Senior Manager, Product Strategy & Operations

Caseware combines over 35 years of industry expertise with AI-powered technology to transform how audit and accounting professionals work. Serving organizations across 130 countries, we bring intelligent automation directly into audit and financial reporting workflows—helping professionals reduce manual work, navigate complexity, and focus on informed decisions. Join our global team and help build technology that strengthens trust in financial information.

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.

Salary range:

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.

What's in it for you:

Shape what’s next with AI: Help transform audit and accounting through AI-powered technology. Explore new ways to bring AI into our own workflows, rethink how work gets done, and turn ideas into meaningful improvements for our teams and customers.

Make an impact that matters: Contribute to solutions that help professionals navigate complexity, make informed decisions, and strengthen trust in financial information around the world.

Bring your voice. Expand your perspective: Collaborate with a diverse global team where your ideas are valued, knowledge is shared, and different perspectives lead to better outcomes.

Build a career that grows with you: Develop your skills, take on new challenges, and explore career opportunities as our business and technology evolve.

Thrive at work and beyond: Enjoy competitive compensation, comprehensive benefits, recognition programs, and performance bonuses, alongside flexible work options, remote opportunities, and generous time off.

Many Voices, One Team:

We’re committed to building teams as diverse as our customers through equitable and inclusive hiring. We welcome candidates of all backgrounds. If you need accommodations or have questions at any stage of the application or interview process, contact our People Operations team at [email protected].

Background Check:

All successful candidates will undergo background screening, which may include identity verification, criminal record checks, and/or reference checks, as appropriate to the role and location and in accordance with applicable law.

Security and Fraud:

All employees are expected to apply security best practices and work within secure handling guidelines to perform assigned responsibilities when accessing data and business information.

Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.com and our open positions are always listed on reputable job boards and on our website https://jobs.lever.co/caseware. We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.