortable presenting to, and pushing back on, C-level stakeholders.
Hands-on fluency with modern AI tools (such as Claude).
Experience with B2B SaaS, fintech, audit/accounting, or another regulated software environment.
Experience contributing to Board-level or C-suite materials.
Familiarity with pricing & packaging or product lifecycle decisions.

Responsibilities

Own the Product Board narrative end-to-end: build the storyline, synthesize the insight, sharpen the message, and prepare the CPO and Product leadership to deliver it.
Lead priority strategy initiatives end-to-end: Product maintains a standing pipeline of our highest-stakes strategy questions, and this role owns taking each from ambiguous problem to executive decision.
Drive the strategy layer of annual planning: design the frameworks, synthesize inputs from our teams worldwide, and produce the core strategy artifacts leadership decides on.
Turn ambiguity into decisions: structure multi-stakeholder questions into crisp narratives, and decision documents that executives act on.
Operate as a trusted thought partner to the Director of Global Product Operations and the CPO's leadership team, in conversations that set Product's direction.