Senior Manager, Product Strategy & Operations

Job description

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles! 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. What the seat offers: Board-level narrative ownership, direct C-suite proximity, on a team that works AI-natively, with Claude in the workflow every day. ❗ This is a Full-time permanent position ❗ This is a new position 📍 Location: This is a hybrid role requiring the successful candidate to work 3 days a week in our Toronto office, located at 351 King St E, Suite 1100, Toronto, ON. ### What you will be doing: - 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. ### What you will bring: - 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.