Senior Manager, Product Strategy & Operations

CaseWare; Toronto; Hybrid; CAD 115,000 - 130,000; Full time

Benefits offered by this job

Discretionary bonus

Commission potential

Flexible work options

Generous time off

Competitive benefits

Job summary

Caseware, a global leader in AI-powered audit and accounting software, is seeking a Senior Manager, Product Strategy & Operations. This hybrid Toronto role shapes the product strategy, informs pricing and packaging, and guides global portfolio decisions alongside the C-suite.

You’ll own board narratives, drive senior-level strategy initiatives, and coordinate input from teams worldwide to deliver clear, decision-ready recommendations and artifacts for leadership.

Qualifications

• 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 youdroveand 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).
• ExperiencewithB2B 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: manage a standing pipeline of high-stakes questions and drive executive decisions.
• Drive the strategy layer of annual planning: design frameworks, synthesize inputs, and produce core strategy artifacts.
• Turn ambiguity into decisions: structure multi-stakeholder questions into crisp narratives and documents for executives.
• Operate as a trusted thought partner to the Director of Global Product Operations and CPO's leadership team.

Skills

Executive communication

Strategic leadership

AI fluency

B2B SaaS

Pricing & packaging

Board-level materials

Tools

Claude

Job description

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, ProductStrategy &Operations, you willownhowdrivetheproductstrategy 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, locatedat 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 theinsight, sharpen the message, and prepare the CPO and Product leadership to deliver it.
• Lead priority strategy initiatives end-to-end: Productmaintainsa standing pipelineof ourhighest-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 fromour teamsworldwide, and producethe corestrategyartifacts leadership decides on.
• Turn ambiguity into decisions: structure multi-stakeholder questions into crispnarratives,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 youdroveand 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).
• ExperiencewithB2B 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 [e-mail].

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.