Director, Product Management - Head of Cal AI
•Myfitnesspal· 10h
📦 Product📝 Contract👔 Executive💰 $200k-290k🇺🇸 USA
10h ago
Caseware·12 days ago
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.
Own the strategic relationship for key enterprise accounts, acting as the CPO's forward-deployed product resource on migrations, roadmap negotiations, and escalations.
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.
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.
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.
Identify gaps in visibility and build the tools and dashboards needed to close them, driving adoption across product and account teams.
Turn ambiguous, multi-stakeholder input into clear initiatives, epics, and decisions — you set the direction, not just document it.
Drive cross-functional alignment across Product, Engineering, Design, and Commercial teams, and be comfortable pushing back when priorities don't align.
3+ years of experience in product management, account/strategic partnership management, or consulting, ideally within SaaS or technology.
Proven ownership of ambiguous, cross-functional initiatives from discovery through resolution, with minimal oversight.
Strong executive-level communication skills — comfortable presenting synthesis and recommendations directly to senior leadership.
Comfort managing multiple senior external stakeholder relationships simultaneously, with the judgment to know when to escalate and when to resolve independently.
Working familiarity with Jira and Confluence, or equivalent project and documentation tools.
Comfort working with data to build dashboards or trackers that drive decision-making (Excel proficiency required; SQL or BI tool experience a plus).
High agency: you identify what needs to happen, move without waiting to be told, and take ownership of outcomes rather than just activities.
Experience in or exposure to accounting, audit, or other regulated industries is a plus.
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.