Product Manager, Office of the CPO

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!

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.  

The audit and assurance profession is the foundation of trust in our financial system and global economy — an essential mission undergoing profound transformation. In a rapidly evolving technology landscape, accountants require world-class tools to enhance trust, drive efficiency, strengthen their capability, and elevate their impact.  

We are looking for a Product Manager to join our CPO's Office and own execution across some of Caseware's most strategic enterprise account relationships and cross-functional initiatives. You will work directly with the CPO, driving account strategy, roadmap alignment, and go-to-market execution across Caseware's most complex and highest-visibility partner relationships.  

This role requires high agency. You will operate with significant autonomy, drive decisions without waiting for permission, and take full ownership of outcomes across the accounts and initiatives you own.  

❗ This is a full-time permanent 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, Toronto, ON.

What you will be doing:

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  Own the strategic relationship for key enterprise accounts, acting as the CPO's forward-deployed product resource on migrations, roadmap negotiations, and escalations.  

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  Drive Product and Commercial alignment, owning the reconciliation of product prioritization against the roadmap and resolving conflicts in partnership with the CPO and cross-functional leadership.  

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  Set go-to-market and customer lifecycle strategy for major account segments, owning account-mapping dashboards and using them to drive prioritization decisions, not just track status.  

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  Own client escalations end-to-end — diagnosing root cause, aligning engineering and technical stakeholders on a resolution path, and making the call on trade-offs when priorities conflict.  

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  Identify gaps in visibility and build the tools and dashboards needed to close them, driving adoption across product and account teams.  

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  Turn ambiguous, multi-stakeholder input into clear initiatives, epics, and decisions — you set the direction, not just document it.  

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  Drive cross-functional alignment across Product, Engineering, Design, and Commercial teams, and be comfortable pushing back when priorities don't align.  

What you will bring:

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  3+ years of experience in product management, account/strategic partnership management, or consulting, ideally within SaaS or technology.  

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  Proven ownership of ambiguous, cross-functional initiatives from discovery through resolution, with minimal oversight.  

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  Strong executive-level communication skills — comfortable presenting synthesis and recommendations directly to senior leadership.  

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  Comfort managing multiple senior external stakeholder relationships simultaneously, with the judgment to know when to escalate and when to resolve independently.  

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  Working familiarity with Jira and Confluence, or equivalent project and documentation tools.  

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  Comfort working with data to build dashboards or trackers that drive decision-making (Excel proficiency required; SQL or BI tool experience a plus).  

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  High agency: you identify what needs to happen, move without waiting to be told, and take ownership of outcomes rather than just activities.  

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  Experience in or exposure to accounting, audit, or other regulated industries is a plus.  

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  An MBA or equivalent business training is a plus but not required.  

Salary Range:

The annual base salary for this position is between $105,000 CAD and $115,000 CAD per year. 

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:

▪️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:

Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our 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 Caseware's core values is Many Voices, One Team and with that in mind, we're 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 [email protected] .

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 Certn.co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.co 

Security and Fraud:

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 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.