We’re looking for a high‑agency builder‑operator to drive execution across product and cross‑functional initiatives. This role focuses on turning defined problems into delivered outcomes fast. You’ll thrive if you’re a self‑learner, highly adaptable, and take extreme ownership, especially in ambiguous, fast‑moving environments.

Location: Hybrid role – 3 days a week in our Toronto office at 351 King St E, Toronto, ON.

What you will be doing

- 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, 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

What you bring

- 3+ years of experience in tech/product roles with strong execution ownership
- Direct experience building and running evaluation 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

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.

Benefits

- Innovation is at our core – we work with cutting‑edge technology in accounting and financial reporting
- Collaborative culture – your ideas are valued and knowledge sharing is encouraged within a supportive, inclusive team
- Work‑life balance – flexible work options, remote opportunities, and generous time‑off policies
- Competitive compensation – including health insurance and retirement plans
- Impactful work – your contributions directly affect how our clients manage financial processes
- Recognition and rewards – performance bonuses and opportunities for growth opportunities
- Global opportunities – work on international projects with a diverse team

We welcome and encourage candidates of all backgrounds. If you require accommodations or have any questions during the application or interview process, please contact our People Operations team.

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📌 Product Manager, Growth (Toronto)
🏢 Medium
📍 Toronto