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Senior Manager, Product Strategy & Operations

Caseware

Job Location:

Toronto - Canada

Monthly Salary: Not provided by the employer

Posted: 9 August 2026 (Yesterday)

Application Deadline: 7 November 2026

Vacancies: 1 Vacancy

Job Summary

Caseware is one of Canadas original Fintech companies having led the global audit and accounting software industry for over 30 years with more than 500000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

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 ahybridrole requiring the successful candidate to work3 days a week in our Toronto officelocatedat351 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 questionsand 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 crispnarrativesand decision documents that executives act on.

Operate as a trusted thought partnerto the Director of Global Product Operations and the CPOs leadership team in conversations that set Products direction.

What you will bring:

35 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$115000 and CAD$130000 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.

Whats in it for you:

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 recognition programs performance bonuses and opportunities for career growth.

We embrace global opportunities. Work on international projects and collaborate with a diverse global team.

About Caseware:

Casewares cutting-edge software products are meticulously designed for accounting firms corporations and teams are continually collaborating innovating and building upon our existing suite of products. With a customer-focused mindset we are building technology that is shaping what the future of audits financial reporting and financial data analytics will look like.

With a recent strategic investment from Hg Capital in 2020 Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date.

One of Casewares core values is Many Voices One Team and with that in mind were dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process please e-mail our People Operations team at emailprotected.

AI Usage:

The recruitment process may use AI assisted tools but not for candidate screening or assessment. All final hiring decisions are made by humans to ensure fairness transparency and oversight.

Background Check:

Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residingin the Netherlands and Germany are excluded from undergoing background checks via

Security and Fraud:

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

We may use artificial intelligence (AI) tools to support parts of the hiring process such as reviewing applications analyzing resumes or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed please contact us.

Required Experience:

Senior Manager

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About Company

Caseware

Accounting, audit, analytics and compliance software built by seasoned accountants. Manage your audit and financial reporting more efficiently with less risk.

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