About the role

Senior Manager shaping product strategy and operations for Caseware, a Canadian audit and accounting fintech. Owning board narratives, strategic initiatives, annual planning, and executive decision materials from Toronto.

Responsibilities

Own the Product Board narrative end-to-end by building storylines, synthesizing insights, sharpening messages, and preparing the CPO and Product leadership to deliver it
Lead priority strategy initiatives from ambiguous problem to executive decision
Drive the strategy layer of annual planning by designing frameworks, synthesizing worldwide team inputs, and producing core strategy artifacts
Turn ambiguous, multi-stakeholder questions into crisp narratives and decision documents for executive action
Serve as a trusted thought partner to the Director of Global Product Operations and the CPO's leadership team
Shape product strategy covering AI-native transformation, portfolio decisions, pricing and packaging, and global market strategies

3–5 years of experience spanning top-tier management consulting and/or in-house corporate strategy of comparable rigor
Demonstrated leadership of strategic workstreams and ability to defend analyses and storylines to senior executives
Structured problem-solving fluency, including hypothesis-driven storylines, top-down communication, and synthesis of ambiguous inputs
Excellent written communication for decision documents and executive materials
Executive presence and comfort 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 and packaging or product lifecycle decisions