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

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

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.