Senior Manager, Product Strategy & Operations

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 Linked In profiles!

Full‑time permanent position

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 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.

• 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.

• 3–5 years of experience spanning top‑tier management consulting and/or in‑house corporate strategy of comparable rigor.
• Demonstrated leadership of strategic work streams: 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.

The salary range for this position would be between CAD $115,000 and CAD $130,000, depending on experience level. This role is also eligible for discretionary bonus and/or commission, as well as other benefits. Actual pay within the listed range will be determined based on factors such as transferable skills, relevant experience, market conditions, and primary work location. The posted range is subject to change and may be updated periodically.

• Innovation is at our core. We work with cutting‑edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions.
• We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team.
• Work‑life balance is important to us. We offer flexible work options, remote opportunities, and generous time‑off policies to ensure a healthy work‑life balance.
• We offer competitive compensation, including a competitive salary and comprehensive benefits such as health insurance and retirement plans.
• We are driven by impactful work. Your contributions directly affect how our clients manage financial processes and drive their success.
• Recognition and rewards matter to us. We celebrate hard work through…