Group Product Manager, AI Platform

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! As Group Product Manager for the AI Platform, you sit at the center of the team building Caseware's core AI surfaces — the agents and agent builder practitioners use to do real work, the eval builder and eval roadmap that let us measure quality, and the pods bringing each of these to life. You don't own the AI platform vision alone — that sits with platform leadership — but you make it real: you lead the team of product managers who each own a piece of it, sequence their overlapping roadmaps into one coherent delivery plan, and make sure the whole is moving faster and more coherently than the sum of its parts. What makes this role unique is the balance it demands: enough product depth to genuinely partner with each PM on their space, and enough leadership craft to manage, coordinate, and unblock a team of product owners rather than owning a single roadmap yourself. You are the person who turns four parallel workstreams into one delivery story. ❗ This a full-time, permanent position ❗ This a new vacancy ❗This role is hybrid. You will be required to work from our Toronto office 3-days a week, located at 351 King Street East, Toronto, ON Talent Partner : Taha Usmani What you will be doing: Roadmap Delivery & Team Development: Partner with the Principal Product Manager who owns the AI Platform roadmap to keep the roadmap aligned with organizational goals, and drive it to execution. Maintain deep knowledge of AI capabilities, agent patterns, and model limitations relevant to audit work, including how they compare to emerging market solutions. Continually assess and refine the AI product suite, identifying new opportunities for automation within audit workflows and the right resourcing to pursue them. Cultivate deep expertise in AI to grasp the full scope of what's technically feasible, and use that expertise to coach the Principal Product Manager toward greater ownership of roadmap strategy over time. Influence and Leadership: Foster a culture of process improvement and employee engagement within and across the AI product, engineering, and applied science teams. Mentor team members and other employees, ensuring the inclusion of relevant stakeholders — including audit practitioners — in decision-making processes. Build a supportive culture that empowers teams to take on more responsibility as AI capabilities mature — including actively developing the Principal Product Manager's ability to own strategy and roadmap definition. Execution and Collaboration: Partner closely with engineering and applied science teams to translate audit pain points into scoped AI features, requirements, and acceptance criteria. Articulate the concept of incremental value delivery to a wide range of stakeholders, including customers, partners, and internal teams. Engage with strategic key accounts and partner firms to understand how AI capabilities are used in practice and what's driving or limiting adoption. Diligently track and proactively manage KPIs and product metrics — including AI accuracy, adoption, and trust — to optimize performance and drive strategic decision-making. Practitioner Insight and Trust: Champion a culture of data-driven decision-making grounded in real audit practice. Serve as an authority on how practitioners will actually use and judge AI outputs, leveraging that insight for product enhancements. Partner with the Principal Product Manager to define the practitioner-credibility standard for AI outputs — not just whether an output is technically accurate, but whether it meets the bar a qualified auditor would need before relying on it. Ensure consistent integration of practitioner and user research into decision-making, shaping product requirements, design, and development accordingly. What you will bring: 5+ years of product management experience, including experience leading, mentoring, or managing other product managers. Proven ability to coordinate multiple concurrent workstreams with overlapping dependencies, and to resolve conflicts between them without needing to personally own each one. Comfortable operating as an orchestrator and multiplier rather than a sole roadmap owner — your success is measured by the team's throughput and coherence, not just your own output. Experience with AI or ML-driven products strongly preferred; enough technical fluency to have substantive conversations with engineering and applied science. Excellent written and verbal communication — able to turn several parallel workstreams into one clear story for leadership. Confidence making sequencing and prioritization calls under ambiguity, and comfortable being the one who says “no, not yet” to a pod on behalf of the group's overall plan. Salary Range: The annual base salary for this position is between $145,000 CAD and $160,000 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 talent@caseware.com. 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 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.