Senior Product Manager owning provider experience and clinical operations products at Maple, Canada’s on - demand healthcare platform. Driving scalable workflows and AI - enabled care delivery improvements.
About the role
- Lead product initiatives at Caseware, a Canadian fintech innovator in accounting software. Drive execution, collaborate across teams, and embrace complex problem-solving in tech-focused role.
Responsibilities
- Own end-to-end execution of defined product and business initiatives
- Stay ahead of the AI landscape — monitor model developments, new architectures, emerging agent patterns, and competitor moves, and bring a clear point of view on what matters for Caseware
- Define and own product health metrics for AI features: task completion, correction rates, override frequency, trust signals, and time-to-completion — and use them to drive product decisions.
- Break down ambiguous asks into clear plans, milestones, and deliverables
- Drive cross-functional alignment across product, engineering, design, and business teams
- Proactively identify and remove blockers to keep work moving
- Ensure tight follow-through, nothing falls through the cracks
- Track progress and maintain high delivery velocity across multiple workstreams
Requirements
- 3+ years of experience in tech/product roles with strong execution ownership
- Direct experience building and running eval frameworks for AI products — golden datasets, rubrics, human-in-the-loop validation, and regression tracking across releases.
- Technical fluency in LLMs, RAG, prompt engineering, embeddings, and agentic patterns — enough to have substantive conversations with engineers and know when a product problem is a model problem.
- Strong track record of building and shipping (0→1 projects, internal tools, automations, or similar)
- High ownership mindset—you don’t wait for instructions, you figure things out
- Proven ability to operate in ambiguous, fast-changing environments
- Excellent at structuring chaos into actionable plans
- Strong stakeholder management and cross-functional coordination skills
- Ability to drive outcomes without direct authority
- Experience working closely with founders, senior leadership, or lean teams is a strong signal
- Experience in startups or high-growth environments, operating with limited structure and wearing multiple hats is a strong plus
- A self-learner who can quickly pick up new domains, tools, and contexts
Benefits
- 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.
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